KR20150116337A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving light-emitting efficiency, stability, and lifespan of an element, an organic electronic element using same and an electronic device thereof.

Description

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

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

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a 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.

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 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, 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 optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time.

In order to solve the problem of light emission in the hole transporting layer in recent organic electroluminescent devices, it is necessary to have a light emitting auxiliary layer between the hole transporting layer and the light emitting layer, It is time to develop the layer.

Generally, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.

However, the material used for the hole transport layer has a low HOMO value and therefore has a low T 1 value. As a result, the exciton generated in the light emitting layer is transferred to the hole transport layer. As a result, charge unbalance ) And emits light at the hole transporting layer or at the interface of the hole transporting layer, thereby exhibiting color purity reduction, efficiency reduction, and low lifetime.

In addition, when a material having a high hole mobility is used to make a low driving voltage, the efficiency tends to decrease. This is because the hole mobility is faster than the electron mobility in a general organic electroluminescent device, resulting in a charge unbalance in the light emitting layer, resulting in a reduction in efficiency and a low lifetime.

Therefore, the light-emission-assisting layer has a hole mobility (within a full device blue device driving voltage range) and a high electron (T1) block for having a proper driving voltage capable of solving the problems of the hole transporting layer, Value, and a wide band gap.

However, this can not be achieved simply by the structural properties of the core of the light-emitting auxiliary layer material, but is possible when the properties of the core and sub-substituents of the material are combined. Therefore, in order to improve the efficiency and lifetime of the organic electronic device, development of a light emitting auxiliary layer material having a high T1 value and a wide band gap is desperately required.

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, an electron injecting material, However, the development of a stable and efficient organic material layer for an organic electric device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and development of materials for the light emission-assisting layer and the hole transporting layer is urgently required.

It is an object of the present invention to provide a compound capable of improving a high luminous efficiency, a low driving voltage, a high heat resistance, a color purity and a lifetime of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the invention provides compounds represented by the formula:

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

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

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

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

When a is an integer of 0, 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 illustration of an organic electroluminescent device according to an embodiment of the present invention.

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

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

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

The compound according to the present invention applied to the organic material layer may be a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, It can be used as a material. Preferably, the compound of the present invention may be used as the hole transport layer 140 and / or the light emitting auxiliary layer 151 material.

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

As described above, in order to solve the light emission problem in the hole transporting layer in recent organic electroluminescent devices, it is preferable that the light emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer. It is necessary to develop different luminescent auxiliary layers. On the other hand, in the case of the light-emission-assisting layer, it is difficult to deduce the characteristics of the organic layer to be used even if a similar core is used because the relationship between the hole-transport layer and the light-emitting layer (host)

Accordingly, in the present invention, by forming a hole transporting layer or a light-emitting auxiliary layer using the compound represented by the formula (1), the energy level and T1 value between each organic layer, the mobility of the material, It is possible to simultaneously improve the lifetime and efficiency of the organic electronic device.

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

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

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

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

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochrome 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 Formula 1, R ¹ to R ⁴ are each independently selected from the group consisting of deuterium; Tritium; 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; -L ^a -N (Ar ^a ) (Ar ^b ); A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having from ₆ to ₃₀ carbon atoms.

Provided that at least one of R ¹ to R ⁴ is bonded to adjacent groups to form at least one ring. The ring formed may be an aromatic ring of C ₆ to C ₆₀ , fluorene, or an alicyclic group of C ₃ to C ₆₀ , or a C ₂ to C ₆ group containing at least one heteroatom selected from O, N, S, Si and P It may be heterocyclic date of _60. Herein, the term " combining neighboring groups " means that neighboring R ¹ , neighboring R ² , neighboring R ^3, or neighboring R ⁴ are bonded to each other. The rings may be fused with the benzene ring to which they are attached to form naphthalene, anthracene, phenanthrene, triphenylene, pyrene, and the like.

Here, R ¹ to R ⁴ which do not form a ring may be respectively defined as defined above. For example, when m and n are both 2, adjacent R ^{1 s} may combine with each other to form a ring, and R ² may be an aryl group or a heterocyclic group independently of each other even when adjacent to each other.

On the other hand, in the general formula m, n, o and p may be an integer from 0 to 4, respectively, at least one of which two can be more integer, each of each is 2 or more integer, if a plurality of R ¹ to R ⁴ are each May be the same or different. For example, when m is 2, one of R ¹ may be an aryl group and the other may be a heterocyclic group.

In Formula 1, Ar ¹ and Ar ² are, independently of each other, 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; -L ^a -N (Ar ^a ) (Ar ^b ); A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having from ₆ to ₃₀ carbon atoms,

L ^a independently of one another are a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; C ₂ to C ₆₀ divalent heterocyclic groups containing at least one hetero atom selected from O, N, S, Si and P; A divalent 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 divalent aliphatic hydrocarbon group,

Ar ^a and Ar ^b are, independently of each other, 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; And an alkenyl group having ₂ to ₂₀ carbon atoms.

Specifically, Ar ¹ and Ar ² are independently of each other an aryl group such as phenyl, biphenyl, terphenyl, naphthyl, phenanthrene and the like, or an aryl group such as furyl, thiophene, pyridyl, pyrimidyl, indolyl, quinolyl, Norbornyl, dibenzothiophene, dibenzofuran, and the like, or a fluorenyl group such as dimethylfluorene, diphenylfluorene, spirobifluorene, and the like. At this time, Ar ¹ and Ar ² may be further substituted with the substituents, and in addition to the substituent, they may be further substituted by halogen, deuterium, alkyl, alkenyl, alkoxyl or the like.

In Formula 1, L ¹ and L ² independently represent a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; C ₂ to C ₆₀ divalent heterocyclic groups containing at least one hetero atom selected from O, N, S, Si and P; A divalent fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And bivalent aliphatic hydrocarbon groups, and each of these (other than a single bond) may be selected from the group consisting of deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; -N (Ar ^c ) (Ar ^d ); And an arylalkenyl group having from ₈ to ₂₀ carbon atoms. Wherein Ar ^c and Ar ^d are independently of each other a C ₆ to C ₆₀ aryl group; A fluorenyl group; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

Specifically, L ¹ and L ² are each independently selected from the group consisting of phenyl, biphenyl, naphthalene, dimethylfluorene, diphenylfluorene, pyridine, phenanthrene, benzothiophene, benzofuran, quinoline, dibenzothiophene, dibenzofuran Etc., and these may further be substituted with the substituents and the like.

On the other hand, when R ¹ to R ⁴ , Ar ¹ and Ar ² are an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkoxyl group or an aryloxy group, halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; And an arylalkenyl group having from ₈ to ₂₀ carbon atoms.

When each symbol of the formula (1) or the group in which they are substituted is an aryl group or an arylene group, it may be an aryl group or an arylene group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, In the case of a cyclic group, it may be a heterocyclic ring having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms. In the case of an alkyl group, it may have 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, Preferably an alkyl group having 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms.

Specifically, the formula (1) may be represented by one of the following formulas (2) to (34).

Wherein q, r, s and t are independently integers of 0 to 2, and R ¹ to R ⁴ , Ar ¹ , Ar ² , L ¹ , L ² , m, n, o, p is the same as defined in formula (1).

More specifically, Formula 1 may be one of the following compounds.

In another embodiment, the present invention provides a compound for an organic electroluminescent device represented by the general formula (1).

In another embodiment, the present invention provides an organic electronic device containing the compound represented by the above formula (1).

The organic electroluminescent device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include a compound represented by Formula 1, wherein Formula 1 is a hole injecting layer, a hole transporting layer, Or the light-emitting layer. That is, the compound represented by the formula (1) can be used as a material for the hole injecting layer, the hole transporting layer, the light emission assisting layer or the light emitting layer, and can be preferably used as the hole transporting layer or the light emitting auxiliary layer material. Specifically, the organic electroluminescent device includes one of the compounds represented by Chemical Formulas 2 to 34 in the organic material layer. More specifically, the organic electroluminescent device includes the compound represented by the individual chemical formulas P-1 to P-168, Organic electroluminescent device.

In another embodiment of the present invention, the light efficiency improving layer is formed on at least one side of the one side of the first electrode opposite to the organic layer, or one side of the one side of the second electrode opposite to the organic layer, And an organic electroluminescent 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 compounds according to the invention (Final Products) are prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but are not limited thereto.

<Reaction Scheme 1>

R ¹ to R ⁴ , Ar ¹ , Ar ² , L ¹ , L ² , m, n, o and p are the same as defined in the above formula (1).

I. Sub  Synthesis of 1

Sub 1 of Reaction Scheme 1 can be synthesized by the reaction route of Reaction Schemes 2 to 5, but is not limited thereto.

&Lt; Reaction Formula 2 > When L ¹ and L ² are both a single bond

<Reaction 3> When L ¹ is a single bond and L ² is not a single bond

<Reaction Scheme 4> When L ¹ is not a single bond and L ² is a single bond

<Reaction Scheme 5> When L ¹ and L ² are not a single bond

M &lt; 1 &gt; and M &lt; 2 &gt; in the above Reaction Schemes 2 to 5 can be synthesized by the reaction path of the following Reaction Scheme 6, but are not limited thereto.

<Reaction Scheme 6>

Wherein A is (R ¹ ) m or (R ³ ) o, B is (R ² ) n or (R ⁴ ) p and Z is L ¹ or L ² , no.

Examples of the synthesis of specific compounds belonging to Sub 1 are as follows.

One. Sub  1-1 Synthetic example

<Reaction Scheme 7>

(1) Synthesis of M 1-I-1

The starting material, phenylboronic acid (79.05 g, 648.3 mmol ) of was dissolved in THF in a round bottom flask, 1-bromo-2-nitrobenzene (157.16 g, 778 mmol), Pd (PPh 3) 4 (37.46 g, 32.4 mmol) , K ₂ CO ₃ (268.81 g, 1945 mmol) and 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 118.82 g (yield: 92%) of the product.

(2) Synthesis of M 1-1 Synthesis

M-I-1 (118.82 g, 596.5 mmol) obtained in the above synthesis was dissolved in o-dichlorobenzene in a round bottom flask, and then triphenylphosphine (391.11 g, 1491.1 mmol) was added and stirred at 200 ° C. After the reaction was completed, o-dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 79.79 g (yield: 80%) of the product.

(3) Synthesis of M 1-I-4

2-bromo-1-nitronaphthalene (200.47 g, 795.3 mmol), Pd (PPh ₃ ) ₄ (38.29 g, 33.1 mmol) and K ₂ CO ₃ (274.8 g, 1988.3 mmol), THF, and water. Using the above M 1 -I-1 synthesis method, 138.77 g of the product (yield: 84%) was obtained.

(4) Synthesis of M 1-4

Triphenylphosphine (365.06 g, 1391.8 mmol) and o-dichlorobenzene were added to M 1 -I-4 (138.77 g, 556.7 mmol) obtained in the above synthesis using 93.14 g (yield: 77% .

(5) Sub 1-I-1 synthesis

M 1-1 (40.59 g, 242.7 mmol) obtained in the above synthesis was dissolved in nitrobenzene in a round bottom flask, and 1,3,5-tribromobenzene (114.63 g, 364.1 mmol), 18-crown- mmol), K ₂ CO ₃ (33.55 g, 242.7 mmol) and Cu (15.43 g, 242.7 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 58.42 g (yield: 60%) of the product.

(6) Sub 1-1 Synthesis

Sub-1-I-1 (21.68 g, 54.1 mmol) and 18-crown-6 (0.95 g, 3.6 mmol) were dissolved in nitrobenzene in a round bottom flask. ), K ₂ CO ₃ (4.98 g, 36 mmol) and Cu (2.29 g, 36 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 10.46 g (yield: 54%) of the product.

2. Sub  1-5 Synthetic example

<Reaction Scheme 8>

(1) Synthesis of M 1-I-12

The starting material, phenanthren-9-ylboronic acid (43.72 g, 196.9 mmol) 1-bromo-2-nitrobenzene in (47.73 g, 236.3 mmol), Pd (PPh 3) 4 (11.38 g, 9.8 mmol), K 2 CO 3 (81.64 g, 590.7 mmol), THF and water were obtained 57.17 g (yield: 97%) of the product using the M 1 -I-1 synthesis method described above.

(2) M 1-12 Synthesis

Triphenylphosphine (125.24 g, 477.5 mmol) and o-dichlorobenzene were added to the obtained compound M-I-12 (57.17 g, 191 mmol) .

(3) Sub 1-5 synthesis

Sub-1-I-1 (18.64 g, 46.5 mmol), 18-crown-6 (0.82 g, 3.1 mmol) and K ₂ CO ₃ (4.28 g, 3.1 mmol) were added to M 1-12 , 31 mmol), Cu (1.97 g, 31 mmol), and nitrobenzene were used to obtain 9.46 g of the product (yield: 52%).

3. Sub  1-21 Synthetic example

<Reaction Scheme 9>

(1) Synthesis of M 1-I-8

The starting material, naphthalen-1-ylboronic acid (29.73 g, 172.9 mmol) for 3-bromo-4-nitro- 1,1'-biphenyl (57.69 g, 207.4 mmol), Pd (PPh 3) 4 (9.99 g, 8.6 mmol), K ₂ CO ₃ (71.67 g, 518.6 mmol), THF and water were used to obtain 46.68 g (yield: 83%) of the product using the above M 1 -I-1 synthesis method.

(2) M 1-8 Synthesis

Triphenylphosphine (94.08 g, 358.7 mmol) and o-dichlorobenzene were added to 29.88 g (Yield: 71%) of the product M 1-I-8 (46.68 g, 143.5 mmol) .

(3) Sub 1-21 synthesis

The starting material, 1,3,5-tribromobenzene (12.69 g, 40.3 mmol) was dissolved in nitrobenzene in a round bottom flask and then M-8 (23.65 g, 80.6 mmol) and 18-crown-6 (4.26 g, 16.1 mmol ), K ₂ CO ₃ (44.57 g, 322.5 mmol) and Cu (10.25 g, 161.2 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 10.14 g (yield: 34%) of the product.

4. Sub  1-25 Synthetic example

<Reaction formula 10>

(1) Synthesis of M 1-I-7

The starting material, naphthalen-1-ylboronic acid 1- bromo-2-nitrobenzene in (92.08 g, 535.4 mmol) ( 129.78 g, 642.5 mmol), Pd (PPh 3) 4 (30.93 g, 26.8 mmol), K 2 CO 3 (221.98 g, 1606.1 mmol), THF, and water, 126.78 g of the product (yield: 95%) was obtained using the above M 1 -I-1 synthesis method.

(2) M 1-7 Synthesis

Triphenylphosphine (333.52 g, 1271.6 mmol) and o-dichlorobenzene were added to 88.1 g (Yield: 80%) of the product using the above M 1-1 synthesis method, to M 1 -I-7 (126.78 g, 508.6 mmol) .

(3) Synthesis of M 1-I-9

2-bromo-3-nitronaphthalene (24.16 g, 95.9 mmol), Pd (PPh ₃ ) ₄ (4.62 g, 4 mmol) and K ₂ CO ₃ (33.12 g, 239.6 mmol), THF, and water. Using the above M 1 -I-1 synthesis method, 17.12 g (yield: 86%) of the product was obtained.

(4) M 1-9 Synthesis

Triphenylphosphine (45.04 g, 171.7 mmol) and o-dichlorobenzene were added to 11.1 g (Yield: 77%) of the product using the above M 1-1 synthesis method, to M 1 -I-9 (17.12 g, 68.7 mmol) .

(5) Sub 1-I-25 synthesis

(117.25 g, 372.5 mmol), 18-crown-6 (6.56 g, 24.8 mmol) and K ₂ CO ₃ (34.32 g, 24.8 mmol) were added to M 1-7 g, 248.3 mmol), Cu (15.78 g, 248.3 mmol), and nitrobenzene were obtained in 64.17 g (yield: 58%) of the product using the Sub 1-I-1 synthesis method.

(6) Sub 1-25 Synthesis

In M 1-9 (6.79 g, 31.3 mmol ) obtained in the above Synthesis Sub 1-I-25 (21.15 g, 46.9 mmol), 18-crown-6 (0.83 g, 3.1 mmol), K 2 CO 3 (4.32 g , 31.3 mmol), Cu (1.99 g, 31.3 mmol), and nitrobenzene were obtained using the Sub 1-1 synthesis method described above to give 8.26 g (yield: 45%) of the product.

5. Sub  1-33 Synthetic example

<Reaction Scheme 11>

(1) Synthesis of M 1-I-16

The starting material, naphthalen-1-ylboronic acid (68.23 g, 396.7 mmol) 2-bromo-1-nitronaphthalene in (119.99 g, 476.1 mmol), Pd (PPh 3) 4 (22.92 g, 19.8 mmol), K 2 CO 3 (164.49 g, 1190.1 mmol), THF, and water. 109.24 g (yield: 92%) of the product was obtained using the M 1 -I-1 synthesis method described above.

(2) M 1-16 Synthesis

Triphenylphosphine (239.31 g, 912.4 mmol) and o-dichlorobenzene were added to M 1 -I-16 (109.24 g, 365 mmol) obtained in the above synthesis using 74.15 g (yield: 76% .

(3) Sub 1-33 Synthesis

M 1-16 obtained in the synthesis (9.62 g, 36 mmol) in Sub 1-I-25 (24.35 g, 54 mmol), 18-crown-6 (0.95 g, 3.6 mmol), K 2 CO 3 (4.97 g , 36 mmol), Cu (2.29 g, 36 mmol), and nitrobenzene were obtained in the same manner as in Sub 1-1, except that 9.64 g (yield: 42%) of the product was obtained.

6. Sub  1-50 Synthetic example

<Reaction Scheme 12>

(1) Synthesis of M 2-I-5

9.1-dimethyl-9H-fluorene (34.9 g, 87.5 mmol) was dissolved in nitrobenzene in a round bottom flask, Na ₂ SO ₄ (8.28 g, 58.3 mmol), K ₂ CO ₃ (8.06 g, 58.3 mmol) and Cu (1.11 g, 17.5 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 15.34 g (yield: 60%) of the product.

(2) M 2-5 Synthesis

Bisphenolato diboron (9.78 g, 38.5 mmol), Pd (dppf) Cl ₂ (0.86 g, 38.5 mmol) was dissolved in DMF in a round-bottomed flask with M 2 -I- 1 mmol), KOAc (10.3 g, 105 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 13.42 g (yield: 79%) of the product.

(3) Sub 1-50 synthesis

It was dissolved the Sub 1-I-25 (9.67 g, 21.4 mmol) obtained in the synthesis as THF in a round bottom flask, M 2-5 (11.45 g, 23.6 mmol), Pd (PPh 3) 4 (0.74 g, 0.6 mmol), NaOH (2.57 g, 64.3 mmol), water, and the mixture was 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 9.85 g (yield: 63%) of the product.

7. Sub  1-62 Synthetic example

<Reaction Scheme 13>

(1) Synthesis of M 2-I-52

1-bromo-4-iodobenzene (85.61 g, 302.6 mmol), Na ₂ SO ₄ (28.66 g, 201.7 mmol) and K ₂ CO ₃ (27.88 g, 201.7 mmol) were added to M 1-16 , 201.7 mmol), Cu (3.85 g, 60.5 mmol) and nitrobenzene were used in the same manner as in the synthesis of M 2-I-5, to give 57.08 g of the product (yield: 67%).

(2) M 2-52 Synthesis

Bis (pinacolato) diboron (37.75 g, 148.7 mmol), Pd (dppf) Cl ₂ (3.31 g, 4.1 mmol) and KOAc (39.79 g, 405.5 mmol) and DMF were obtained 46.31 g (yield: 73%) of the product using the above M 2-5 synthesis method.

(3) Sub 1-62 Synthesis

To the Sub 1-I-1 (8.82 g, 22 mmol) obtained in the above synthesis, M 2-52 (11.35 g, 24.2 mmol), Pd (PPh ₃ ) ₄ (0.76 g, 0.7 mmol) mmol), THF, and water were used to obtain 11.09 g (yield: 76%) of the product using the Sub 1-50 synthesis method described above.

8. Sub  1-77 Synthetic example

<Reaction Scheme 14>

(1) Synthesis of M 2-I-19

1-bromo-3-iodobenzene (138.88 g, 490.9 mmol), Na ₂ SO ₄ (46.49 g, 327.3 mmol) and K ₂ CO ₃ (45.23 g, 327.3 mmol) were added to M 1-4 , 327.3 mmol), Cu (6.24 g, 98.2 mmol), and nitrobenzene were obtained by using the above M 2-I-5 synthesis method.

(2) M 2-19 Synthesis

Bis (pinacolato) diboron (67.65 g, 266.4 mmol), Pd (dppf) Cl ₂ (5.93 g, 7.3 mmol) and KOAc (71.31 g, 242.2 mmol) were added to M 2 -I- 726.6 mmol) and DMF were obtained 84.29 g (yield: 83%) of the product using the above M 2-5 synthesis method.

(3) Sub 1-I-77 synthesis

Was dissolved the M 2-19 (50.07 g, 119.4 mmol ) obtained in the synthesis as THF in a round bottom flask, 1,3,5-tribromobenzene (75.18 g, 238.8 mmol), Pd (PPh 3) 4 (4.14 g, 3.6 mmol), NaOH (14.33 g, 358.2 mmol), water and the mixture was 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 42.81 g of the product (yield: 68%).

(4) Sub 1-77 Synthesis

M 1-7 (5 g, 23 mmol) obtained in the above synthesis was dissolved in nitrobenzene in a round-bottomed flask and Sub 1-I-77 (18.2 g, 34.5 mmol) and 18-crown- ), K ₂ CO ₃ (3.18 g, 23 mmol) and Cu (1.46 g, 23 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 9.01 g (yield: 59%) of the product.

9. Sub  1-95 Synthetic example

<Reaction Scheme 15>

(1) Synthesis of M 2-I-1

1-bromo-4-iodobenzene (49.28 g, 174.2 mmol), Na ₂ SO ₄ (16.5 g, 116.1 mmol) and K ₂ CO ₃ (16.05 g, 116.1 mmol) were added to M 1-1 , 116.1 mmol), Cu (2.21 g, 34.8 mmol), and nitrobenzene were used to synthesize 29.94 g (yield: 80%) of the product using the above M 2-I-5 synthesis method.

(2) Synthesis of M 2-1

Bisacetate (25.96 g, 102.2 mmol), Pd (dppf) Cl ₂ (2.28 g, 2.8 mmol) and KOAc (27.36 g, 92.9 mmol) were added to M 2 -I- 278.8 mmol) and DMF were obtained 29.35 g (yield: 87%) of the product using the above M 2-5 synthesis method.

(3) Sub 1-95 Synthesis

It was dissolved the Sub 1-I-77 (8.22 g, 15.6 mmol) obtained in the synthesis as THF in a round bottom flask, M 2-1 (6.33 g, 17.1 mmol), Pd (PPh 3) 4 (0.54 g, 0.5 mmol), NaOH (1.87 g, 46.8 mmol), water, and the mixture was 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 8.06 g (yield: 75%) of the product.

10. Sub  1-102 Synthetic example

<Reaction Scheme 16>

(1) Synthesis of M 2-I-38

1-bromo-4-iodobenzene (40.59 g, 143.5 mmol), Na ₂ SO ₄ (13.59 g, 95.7 mmol) and K ₂ CO ₃ (13.22 g, 95.7 mmol) were added to M 1-12 , 95.7 mmol), Cu (1.82 g, 28.7 mmol), and nitrobenzene were used to synthesize 27.47 g (yield: 68%) of the product using the above M 2-I-5 synthesis method.

(2) M 2-38 Synthesis

Bisacetate Bis (pinacolato) diboron (18.17 g, 71.6 mmol), Pd (dppf) Cl ₂ (1.59 g, 2 mmol) and KOAc (19.15 g, 65 mmol) were added to M 2 -I- 195.1 mmol) and DMF were used to obtain 24.73 g (yield: 81%) of the product using the M &lt; 2-5 &gt; synthetic method.

(3) Sub 1-I-102 synthesis

1,3,5-tribromobenzene (26.79 g, 85.1 mmol), Pd (PPh ₃ ) ₄ (1.47 g, 1.3 mmol) and NaOH (5.11 g, 42.5 mmol) were added to M 2-38 127.6 mmol), THF, and water were used to obtain 17.19 g (yield: 70%) of the product using the Sub 1-I-77 synthesis method.

(4) Sub 1-102 Synthesis

M 2-1 (6.28 g, 17 mmol), Pd (PPh ₃ ) ₄ (0.54 g, 0.5 mmol) and NaOH (1.86 g, 46.4 mmol) were added to Sub 1-I- mmol), THF, and water were subjected to the Sub 1-95 synthesis method to obtain 8.35 g (yield: 73%) of the product.

11. Sub  1-122 Synthetic example

<Reaction Scheme 17>

The starting material 1,3,5-tribromobenzene (8.02 g, 25.5 mmol) was dissolved in THF in a round bottom flask and then M 2-19 (21.37 g, 51 mmol), Pd (PPh ₃ ) ₄ (0.88 g, 0.8 mmol), NaOH (6.11 g, 152.9 mmol), water, and the mixture was 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 11.12 g (yield: 59%) of the product.

12. Sub  1-124 Synthetic example

<Reaction Scheme 18>

(1) Synthesis of M 2-I-25

1-bromo-4-iodobenzene (41.15 g, 145.5 mmol), Na ₂ SO ₄ (13.77 g, 97 mmol) and K ₂ CO ₃ (13.4 g, 97 mmol) were added to M 1-7 , 97 mmol), Cu (1.85 g, 29.1 mmol), and nitrobenzene were obtained by the above M 2-I-5 synthesis method.

(2) M 2-25 Synthesis

To a solution of bis (pinacolato) diboron (19.77 g, 77.9 mmol), Pd (dppf) Cl ₂ (1.73 g, 2.1 mmol), KOAc (20.84 g, 212.4 mmol) and DMF were obtained 24.34 g (yield: 82%) of the product using the above M 2-5 synthesis method.

(3) Sub 1-124 Synthesis

In the 1,3,5-tribromobenzene (6.74 g, 21.4 mmol) starting material M 2-25 (17.96 g, 42.8 mmol ), Pd (PPh 3) 4 (0.74 g, 0.6 mmol), NaOH (5.14 g, 128.5 mmol), THF and water were obtained by using the Sub 1-I-122 synthesis method described above to give 10.77 g (yield: 68%) of the product.

13. Sub  1-143 Synthetic example

<Reaction Scheme 19>

To the starting material, 1,3,5-tribromobenzene (7.16 g, 22.7 mmol), M 2-52 (21.35 g, 45.5 mmol), Pd (PPh ₃ ) ₄ (0.79 g, 0.7 mmol) mmol), THF, and water were subjected to the synthesis of Sub 1-I-122 to obtain 11.65 g (yield: 61%) of the product.

On the other hand, the compound belonging to M 1 may be, but not limited to, the following compounds, and Table 1 shows FD-MS values of the compound belonging to M 1.

[Table 1]

On the other hand, the compounds belonging to M 2 may be the following compounds, but are not limited thereto, and Table 2 shows the FD-MS values of the compounds belonging to M 2.

[Table 2]

On the other hand, the compounds belonging to Sub 1 may be, but not limited to, the following compounds, and Table 3 shows FD-MS values of the compounds belonging to Sub 1.

[Table 3]

II . Sub  Synthesis of 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 20, but is not limited thereto.

<Reaction Scheme 20>

Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

One. Sub  2-2 Synthetic example

<Reaction Scheme 21>

The starting material, 1-bromonaphthalene (10.14 g, 49 mmol), was dissolved in toluene in a round bottom flask and then aniline (9.12 g, 97.9 mmol), Pd ₂ (dba) ₃ (1.35 g, 1.5 mmol) t-Bu) ₃ (1.9 ml, 3.9 mmol), NaOt-Bu (14.12 g, 146.9 mmol) and stir at 40 ° 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 8.27 g (yield: 77%) of the product.

2. Sub  2-8 Synthetic example

<Reaction Formula 22>

Aniline (6.52 g, 70 mmol), Pd ₂ (dba) ₃ (0.96 g, 1.1 mmol) and 50% P (t- Bu) ₃ (1.4 ml, 2.8 mmol), NaOt-Bu (10.09 g, 105 mmol) and toluene were used to obtain 7.13 g (yield: 83%) of the product.

3. Sub  2-14 Synthetic example

<Reaction Scheme 23>

4-amine (10.29 g, 60.8 mmol) and Pd ₂ (dba) ₃ (0.84 g, 30.8 mmol) were added to the starting material, 4-bromo-1,1'- , 0.9 mmol), 50% P (t-Bu) 3 (1.2ml, 2.4 mmol), NaOt-Bu (8.77 g, 91.2 mmol), using the Sub 2-2 synthesis of toluene the product 7.72 g (yield: 79%).

4. Sub  2-15 Synthetic example

<Reaction Scheme 24>

(10.5 g, 62 mmol) and Pd ₂ (dba) ₃ (0.85 g, 62 mmol) were added to the starting material, 3-bromo-1,1'- , 9.90 g (0.9 mmol), 50% P (t-Bu) ₃ (1.2 ml, 2.5 mmol), NaOt-Bu (8.94 g, 93.1 mmol) 80%).

5. Sub  2-21 Synthetic example

<Reaction Scheme 25>

Aniline (7.72 g, 82.9 mmol) and Pd ₂ (dba) ₃ (1.14 g, 1.2 mmol) were added to the starting material 5'-bromo-1,1 ': 3', 1 "-terphenyl (12.81 g, 41.4 mmol) 11.32 g (Yield: 85%) of the product was obtained by using the Sub 2-2 synthesis method, 50% P (t-Bu) ₃ (1.6 ml, 3.3 mmol), NaOt-Bu (11.95 g, 124.3 mmol) .

6. Sub  2-32 Synthetic example

<Reaction Scheme 26>

Aniline (6.58 g, 70.7 mmol), Pd ₂ (dba) ₃ (0.97 g, 1.1 mmol) and 50% P (t-Bu) were added to 4- (4-bromophenyl) isoquinoline (10.04 g, 35.3 mmol) ₃ (1.4 ml, 2.8 mmol), NaOt-Bu (10.19 g, 106 mmol) and toluene were obtained 7.43 g (Yield: 71%) of the product using the Sub 2-2 synthesis method described above.

7. Sub  2-36 Synthetic example

<Reaction Scheme 27>

(15 g, 88.6 mmol), Pd ₂ (dba) ₃ (1.22 g, 1.3 mmol), and 50% aqueous solution of 6-bromoquinoline (9.22 g, 44.3 mmol) P (t-Bu) ₃ (1.7 ml, 3.5 mmol), NaOt-Bu (12.78 g, 132.9 mmol) and toluene were used to obtain 8.54 g (yield 65%) of the product.

8. Sub  2-44 Synthetic example

<Reaction Scheme 28>

(10.41 g, 72.7 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), 50% P (dibenzylideneacetoacetate) were added to the starting material, 2-bromodibenzo [b, d] thiophene (yield: 77%) of the product (t-Bu) ₃ (1.4 ml, 2.9 mmol), NaOt-Bu (10.49 g, 109.1 mmol) and toluene using the Sub 2-2 synthesis method described above.

9. Sub  2-50 Synthetic example

<Reaction Scheme 29>

(9.34 g, 65.2 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), 50% P (dibenzylideneacetone) (yield: 80%) of the product (t-Bu) ₃ (1.3 ml, 2.6 mmol), NaOt-Bu (9.41 g, 97.9 mmol) and toluene using the Sub 2-2 synthesis method described above.

10. Sub  2-58 Synthetic example

<Reaction Scheme 30>

4-amine (13.39 g, 79.1 mmol), Pd ₂ (dba) ₃ ( ₃ g) was added to the starting material, 2-bromo-9,9-dimethyl-9H- (1.09 g, 1.2 mmol), 50% P (t-Bu) ₃ (1.5 ml, 3.2 mmol), NaOt-Bu (11.41 g, 118.7 mmol) and toluene using the Sub 2-2 synthesis method (Yield: 82%).

On the other hand, the compounds belonging to Sub 2 may be, but not limited to, the following compounds, and Table 4 shows FD-MS values of the compounds belonging to Sub 2.

[Table 4]

III . Product  synthesis

Sub 1 (1 eq.) Was dissolved in toluene in a round bottom flask and then Sub 2 (1 eq), Pd ₂ (dba) ₃ (0.03 eq), P (t- Bu) ₃ 3 eq.) Was added and stirred at 100 [deg.] 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 subjected to silicagel column and recrystallization to obtain final product.

1. P-1 Synthetic example

<Reaction Scheme 31>

Sub 1-14 (3.08 g, 9.6 mmol) and Pd ₂ (dba) ₃ (0.26 g, 0.3 mmol) were dissolved in toluene in a round bottom flask, (50 ml), 50% P (t-Bu) ₃ (0.4 ml, 0.8 mmol) and NaOt-Bu (2.76 g, 28.7 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 6.41 g (yield: 86%) of the product.

2. P-10 Synthetic example

<Reaction equation 32>

To Sub 1-5 (5.63 g, 9.6 mmol) obtained in the above synthesis, Sub 2-58 (3.46 g, 9.6 mmol), Pd ₂ (dba) ₃ (0.26 g, 0.3 mmol) ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.76 g, 28.7 mmol) and toluene were obtained 6.65 g (Yield: 80%) of the product using the above P-1 synthesis method.

3. P-31 Synthetic example

<Reaction Scheme 33>

To Sub 1-21 (7.67 g, 10.4 mmol) obtained in the above synthesis, Sub 2-36 (3.07 g, 10.4 mmol), Pd ₂ (dba) ₃ (0.28 g, 0.3 mmol) ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.99 g, 31.1 mmol) and toluene were obtained 6.64 g (Yield: 67%) of the product using the above P-1 synthesis method.

4. P-36 Synthetic example

<Reaction formula 34>

Sub 2-21 (3.22 g, 10 mmol), Pd ₂ (dba) ₃ (0.27 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-25 (5.88 g, ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.89 g, 30 mmol) and toluene were obtained 6.46 g (Yield: 78%) of the product using the above P-1 synthesis method.

5. P-44 Synthetic example

<Reaction Scheme 35>

Sub 2-15 (3.03 g, 9.4 mmol), Pd ₂ (dba) ₃ (0.26 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-33 (6.02 g, 9.4 mmol) 3.22 g (Yield: 75%) of the product was obtained by using the above P-1 synthesis method in the same manner as in Example ₁ ( ₃₎ (0.4 ml, 0.8 mmol), NaOt-Bu (2.72 g, 28.3 mmol)

6. P-61 Synthetic example

<Reaction Formula 36>

Sub 2-2 (2.1 g, 9.6 mmol), Pd ₂ (dba) ₃ (0.26 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-50 (6.98 g, 9.6 mmol) ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.76 g, 28.7 mmol) and toluene were obtained 6.73 g (Yield: 81%) of the product using the above P-1 synthesis method.

7. P-73 Synthetic example

(Reaction Scheme 37)

Sub 2-22 (2.8 g, 9.4 mmol), Pd ₂ (dba) ₃ (0.26 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-62 (6.27 g, 9.4 mmol) ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.72 g, 28.3 mmol) and toluene were obtained 6.06 g (yield: 73%) of the product using the above P-1 synthesis method.

8. P-89 Synthetic example

<Reaction Formula 38>

To Sub-77 (5.81 g, 8.8 mmol) obtained in the above synthesis, Sub 2-58 (3.16 g, 8.8 mmol), Pd ₂ (dba) ₃ (0.24 g, 0.3 mmol) ₃ (0.3 ml, 0.7 mmol), NaOt-Bu (2.52 g, 26.3 mmol) and toluene were obtained 6.86 g (Yield: 83%) of the product using the above P-1 synthesis method.

9. P-110 Synthetic example

<Reaction Scheme 39>

Sub 2-50 (2.81 g, 9.1 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-95 (6.27 g, 9.1 mmol) ₃ (0.4 ml, 0.7 mmol), NaOt-Bu (2.62 g, 27.3 mmol) and toluene were obtained 6.43 g (Yield: 77%) of the product using the above P-1 synthesis method.

10. P-117 Synthetic example

<Reaction formula 40>

Sub 2-8 (2.25 g, 9.2 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-102 (6.79 g, 9.2 mmol) ₃ (0.4 ml, 0.7 mmol), NaOt-Bu (2.65 g, 27.5 mmol) and toluene were used to obtain 6.14 g (yield: 74%) of the product using the above P-1 synthesis method.

11. P-139 Synthetic example

<Reaction Scheme 41>

To Sub 1-122 (7.46 g, 10.1 mmol) obtained in the above synthesis, Sub 2-44 (3.28 g, 10.1 mmol), Pd ₂ (dba) ₃ (0.28 g, 0.3 mmol) ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.91 g, 30.3 mmol) and toluene were obtained 6.45 g (Yield: 65%) of the product using the above P-1 synthesis method.

12. P-141 Synthetic example

<Reaction Scheme 42>

Sub 2-21 (2.83 g, 8.8 mmol), Pd ₂ (dba) ₃ (0.24 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-124 (6.51 g, 8.8 mmol) ₃ (0.3 ml, 0.7 mmol), NaOt-Bu (2.54 g, 26.4 mmol) and toluene were obtained 6.73 g (Yield: 78%) of the product using the above P-1 synthesis method.

13. P-161 Synthetic example

<Reaction Scheme 43>

Sub 2-2 (2.24 g, 10.2 mmol), Pd ₂ (dba) ₃ (0.28 g, 0.3 mmol) and 50% P (t-Bu) were added to Sub 1-143 (8.56 g, 10.2 mmol) ₃ (0.4 ml, 0.8 mmol), NaOt-Bu (2.94 g, 30.6 mmol) and toluene were obtained 7.18 g (Yield: 72%) of the product using the above P-1 synthesis method.

The FD-MS values of the compounds P-1 to P-168 of the present invention prepared according to the above synthesis examples are shown in Table 5 below.

[Table 5]

In the meantime, although an exemplary synthesis example of the present invention represented by the general formula (1) has been described above, all of them are represented by Ullmann reaction, Suzuki cross-coupling reaction, PPh ₃ -mediated reductive cyclization reaction (J. Org. ), Miyaura boration reaction and Buchwald-Hartwig cross coupling reaction. In addition to the substituents specified in the specific synthesis example, other substituents (R ¹ to R ⁴ , Ar ¹ , Ar ² , L ¹ , L ² , m , a substituent such as n, o, and p) are bonded to each other, it will be easily understood by those skilled in the art.

For example, in Reaction Scheme 2, the starting material -> Sub 1-I and Sub 1 -I -> Sub 1 reaction, the starting material -> Sub 1-I reaction in Scheme 3, Sub 1 -I -> Sub 1 reaction , Sub 1-I -> Sub 1 reaction in Scheme 3, Starting material -> Sub 1-I reaction in Scheme 4, Reaction Scheme 5 in Scheme 6, and M 1 -> M 2 -I reaction in Scheme 6 are all based on Ullmann reaction. , The starting material -> Sub 1-I and Sub 1-I -> Sub 1 in the starting material -> M 1-I reaction in Scheme 6 are all based on the Suzuki cross-coupling reaction, The I-> M 1 reaction is based on the PPh ₃ -mediated reductive cyclization reaction. Subsequently, in Scheme 6, the M 2 -I -> M 2 reaction is based on the Miyaura boration reaction, the starting material -> Sub 2 reaction in Scheme 20 and the reaction in Scheme 31 to Scheme 43 are based on the Buchwald-Hartwig cross coupling reaction, Even if a substituent not specifically mentioned in these groups is bonded, the above reactions will proceed.

Evaluation of manufacturing of organic electric device

[ Example  I-1] green organic electroluminescent device ( Hole transport layer )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a hole transport layer material. First, 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ") was deposited on the ITO layer (anode) To form a hole injection layer. Then, the compound P-1 of the present invention was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Subsequently, tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy) 2") was used as a host material on the hole transport layer, and 4,4'-N, N'-dicarbazole- ) ₃ ") was used as a dopant material and doped in a ratio of 90:10 by weight to form a light emitting layer by vacuum evaporation to a thickness of 30 nm. Subsequently, 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 vacuum deposited on the hole blocking layer to a thickness of 40 nm to form an electron transporting layer. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example  I-2] to [ Example  I-154] green organic electroluminescent device ( Hole transport layer )

An organic electroluminescence device was produced in the same manner as in Example I-1, except that the compounds P-2 to P-164 of the present invention described in Table 6 below were used instead of the compound P-1 of the present invention as the hole transport layer material Respectively.

[Comparative Example I-1]

An organic electroluminescent device was fabricated in the same manner as in Example I-1, except that the following compound 1 was used instead of the compound P-1 of the present invention as a hole transport layer material.

<Comparative Compound 1>

[Comparative Example I-2]

An organic electroluminescent device was fabricated in the same manner as in Example I-1, except that the following compound 2 was used in place of the compound P-1 of the present invention as a hole transport layer material.

&Lt; Comparative Compound 2 >

[Comparative Example I-3]

An organic electroluminescence device was fabricated in the same manner as in Example I-1, except that the following compound 3 was used instead of the compound P-1 of the present invention as a hole transport layer material.

&Lt; Comparative Compound 3 >

[Comparative Example I-4]

An organic electroluminescence device was fabricated in the same manner as in Example I-1, except that the following compound 4 was used instead of the compound P-1 of the present invention as a hole transport layer material.

<Comparative Compound 4>

The organic electroluminescent devices prepared in Examples I-1 to I-154 and Comparative Examples I-1 to I-4 of the present invention were subjected to photolithographic PR- 650, and the T95 lifetime was measured by a lifetime measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 5000 cd / m ^2. The measurement results are shown in Table 6 below.

[Table 6]

As can be seen from the results of Table 6, when the material for an organic electroluminescent device of the present invention is used as a hole transporting layer material, the luminous efficiency and lifetime of the organic electroluminescent device can be remarkably improved.

In particular, Comparative Compounds 2 to 4 having one or two carbazole cores showed higher luminous efficiency than Comparative Compound 1, which was NPB, and the result was that the aromatic rings were additionally condensed in the two carbazole cores The compounds of the present invention exhibited higher luminescent efficiency and higher lifetime than the comparative compounds 2 to 4.

In the case of Comparative Compounds 2 to 4 in which one or two carbazole cores are introduced, it is possible to confirm that the efficiency of blocking electrons is improved by increasing the T1 value to a value higher than that of Comparative Compound 1, It shows high hole mobility and causes a charge unbalance in the light emitting layer, so that the efficiency and lifetime of the compound of the present invention are reduced as compared with the compound of the present invention.

On the other hand, the compound of the present invention in which the aromatic rings are further fused to the two carbazole cores has a high T1 value and high thermal stability, and the ability to trap holes in the carbazole core is improved, 4 has a hole mobility that is easy to achieve charge balance.

As described above, by further fusing an aromatic ring to the carbazole core, the band gap, electrical characteristics, interface characteristics, and the like are largely changed, which can be confirmed as a major factor in improving the performance of the device.

Further, in the case of the hole transporting layer, it is necessary to grasp the correlation with the light emitting layer (host), and even if similar cores are used, it is very difficult for the ordinary technologists to deduce the characteristics shown in the hole transporting layer in which the compound according to the present invention is used .

[ Example II -One] Red organic electroluminescent device  ( The light- )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer. Then, NPB was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer Respectively. Subsequently, Compound P-1 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emission-assisting layer. Then, CBP (bis- (1-phenylisoquinolyl) Iridium (III) acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir (acac)") as a dopant was doped at a weight ratio of 95: 5 and vacuum deposited to a thickness of 30 nm to form a light emitting layer. Subsequently, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer, and Alq ₃ was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example II -2] to [ Example II -76] Red organic electroluminescent device  ( The light- )

Except that the compounds P-2 to P-164 of the present invention described in the following Table 7 were used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material in Example II-1, Respectively.

[Comparative Example II-1]

An organic electroluminescence device was fabricated in the same manner as in Example II-1 except that the above-mentioned Comparative Compound 2 was used instead of the compound P-1 of the present invention as a light-emitting auxiliary layer material.

[Comparative Example II-2]

An organic electroluminescence device was fabricated in the same manner as in Example II-1 except that the compound of Comparative Example 3 was used instead of the compound of the present invention P-1 as the luminescent auxiliary layer material.

[Comparative Example II-3]

An organic electroluminescent device was fabricated in the same manner as in Example II-1 except that the compound of the present invention was used in place of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example II-4]

An organic electroluminescent device was fabricated in the same manner as in Example II-1, except that the luminescent auxiliary layer was not formed.

The organic electroluminescent devices prepared according to Examples II-1 to II-76 and Comparative Examples II-1 to II-4 of the present invention were subjected to PR-DC voltage application by photo- 650, and the T95 lifetime was measured through a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 2500 cd / m ^2. The measurement results are shown in Table 7 below.

[Table 7]

[ Example III -1] green organic electroluminescent device ( The light- )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer. Then, NPB was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer Respectively. Subsequently, the compound P-1 of the present invention on the hole transport layer and then forming a vacuum-deposited to the light-emitting auxiliary layer with a thickness of 20 nm, CBP on the light emitting auxiliary layer as a host material, dopant, the Ir (ppy) ₃ And doped in a weight ratio of 90:10, followed by vacuum evaporation to a thickness of 30 nm to form a light emitting layer. Subsequently, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer, and Alq ₃ was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example III -2] to [ Example III -124] green organic electroluminescent device ( The light- )

Except that the compounds P-2 to P-164 of the present invention described in the following Table 8 were used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material in Example III-1, Respectively.

[Comparative Example III-1]

An organic electroluminescent device was fabricated in the same manner as in Example III-1 except that the compound of the present invention was used in place of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example III-2]

An organic electroluminescent device was fabricated in the same manner as in Example III-1 except that the above-mentioned Comparative Compound 3 was used in place of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example III-3]

An organic electroluminescent device was fabricated in the same manner as in Example III-1 except that the compound 4 was used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example III-4]

An organic electroluminescent device was fabricated in the same manner as in Example III-1, except that the luminescent auxiliary layer was not formed.

Photoreceptor PR-1 was prepared by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples III-1 to III-124 and Comparative Examples III-1 to III-4 of the present invention. 650, and the T95 lifetime was measured through a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 5000 cd / m ^2. The measurement results are shown in Table 8 below.

[Table 8]

[ Example IV -One] Blue organic electroluminescent device  ( The light- )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. First, 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer, and N, N'-bis (1-naphthalenyl) -N N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as "NPB") was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, Compound P-1 of the present invention was vacuum deposited on the hole transport layer to a thickness of 20 nm to form an emission assist layer, and 9,10-Di (2-naphthyl) anthracene (Hereinafter abbreviated as "ADN &quot;) was used as a host material and BD-052X (manufactured by Idemitsu Kosan) was used as a dopant in a ratio of 93: 7 by weight to form a light emitting layer by vacuum deposition to a thickness of 30 nm. Subsequently, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer, and Alq ₃ was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example IV -2] to [ Example IV -40] Blue organic electroluminescent device  ( The light- )

Except that the compounds P-2 to P-164 of the present invention described in the following Table 9 were used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material, Respectively.

[Comparative Example IV-1]

An organic electroluminescent device was fabricated in the same manner as in Example IV-1 except that the compound of the present invention was used in place of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example IV-2]

An organic electroluminescent device was fabricated in the same manner as in Example IV-1 except that the compound 3 was used in place of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example IV-3]

An organic electroluminescent device was fabricated in the same manner as in Example IV-1 except that the compound 4 was used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material.

[Comparative Example IV-4]

An organic electroluminescence device was fabricated in the same manner as in Example IV-1, except that the luminescent auxiliary layer was not formed.

Photovoltaic cells were prepared by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples IV-1 to IV-40 and Comparative Examples IV-1 to IV-4 of the present invention, 650, and the T95 lifetime was measured through a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 500 cd / m ^2. The measurement results are shown in Table 9 below.

[Table 9]

As can be seen from the results of Tables 7 to 9, the organic electroluminescent device using the compound of the present invention as the material of the light-emission-assisting layer has higher luminous efficiency than the organic electroluminescent devices of Comparative Examples II-1 to IV- And the life span was remarkably improved.

These results show that devices using Comparative Compounds 2 to 4 and the compound of the present invention as a light-emission-assisting layer have improved luminous efficiency and lifetime, compared with devices not having a light-emitting auxiliary layer. Among them, It can be confirmed that the result is much higher in terms of luminous efficiency and life span. This is because the addition of condensed aromatic rings to the two carbazole cores serves as a major factor in enhancing the performance of the device not only in the hole transport layer but also in the emission auxiliary layer (blue fluorescence, green phosphorescence, and red phosphorescence) And it plays an effective electronic blocking role.

In particular, the compound of the present invention, which is used as a light-emitting auxiliary layer, can form a twisted structure when introducing a phenylene group into L ¹ and L ² , and adjust the packing density between materials in the light- It can be confirmed that the hole mobility is relatively lowered and consequently the charge balance can be easily established within the light emitting layer, thereby exhibiting the highest light emitting efficiency and lifetime.

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

100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (8)

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

[In the above formula (1)
R ¹ to R ⁴ independently of one another are deuterium; Tritium; 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; -L ^a -N (Ar ^a ) (Ar ^b ); A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group of C ₆ to C ₃₀ , provided that at least one of R ¹ to R ⁴ is adjacent to each other to form at least one ring,
m, n, o, and p are each an integer of 0 to 4, and when each of these is an integer of 2 or more, a plurality of R ¹ to R ⁴ are the same or different from each other,
Ar ¹ and Ar ² are, independently of each other, 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; -L ^a -N (Ar ^a ) (Ar ^b ); A C ₁ to C ₃₀ alkoxyl group; And an aryloxy group having from ₆ to ₃₀ carbon atoms,
L ^a is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; C ₂ to C ₆₀ divalent heterocyclic groups containing at least one hetero atom selected from O, N, S, Si and P; A divalent 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 divalent aliphatic hydrocarbon group,
Ar ^a and Ar ^b are, independently of each other, 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 C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; And an alkenyl group having ₂ to ₂₀ carbon atoms,
L ¹ and L ² independently of one another are a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; C ₂ to C ₆₀ divalent heterocyclic groups containing at least one hetero atom selected from O, N, S, Si and P; A divalent 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 divalent aliphatic hydrocarbon group, each of them (excluding a single bond) is selected from the group consisting of deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; -N (Ar ^c ) (Ar ^d ); And an arylalkenyl group having from ₈ to ₂₀ carbon atoms, which may be further substituted with at least one substituent selected from the group consisting of
Ar ^c and Ar ^d are independently of each other a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P;
An aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkoxyl group and an aryloxy group of R ¹ to R ⁴ , Ar ¹ and Ar ² are respectively deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; And an arylalkenyl group having from ₈ to ₂₀ carbon atoms. The method according to claim 1,
Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

Q, r, s and t are independently integers of 0 to 2, and R ¹ to R ⁴ , Ar ¹ , Ar ² , L ¹ , L ² , m, n, o And p are the same as defined in claim 1. The method according to claim 1,
Lt; / RTI &gt; is one of the following compounds.

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 contains the compound of any one of claims 1 to 3. 5. The method of claim 4,
Wherein the compound is contained in at least one of the hole injection layer, the hole transporting layer, the light emission-assisting layer and the light-emitting layer of the organic material layer. 5. The method of claim 4,
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 including the organic electroluminescent device of claim 4; And
And a control unit for driving the display device. 8. The method of claim 7,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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