KR20190011463A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed is an organic electronic device comprising: a compound represented by chemical formula 1; a first electrode; a second electrode; an organic electronic element comprising an organic layer between the first electrode and the second electrode; and an electronic device comprising the same. The present invention can lower a driving voltage of the organic electronic and improve luminous efficiency and a lifetime by including the compound represented by chemical formula 1 in the organic layer.

Description

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

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

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

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

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is an important factor for portable displays, which have a limited power source, such as a battery, and efficiency and longevity are also important factors to be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage drops and the driving voltage drops. As a result, 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 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 recent years, a method of using a light-emitting auxiliary layer between a hole transporting layer and a light emitting layer has been studied in order to solve the problem of light emission in a hole transporting layer in an organic electroluminescent device. The material properties are different, and it is necessary to develop the light-emission assisting layer for each light-emitting 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 interface of the hole transport layer or the hole transport layer, Resulting in light emission at the interface or charge unbalance in the light emitting layer, resulting in light emission at the interface of the hole transporting layer.

When light is emitted from the interface of the hole transporting layer, the color purity and efficiency of the organic electronic device are lowered and the lifetime is shortened. Therefore, it should be a material having a HOMO level between the HOMO energy level of the hole transporting layer and the HOMO energy level of the light emitting layer, and has a high T1 value and a hole mobility (within a driving voltage range of a full device blue device) mobility of the light-emitting layer.

However, this can not be achieved simply by the structural characteristics of the core of the light-emitting auxiliary layer material, and the proper combination of the characteristics of the core and the sub-substituent of the light-emitting auxiliary layer material and between the light emitting auxiliary layer, the hole transport layer, A high efficiency and a high number of devices can be realized.

Meanwhile, it is also necessary to develop a light emitting layer and a light emitting auxiliary layer material having stable characteristics, that is, a high glass transition temperature, against joule heating generated when a device is driven. The low glass transition temperature of the light emitting layer and the light emitting auxiliary layer material lowers the uniformity of the surface of the thin film during device operation, and the material may be deformed due to heat generated when the device is driven.

In addition, OLED devices are mainly formed by a deposition method, and it is necessary to develop a material that can withstand a long period of time, that is, a material having high heat resistance characteristics.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electronic device, it is required that a material constituting the organic material layer in the device, for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, However, the development of a stable and efficient organic material layer for an organic electric device has not been sufficiently developed yet. Accordingly, development of new materials is continuously required, and development of a material used for a light-emission-assisting layer, a light-emitting layer, and the like is urgently required.

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

In one aspect, the 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 embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity and lifetime of the device can be greatly improved.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The terms " aryl group " and " arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.

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

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

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

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

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

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

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

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

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

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

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

When a is an integer of 0, the substituent R ¹ is absent. That is, when a is 0, it means that all of the carbons forming the benzene ring are bonded to hydrogen. In this case, And the chemical formula or compound may be described. When a is an integer of 1, one substituent R < ¹ > is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3, for example, , R < ¹ > may be the same or different from each other when a is an integer of 2 or more.

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

1, an organic electroluminescent device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 formed on a substrate 110, And an organic material layer containing a compound according to the present invention is provided between the two electrodes 180. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer 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, an electron transporting auxiliary layer, a buffer layer 141, It may also serve as a hole blocking layer.

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

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

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

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

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. A light emitting auxiliary layer 151 may be further formed between the hole transporting layer 140 and the light emitting layer 150 and an electron transporting auxiliary layer may be further formed between the light emitting layer 150 and the electron transporting layer 160.

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

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

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

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

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

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

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

≪ Formula 1 >

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

A rings are independently of each other C ₆ -C ₆₀ aromatic hydrocarbons; Fluorene; _{O, N, S, C 2} ~ C ₆₀ heteroaryl rings containing Si and P, at least one of the hetero atoms in the; And a fused ring of a C ₆ to C ₆₀ aromatic ring and a C ₃ to C ₆₀ aliphatic ring.

A ring is deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; Aryl alkenyl group of C ₈ -C _20; -L ² -N (R _a ) (R _b ); And a combination of these.

When the ring A is an aromatic hydrocarbon, it may preferably be a C ₆ -C ₃₀ aromatic hydrocarbon, more preferably a C ₆ -C ₁₄ aromatic hydrocarbon, specifically, benzene, naphthalene, phenanthrene, and the like.

X ₁ and X ₂ independently represent a single bond, N (L ¹ ) (Ar ¹ ), O, S, C (R ') (R ") or Si (R') (R").

L ¹ represents a single bond of C ₆ to C ₆₀ ; An arylene group; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ .

When L ¹ is an arylene group, it may preferably be an arylene group having ₆ to ₃₀ carbon atoms, more preferably an arylene group having ₆ to ₁₂ carbon atoms, specifically, phenyl, naphthalene, biphenyl, and the like. When L ¹ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₃ heterocyclic group, specifically, pyridine, pyrimidine, triazine, quinazoline, Quinoxaline, phthalazine, carbazole, pyridopyrimidine, benzoquinoline, phenanthridine benzothienopyrimidine, benzopuropyrimidine, and the like.

Ar ¹ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And -L ² -N (R _a ) (R _b ).

When Ar ¹ is an aryl group, it may preferably be an aryl group of C ₆ to C ₃₀ , more preferably a C ₆ to C ₁₂ aryl group, specifically, phenyl, biphenyl, naphthyl, and the like. When Ar ¹ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group, specifically, pyridine, pyrimidine, triazine, quinazoline, benzothiazole, Benzopyrimidine, benzoquinazoline, quinoxaline, phthalazine, carbazole, pyridopyrimidine, benzoquinoline, phenanthridine, indolocarbazole, dibenzofurane, and the like.

Wherein R 'and R " are independently selected from the group consisting of a C ₁ to C ₅₀ alkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₆₀ alkyl group having at least one heteroatom selected from O, N, S, , And R 'and R " may be bonded to each other to form a ring.

R ¹ to R ⁹ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 ² -N (R _a ) (R _b ), and neighboring groups may be bonded to each other to form a ring.

L < ² > is a single bond; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ .

R _a and R _b are each independently a C ₆ to C ₆₀ aryl group; 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 hetero atom selected from the group consisting of O, N, S, Si and P, and R _a and R _b may be bonded to each other to form a ring have.

An aryl group, an aryl group, an aromatic hydrocarbon, a fluorenyl group, a fluorenylene group, a fluorene, a heterocyclic group, a heterocyclic ring, a fused ring group, a fused ring, an alkyl group, an alkenyl group, an alkynyl group, , R ¹ to R ⁹ adjacent group ring formed by binding to formed ring, R 'and R "combine with each other to each other in a, and R _a and ring R _b is formed by bonding to each other are each heavy hydrogen; halogen; C ₁ - C ₂₀ alkyl group or a C ₆ aryl group a substituted or unsubstituted silane group of the -C _20; siloxane group; a boron group; germanium group; cyano group; nitro group; an alkylthio import of C ₁ -C _20; C ₁ -C ₂₀ alkoxyl group; an alkyl group of C ₁ -C _20; a C ₂ -C ₂₀ alkenyl; of a C ₆ -C ₂₀ substituted with heavy hydrogen; alkynyl of C ₂ -C _20; an aryl group of C ₆ -C ₂₀ An aryl group, a fluorenyl group, a C ₂ -C ₂₀ hetero atom containing at least one hetero atom selected from the group consisting of O, N, S, 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, and combinations thereof.

Specifically, the formula (1) may be represented by one of the following formulas (2) to (41).

   &Lt; Formula 2 > < EMI ID =

   &Lt; Formula 5 > < EMI ID =

&Lt; Formula 8 > < EMI ID =

&Lt; Formula 10 > < EMI ID =

&Lt; Formula 13 > < EMI ID =

&Lt; Formula 16 > < EMI ID =

&Lt; Formula 18 > < EMI ID =

&Lt; Formula 21 > < EMI ID =

&Lt; Formula 24 > < EMI ID =

&Lt; Formula 26 >

&Lt; Formula 29 > < EMI ID =

&Lt; Formula 32 > < EMI ID =

&Lt; Formula 34 > < EMI ID =

&Lt; Formula 37 > < EMI ID = 38.0 >

&Lt; Formula 40 > < EMI ID =

Wherein X ₁ and X ₂ are the same as defined in Formula (1), and in Formulas (10) to (17), R ¹ to R ⁹ are as defined in Formula , Ar ¹ is as defined in formula (1), and R 'and R "in the above formulas (18) to (25) are as defined in formula (1).

In the above Chemical Formulas 2 to 41, R ¹⁰ to R ¹⁷ independently represent 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 ² -N (R _a ) (R _b ), wherein L ² , R _a and R _b are as defined in formula (1).

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

In another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode.

The organic material layer is at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, and a light emitting layer, and the organic material layer may include at least one of the compounds. The organic material layer may include one or more compounds represented by the formula (1), and the compound represented by the formula (1) may be used as a material for the emission coarsening layer or a host material for the emission layer, in particular, a red phosphorescent host material .

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

The compound of formula (1) according to the present invention can be prepared by a reaction route as shown in the following reaction formula (1), but is not limited thereto.

(Reaction Scheme 1) When X ₁ or X ₂ is N (Ar ¹ )

In the Core, _one of Z ₁ and Z ₂ is -NH and the other is a single bond.

I. Synthesis of Core

1. Core-1's Synthetic example

Synthesis of Core-1-a

1-ene-1-one (10.00 g, 51.64 mmol) and (4-bromobut-1-en-1-yl) benzene (11.99 g, 56.81 mmol), K ₂ CO ₃ (10.71 g, 77.47 mmol) and acetone (200 ml) were added, and the mixture was refluxed at 60 ° C for 12 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with EA, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 16.05 g (96%) of the product.

Synthesis of Core-1-b

Pyridine (5 ml) and acetone (120 ml) are added to Core-1-a (5.10 g, 15.75 mmol) and irradiated with light with a wavelength of 300 nm or more at room temperature. After the reaction was completed, the solvent was removed from the reaction mixture, and the resulting organic material was separated using a silicagel column to obtain 3.33 g (87%) of the product.

Synthesis of Core-1-c

2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (5.97 g, 26.30 mmol) and MC (50 ml) were added to Core-1-b (3.20 g, 13.15 mmol) and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, NaHCO ₃ aqueous solution (50 ml) was added, extracted with MC 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 2.86 g (90%) of product.

Synthesis of Core-1-d

N- bromosuccinimide (3.33 g, 18.71 mmol) and DMF (50 mL) were added to a solution of Core-1-c (4.3 g, 17.82 mmol) and the mixture was stirred at room temperature for 6 hours. When the reaction was completed, it was extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 4.39 g (77%) of the product.

Synthesis of Core-1-e

2-chloroaniline (2.19 g, 17.18 mmol), Pd ₂ (dba) ₃ (0.47 g, 0.52 mmol), t-BuONa (1.82 g, 18.90 mmol), P (t-bu) ₃ (0.35 g, 1.72 mmol) and toluene (50 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel filter to obtain 5.48 g (87%) of product.

Synthesis of Core-1

P (OAc) ₂ (0.12 g, 0.52 mmol), P (t-Bu) ₃ (0.30 g, 1.04 mmol), K ₂ CO ₃ (4.29 g, 31.08 mmol) and DMA (50 ml), and the mixture is refluxed at 170 ° C for 12 hours. When the reaction is complete, cool the reaction mixture to room temperature, extract with MC, and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 2.74 g (80%) of the product.

2. Core-2's Synthetic example

Synthesis of Core-2-a

To a round bottom flask was added Core-1-d (3.9 g, 12.18 mmol), 1-chloronaphthalen-2-amine (2.16 g, 12.18 mmol), Pd ₂ (dba) ₃ (0.33 g, 4.27 g (84%) of the product was obtained using the above Core-1-e synthesis method by adding 1.29 g, 13.40 mmol), P (t-bu) ₃ (0.25 g, 1.22 mmol) and toluene (50 ml).

Synthesis of Core-2

Core-2-a (3.10 g , 7.44 mmol), Pd (OAc) 2 (0.08 g, 0.37 mmol), P (t-Bu) 3 (0.22 g, 0.74 mmol), K 2 CO 3 (3.08 g, 22.31 mmol) and DMA (50 ml) were subjected to the synthesis of Core-1 to obtain 2.32 g (82%) of the product.

3. Core-3's Synthetic example

Synthesis of Core-3-a

3-chloronaphthalen-2-amine (3.11 g, 17.49 mmol), Pd ₂ (dba) ₃ (0.48 g, 0.52 mmol) and t-BuONa (1.85 g, 19.24 5.91 g (81%) of the product was obtained using the above Core-1-e synthesis method with the addition of P (t-bu) ₃ (0.35 g, 1.75 mmol) and toluene (70 ml).

Synthesis of Core-3

(3.70 g, 8.87 mmol), Pd (OAc) ₂ (0.10 g, 0.44 mmol), P (t-Bu) ₃ (0.26 g, 0.89 mmol), K ₂ CO ₃ (3.68 g, 26.62 mmol) and DMA (50 ml) were used to obtain 4.4 g (64%) of the product using the above Core-1 synthesis method.

4. Core-4 Synthetic example

Synthesis of Core-4-a

2-chloronaphthalen-1-amine (1.39 g, 7.81 mmol), Pd ₂ (dba) ₃ (0.21 g, 0.23 mmol) and t-BuONa (0.83 g, 8.59 2.54 g (78%) of the product was obtained using the above Core-1-e synthesis method with the addition of P (t-bu) ₃ (0.32 g, 0.78 mmol) and toluene (50 ml).

Synthesis of Core-4

P (t-Bu) ₃ (0.46 g, 1.58 mmol), K ₂ CO ₃ (6.56 g, 47.49 mmol), Pd (OAc) ₂ (0.18 g, 0.79 mmol) mmol) and DMA (80 ml) were obtained 4.52 g (75%) of the product using the above core-1 synthesis method.

5. Core-5 Synthetic example

Synthesis of Core-5-a

The Core-1-d (12.30 g , 38.41 mmol) (2-nitrophenyl) boronic acid (6.41 g, 38.41 mmol), Pd (PPh 3) 4 (1.33 g, 1.15 mmol), K 2 CO 3 (7.96 g, 57.62 mmol), THF (150 ml) and H ₂ O (80 ml) were added, and the mixture was refluxed at 90 ° C for 12 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 12.25 g (88%) of the product.

Synthesis of Core-5

Triphenylphosphine (28.05 g, 106.93 mmol) and o-dichlorobenzene (o-DCB) (150 ml) were added to Core-5-a (15.50 g, 42.77 mmol) and refluxed at 180 ° C for 6 hours. When the reaction is complete, the temperature of the reaction is cooled to room temperature and o-DCB is removed. The resulting organic material was separated by silicagel column to obtain 13.00 g (92%) of product.

6. Core-6 Synthetic example

Synthesis of Core-6-a

Core-1-d (7.80 g , 24.36 mmol) in (2-nitronaphthalen-1-yl ) boronic acid (5.29 g, 24.36 mmol), Pd (PPh 3) 4 (0.84 g, 0.73 mmol), K 2 CO 3 8.44 g (84%) of the product was obtained by using the above Core-5-a synthesis method with 5.05 g (36.54 mmol), THF (100 ml) and H ₂ O (50 ml)

Synthesis of Core-6

Dichloro benzene (o-DCB) (100 ml) was reacted with 6.50 g (87%) of Core-6-a (8.10 g, 19.64 mmol), triphenylphosphine (12.88 g, 49.10 mmol) ).

7. Core-7's Synthetic example

Synthesis of Core-7-a

The Core-1-d (5.30 g , 16.55 mmol) (3-nitronaphthalen-2-yl) boronic acid (3.59 g, 16.55 mmol), Pd (PPh 3) 4 (0.57 g, 0.50 mmol), K 2 CO 3 6.08 g (89%) of the product was obtained by using the above Core-5-a synthesis method with the above compound (3.43 g, 24.83 mmol), THF (100 ml) and H ₂ O (50 ml)

Synthesis of Core-7

Dichlorobenzene (o-DCB) (70 ml) was reacted with 4.84 g (89%) of Core-7-a (5.90 g, 14.30 mmol), triphenylphosphine (9.38 g, 35.76 mmol) ).

8. Core-8 Synthetic example

Synthesis of Core-8-a

Core-1-d (6.20 g , 19.36 mmol) (1-nitronaphthalen-2-yl) the boronic acid (4.20 g, 19.36 mmol ), Pd (PPh 3) 4 (0.67 g, 0.58 mmol), K 2 CO 3 7.03 g (88%) of the product was obtained by using the Core-5-a synthesis method described above (4.01 g, 29.05 mmol), THF (100 ml) and H ₂ O (50 ml).

Synthesis of Core-8

Dichloro benzene (o-DCB) (50 ml) was reacted with 2.19 g (82%) of Core-8-a (2.90 g, 7.03 mmol), triphenylphosphine (4.61 g, 17.58 mmol) ).

&Lt; Reaction Formula 2 > When X ₁ and X ₂ are S, O, or CR'R ''

One of X ₁ and X ₂ is S, O or CR'R "and the other is a single bond.

9. Core-9's Synthetic example

Synthesis of Core-9-a

N -iodosuccimide (9.11 g, 40.47 mmol) and DMF (150 mL) were added to a solution of Core-1-c (9.30 g, 38.54 mmol) and the mixture was stirred at room temperature for 6 hours. When the reaction was completed, it was extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 9.26 g (75%) of the product.

Synthesis of Core-9-b

2,5-dibromobenzenethiol (2.99 g, 11.17 mmol), Pd ₂ (dba) ₃ (0.31 g, 0.33 mmol), Oxydi-2,1-phenylene bis (DPEPhos) (0.60 g, 1.12 mmol), t-BuONa (1.18 g, 12.28 mmol) and toluene (100 ml) were added and refluxed at 60 ° C for 2 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel filter to obtain 1.62 g (40%) of the product.

Synthesis of Core-9-c

Pd (OAc) ₂ (0.09 g, 0.38 mmol), P (t-Bu) ₃ (0.22 g, 0.77 mmol), K ₂ CO ₃ (3.19 g, 23.07 mmol) and DMA (50 ml) were obtained 2.23 g (68%) of the product using the above Core-1 synthesis method.

Synthesis of Core-9

To a solution of bis (pinacolato) diboron (5.30 g, 18.91 mmol), PdCl ₂ (dppf) ₂ (0.59 g, 0.73 mmol), KOAc (4.28 g, 43.63 mmol), DMF (100 ml), and the mixture is refluxed at 120 ° C for 6 hours. When the reaction is complete, cool the reaction mixture to room temperature, extract with MC, and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resultant organics were separated using a silicagel column to obtain 6.06 g (88%) of the product.

10. Core-10 Synthetic example

Synthesis of Core-10-a

PdCl ₂ (dppf) ₂ (1.20 g, 1.47 mmol), KOAc (8.64 g, 88.07 mmol), DMF (10.64 g, (100 ml) was obtained 9.06 g (84%) of the product using the above-described synthesis of Core-9

Synthesis of Core-10-b

Core-10-a (7.90 g , 21.51 mmol) in 2,4-dibromophenol (5.42 g, 21.51 mmol), Pd (PPh 3) 4 (0.75 g, 0.65 mmol), K 2 CO 3 (4.46 g, 32.27 mmol ), THF (100 ml), EtOH (50 ml) and H ₂ O (50 ml) were added, and the mixture was refluxed at 90 ° C for 12 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC 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 4.88 g (55%) of the product.

Synthesis of Core-10-c

3-nitropyridine (0.06 g, 0.50 mmol), BzOOtBu (tert-butyl peroxybenzoate) (3.86 g, 19.89 mmol), Pd (OAc) ₂ (0.10 g, ), C ₆ F ₆ (hexafluorobenzene) (100 ml) and DMI (N, N'-dimethylimidazolidinone) (65 ml) were added and refluxed at 90 ° C. for 3 hours. When the reaction is complete, the reaction temperature is cooled to room temperature, extracted with EA, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 1.88 g (46%) of the product.

Synthesis of Core-10

PdCl ₂ (dppf) ₂ (0.28 g, 0.34 mmol), KOAc (2.01 g, 20.47 mmol), DMF (2.08 g, (50 ml) was obtained 2.75 g (88%) of the product using the above-described synthesis of Core-9.

11. Core-11 Synthetic example

Synthesis of Core-11-a

Core-10-a (6.80 g , 18.52 mmol) to methyl 5-bromo-2-iodobenzoate (6.31 g, 18.52 mmol), Pd (PPh 3) 4 (0.64 g, 0.56 mmol), K 2 CO 3 (3.84 g , 27.77 mmol), THF (100 ml) and H ₂ O (50 ml) were used to synthesize Core-10-b to give 3.53 g (42%) of the product.

Synthesis of Core-11-b

Core-11-a (3.40 g, 7.48 mmol) and THF (50 ml) were added. 1.6 M methylmagnesium bromide (11.7 ml) was added at 0 ° C and the mixture was stirred at room temperature for 24 hours. When the reaction is complete, add 1 N HCl and stir for 10 minutes, then extract with EA and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 2.35 g (69%) of the product.

Synthesis of Core-11-c

After dissolving Core-11-b (4.20 g, 9.24 mmol) in THF (100 ml), 4 ml of methanesulfonic acid was slowly added at 0 ° C and stirred at room temperature for 1 hour. After the reaction is completed, add sodium carbonate aqueous solution (100 ml), stir for 10 minutes, extract with MC and wipe with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was separated using a silicagel column to obtain 2.58 g (64%) of the product.

Synthesis of Core-11

(4.49 g, 15.49 mmol), PdCl ₂ (dppf) ₂ (0.49 g, 0.60 mmol), KOAc (3.51 g, 35.75 mmol), DMF (70 ml) was obtained 5.13 g (89%) of the product using the above-described synthesis of Core-9.

Ⅱ. Example of Sub 1

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

[Table 1]

III. Product synthesis

1. P-3 Synthetic example

Sub-1-45 (2.67 g, 9.99 mmol), Pd ₂ (dba) ₃ (0.27 g, 0.30 mmol) and t-BuONa (1.06 g, 9.99 mmol) were placed in a round bottom flask, 10.99 mmol), P (t-bu) ₃ (0.54 g, 1.08 mmol) and toluene (50 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with MC and wiped with water. The organic layer was dried over MgSO ₄ and concentrated. After separating the resulting organic material with silicagel filter, 4.60 g (82%) of the product was obtained.

2. P-30 Synthetic example

Sub-1-51 (2.47 g, 10.25 mmol), Pd ₂ (dba) ₃ (0.28 g, 0.31 mmol), t-BuONa (1.08 g, 11.28 mmol), P (t-bu) ₃ (0.55 g, 1.03 mmol) and toluene (50 ml) were used to obtain 4.84 g (84%) of the product.

3. P-37 Synthetic example

Pd ₂ (dba) ₃ (0.20 g, 0.22 mmol), t-BuONa (0.78 g, 8.10 mmol), P-1 -44 (2.33 g, 7.36 mmol) (t-bu) ₃ (0.40 g, 0.74 mmol) and toluene (40 ml) were used to obtain 2.69 g (65%) of the product.

4. P-53 Synthetic example

(1.68 g, 5.78 mmol), Pd ₂ (dba) ₃ (0.16 g, 0.17 mmol), t-BuONa (0.61 g, 6.36 mmol), P (t-bu) ₃ (0.31 g, 0.62 mmol) and toluene (30 ml) were obtained 3.19 g (87%) of the product using the above synthesis method of P-1-7.

5. P-73 Synthetic example

Pd ₂ (dba) ₃ (0.34 g, 0.37 mmol), t-BuONa (1.31 g, 13.65 mmol), P-1 -46 (3.68 g, 12.41 mmol) (t-bu) ₃ (0.67 g, 1.24 mmol) and toluene (50 ml) were obtained 6.74 g (92%) of the product using the above synthesis method of P-3.

6. P-88 Synthetic example

Sub-1-2 (3.30 g, 12.35 mmol), Pd ₂ (dba) ₃ (0.34 g, 0.37 mmol), t-BuONa (1.31 g, 13.59 mmol), P (t-bu) ₃ (0.67 g, 1.24 mmol) and toluene (50 ml) were subjected to the synthesis of P-3 to obtain 5.96 g (79%) of the product.

7. P-110 Synthetic example

Sub-1-72 (1.62 g, 5.78 mmol), Pd ₂ (dba) ₃ (0.16 g, 0.17 mmol), t-BuONa (0.61 g, 6.36 mmol), P (t-bu) ₃ (0.31 g, 0.62 mmol) and toluene (30 ml) were obtained 3.29 g (91%) of the product using the synthesis of P-3.

8. P-120 Synthetic example

Sub-1-32 (3.33 g, 10.51 mmol), Pd ₂ (dba) ₃ (0.29 g, 0.32 mmol), t-BuONa (1.11 g, 11.57 mmol), P (t-bu) ₃ (0.57 g, 1.05 mmol) and toluene (50 ml) were subjected to the synthesis of P-3 to obtain 5.97 g (86%) of the product.

9. P-16 Synthetic example

Core-9 (3.30 g, 6.97 mmol), Sub-1-62 (1.95 g, 6.97 mmol), Pd (PPh 3) 4 (0.24 g, 0.21 mmol), K 2 CO 3 (1.45 g, 10.46 mmol), THF (80 ml) and H ₂ O (40 ml) were used to synthesize Core-5-a to obtain 3.62 g (88%) of the product.

10. P-19 Synthetic example

Core-10 (6.50 g, 14.21 mmol), Sub 1-67 (8.55 g, 14.21 mmol), Pd (PPh 3) 4 (0.49 g, 0.43 mmol), K 2 CO 3 (2.95 g, 21.32 mmol), THF (80 ml) and H ₂ O (40 ml) were subjected to the synthesis of Core-5-a to obtain 6.47 g (85%) of the product.

11. P-20 Synthetic example

Core-11 (3.60 g, 7.45 mmol), Sub-1-14 (2.37 g, 7.45 mmol), Pd (PPh 3) 4 (0.26 g, 0.22 mmol), K 2 CO 3 (1.54 g, 11.17 mmol), THF (100 ml) and H ₂ O (50 ml) were subjected to the synthesis of Core-5-a to obtain 3.90 g (82%) of the product.

The FD-MS values of the final compounds synthesized by the above synthesis method are shown in Table 2 below.

[Table 2]

Evaluation of manufacturing of organic electric device

[ Example  One] Red organic electroluminescent device (Phosphorescent host)

A 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ") film was vacuum deposited on the ITO layer (anode) After the formation of the injection layer, a 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) film was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Then, the compound P-1 of the present invention was used as a host material on the hole transport layer and bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter referred to as "(piq) ₂ Ir (acac)") (1, 1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum hereinafter "BAlq" as abbreviated) of 10 nm in thickness by vacuum vapor deposition to form a hole blocking layer, tris- (8-hydroxyquinoline) aluminum on the hole blocking layer (hereinafter "Alq _3" abbreviated to) 40 nm Vacuum evaporation to a thickness of &lt; RTI ID = 0.0 &gt; Then, LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer. Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode Thereby preparing an organic electroluminescence device.

[ Example  2] to [ Example  53]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 3 was used instead of the compound P-1 of the present invention as a host material of the light emitting layer.

[ Comparative Example  1] to [ Comparative Example  3]

An organic electroluminescence device was prepared in the same manner as in Example 1 except that one of the following Comparative Compounds A to C was used in place of the compound P-1 of the present invention as a host material in the light emitting layer.

  &Lt; Comparative Compound A > < Comparative Compound B > < Comparative Compound C &

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 53 and Comparative Examples 1 to 3 of the present invention And the T95 lifetime was measured using a life measuring instrument manufactured by Mac Science Inc. at a luminance of 2500 cd / m ^2. The measurement results are shown in Table 3 below.

[Table 3]

As can be seen from the results of Table 3, the organic electroluminescent device using the compound of the present invention as a phosphorescent host material has a lower driving voltage and significantly improved luminous efficiency and lifetime than the case of using a comparative compound.

Compared with Comparative Compound A, which is a CBP mainly used as a host material, when the indolopyrrolocarbazole was the main skeleton of Comparative Compound B and Comparative Compound C were used as the host material, the device characteristics were improved, and Comparative Compound B and Comparative Compound C, the device characteristics were further improved when the compound of the present invention was used as a host material.

Compounds of the present invention are more fused with one or more benzene in the main skeleton than the comparative compounds B and C. As the compound of the present invention, one or more benzene is fused in the main skeleton, and physical properties such as HOMO value, T 1 value, and thermal stability are changed. The difference in physical properties is a main factor Energy balance), resulting in different device results.

[ Example  54] Red organic electroluminescent device ( The light- )

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 NPB was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Subsequently, the compound P-18 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, and then 4,4'-N, N'-dicarbazole- biphenyl (hereinafter abbreviated as " CBP &quot;) was doped with 95: 5 by weight of dopant (piq) ₂ Ir (acac) to form a 30 nm thick light emitting layer. Next, BAlq was vacuum-deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq ₃ was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer. Then, LiF, which is 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 Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example  55] to [ Example  62]

An organic electroluminescent device was prepared in the same manner as in Example 54 except that the compound of the present invention described in Table 4 was used instead of the compound P-18 of the present invention as a material of the luminescent auxiliary layer.

[ Comparative Example  4]

An organic electroluminescent device was prepared in the same manner as in Example 54 except that no luminescent auxiliary layer was formed.

[ Comparative Example  5] and [ Comparative Example  6]

An organic electroluminescence device was prepared in the same manner as in Example 54, except that the following compound D or Comparative Compound F was used in place of the compound P-18 of the present invention as a material of the luminescent auxiliary layer.

 &Lt; Comparative Compound D > < Comparative Compound F >

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 54 to 62 and Comparative Examples 4 to 6 of the present invention And the T95 lifetime was measured using a life measuring apparatus manufactured by Mac Science Inc. at a luminance of 2500 cd / m ^2. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, the red organic light emitting device using the compound of the present invention as the light emitting auxiliary layer material has a lower driving voltage than the comparative example in which no luminescent auxiliary layer is formed or Comparative Compound D and Comparative Compound F are used The efficiency, and the life span were remarkably improved.

The device characteristics of Comparative Example 5 and Comparative Example 5 using the comparative compound D or the comparative compound F were superior to those of the comparative example 4 in which the luminescent auxiliary layer was not used. When the compound of the present invention was used in comparison with the comparative compound D or the comparative compound F The device characteristics were the best.

This suggests that if more than one benzene is fused to the core of Comparative Compound C or Comparative Compound F as described in Table 3, the chemical and physical properties of the compound may be different, thereby resulting in different element results have.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, 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 equivalents should be construed as falling within the scope of the present invention.

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

Claims (13)

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

In Formula 1,
A rings are independently of each other C ₆ -C ₆₀ aromatic hydrocarbons; Fluorene; _{O, N, S, C 2} ~ C ₆₀ heteroaryl rings containing Si and P, at least one of the hetero atoms in the; And a fused ring of a C ₆ to C ₆₀ aromatic ring and a C ₃ to C ₆₀ aliphatic ring,
X ₁ and X ₂ independently represent a single bond, N (L ¹ ) (Ar ¹ ), O, S, C (R ') (R ") or Si (R') (R"
R ¹ to R ⁹ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 ² -N (R _a ) (R _b ), adjacent groups may be bonded to each other to form a ring,
Ar ¹ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And it is selected from the group consisting of _{^{-L 2 -N (R a) (}} R b),
L ¹ and L ² are independently a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ;
Wherein R 'and R " are independently selected from the group consisting of a C ₁ to C ₅₀ alkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₆₀ alkyl group having at least one heteroatom selected from O, N, S, And R 'and R " may be bonded to each other to form a ring,
R _a and R _b are each independently a C ₆ to C ₆₀ aryl group; 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 hetero atom selected from the group consisting of O, N, S, Si and P, and R _a and R _b may be bonded to each other to form a ring In addition,
A heterocyclic group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, R ¹ to R ⁹ a ring group, R 'combine with each other formed in a small neighborhood and R "the ring formed by combining each other, and R _a and R _b combine with each other are formed, each ring is heavy hydrogen; halogen; C ₁ -C ₂₀ alkyl group or C A silyl group substituted or unsubstituted with an aryl group of _{6 to 20} carbon atoms, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C _{1 to} C ₂₀ alkylthio group, a C _{1 to} C ₂₀ alkoxyl group, ₁ -C ₂₀ alkyl group; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; C ₂ -C ₂₀ alkynyl of;; C ₆ aryl group of C ₂ -C ₂₀ alkenyl group ₂₀ -C fluorene group ; O, N, S, Si, and a heterocyclic group of C ₂ -C ₂₀ containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ cycloalkyl ; C ₇ -C ₂₀ aryl alkyl groups; C ₈ -C ₂₀ aryl alkenyl group _{^{of; -L 2 -N (R a)}} (R b); and be further substituted with one or more substituents selected from the group consisting of . The method according to claim 1,
(1) is represented by one of the following formulas (2) to (9):
&Lt; Formula 2 >< EMI ID =

&Lt; Formula 5 &gt;&lt; EMI ID =

&Lt; Formula 8 >< EMI ID =

In the above Chemical Formulas 2 to 9,
R ¹ to R ⁹ , X ₁ and X ₂ are the same as defined in claim 1,
R ¹⁰ to R ¹⁷ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 it is selected from the group consisting of _{^{-L 2 -N (R a) (}} R b),
Wherein L ² , R _a and R _b are as defined in claim 1. The method according to claim 1,
The compound of formula (I) is represented by one of the following formulas (10) to (17):
&Lt; Formula 10 >< EMI ID =

&Lt; Formula 13 &gt;&lt; EMI ID =

&Lt; Formula 16 >< EMI ID =

In the above Chemical Formulas 10 to 17,
R ¹ to R ⁹ , Ar ¹ are as defined in claim 1,
R ¹⁰ to R ¹⁷ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 it is selected from the group consisting of _{^{-L 2 -N (R a) (}} R b),
Wherein L ² , R _a and R _b are as defined in claim 1. The method according to claim 1,
The compound of formula (I) is represented by one of the following formulas (18) to (25):
&Lt; Formula 18 >< EMI ID =

&Lt; Formula 21 &gt;&lt; EMI ID =

&Lt; Formula 24 >< EMI ID =

In the above Chemical Formulas 18 to 25,
R ¹ to R ⁹ , R ', R "are the same as defined in claim 1,
R ¹⁰ to R ¹⁷ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 it is selected from the group consisting of _{^{-L 2 -N (R a) (}} R b),
Wherein L ² , R _a and R _b are as defined in claim 1. The method according to claim 1,
The compound of formula 1 is represented by one of the following formulas 26 to 33:
&Lt; Formula 26 >

&Lt; Formula 29 >< EMI ID =

&Lt; Formula 32 &gt;&lt; EMI ID =

In the above Chemical Formulas 26 to 33,
R ¹ to R ⁹ are as defined in claim 1,
R ¹⁰ to R ¹⁷ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 it is selected from the group consisting of _{^{-L 2 -N (R a) (}} R b),
Wherein L ² , R _a and R _b are as defined in claim 1. The method according to claim 1,
The compound of formula (I) is represented by one of the following formulas (34) to (41):
&Lt; Formula 34 >< EMI ID =

&Lt; Formula 37 &gt;&lt; EMI ID = 38.0 &gt;

&Lt; Formula 40 &gt;&lt; EMI ID =

In Formulas 34 to 41,
R ¹ to R ⁹ are as defined in claim 1,
R ¹⁰ to R ¹⁷ 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 aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl 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 it is selected from the group consisting of _{^{-L 2 -N (R a) (}} R b),
Wherein L ² , R _a and R _b are as defined in claim 1. The method according to claim 1,
Wherein the compound of formula (I) is one of the following compounds:

. A first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode and containing a compound according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer,
The compound is contained in at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting supporting layer, an electron transporting layer and an electron injecting layer, And an organic electroluminescent device. 10. The method of claim 9,
Wherein the compound is contained in the light-emission-assisting layer or is used as a host material of the light-emitting layer. 9. The method of claim 8,
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 8; And
And a control unit for driving the display device. 13. The method of claim 12,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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