KR20160012895A - An organic electronic element and an electronic device comprising it - Google Patents

Abstract

Disclosed is an organic electric element comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode. The organic layer comprises a compound represented by chemical formula 1 and chemical formula 2. The element has low driving voltage and has improved light emitting efficiency, color purity and lifespan, by including the compound represented by the chemical formula 1 and the chemical formula 2 in the organic layer.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to an organic electroluminescent device,

The present invention relates to an organic electronic device and an electronic device including the same.

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 moves to the wavelength of the dopant, light of the desired wavelength can be obtained according to the type of the dopant used.

Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption becomes a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues 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, 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 and the intrinsic properties (mobility, interfacial characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved 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 sufficiently 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 And it is urgently required to develop a material capable of ideal combination of a host material of a light emitting auxiliary layer material, a hole transporting layer material and a light emitting layer.

An object of the present invention is to provide an organic electroluminescent device having improved luminous efficiency, color purity and lifetime and low driving voltage, and an electronic device including the same.

In one aspect, the present invention relates to a light-emitting device, wherein at least one of the luminescent auxiliary layer and the hole transporting layer contains one or more compounds represented by the following formula (1) Organic electroluminescent device comprising at least one kind of organic electroluminescent material.

≪ Formula 1 > (2)

In another aspect, the present invention provides an electronic device comprising the organic electric device.

Industrial Applicability According to the present invention, it is possible to provide an organic electronic device having improved luminous efficiency, color purity, life span, and the like and a low driving voltage, and an electronic device including the organic electronic 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 numerals even though 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.

In the present specification, a monovalent or divalent functional group is referred to as a functional group name or a maleic acid is written in front of a parent compound. For example, "divalent benzothiophene" means a divalent functional group of a benzothiophene which is a parent compound, similarly, "divalent dibenzothiophene" means a divalent functional group of a dibenzothiophene, Furan "refers to the bivalent functional group of the parent compound," bivalent dibenzofuran "refers to the divalent functional group of the dibenzofurane, which is the parent compound, and" bivalent pyrimidine "refers to the bivalent functional group of the parent compound, pyrimidine .

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. In this case, the atoms shared in the two rings are called 'spyro atoms', and depending on the number of spyro atoms contained in one compound, they are referred to as' monospyros,' 'diospyros,' ' '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.

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, 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, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

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 110 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 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, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, etc., and the electron transporting layer 160 may serve as a hole blocking layer You can do it.

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 material layer includes a hole injecting layer 130, a hole transporting layer 140, an electron transporting layer 160, an electron injecting layer 170, a light emitting layer 150, The light-emitting auxiliary layer 151 and the like. For example, the compound of the present invention can be used for the hole transport layer 140, the emission auxiliary layer 151, the light emitting layer 150, and the like.

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.

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, an organic electroluminescent device according to one aspect of the present invention will be described.

An organic electroluminescent device according to an embodiment of the present invention includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer including a light emitting layer, And a hole transport layer formed between the first electrode and the luminescent auxiliary layer.

At least one of the light-emission-assisting layer and the hole-transporting layer contains at least one compound represented by the following general formula (1), or two or more compounds represented by the following general formula (2)

≪ Formula 1 > (2)

In the above formulas (1) and (2), each symbol can be defined as follows.

Ar ¹ to Ar ⁶ 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'-N (R ^a ) (R ^b ). o and p are 0 or 1, provided that at least one of o and p is 1; That is, o + p = 1 or an integer of 2.

Preferably, at least one of Ar ² to Ar ⁵ is a C ₂ to C ₆₀ heterocyclic group.

,

,

등일 수 있다.Preferably, Ar ¹ to Ar ⁵ may be a C ₆ -C ₁₈ aryl group, a fluorenyl group, a C ₃ -C ₁₆ heterocyclic group, or a combination thereof, and preferably C ₆ , C ₁₀ , A C ₁₂ , C ₁₈ aryl group, a C ₃ , C ₄ , C ₅ , C ₇ , C ₈ , C ₁₀ , C ₁₂ , C ₁₆ heterocycle. Specifically, Ar ¹ to Ar ⁵ are a phenyl group, naphthyl group, biphenyl group substituted or unsubstituted with deuterium, a terphenyl group substituted or unsubstituted with deuterium, a 9,9-dimethyl-9H-fluorenyl group, Substituted or unsubstituted carbazolyl groups such as a 9-diphenyl-9H-fluorenyl group, a 9,9'-spirobifluorenyl group, a dibenzothienyl group, a dibenzofuryl group, a phenyl group, a naphthyl group, A pyridyl group, a pyrimidinyl group substituted or unsubstituted with phenyl,

,

,

And so on.

,

등일 수 있고, 이들 각각은 페닐, 나프틸, 피리딜기,

,

등으로 더 치환될 수 있다.In addition, preferably, Ar ⁶ may be a C ₆ aryl group, a C ₃ -C ₁₀ heterocyclic group, or a combination thereof, and specifically includes a phenyl group, a pyridyl group, a pyrimidinyl group, a traazinyl group,

,

Etc., each of which may be phenyl, naphthyl, pyridyl,

,

And the like.

Preferably, Ar ¹ to Ar ⁶ are independently selected from the group consisting of deuterium, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C ₁ -C ₂₀ alkylthio group, a C ₁ -C ₂₀ alkoxy group , A C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₆ -C ₂₀ An 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, NS, Si and P, And may further be substituted with at least one substituent selected from the group consisting of a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, an arylamine group, and a heteroarylamine group.

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 ); a, b, c and m are integers of 1 to 4, and n is an integer of 1 to 3.

When each of a, b, c, m and n is an integer of 2 or more, a plurality of R ¹ to R ⁵ may be the same or different and adjacent groups may combine with each other to form a ring. The ring formed at this time may be an aromatic ring or a heteroaromatic ring, and may be a C ₆ aromatic ring, that is, a benzene ring. Therefore, naphthalene, phenanthrene, etc. may be formed together with the benzene ring to which they are bonded.

Preferably, R ¹ to R ⁵ is a deuterium, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, an alkylthio import of _{C 1 -C 20, C 1 -C} 20 alkoxy group , A C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₆ -C ₂₀ An 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, NS, Si and P, And may further be substituted with at least one substituent selected from the group consisting of a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, an arylamine group, and a heteroarylamine group.

In Formula 1, L ¹ represents a divalent or trivalent C ₆ -C ₆₀ aromatic hydrocarbon group; A divalent or trivalent fluorene group; It may be selected from the group consisting of; and O, N, S, Si and P, at least one of the second containing a hetero atom or a trivalent C ₂ ~ C ₆₀ heterocyclic group of. Preferably, L ¹ is a divalent or trivalent C ₆ to C ₁₂ aromatic hydrocarbon group; A divalent or trivalent fluorene group; Or a divalent or trivalent C ₂ to C ₁₂ heterocyclic group, specifically a divalent or trivalent phenyl, biphenyl, pyridine, triazine, dibenzothiophene, 9, 9-dimethyl-9H-fluorene, and the like.

In Formula 2, X and Y are single bonds, S, O, NR ', CR'R "except that when X and Y are both a single bond, R' and R" are hydrogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of O, N, S, Si, and C ₃ ~ containing at least one hetero atom in the P C _60; And a C ₁ to C ₅₀ alkyl group.

When Ar ¹ to Ar ⁶ and R ¹ to R ⁵ are -L'-N (R ^a ) (R ^b ), L 'is 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 ; And a C ₂ to C ₆₀ heterocyclic group; and R ^a and R ^b are independently selected from the group consisting of C ₆ to C ₆₀ aryl groups; A fluorenyl 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

When each of the symbols is an aryl group, a fluorenyl group, a fused ring group, a heterocyclic group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxyl group, an aromatic hydrocarbon group and a fluorene group, a halogen, a silane group, a siloxane group, an alkyl group of the boron group, a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ a, C ₂ - an aryl group of C ₂₀ alkenyl, C ₂ -C ₂₀ alkynyl, C ₆ -C ₂₀ substituted with a C ₆ aryl group, a heavy hydrogen of -C ₂₀ of, fluorene group, O, N, S, Si and P a heterocyclic group of C ₂ -C ₂₀ containing at least one heteroatom selected from the group consisting of, a cycloalkyl group of C ₃ -C _20, arylalkyl groups, C ₇ -C _20, alkenyl of C ₈ -C ₂₀ aryl group , An arylamine group, and a heteroarylamine group.

The formula (1) may be represented by the following formula (3) or (4).

(3) ≪ Formula 4 >

In the above formulas (3) and (4), each symbol is as defined in formula (1). For example, Ar ¹ to Ar ⁵ , L, R ¹ , R ² , m and n are as defined in formula (1).

Specifically, the above-mentioned formulas (1), (3) and (4) may be one of the following compounds.

The formula (2) may be represented by the following formula (5) or (6). Formula 5 is a case where Y is a single bond, and Formula 6 is a case where X is a single bond.

    &Lt; Formula 5 > < EMI ID =

In the above Formulas (5) and (6), each symbol is the same as defined in Formula (2). For example, Ar ⁶ , X, Y, R ³ to R ⁵ , a, b and c are as defined in formula (2).

Specifically, the above-mentioned formulas (2), (5) and (6) may be one of the following compounds.

.

.

Preferably, the luminescent auxiliary layer contains one or more compounds represented by Formula 1, and the hole transport layer may include one or more compounds represented by Formula 7 below.

&Lt; Formula 7 >

In the above formula (7), Ar ⁹ is one of the following formulas (7-1) to (7-3).

&Lt; Formula <Formula 7-2> <Formula 7-3>

In the formulas (7) and (7-1) to (7-3), each symbol can be defined as follows.

Ar ⁷ , Ar ⁸ , Ar ¹⁰ , Ar ¹¹ and Ar ¹² 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; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R ^a ) (R ^b ); Preferably, Ar ⁷ , Ar ⁸ , Ar ¹⁰ , Ar ¹¹ and Ar ¹² are each independently a C ₆ to C ₁₂ aryl group; A fluorenyl group; Or a C ₂ to C ₁₂ heterocyclic group, specifically, phenyl optionally substituted with a naphthyl, methoxyl, pyrimidinyl or tert-butyl group, biphenyl, naphthyl optionally substituted with fluorine, Dibenzothienyl group, dibenzofuryl group, 9,9-dimethyl-9H-fluorenyl group, 9,9-diphenyl-9H-fluorenyl group, 9,9'-spirobifluorenyl group and the like .

R ⁶ to R ⁸ independently of one another 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 ); f, g and h are integers of 1 to 4, and when each of these is an integer of 2 or more, R ⁶ to R ⁸ may be the same or different from each other, and a plurality of R ⁶ to R ⁸ may be the same or different, , Neighboring groups may be joined together to form a ring. In this case, the ring formed may be an aromatic ring or heteroaromatic ring, preferably a C ₆ aromatic ring, that is, a benzene ring, so that naphthalene, phenanthrene, etc. may be formed together with the benzene ring to which they are bonded.

Preferably, R ⁶ to R ⁸ are selected from the group consisting of deuterium, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C ₁ -C ₂₀ alkylthio group, a C ₁ -C ₂₀ alkoxy group , A C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₆ -C ₂₀ An 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, NS, Si and P, A C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, and a C ₈ -C ₂₀ arylalkenyl group.

When R ⁶ to R ⁸ are -L'-N (R ^a ) (R ^b ), L 'is 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 ; And a C ₂ to C ₆₀ heterocyclic group; and R ^a and R ^b are independently selected from the group consisting of C ₆ to C ₆₀ aryl groups; A fluorenyl 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

In the general formulas (7-1) and (7-3), L ² and L ⁴ are C ₆ to C ₆₀ arylene groups; 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si, and P, and L ³ is selected from the group consisting of C ₆ A single bond of C ₆₀ ; An arylene group; 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

Preferably, Ar ⁷ , Ar ⁸ , Ar ¹⁰ , Ar ¹¹ , Ar ¹² and R ⁶ to R ⁸ are each an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, group, and aryloxy group, if and, L ¹ to L ³ is an aryl group, a fluorenyl group, a fusion ring group, and when a heterocyclic group, each of which is heavy hydrogen, a halogen, a silane group, a siloxane group, a boron group, a germanium group , a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ alkynyl of the A C ₆ -C ₂₀ aryl group, a C ₆ -C ₂₀ aryl group substituted with deuterium, a fluorenyl group, and at least one hetero atom selected from the group consisting of O, N, S, Si and P A C ₂ -C ₂₀ heterocyclic group, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, an arylamine group and a heteroarylamine group Lt; / RTI &gt; may be further substituted with one or more substituents selected from the group consisting of

Specifically, Formula 7 may be one of the following compounds.

Preferably, the organic material layer may be 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.

In another embodiment of the present invention, a light efficiency improving layer is formed on at least one side of the 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 Thereby providing an organic electric device. Preferably, the light-efficiency-improvement layer may include a compound represented by the general formula (1).

In another embodiment of the present invention, the present invention provides an electronic device including a display device including an organic electronic device including an organic layer containing a compound according to the present invention, and a control unit for controlling the display device. The organic electrical device may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

Hereinafter, the synthesis examples of the compound represented by the formula according to the present invention and the production example of the organic electric device will be concretely described by way of examples, but the present invention is not limited to the following examples.

Synthetic example

The compound of formula (1) according to the present invention can be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

Synthetic example of Sub 1

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

<Reaction Scheme 2>

Synthetic example of Sub 1-I

4-bromo-1-iodo-2-nitrobenzene (309.96 g, 945.3 mmol) and Pd (PPh ₃ ) ₄ (prepared as described in Example 1) were dissolved in 2780 mL of THF in a round bottom flask. 36.41 g, 31.5 mmol), K ₂ CO ₃ (261.3 g, 1890.6 mmol) and 1390 mL of water were added and stirred at 80 ° 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 122.68 g of the product (yield: 70%).

Examples of synthesis of Sub 1- II

Sub-1-I-1 (122.68 g, 441.1 mmol) obtained in the above synthesis was dissolved in 1810 mL of o- dichlorobenzene in a round bottom flask, and then triphenylphosphine (289.26 g, 1102.8 mmol) was added and stirred at 200 ° C. When the reaction was complete, o- dichlorobenzene was removed by distillation 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 80.34 g (yield: 74%) of the product.

Synthesis Example of Sub 1- III (1)

Sub I-II-1 (80.34 g, 326.5 mmol) obtained in the above synthesis was dissolved in 653 mL of nitrobenzene in a round bottom flask and then iodobenzene (99.9 g, 489.7 mmol), Na ₂ SO ₄ (46.37 g, 326.5 mmol) K ₂ CO ₃ (45.12 g, 326.5 mmol) and Cu (6.22 g, 97.9 mmol) were added and stirred at 200 ° C. When the reaction was complete, nitrobenzene was removed by distillation 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 76.78 g (yield: 73%) of the product.

Synthesis Example of Sub 1- III (2)

2-iodo-9,9-diphenyl-9H-fluorene (189.6 g, 426.7 mmol) and Na ₂ SO ₄ (2 mL) were dissolved in 70 mL of nitrobenzene and 5 mL of Sub 1-II- 108.8 g (Yield: 68%) of the product was obtained by the same synthetic method as in Sub 1-III-1, with potassium carbonate (40.4 g, 284.4 mmol), K ₂ CO ₃ (39.3 g, 284.4 mmol) .

Examples of synthesis of Sub 1- IV

After the Sub 1-III-1 (76.78 g, 238.3 mmol) obtained in the above synthesis in a round bottom flask was dissolved in DMF, Bis (pinacolato) diboron ( 66.57g, 262.1 mmol), Pd (dppf) Cl 2 (5.84 g, 7.1 mmol), KOAc (70.16 g, 714.9 mmol) was added and stirred at 90 [deg.] C. When the reaction was complete, DMF was removed by distillation 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 73.92 g (yield: 84%) of the product.

Example of synthesis of Sub 1 (when o = 1, p = 0) (1)

Obtained in the above Synthesis Sub 1-IV-1 (73.92 g, 200.2 mmol) of was dissolved in 880 mL THF in a round bottom flask, 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd (PPh 3) 4 (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol) and 440 mL of water were added and stirred at 80 ° 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 55.8 g (yield: 70%) of the product.

Example of synthesis of Sub 1 (when o = 1 and p = 0) (2)

Obtained in the above Synthesis Sub 1-IV-14 (80.6 g, 132.3 mmol), THF 582 mL, 1-bromo-2-iodobenzene (56.2 g, 198.6 mmol), Pd (PPh 3) 4 (7.65 g, 6.62 mmol) , K ₂ CO ₃ (54.9 g, 397.2 mmol) and 291 mL of water were used to obtain 52.4 g (yield: 62%) of the product using the synthesis of Sub 1-1.

Example of synthesis of Sub 1 (when o = 1, p = 0) (3)

Obtained in the above Synthesis Sub 1-IV-17 (65.9 g, 126.4 mmol), THF 556 mL, 1-bromo-2-iodobenzene (53.8 g, 190 mmol), Pd (PPh 3) 4 (7.3 g, 6.32 mmol) , K ₂ CO ₃ (52.4 g, 319.1 mmol) and water (278 mL) were subjected to the synthesis of Sub 1-1 to obtain 45.2 g of the product (yield: 65%).

Synthesis example of Sub 1-2 (when o = 1, p = 1)

It was dissolved the Sub 1-IV-1 (73.92 g, 200.2 mmol) obtained in the above synthesis in 880 mL THF in a round bottom flask, 1,3-dibromo-5-iodobenzene (108.65 g, 300.3 mmol), Pd (PPh 3 ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol) and 440 mL of water were added and stirred at 80 ° 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 69.7 g (yield: 73%) of the product.

Examples of Sub 1 are as follows, and the FD-MS values thereof are as shown in Table 1 below.

[Table 1]

Synthetic example of Sub 2

Sub 2 of Scheme 1 may be synthesized by the reaction path of Scheme 3, but is not limited thereto.

<Reaction Scheme 3>

Example of synthesis of Sub 2-1

Then put the bromobenzene (37.1 g, 236.2 mmol) in a round bottom flask was dissolved in toluene (2200 mL) aniline (20 g, 214.8 mmol), Pd 2 (dba) 3 (9.83 g, 10.7 mmol), P (t -Bu ) ₃ (4.34 g, 21.5 mmol) and NaO t- Bu (62 g, 644.3 mmol) were added in this order and stirred at 100 ° C. 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 compound was purified by silicagel column and recrystallized to obtain 28 g of product (yield: 77%).

Synthetic Example of Sub 2-13

3-bromodibenzo [b, d] thiophene (42.8 g, 162.5 mmol), toluene (1550 mL), [1,1'-biphenyl] -4-amine (25 g, 147.7 mmol), Pd 2 (dba) 3 ( (37.6 g, 162.5 mmol), P ( t- Bu) ₃ (3 g, 14.8 mmol) and NaO t- Bu (42.6 g, 443.2 mmol) 73%).

Examples of Sub 2 are as follows, and their FD-MS values are as shown in Table 2 below.

[Table 2]

Synthesis Example of Final Compound 1

P1-1 synthesis example

Sub 2-1 (6.4 g, 47.3 mmol) was added to a round bottom flask and dissolved in toluene (500 mL). Sub 1-1 (20.7 g, 52.0 mmol) and Pd ₂ (dba) ₃ ), P ( t- Bu) ₃ (1 g, 4.73 mmol) and NaO t- Bu (13.6 g, 141.8 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 16.2 g (yield: 70%) of the product.

Example of P1-53 synthesis

(20.7 g, 52.0 mmol) and Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol) were dissolved in toluene (500 mL) ), P ( t- Bu) ₃ (1 g, 4.73 mmol) and NaO t- Bu (13.6 g, 141.8 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 28.8 g (yield: 70%) of the product.

Example of P1-70 synthesis

Sub 2-2 (11.6 g, 47.3 mmol) was added to a round bottom flask and dissolved in toluene (500 mL), Sub 1-2 (24.8 g, 52.0 mmol) and Pd ₂ (dba) ₃ ), P ( t- Bu) ₃ (1 g, 4.73 mmol) and NaO t- Bu (13.6 g, 141.8 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 25.0 g (yield: 75%) of the product. Sub2-2 (6.6 g, 24 mmol) was added to the obtained compound, and the reaction proceeded as in the above reaction formula using P1-1 synthesis method to obtain 22.0 g (yield: 74%) of the product.

 [Table 3]

Synthesis Example of Final Compound 2

The final product 2 represented by formula 2 according to the present invention can be prepared by reacting Sub 3 and Sub 4 according to the following reaction formula 4, but is not limited thereto.

<Reaction Scheme 4>

Example of synthesis of Sub 3

Sub 3 of Scheme 4 can be synthesized by, but not limited to, Scheme 5.

<Reaction Scheme 5>

Sub 3 (1) Synthetic example (when X = S, Y = single bond)

Sub 3-2-1 synthesis example

(50 g, 0.16 mol), bis (pinacolato) diboron (48.65 g, 0.19 mol), KOAc (47 g, 0.48 mol), PdCl ₂ (dppf), 5-bromobenzo [ b ] naphtha [1,2- d ] thiophene (5.21 g, 4 mol%) was dissolved in DMF solvent, and the mixture was refluxed at 120 ° C for 12 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. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic layer was recrystallized from CH ₂ Cl ₂ and methanol to obtain the desired Sub 3-2-1 (46 g, 80%).

Sub 3-4-1 Synthetic Example

Sub 3-2-1 (40 g, 0.11 mol ), bromo-2-nitrobenzene (26.91 g, 0.13 mol), K 2 CO 3 (46.03 g, 0.33 mol), Pd (PPh 3) 4 (5.13 g, 4 mol%) was dissolved in anhydrous THF and a small amount of water, and the mixture was refluxed at 80 DEG C for 12 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. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using silicagel column to obtain the desired Sub 3-4-1 (27.62 g, 70%).

Sub 3 (1) Synthetic example

Sub 3-4-1 (20 g, 0.05 mol) and triphenylphosphine (44.28 g, 0.17 mol) were dissolved in o- dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was recrystallized by silicagel column to obtain the desired Sub 3 (1) (26.68 g, 75%).

Sub 3 (2) Synthetic example (when X = single bond, Y = S)

Sub 3-2-2 Synthetic Example

(50 g, 0.16 mol), bis (pinacolato) diboron (48.65 g, 0.19 mol), KOAc (47 g, 0.48 mol), PdCl ₂ (dppf), 5-bromobenzo [b] naphtho [2,1-d] thiophene (5.21 g, 4 mol%) was dissolved in DMF solvent, and the mixture was refluxed at 120 ° C for 12 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. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic layer was recrystallized from CH ₂ Cl ₂ and methanol to obtain the desired Sub 3-2-2 (45 g, 78%).

Sub 3-4-2 Synthetic Example

Sub 3-2-2 (40 g, 0.11 mol ), bromo-2-nitrobenzene (26.91 g, 0.13 mol), K 2 CO 3 (46.03 g, 0.33 mol), Pd (PPh 3) 4 (5.13 g, 4 mol%) was dissolved in anhydrous THF and a small amount of water, and the mixture was refluxed at 80 DEG C for 12 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. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated by silicagel column to obtain the desired Sub 3-4-2 (25.4 g, 65%).

Sub 3 (2) Synthetic examples

Sub 3-4-2 (20 g, 0.05 mol) and triphenylphosphine (44.28 g, 0.17 mol) were dissolved in o- dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was recrystallized by silicagel column to obtain the desired Sub 3 (2) (23.48 g, 66%).

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

[Table 4]

Examples of compounds of Sub 4

Examples of Sub 4 include, but are not limited to, the following FD-MS values.

[Table 5]

Synthesis Example of Final Compound 2

Example of P2-4 synthesis

Sub 4-15 (14.8 g, 52.0 mmol) and Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol) were dissolved in toluene (500 mL) mmol), P ( t- Bu) ₃ (1 g, 4.73 mmol) and NaO t- Bu (13.6 g, 141.8 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 17.0 g (yield: 68%) of the product.

Example of P2-25 synthesis

Sub 4 (5) (16.2 g, 52.0 mmol), Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol) were dissolved in toluene (500 mL) mmol), P ( t- Bu) ₃ (1 g, 4.73 mmol) and NaO t- Bu (13.6 g, 141.8 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 20.3 g (yield: 70%) of the product.

The FD-MS values of the final compounds P2-1 to P2-28 are shown in Table 6 below.

[Table 6]

Example of Synthesis of Final Compound 3

The final product 3 represented by formula (7) according to the present invention can be prepared by reacting Sub 5 or Sub 6 with Sub 2 as shown in Reaction Scheme 6 below, but is not limited thereto.

<Reaction Scheme 6>

In the final compound 3, L is L ² to L ⁴ defined in formulas (7-1) to (7-3), and Ar corresponds to Ar ⁷ and Ar ⁸ .

1. Synthetic Example of Sub 5

<Reaction Scheme 7>

Examples of the Sub 5 may include the compounds of the following S1 to S7.

Sub 5-1-1 Synthesis Example (L = biphenyl)

4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na ₂ SO ₄ (42.6 g, 300 mmol), K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were added and stirred at 200 ° C. When the reaction was complete, nitrobenzene was removed by distillation 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 80.05 g (yield: 67%) of the product.

Sub 5-1-2 Synthesis Example (L = 9,9-dimethyl-9H-fluorene)

2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol) and Na ₂ SO ₄ (42.6 g, 300 mmol) were added to the starting material, 9H-carbazole (50.16 g, , K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were added thereto to obtain 88.11 g (yield: 67%) of the product using Sub 5-1-1.

Sub 5-1-3 Synthesis Example (L = 9,9-dimethyl-9H-fluorene)

4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na ₂ SO ₄ (42.6 g, 300 mmol) was added to the starting material, 7H-benzo [ mmol), K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were added and 92.8 g of the product (yield: 69%) was obtained using the synthesis method of Sub 5-1-1 .

Sub 5-1-4 Synthesis Example (L = 9,9-dimethyl-9H-fluorene)

7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol) and Na ₂ SO ₄ (42.6 g, 300 mmol) were added to the starting material, 7H-benzo [ , 95.24 g (Yield: 65%) of the product was obtained by the method of Sub 5-1-1, by adding K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, .

Sub 5-1-5 Synthesis Example (L = biphenyl)

4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na ₂ SO ₄ (42.6 g, 300 mmol) was added to the starting material, 11H-benzo [ mmol), K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were added and 80.05 g (Yield: 62%) of the product was obtained using the synthesis method of Sub 5-1-1 .

Sub 5-1-6 Synthesis Example (L = 9,9-dimethyl-9H-fluorene)

7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol) and Na ₂ SO ₄ (42.6 g, 300 mmol) were added to the starting material, 5H-benzo [ 93.78 g (Yield: 64%) of the product was obtained by the method of Sub 5-1-1, by adding K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, .

Sub 5-1-7 Synthesis Example (L = biphenyl)

4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol) and Na ₂ SO ₄ (42.6 g, 300 mmol) were added to the starting material, 9H-dibenzo [a, 98.7 g (Yield: 66%) of the product was obtained using Sub 5-1-1 synthesis method by adding K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, .

Sub 5-1-8 Synthesis Example (L = biphenyl)

4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na ₂ SO ₄ (42.6 g, 300 mmol) was added to the starting material N-phenylnaphthalen- mmol), K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were added and 89.2 g (Yield: 66%) of the product was obtained using the synthesis method of Sub 5-1-1 .

Sub 5-1-9 Synthesis Example (L = 9,9-dimethyl-9H-fluorene)

2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na ₂ SO ₄ (80 mmol) was added to the starting material, 7H-dibenzo [ (42.4 g, 300 mmol), K ₂ CO ₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were added and the product, 98.5 g %).

2. Synthetic examples of Sub 6

<Reaction Scheme 8>

M2-2-1 Synthesis Example (h = 0, Ar ¹⁰ = Phenyl)

After dissolving 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in 980 mL of DMF, bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol) 41.3 g, 420 mmol) were added in this order, followed by stirring for 24 hours to synthesize a borate compound. The resulting compound was separated by silicagel column and recrystallization to obtain 35.2 g (68%) of a borate compound.

M2-2-2 Synthesis Example (h = 0, Ar ¹⁰ = biphenyl)

Using the above synthesis method of M2-2-1, 40 g (64%) was obtained. 3-bromo-9-biphenyl-9H-carbazole (45.1 g, 140 mmol) was used instead of 3-bromo-9-phenyl-9H-carbazole (55.76 g, It differs only in the point of use.

Sub 6-1-1 Synthesis Example (h = 0, Ar ¹⁰ = Phenyl, L ³ = biphenyl (linear))

M2-2-1 (29.5 g, 80 mmol) was dissolved in THF 360 mL, 4-bromo- 4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3) 4 ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL), 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 26.56 g (70%) of the product.

Sub 6-1-2 Synthesis Example (h = 0, Ar ¹⁰ = Phenyl, L ³ = phenyl)

M2-2-1 (29.5 g, 80 mmol) , THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd (PPh 3) 4 (2.8 g, 2.4mmol), NaOH (9.6 g , 240 mmol) and water (180 mL), 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 purified by silicagel column and recrystallized to obtain 22.9 g (72%) of the product.

Sub 6-1-3 Synthesis Example (h = 0, Ar ¹⁰ = Phenyl, L ³ = biphenyl (non-linear))

M2-2-1 (29.5 g, 80 mmol) was dissolved in THF 360 mL, 4'-bromo- 3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3) 4 ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL), 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 24.7 g (65%) of the product.

Sub 6-1-4 Synthesis Example (h = 0, Ar ¹⁰ = biphenyl, L ³ = biphenyl (linear))

After dissolving M2.2-2 (35.63 g, 80 mmol) obtained in the above synthesis in 360 mL of THF, 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL), 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 purified by silicagel column and recrystallized to obtain 29.51 g (67%) of the product.

Synthesis Example of Final Compound 3

Synthesis Example of Compound 3-17

After dissolving 9- (4'-bromo- [1,1'-biphenyl] -4-yl) -9H-carbazole (9.6 g, 24 mmol) in toluene, di ([ yl) amine (6.4g, 20mmol) , Pd 2 (dba) 3 (0.05 eq.), PPh ₃ (0.1 equiv), NaO t -Bu (after addition of 3 eq.), respectively, stirred for 24 hours at 100 ℃ refluxed . 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 12.9 g (yield: 84%) of the final compound.

Synthesis Example of Compound 3-32

After 9- (4-bromophenyl) -9-phenyl-9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene, 9H-fluoren-2-amine ( 7.2g, 20mmol), Pd 2 (dba) 3 (0.05 eq.), PPh ₃ (0.1 eq.), then the addition of NaO t -Bu (3 equiv), respectively, at 100 ℃ 24 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 13.8 g (yield: 85%) of the final compound.

Synthesis Example of Compound 3-61

After dissolving N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-1 -amine (10.8 g, 24 mmol) in toluene, N-phenylnaphthalen- (0.05 eq.), Pd ₂ (dba) ₃ (0.05 eq.), PPh ₃ (0.1 eq.) and NaO t- Bu (3 eq.) were added thereto. 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 11.4 g (yield: 81%) of the final compound.

The FD-MS values of some compounds of the compounds 3-1 to 3-71 are shown in Table 7 below.

[Table 7]

Evaluation of manufacturing of organic electric device

[ Example  One] Red organic light emitting device

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 -phenylbenzene -1,4-diamine (hereinafter referred to as "2-TNATA") was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Then, the compound P1-4 of the present invention was coated on the hole injection layer to a thickness of 60 nm To form a hole transporting layer. (II) acetylacetonate] (hereinafter, referred to as "(piq) ₂ Ir (acac)") as a host material on the hole transport layer using the compound P2-4 of the present invention as a dopant substance To a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, aluminum (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter referred to as "BAlq") was vacuum deposited on the light emitting layer to a thickness of 10 nm Thereby forming a hole blocking layer. Next, tris (8-quinolinol) aluminum (hereinafter referred to as "Alq ₃ ") was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Then, LiF as an alkali metal halide was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm as a cathode to produce an organic electroluminescence device.

[ Example  2] to [ Example  49] Red organic light emitting device

The compound described in the following Table 8 was used as the hole transport layer material instead of the compound P1-4 of the present invention except that the compound of the present invention described in the following Table 8 was used instead of the compound P2-4 of the present invention as the host material of the light emitting layer An organic electroluminescent device was prepared in the same manner as in Example 1.

[ Comparative Example  1] to [Comparative Example 5]

Organic electroluminescent devices were manufactured in the same manner as in Example 1 except that the compounds A to C, the compounds P2-28 and the compounds P1-53 were used as the phosphorescent host materials of the hole transporting layer and the light emitting layer as shown in Table 8 below Respectively.

Electroluminescence (EL) characteristics of the organic EL devices of Examples 1 to 49 and Comparative Examples 1 to 5 thus prepared were measured by applying a forward bias DC voltage and using PR-650 of a photoresearch company , T95 lifetime was measured through a life measuring apparatus manufactured by Mac Science Inc. at a reference brightness of 2500 cd / m ² , and the measurement results are shown in Table 8 below.

[Table 8]

From the results of the above Table 8, it can be seen that when the material for an organic electroluminescence device of the present invention represented by Chemical Formula 1 is used as a hole transport layer and the material for an organic electroluminescence device of the present invention represented by Chemical Formula 2 is used as a phosphorescent host, It can be confirmed that the driving voltage is lowered and the efficiency and the life span are improved as compared with Examples 1 to 5.

That is, one of the comparative compounds A and B was used as the hole transport layer and the comparative compound C was used as the phosphorescent host, and one of the comparative compounds A and B was used as the hole transport layer. Compared with Comparative Example 3 and Comparative Example 4 using the compound to be displayed, and Compound 5 represented by Formula 1 were used as the hole transporting layer and Comparative Example 5 using the Comparative Compound C as the phosphorescent host, Examples 1 to 49 using the compound represented by Chemical Formula 2 as a phosphorescent host as a transport layer showed excellent results in terms of driving voltage, efficiency, and lifetime.

Compounds of the present invention represented by the formula (I) have properties such as a high mobility and a wide band gap as compared with the comparative compounds A and B, and the compounds represented by the formula (2) As compared with the former, there are not only electrons but also stability to holes and high T1.

Therefore, when the organic electroluminescent device is manufactured by appropriately combining the compounds represented by the formulas (1) and (2), more holes are transferred to the luminescent layer quickly and easily, and the charge balance in the luminescent layer of holes and electrons is increased Light emission is well performed inside the light emitting layer rather than at the interface of the hole transporting layer, thereby deteriorating the deterioration at the ITO and HTL interfaces, thereby lowering the driving voltage of the entire device, and improving the efficiency and lifetime. That is, when the compounds represented by the formulas (1) and (2) are appropriately combined, the synergistic action occurs electrochemically and the performance of the entire device is improved.

[Example 50] Red organic light emitting element

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, Compound 3-17 of the present invention was vacuum-deposited to a thickness of 60 nm on the hole injection layer Thereby forming a hole transporting layer. Compound P1-53 of the present invention was vacuum deposited on the hole transport layer to form a light emitting auxiliary layer having a thickness of 60 nm. The compound P2-4 of the present invention was used as a host material and (piq) ₂ Ir ( acac) as a dopant material was doped at a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, 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 deposited to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer. Then, LiF as an alkali metal halide was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm as a cathode to produce an organic electroluminescence device.

[Examples 51 to 79] Red organic electroluminescent devices

The compound 3-17 of the present invention or the compound described in the following Table 9 can be used as the hole transporting layer material, the compound P1-53 of the present invention or the compound described in the following Table 9 as the luminescent auxiliary layer material as the host material of the light emitting layer, An organic electroluminescence device was prepared in the same manner as in Example 50 except that the compound of the present invention described in Table 9 was used.

[Comparative Example 6] to [Comparative Example 15]

An organic electroluminescent device was prepared in the same manner as in Example 50 except that a hole transport layer, a light emitting auxiliary layer and a phosphorescent host material were used as shown in Table 9 below.

Electroluminescence (EL) characteristics of the organic EL devices of Examples 50 to 79 and Comparative Examples 6 to 15 thus prepared were measured by PR-650 of a photoresearch company by applying a forward bias DC voltage , T95 lifetime was measured through a life measuring apparatus manufactured by Mac Science Inc. at a reference brightness of 2500 cd / m ² , and the measurement results are shown in Table 9 below.

[Table 9]

It can be seen from Table 9 that the compound represented by the general formula (7) of the present invention is used as the hole transport layer material and the compound represented by the general formula (1) is used as the luminescent auxiliary layer material and the compound represented by the general formula (In Comparative Example 6 in Table 9, the materials of the light-emission-assisting layer and the hole-transporting layer are indicated as being the same, but this is for comparison with devices of the same thickness, (Comparative Example 7 to Comparative Example 12), or Comparative Compound C was used as the phosphorescent host material (Comparative Example 7), or Comparative Example 7 was used as the light- (Comparative Examples 13 to 15) It can be seen that the driving voltage of the device is lower than that of the comparative example, and the efficiency and lifetime are improved.

When the compound represented by Formula 1 of the present invention is used alone as a light-emitting auxiliary layer material, it has a high T1 energy level and a deep HOMO energy level, so that the hole and electron have a charge balance and a hole transport layer interface Emitting layer is formed within the light emitting layer, thereby maximizing the efficiency. Further, by using the compound represented by the general formula (3) of the present invention as a phosphorescent host material, the proper combination of the luminescent auxiliary layer and the phosphorescent host material electrochemically shows a synergistic action to improve the performance of the entire device. &Lt; tb &gt; &lt; TABLE &gt;

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)

An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode,
Wherein the organic material layer includes a light emitting layer, a light emitting auxiliary layer formed between the first electrode and the light emitting layer, and a hole transporting layer formed between the first electrode and the light emitting auxiliary layer,
Wherein at least one of the light-emission-assisting layer and the hole-transporting layer contains at least one compound represented by the following formula (I) or a mixture of two or more compounds represented by the following formula (II) An organic electroluminescent device characterized by comprising:
&Lt; Formula 1 >< EMI ID =

In the above Formulas 1 and 2,
Ar ¹ to Ar ⁶ 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'-N (R ^a ) (R ^b ); o and p are 0 or 1, with the proviso that at least one of o and p is 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); is selected from the group consisting of, adjacent to each other a group bonded to each other can form a ring, a, b, c, m is an integer from 1 to 4; , n is an integer of 1 to 3;
L 'is 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 ; And a C ₂ to C ₆₀ heterocyclic group; and R ^a and R ^b are independently selected from the group consisting of C ₆ to C ₆₀ aryl groups; A fluorenyl 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 ; It is selected from the group consisting of; and O, N, S, Si, and heterocyclic of C ₂ ~ C ₆₀ group containing at least one hetero atom in the P;
In Formula 1, L ¹ represents a divalent or trivalent C ₆ -C ₆₀ aromatic hydrocarbon group; A divalent or trivalent fluorene group; And O, N, S, Si and at least one heteroatom divalent or trivalent C ₂ ~ C ₆₀ heterocyclic group containing from P; is selected from the group consisting of;
In Formula 2, X and Y are single bonds, S, O, NR ', CR'R "except that when X and Y are both a single bond, R' and R" are hydrogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of O, N, S, Si, and C ₃ ~ containing at least one hetero atom in the P C _60; And a C ₁ to C ₅₀ alkyl group;
The aryl group, the fluorenyl group, the fused ring group, the heterocyclic group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxyl group, the aromatic hydrocarbon group and the fluorene group may be replaced by deuterium, a halogen, a silane group, group, a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, an alkenyl group, a C ₂ C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ a- for C ₂₀ alkynyl, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one heteroatom selected from the group consisting of Si and P aryl of heterocyclic group of C ₂ -C ₂₀ containing atoms, C ₃ -C ₂₀ cycloalkyl, C ₇ -C ₂₀ arylalkyl groups, C ₈ -C ₂₀ in the alkenyl group, an arylamine group, and a heteroaryl amine groups And may be further substituted with one or more substituents selected from the group consisting of The method according to claim 1,
(1) is represented by the following formula (3) or (4): < EMI ID =
&Lt; Formula 3 &gt;&lt; Formula 4 &gt;

Wherein Ar ¹ to Ar ⁵ , L, R ¹ , R ² , m and n are as defined in claim 1. The method according to claim 1,
Wherein at least one of Ar ² to Ar ⁵ in Formula 1 is a C ₂ to C ₆₀ heterocyclic group. The method according to claim 1,
(2) is represented by the following general formula (5) or (6): < EMI ID =
&Lt; Formula 5 &gt;&lt; EMI ID =

Wherein Ar ⁶ , X, Y, R ³ to R ⁵ , a, b and c are as defined in claim 1. The method according to claim 1,
(1) is one of the following compounds:

. The method according to claim 1,
(2) is one of the following compounds:

. The method according to claim 1,
Wherein at least one of the compounds represented by Formula 1 is contained in the light-emission-assisting layer. The method according to claim 1,
The light-emitting layer may include one or more compounds represented by Formula 1,
Wherein the hole transport layer contains one or more compounds represented by the following general formula (7): < EMI ID =
&Lt; Formula 7 &gt;

In the above formula (7), Ar ⁹ is one of the following formulas (7-1) to (7-3)
<Formula 7-1> Formula 7-2> Formula 7-3>

In Formulas 7 and 7-1 to 7-3,
Ar ⁷ , Ar ⁸ , Ar ¹⁰ , Ar ¹¹ and Ar ¹² 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; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R ^a ) (R ^b );
In the above formulas (7-1) to (7-3)
R ⁶ to R ⁸ independently of one another 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 is selected from the group consisting of, it is possible to form a ring adjacent to each other a group bonded to each other, f, g, and h is an integer from 1 to 4; and ^{-L'-N (R a) (} R b)
L ² and L ⁴ are C ₆ to C ₆₀ arylene groups; 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P;
L ³ is a single bond of C ₆ to C ₆₀ ; An arylene group; 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P;
Wherein L ', R ^a and R ^b are as defined in claim 1,
^{Ar 7, Ar 8, Ar 10} , Ar 11, Ar 12, R 6 to R ⁸ are each an aryl group, a fluorenyl group, a heterocyclic group, a fusion ring group, an alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryl If the case-oxy group, the L ¹ to L ³ an aryl group, a fluorenyl group, a fused ring group and a heterocyclic group, each of which is heavy hydrogen, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, an alkylthio import of C ₁ -C _20, alkynyl of C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ a of, C ₆ aryl groups -C ₂₀ aryl group, a C ₆ -C ₂₀ substituted with a heavy hydrogen, fluorene group, O, N, S, C ₂ -C comprising at least one heteroatom selected from the group consisting of Si and P ₂₀ heterocyclic group, C ₃ -C ₂₀ cycloalkyl, C ₇ -C ₂₀ arylalkyl groups, C ₈ -C ₂₀ aryl alkenyl group, an arylamine group, and a heteroaryl amine by a group selected from the group consisting of Which may be further substituted with one or more substituents. 9. The method of claim 8,
(7) is one of the following compounds.

The method according to claim 1,
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. The method according to claim 1,
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. A display device comprising the organic electroluminescent device according to claim 1,
And a control unit for driving the display device. 13. The method of claim 12,
Wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a device for monochromatic or white illumination.

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