KR20200117556A - Compound for organic electric element and organic electric device comprising the same - Google Patents

Abstract

Embodiments of the present invention relate to a compound for an organic electric device capable of providing high luminous efficiency, low driving voltage, and high heat resistance, and improving color purity or lifespan, and an organic electric device using the same.

Description

Compound for organic electric device and organic electric device using the same {COMPOUND FOR ORGANIC ELECTRIC ELEMENT AND ORGANIC ELECTRIC DEVICE COMPRISING THE SAME}

Embodiments of the present invention relate to a compound for an organic electric device and an organic electric device using the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic electric device using an organic light emission phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as an organic material layer in an organic electronic device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

In addition, the light-emitting material can be classified into a high-molecular type and a low-molecular type according to the molecular weight, and according to the light-emitting mechanism, the fluorescent material derived from the singlet excited state of the electron and the phosphorescent material derived from the triplet excited state of the electron can be classified I can. In addition, the light-emitting materials may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a long wavelength due to the interaction between molecules, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect. A host/dopant system may be used as a light-emitting material in order to increase the luminous efficiency through. The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light-emitting layer is mixed in the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant to emit highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is increasing in size as a large-area display. Since the portable display has a battery, which is a limited power supply, more efficient power consumption than the power consumption required in the existing portable display is required. In addition, in addition to the efficient power consumption, the problem of luminous efficiency and lifespan must be solved.

In organic electronic devices, efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased, and when the driving voltage is decreased, the organic material is crystallized by Joule heating. As a result, the lifespan tends to increase as is reduced. However, simply improving the organic material layer cannot maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the optimum combination of energy level and T1 value between each organic material layer, and intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved. Accordingly, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer.

In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. Although this should be preceded, development of a stable and efficient organic material layer material for organic electric devices has not been sufficiently achieved.

In general, 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, thereby generating excitons through recombination.

However, since holes move faster than electrons, excitons generated in the emission layer are transferred to the electron transport layer, resulting in charge unbalance in the emission layer, thereby emitting light at the interface of the electron transport layer. When light is emitted at the interface of the electron transport layer, there is a problem that the color purity and efficiency of the organic electronic device are deteriorated. In particular, when the organic electronic device is manufactured, the high temperature stability is deteriorated and the life of the organic electronic device is shortened. Therefore, the electron transport material having high temperature stability and high electron mobility (within the range of the driving voltage of a blue device of a full device) and a low HOMO value to improve the hole blocking ability. It is time for development.

On the other hand, in the case of a cyclic compound containing a hetero atom, the difference in characteristics according to the material structure is very large, and thus, it is applied to various layers as an OLED material. In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, and physical properties are different depending on the number of rings and the fused position, and the type and arrangement of heteroatoms. Development has been applied to various OLED layers using this. come. In addition, recently, OLED material development for the type, number, and position of heteroatoms of cyclic compounds is actively progressing.

In recent years, not only researches to improve device characteristics by changing the performance of each material, but also to improve the color purity and increase efficiency by the optical thickness optimized between the anode and the cathode in the top device of the resonance structure It is one of the important factors in improving the performance. Compared to the non-resonant bottom device structure, the top device structure has a large optical energy loss due to the surface plasmon polariton (SPP) because the formed light is reflected by the anode, which is a reflective film, and light is emitted toward the cathode.

Therefore, one of the important methods for improving the shape and efficiency of the EL Spectral is a method of using a capping layer for the top cathode. In general, SPP mainly uses four metals: Al, Pt, Ag, and Au for electron emission, and surface plasmon is generated on the surface of the metal electrode. For example, when the cathode is used as Ag, the light emitted by Ag of the cathode is quenched by SPP (loss of light energy due to Ag), thereby reducing efficiency.

On the other hand, when the capping layer is used, SPP is generated at the interface between the MgAg electrode and the organic material having high refractive index. Among them, the transverse electric (TE) polarized light is extinguished on the surface of the capping layer in the vertical direction by the evanescent wave. Transverse magnetic (TM) polarized light moving along the capping layer causes an amplification of the wavelength due to surface plasma resonance, which increases the intensity of the peak, resulting in high efficiency and effective efficiency. Color purity can be adjusted.

Embodiments of the present invention can provide a compound capable of improving 　 high heat resistance, color purity, and lifespan while lowering 　 driving voltage of a device, an organic electric device using the same, and an electronic device thereof.

In one aspect, embodiments of the present invention can provide a compound represented by the following formula (1), an organic electric device including the same, and an electronic device thereof.

Formula (1)

According to the embodiments of the present invention, by using the compound according to the embodiments of the present invention, it is possible to achieve high luminous efficiency, low driving voltage, and high heat resistance of the device, and the color purity and lifespan of the device are greatly improved. Device can be provided.

1 to 3 are schematic views of organic electric devices according to embodiments of the present invention.

Hereinafter, some embodiments of the present invention will be described in detail with reference to exemplary drawings.

In adding reference numerals to elements of each drawing, the same elements may have the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, when it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof may be omitted. When "include", "have", "consists of" and the like mentioned in the present specification are used, other parts may be added unless "only" is used. In the case of expressing the constituent elements in the singular, the case including plural may be included unless there is a specific explicit description.

In addition, in describing the constituent elements of the present invention, terms such as first, second, A, B, (a) and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, order, or number of the component is not limited by the term.

In the description of the positional relationship of the components, when two or more components are described as being "connected", "coupled" or "connected", the two or more components are directly "connected", "coupled" or "connected" "It may be, but it should be understood that two or more components and other components may be further "interposed" to be "connected", "coupled" or "connected". Here, the other components may be included in one or more of two or more components "connected", "coupled" or "connected" to each other.

In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, it is not only "directly over" another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is "directly above" another part, it means that there is no other part in the middle.

In the description of the temporal flow relationship related to the components, the operation method or the manufacturing method, for example, the temporal predecessor relationship such as "after", "after", "after", "before", etc. Alternatively, a case where a flow forward and backward relationship is described may also include a case that is not continuous unless "direct" or "direct" is used.

On the other hand, when a numerical value for a component or its corresponding information is mentioned, the numerical value or its corresponding information may be caused by various factors (e.g., process factors, internal or external shock, noise, etc.) It can be interpreted as including a possible error range.

The term "halo" or "halogen" as used in the present application includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used in the present application has 1 to 60 carbons connected by a single bond unless otherwise specified, and a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted It may mean a radical of a saturated aliphatic functional group including a cycloalkyl group and a cycloalkyl-substituted alkyl group.

The terms "haloalkyl group" or "halogenalkyl group" as used in the present application may mean an alkyl group in which halogen is substituted unless otherwise specified.

The terms "alkenyl" or "alkynyl" used in the present application each have a double bond or a triple bond, unless otherwise specified, include a straight or branched chain group, and may have 2 to 60 carbon atoms.

The term "cycloalkyl" used in the present application may mean an alkyl forming a ring having 3 to 60 carbon atoms unless otherwise specified.

The term "alkoxy group" or "alkyloxy group" as used herein refers to an alkyl group to which an oxygen radical is bonded, and may have 1 to 60 carbon atoms unless otherwise specified.

The terms "alkenyl group", "alkenoxy group", "alkenyloxy group", or "alkenyloxy group" as used in the present application mean an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 May have carbon number of.

The terms "aryl group" and "arylene group" as used in the present application each have 6 to 60 carbon atoms, but are not limited thereto. In the present application, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a conjugated multiple ring system, a spiro compound, and the like. For example, the aryl group may refer to a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group.

In the present application, the terms "fluorenyl group" or "fluorenylene group" may each mean a monovalent or divalent functional group of fluorene unless otherwise specified. "Substituted fluorenyl group" or "substituted fluorenylene group" may mean a monovalent or divalent functional group of substituted fluorene. "Substituted fluorene" may mean that at least one of the following substituents R, R', R" and R'" is a functional group other than hydrogen. It may include the case where R and R'are bonded to each other to form a spy compound with the carbon to which they are bonded.

The term "spyro compound" as used in the present application has a'spiro union', and the spiro linkage refers to a connection made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It can be called a compound.

The term "heterocyclic group" as used in the present application includes not only an aromatic ring such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and unless otherwise stated, the number of carbon atoms each containing one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used in the present application represents N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type including a heteroatom, a ring aggregate, a conjugated ring system, spy It may mean a compound or the like.

In addition, the "heterocyclic group" may also include a ring including SO ₂ instead of carbon forming a ring. For example, the "heterocyclic group" may include the following compounds.

The term “ring” used in the present application includes monocyclic and polycyclic rings, and includes a heterocycle including at least one heteroatom as well as a hydrocarbon ring, and may include aromatic and non-aromatic rings.

The term "polycyclic" as used in the present application includes ring assemblies, fused ring systems and spiro compounds, and includes not only aromatic but also non-aromatic, hydrocarbon rings as well as at least one hetero It may contain a heterocycle containing an atom.

The term "aliphatic ring group" used in the present application refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic types, ring aggregates, conjugated ring systems, spiro compounds, etc., unless otherwise stated, It may mean 3 to 60 rings. For example, benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.

The term "ring assemblies" as used in this application means that two or more ring systems (single ring or fused ring system) are directly connected to each other through a single bond or a double bond. For example, in the case of an aryl group, it may be a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

The term "conjugated multiple ring systems" as used in the present application refers to a fused ring type that shares at least two atoms. For example, the aryl group may be a naphthalenyl group, a phenanthrenyl group, or a fluorenyl group, but is not limited thereto.

In addition, when the prefixes are named consecutively, it may mean that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonylalkenyl group, it may mean an alkenyl group substituted with an arylcarbonyl group. have. Here, the arylcarbonyl group may be a carbonyl group substituted with an aryl group.

In addition, unless expressly stated, the term "substituted or unsubstituted" used in the present application "substituted" refers to deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group of, 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 It means substituted with one or more substituents selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group including a group, a germanium group, and at least one heteroatom selected from the group consisting of O, N, S, Si and P Can be, but is not limited to these substituents.

In the present application, the'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe the'name of the functional group reflecting the number', but it is described as the'parent compound name' You may. For example, in the case of'phenanthrene,' a kind of aryl group, the monovalent'group' is'phenanthryl (group)', and the divalent group is labeled with the name of the group by dividing the valence such as'phenanthrylene (group)'. Although it can be done, it can also be described as'phenanthrene', which is the name of the parent compound regardless of the valence. Similarly, in the case of pyrimidine, it is described as'pyrimidine' regardless of the valence, or in the case of monovalent, the'group' of the corresponding valency, such as pyrimidinyl (group), and in the case of divalent, pyrimidinylene (group) You can also write it as'name'. Therefore, when the type of the substituent is described as the parent compound name in the present application, it may mean an n-valent'group' formed by desorbing a carbon atom and/or a hydrogen atom bonded to a heteroatom of the parent compound.

In addition, unless there is an explicit description, the formula used in this application may be applied in the same manner as the definition of the substituent 　 in the index definition of the following formula.

Here, when a is 0, the substituent R ¹ means that the substituent R ¹ is absent, which means that all hydrogens are bonded to the carbon forming the benzene ring, and at this time, the indication of hydrogen bonded to the carbon is omitted and the formula or compound Can be described. In addition, when a is 1, one substituent R ¹ is bonded to any one of the carbons forming a benzene ring, and when a is 2 or 3, each can be bonded as follows, and a is 4 to 6 In the case of an integer, it is bonded to the carbon of the benzene ring in a similar manner. When a is an integer of 2 or more, R ¹ may be the same or different from each other.

In the present application, that substituents are bonded to each other to form a ring means that adjacent groups are bonded to each other to form a single ring or multiple conjugated rings, and the single ring and the formed conjugated multiple rings are hydrocarbon rings as well as at least one hetero It includes a heterocycle containing an atom, and may include aromatic and non-aromatic rings.

In the present application, the organic electric device may mean a component(s) between an anode and a cathode, or an organic light emitting diode including an anode and a cathode, and component(s) positioned therebetween.

In addition, in some cases, the organic electric device in the present application may refer to an organic light-emitting diode and a panel including the same, or may refer to an electronic device including a panel and a circuit. Here, for example, the electronic device is a display device, a lighting device, a solar cell, a portable or mobile terminal (eg, a smart phone, a tablet, a PDA, an electronic dictionary, a PMP, etc.), a navigation terminal, a game machine, various TVs, and various computers. Any type of device may be included as long as it includes all of the monitors and the like, but is not limited thereto.

Organic Electric Device FIGS. 1 to 3 are exemplary views of organic electric devices according to embodiments of the present invention.

First, referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). An organic material layer including the compound according to the present invention may be included between the and the second electrode 170, and the capping layer 180 may or may not be additionally formed.

The first electrode 110 of FIG. 1 may be an anode (anode), and the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode. .

The organic material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially disposed on the first electrode 110.

In addition, referring to FIG. 2, the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 220, a hole transport layer 230, and a buffer layer sequentially disposed on the first electrode 210. 243), a light emission auxiliary layer 253, a light emission layer 240, an electron transport layer 250, an electron injection layer 260, and a second electrode 270 may be included, and an additional capping layer 280 may be formed. Yes, it may not be formed.

Meanwhile, although not shown in FIG. 2, an electron transport auxiliary layer may be further disposed between the light emitting layer 240 and the electron transport layer 250.

In addition, referring to FIG. 3, in the organic electric device 300 according to another embodiment of the present invention, a stack of multilayer organic material layers ST1 and ST2 is formed between the first electrode 310 and the second electrode 370. More than one set can be placed. For example, a first stack ST1 is disposed on the first electrode 310, a second stack ST2 is disposed on the first stack ST1, and a second stack ST2 is disposed on the second stack ST2. The electrode 370 may be disposed. A charge generation layer (CGL) may be disposed between the first stack ST1 and the second stack ST2. Additionally, the capping layer 380 may or may not be formed on the second electrode 370.

Specifically, in the present application, the organic electric device 300 includes a first electrode 310, a first stack ST1, a charge generation layer CGL, a second stack ST2, a second electrode 370, and a capping layer. (380) may be included.

The first stack ST1 is an organic material layer formed on the first electrode 310, which is a first hole injection layer 321, a first hole transport layer 331, a first emission layer 341 and a first electron transport layer 351 ), and the second stack ST2 may include a second hole transport layer 332, a second emission layer 342, and a second electron transport layer 352. Additionally, an electron injection layer 360 may be included between the second electrode and the second electron transport layer. As described above, the first stack and the second stack may be organic material layers having the same stacked structure.

The charge generation layer CGL may include a first charge generation layer 390 and a second charge generation layer 391. Since the charge generation layer CGL is disposed between the first and second emission layers 341 and 342, the current efficiency generated in each emission layer may be increased, and electric charges may be smoothly distributed.

The first emission layer 341 may include a light emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 342 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first and second emission layers 341 and 342 according to an embodiment of the present invention is not limited thereto.

The charge generation layer CGL and the second stack ST2 may be repeatedly positioned n times, which is a positive integer. For example, n may be an integer of 1 to 5. For example, when n is 2, a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.

In the drawing, a capping layer 180 is formed on at least one of one surface of the first electrode 110, 210, and 310 opposite to the organic material layer and one surface of the second electrode 170, 270, 370 opposite to the organic material layer. , 280, 380) may be formed.

In addition, when the capping layer is formed, the light efficiency of the organic electric device may be improved.

In the case of a top emission organic light emitting device, the capping layers 180, 280, 380 play a role in reducing optical energy loss due to surface plasmon polaritons (SPPs) in the second electrodes 170, 270, 370. can do. In the case of a bottom emission organic electric device, the capping layers 180, 280, and 380 may serve as a buffer for the second electrodes 170, 270, and 370.

On the other hand, when a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electric device in which white light is emitted by a mixing effect of light emitted from each light emitting layer.

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 220, 321), a hole transport layer (130, 230, 331, 332), a buffer layer (243), a light emission auxiliary layer (253), an electron transport layer (150). , 250, 351, 352), electron injection layers 160, 260, 360, light emitting layers 140, 240, 341, 342, or capping layers 180, 280, 380. For example, the compound of the present invention may be used as a material for the electron transport layers 150, 250, 351, 352, the host of the emission layers 140, 240, 341, 342, and the capping layers 180, 280, 380.

On the other hand, even with the same core, the band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position, so the selection of the core and the combination of sub-substituents bonded thereto may be changed. Research is needed. In particular, long life and high efficiency can be achieved at the same time when the optimum combination of energy level and T1 value between each organic material layer, and intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved.

The organic electric device according to the embodiments of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD (Physical Vapor Deposition) or CVD (Chemical Vapor Deposition), for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to deposit the anodes 110, 210, 310), and hole injection layers (120, 220, 321), hole transport layers (130, 230, 331, 332), light emitting layers (140, 240, 341, 342), electron transport layers (150, 250, 351) thereon. After forming an organic material layer including the, 352 and electron injection layers 160, 260, and 360, it may be manufactured by depositing a material that can be used as the cathodes 170, 270, and 370 thereon.

In addition, the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading. It can be manufactured with fewer layers by a method such as a process, a screen printing process, or a thermal transfer method. 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 electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.

WOLED (White Organic Light Emitting Device) is easy to realize high resolution and excellent processability, while there is an advantage that can be manufactured using the existing LCD color filter technology. Various structures for white organic electric devices mainly used as backlight devices have been proposed and patented. Typically, R(Red), G(Green), B(Blue) light emitting parts are arranged side-by-side in a mutually planar way, and R, G, B light emitting layers are stacked up and down. In addition, there is a color conversion material (CCM) method that uses electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom. May be applied to such WOLED.

Hereinafter, a compound according to an aspect of the present invention will be described. A compound according to an aspect of the present invention is represented by the following formula (1).

A compound represented by the following formula (1):

Formula (1)

In the above formula (1),

a is an integer of 1 or 2, and b may be an integer of 0 to 3.

When a is 1, Y is each independently deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; It may be selected from the group consisting of C ₆ ~ C ₃₀ aryloxy group, -L'-N(R ^a )(R ^b ) and -L ^a -Ar ^a .

For example, when a is 1, Y is a C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, Y is a C ₆ ~ C ₆₀ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, Y is a C ₆ ~ C ₂₄ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₂₆ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

When a is 2, b is an integer of 1, and Y is, each independently, a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₁ ~ C ₅₀ alkylene group; C ₃ ~ C ₆₀ aliphatic ring group; And it may be selected from the group consisting of a fused ring of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

For example, Y is a single bond; C ₆ ~ C ₆₀ arylene group; It may be selected from the group consisting of a fluorenylene group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, Y is a C ₆ ~ C ₂₄ arylene group; It may be selected from the group consisting of a fluorenylene group and a C ₂ ~ C ₂₆ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

When a is 1 and b is 2 or 3, adjacent Ys may be bonded to each other to form a ring.

X ¹ and X ² may each independently be selected from the group consisting of CR'R", NR ^c , O and S.

R′ and R” are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ to C ₅₀ alkyl group; C ₁ to C ₃₀ alkoxy group; C ₆ to C ₆₀ aryl group; flu Orenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group and C ₆ ~ C ₃₀ It may be selected from the group consisting of aryloxy group.

For example, R'and R" are each independently hydrogen; C ₁ to C ₅₀ alkyl group; C ₆ to C ₆₀ aryl group; fluorenyl group and at least one hetero from O, N, S, Si and P It may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing an atom.

For example, R'and R" may each independently be selected from the group consisting of a C ₁ to C ₅₀ alkyl group; a C ₆ to C ₆₀ aryl group and a fluorenyl group.

For example, R'and R" may each independently be selected from the group consisting of a C ₁ to C ₅ alkyl group, benzene, naphthalene, and biphenyl.

R′ and R” may be bonded to each other to form a ring. When R′ and R” are bonded to each other to form a ring, the compound represented by Formula (1) may contain a spiro structure. have.

R ^c is, each independently, deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₃₀ aryloxy group; -L'-N(R ^a ) (R ^b ); And -L ^a -Ar ^a may be selected from the group consisting of.

For example, R ^c is each independently a C ₁ to C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, R ^c is each independently a C ₆ ~ C ₆₀ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, R ^c is each independently a C ₆ ~ C ₂₄ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₂₆ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

m and n are integers of 0 or 1, when m or n is 0, it means that no bridging bond exists, and o is an integer of 0 to 5.

When n is 0, it may mean that X ¹ does not exist, and when m is 0, it may mean that X ² does not exist.

Z is, each independently, deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₃₀ aryloxy group; -L'-N(R ^a ) (R ^b ); And -L ^a -Ar ^a may be selected from the group consisting of.

For example, Z is each independently a C ₁ to C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, Z is, each independently, a C ₆ ~ C ₂₄ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₂₆ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

It may be possible to form a ring between adjacent Z.

When a is 1, at least one of R ^c , Y and Z may be -L ^a -Ar ^a .

L ^a is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; And O, N, S, Si and P may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom.

Ar ^a may be a C ₂ ~ C ₆₀ heterocyclic group containing at least one N.

For example, Ar ^a may be a C ₂ ~ C ₆₀ heterocyclic group containing two or more N.

For example, Ar ^a can be pyrimidine, pyrazine, triazine, quinazoline, quinoxaline, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine or phenanthroline. .

L'is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; And O, N, S, Si and P may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom.

R ^a and R ^b are deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ It may be selected from the group consisting of aryloxy group.

In the above Y, R ^a , R ^b , Ar ^a , R', R", R ^c , Z and L ^a , L', the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group , Alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkylene group, arylene group and fluorenylene group, respectively, deuterium; nitro group; nitrile group; halogen group; amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₆ ~ C ₂₀ aryl group; C ₆ substituted with deuterium -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ heterocyclic group; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group and C ₈ -C ₂₀ arylalkenyl group One or more substituents selected from the group may be further substituted, and the additionally substituted substituents may be bonded to each other to form a ring, and the additionally substituted substituents are each deuterium; nitro group; nitrile group; halogen group ; amino; C ₁ ~ Import alkylthio of C _20; C ₁ ~ alkoxy group of C _20; C ₁ ~ alkyl group of C _20; C ₂ ~ of the C ₂₀ alkenyl; C ₂ ~ alkynyl of C _20; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ aryl One or more substituents selected from the group consisting of an alkyl group and a C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and these substituents may be bonded to each other to form a ring.

The compound represented by formula (1) may be represented by any one of the following formulas (2) to (6).

Formula (2) Formula (3)

Formula (4) Formula (5)

Formula (6)

In the above formulas (2) to (6), X ¹ , X ² , Z, Y, bn, m and o are the same as those defined in formula (1).

In the case of Formula (2) or Formula (3), when Formula (2) or Formula (3) is used as an electron transport layer, a light emitting layer, or a capping layer, an organic electric device having excellent driving voltage, luminous efficiency and lifetime characteristics can be manufactured. I can.

In the case of Formula (4), Formula (5), or Formula (6), when Formulas (4) to (5) are used as an electron transport layer or a capping layer, an organic electric device having excellent driving voltage, luminous efficiency and lifetime characteristics Can be manufactured.

When n and m in Formula (1) are simultaneously 0, when Formula (1) is used as a capping layer, an organic electric device having excellent luminous efficiency and lifetime characteristics can be manufactured.

In particular, when n and m in Formula (1) are equal to 0 at the same time, when Formula (1) is used as a capping layer of a top-emitting organic electrical device, an organic electronic device having excellent luminous efficiency and lifetime characteristics can be manufactured.

The compound represented by Formula (1) may be represented by any one of Formulas (7) to (50) below.

Formula (7) Formula (8) Formula (9) Formula (10)

Formula (11) Formula (12) Formula (13) Formula (14)

Formula (15) Formula (16) Formula (17) Formula (18)

Formula (19) Formula (20) Formula (21) Formula (22)

Formula (23) Formula (24)

Formula (25) Formula (26)

Formula (27) Formula (28)

Formula (29) Formula (30)

Formula (31) Formula (32)

Formula (33) Formula (34)

Formula (35) Formula (36)

Formula (37) Formula (38)

Formula (39) Formula (40)

Formula (41) Formula (42)

Formula (43) Formula (44)

Formula (45) Formula (46)

Formula (47) Formula (48)

Formula (49) Formula (50)

In the above formulas (7) to (50), X ¹ , X ² , Z, Y, R ^c , R', R", b and o are the same as defined in formula (1).

In the case of the formulas (7) to (14), when used as an electron transport layer, a light emitting layer, or a capping layer, an organic electric device having excellent driving voltage, light emission efficiency, and lifespan characteristics can be manufactured.

In the case of Formulas (15) to (50), when used as an electron transport layer or a capping layer, an organic electric device having excellent driving voltage, luminous efficiency, and lifetime characteristics can be manufactured.

The compound represented by Formula (1) may be one of the following chemicals, but the compound represented by Formula (1) is not limited thereto.

As another embodiment, the present invention provides an organic electric device including the compound represented by the formula (1).

The organic electric device may include a first electrode, a second electrode, an organic material layer positioned between the first electrode and the second electrode, and may include a compound represented by Formula (1) in the organic material layer.

In another aspect, the organic electric device includes a first electrode, a second electrode, an organic material layer positioned between the first electrode and the second electrode, and one surface of the first electrode opposite to the organic material layer, and the second electrode. A capping layer may be disposed on one or more of one or more of one surface of the organic material layer opposite to the organic material layer, and at least one of the organic material layer and the capping layer may include a compound represented by Formula (1).

The organic material layer and the capping layer may have a single layer or multilayer structure.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and a hole injection layer, a hole transport layer, and a light emission auxiliary included in the organic material layer At least one of a layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, or an electron injection layer may include a compound represented by Formula (1).

Specifically, at least one of the electron transport auxiliary layer, the electron transport layer and the electron injection layer included in the organic material layer may include a compound represented by Formula (1).

In another embodiment, the compound represented by Formula (1) may be included in at least one emission layer included in the organic material layer.

In other words, an organic electric device including one of the compounds represented by the formula (1) is provided in the organic material layer, and more specifically, a compound represented by the individual formulas (P-1 to P-140) in the organic material layer It provides an organic electric device comprising a.

In another embodiment, the compound alone is included in at least one of the hole injection layer, the hole transport layer, the emission auxiliary layer, the emission layer, the electron transport layer, and the electron injection layer of the organic material layer, or the It provides an organic electric device, characterized in that the compound is included in a combination of two or more different compounds, or the compound is included in a combination of two or more different compounds.

In another embodiment, the compound is included alone, the compound is included in a combination of two or more different from each other, or a layer in which the compound is included in a combination of two or more different compounds may be a light emitting layer.

In other words, each of the layers may contain a compound corresponding to formula (1) alone, or a mixture of two or more compounds of formula (1), and a compound of formula (1), corresponding to the present invention. Mixtures with compounds that do not. Herein, the compound not applicable to the present invention may be a single compound or two or more compounds. In this case, when the compound is included in a combination of two or more of the other compounds, the other compound may be a known compound of each organic material layer or a compound to be developed in the future. In this case, the compound included in the organic material layer may be composed of only the same type of compound, but may be a mixture of two or more different types of compounds represented by Formula (1).

For example, in the organic material layer, two types of compounds having different structures among the compounds may be mixed in a molar ratio of 99:1 to 1:99.

In another embodiment of the present invention, the present invention provides a capping layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device further comprising. The capping layer may include the compound represented by Formula (1) according to the present invention.

Organic electricity, characterized in that the compound of the present invention is included in the capping layer alone, the compound of the present invention is included in a combination of two or more different compounds, or the compound of the present invention is included in a combination of two or more different compounds Device.

The emission layer may further include one or more compounds represented by any one of the following formulas (51) to (53).

Formula (51) Formula (52) Formula (53)

In the above formulas (51) to (53),

X ³ may be NAr ⁹ , CR ⁵ R ⁶ , O or S.

Ar ¹ to Ar ⁹ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; C ₁ ~ C ₂₀ alkyl group; C ₁ ~ C ₂₀ alkoxy group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₂₀ heterocyclic group containing at least one hetero atom of P; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And C ₈ ~ C ₂₀ It may be selected from the group consisting of arylalkenyl group.

For example, Ar ¹ to Ar ⁹ are each independently a C ₆ to C ₆₀ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₂₀ heterocyclic group including at least one hetero atom of O, N, S, Si and P.

For example, Ar ¹ to Ar ⁹ are each independently a C ₆ to C ₂₄ aryl group; It may be selected from the group consisting of a fluorenyl group and a C ₂ ~ C ₂₆ heterocyclic group including at least one hetero atom of O, N, S, Si and P.

L ¹ is a C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group,

For example, L ¹ is a C ₆ ~ C ₆₀ arylene group; It may be selected from the group consisting of a fluorenylene group and a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

For example, L ¹ is a C ₆ ~ C ₂₄ arylene group; It may be selected from the group consisting of a fluorenylene group and a C ₂ ~ C ₂₆ heterocyclic group including at least one heteroatom of O, N, S, Si and P.

L ² is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

For example, L ² is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and P may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom.

For example, L ² is a single bond; C ₆ ~ C ₂₄ arylene group; Fluorenylene group; O, N, S, Si, and P may be selected from the group consisting of C ₂ ~ C ₂₆ heterocyclic group containing at least one heteroatom.

For example, L ² may be a single bond.

R ¹ to R ⁴ are each independently deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, adjacent R ¹ to R ⁴ may be bonded to each other to form a ring.

R ⁵ and R ⁶ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, R ⁵ and R ₆ may be bonded to each other to form a ring.

t and w are integers from 0 to 4, and u and v may be integers from 0 to 3.

In the above Ar ¹ to Ar ⁹ , L ¹ , L ² and R ¹ to R ⁶ , the aryl group, fluorenyl group, heterocyclic group, alicyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, cycloalkyl group , Arylalkyl group, arylalkenyl group, arylene group, and fluorenylene group are each deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and the additionally substituted substituents may be bonded to each other to form a ring. And each of the additionally substituted substituents is deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and these substituents may be bonded to each other to form a ring.

Formula (51) may be a compound represented by the following formula (54).

Chemical Formula (54)

In the above formula (54),

X ⁴ may be O, S, NAr ¹⁰ or CR ⁵ R ⁶ .

Ar ² and Ar ³ may be the same as defined in Formula (51).

R ⁵ and R ⁶ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, R ⁵ and R ⁶ may be bonded to each other to form a ring.

Ar ¹⁰ may be the same as the definition of Ar ⁹ in Formulas (51) to (53).

R ⁷ and R ⁸ may be the same as the definition of R ¹ in Formulas (51) to (53).

k is an integer of 0 to 4, and l may be an integer of 0 to 3.

The compound represented by Formula (51) may be one of the following compounds, but the compound represented by Formula (51) is not limited thereto.

The compound represented by Formula (52) may be one of the following compounds, but the compound represented by Formula (52) is not limited thereto.

The compound represented by Formula (53) may be one of the following compounds, but the compound represented by Formula (53) is not limited thereto.

In another aspect, the present invention provides an organic electric device, characterized in that the compounds represented by formula (1) and formula (51) are mixed in a ratio of 1:9 to 9:1 and used in the light emitting layer. .

In another aspect of the present application, the present invention is an organic electric device, characterized in that the compounds represented by formula (1) and formula (52) are mixed in a ratio of 1:9 to 9:1 and used in the light emitting layer. Provides.

In another aspect of the present application, the present invention is an organic electroluminescent device, characterized in that the compounds represented by the formula (1) and formula (53) are mixed in any one ratio of 1:9 to 9:1 and used in the light emitting layer Provides.

Hereinafter, examples for synthesizing the compound represented by Formula (1) according to the present invention and an example for preparing an organic electric device according to the present invention will be described in detail, but the present invention is not limited to the following examples.

[Synthesis Example 1]

The compound represented by Formula (1) according to the present invention (final product 1, final product 2) is synthesized as shown in Scheme 1 or Scheme 2 below, but is not limited thereto.

However, X ¹ , X ² , Y, Z, a, b, n, m, o are the same as defined in Formula (1), and Hal ¹ , Hal ² = Cl, Br, and Hal ³ to Hal ⁵ are Cl, Br, I, and e+f=o, g+h=b.

When f+h is 1 or more, it is synthesized by the synthesis route of Scheme 1, and when X ¹ and X ² are N and f+h is 0, it is synthesized by the synthesis route of Scheme 2.

<Reaction Scheme 1>

<Reaction Scheme 2>

I. Synthesis of Sub1 and Sub2

Sub1 in Scheme 1 is synthesized by the reaction route of Scheme 3 below, but is not limited thereto.

However, X ¹ , X ² , Y, Z, R', R", a, b, n, m, o are the same as defined in Formula (1), and Hal ¹ , Hal ² = Cl, Br, e+f=o, g+h=b,

When X ¹ and X ² are N and f+h is 0, Sub1-h is Sub2.

<Reaction Scheme 3>

1. Sub1-2, Sub1-16 synthesis example

(1) Sub1-1-a synthesis example

1,10-phenanthrolin-4-ol (700 g, 3.57 mol) was added to an excess of trifluoromethane-sulfonic acid, stirred at room temperature for 24 hours, and then water and pyridine (8:1) were slowly added. Reflux for 30 minutes. The temperature was lowered and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting product was obtained by Silicagel column and recrystallization to obtain 843 g (yield: 72%) of the product.

(2) Sub1-1-b synthesis example

After dissolving Sub1-1-a (843 g, 2.57 mol) obtained in the above synthesis in DMF (Dimethylformamide) (9 L), bis (pinacolato) diboron (718 g, 2.83 mol), KOAc (756 g, 7.71 mol) , PdCl ₂ (dppf) (56.4 g, 77.1 mmol) was added and stirred at 120 ^o C. When the reaction is complete, DMF is removed through distillation and extracted with CH ₂ Cl ₂ and water. When extraction is complete, the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 574 g (yield: 73%) of the product.

(3) Sub1-2-c synthesis example

After dissolving Sub1-1-b (50.0 g, 163 mmol) obtained in the above synthesis in THF (Tetrahydrofuran) (820 mL), (2-bromo-5-chlorophenyl) (methyl)sulfane (38.8 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd(PPh ₃ ) ₄ (11.3 g, 9.80 mmol), and water (410 mL) were added and stirred at 80 ^o C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 46.8 g (yield: 85%) of the product.

(4) Example of Sub1-2-d synthesis

Add acetic acid (555 mL) to Sub1-2-c (46.8 g, 139 mmol) obtained in the above synthesis, add 35% Hydrogen peroxide (H ₂ O ₂ ) (39.7 mL), and stir at room temperature. When the reaction was completed, it was neutralized with an aqueous NaOH solution, followed by extraction with ethylacetate (EA) and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a Silicagel column to obtain 44.6 g (yield: 91%) of the product.

(5) Example of Sub1-2, Sub1-16 synthesis

Sub1-2-d (44.6 g, 126 mmol) obtained in the above synthesis was added to an excess of trifluoromethane-sulfonic acid, stirred at room temperature for 24 hours, and then water and pyridine (8:1) were slowly added. Reflux for 30 minutes. The temperature was lowered and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting product was obtained by using a Silicagel column and recrystallization to obtain 17.4 g (yield: 43%) of the product Sub1-2 and 11.8 g (yield: 29%) of the product Sub1-16.

2. Sub1-3, Sub1-17 Synthesis Example

(1) Sub1-3-c synthesis example

Sub1-1-b (50.0 g, 163 mmol), (2-bromo-4-chlorophenyl)(methyl)sulfane (38.8 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd(PPh) obtained in the above synthesis ₃ ) ₄ (11.3 g, 9.80 mmol) was obtained as a product 45.1 g (yield: 82%) using the synthesis method of Sub1-2-c.

(2) Sub1-3-d synthesis example

Sub1-3-c (45.1 g, 134 mmol), acetic acid (536 mL), 35% Hydrogen peroxide (H ₂ O ₂ ) (38.3 mL) obtained in the above synthesis was used in the synthesis method of Sub1-2-d. Thus, the product 43.9 g (yield: 93%) was obtained.

(3) Example of Sub1-3, Sub1-17 synthesis

Sub1-2-d (43.9 g, 125 mmol) obtained in the above synthesis was 17.6 g of the product Sub1-3 (yield: 44%) and 12.0 g of the product Sub1-17 using the synthesis method of Sub1-2 (yield : 30%).

3. Sub1-6 synthesis example

(1) Sub1-6-a synthesis example

2-phenyl-1,10-phenanthrolin-4-ol (50.0 g, 272 mmol) was obtained by using the synthesis method of Sub1-1-a, 54.2 g (yield: 73%) of the product.

(2) Example of Sub1-6-b synthesis

Sub1-6-a (54.2 g, 134 mmol), bis(pinacolato) diboron (37.4 g, 147 mmol), KOAc (39.5 g, 402 mmol), PdCl ₂ (dppf) (2.94 g, 4.02 mmol) obtained in the above synthesis ) Was obtained by using the synthesis method of Sub1-1-b.

(3) Sub1-6-c synthesis example

Sub1-6-b (36.4 g, 95.2 mmol), (2-bromo-5-chlorophenyl) (methyl)sulfane (22.6 g, 95.2 mmol), NaOH (11.4 g, 286 mmol), Pd(PPh) obtained in the above synthesis ₃ ) ₄ (6.60 g, 5.71 mmol) was obtained as a product 33.0 g (yield: 84%) using the synthesis method of Sub1-2-c.

(4) Example of Sub1-6-d synthesis

Sub1-6-c (33.0 g, 80.0 mmol), acetic acid (320 mL), 35% Hydrogen peroxide (H ₂ O ₂ ) (22.9 mL) obtained in the synthesis was used as the synthesis method of Sub1-2-d. Using the product 30.9 g (yield: 90%) was obtained.

(5) Example of Sub1-6 synthesis

Sub1-6-d (30.9 g, 72.0 mmol) obtained in the above synthesis was obtained as a product 13.1 g (yield: 46%) using the synthesis method of Sub1-2.

4. Sub1-32, Sub1-44 synthesis example

(1) Synthesis example of Sub1-32-e

Sub1-1-b (50.0 g, 163 mmol), 2-bromo-4-chlorophenol (33.9 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd(PPh ₃ ) ₄ (11.3 g) obtained in the above synthesis , 9.80 mmol) was obtained as a product 41.6 g (yield: 83%) using the synthesis method of Sub1-2-c.

(2) Example of Sub1-32, Sub1-44 synthesis

Sub1-32-e (41.6 g, 136 mmol) obtained in the above synthesis Pd(OAc) ₂ (1.52 g, 6.78 mmol), 3-nitropyridine (0.84 g, 6.78 mmol), BzOO t -Bu (tert-butyl peroxybenzoate) ) (52.7 g, 271 mmol), C ₆ F ₆ (hexafluorobenzene) (200 mL), and DMI (N,N'-dimethylimidazolidinone) (140 mL) were added and refluxed at 90 ^o C for 3 hours. When the reaction was completed, the temperature of the reaction product was cooled to room temperature, and extracted with EA and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a Silicagel column to obtain 16.6 g (yield: 40%) of the product Sub1-32 and 11.1 g (yield: 27%) of the product Sub1-44.

5. Sub1-55 Synthesis Example

(1) Sub1-55-e synthesis example

Sub1-1-b (50.0 g, 163 mmol), 1-bromo-4-chloronaphthalen-2-ol (42.1 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd (PPh ₃ ) obtained in the above synthesis ₄ (11.3 g, 9.80 mmol) was obtained as a product 49.5 g (yield: 85%) using the synthesis method of Sub1-2-c.

(2) Sub1-55 synthesis example

Sub1-55-e (49.5 g, 139 mmol) obtained in the above synthesis Pd(OAc) ₂ (1.56 g, 6.94 mmol), 3-nitropyridine (0.86 g, 6.94 mmol), BzOO t -Bu (tert-butyl peroxybenzoate) ) (53.9 g, 278 mmol), C ₆ F ₆ (hexafluorobenzene) (210 mL), and DMI (N,N'-dimethylimidazolidinone) (140 mL) using the synthesis method of Sub1-32, the product 10.5 g (yield 25%).

6. Sub1-75, Sub1-91 Synthesis Example

(1) Sub1-75-f synthesis example

Sub1-1-b (50.0 g, 163 mmol), 2-(2-bromo-4-chlorophenyl)propan-2-ol (57.0 g, 163 mmol), NaOH (19.6 g, 490 mmol) obtained in the above synthesis, Pd(PPh ₃ ) ₄ (11.3 g, 9.80 mmol) was obtained by using the synthesis method of Sub1-2-c as the product 33.8 g (yield: 83%).

(2) Example of Sub1-75, Sub1-91 synthesis

Sub1-75-f (33.8 g, 136 mmol) obtained in the above synthesis was added to a round bottom flask, acetic acid (339 mL) and sulfuric acid (54 mL) were additionally added, followed by stirring at 120° C. for 12 hours. Upon completion of the reaction, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized in a silicagel column and 14.8 g of the product Sub1-75 (yield: 33%) and the product Sub1-91. 9.9 g (yield: 22%) was obtained.

7. Sub1-102 synthesis example

(1) Synthesis example of Sub1-102-f

Sub1-1-b (50.0 g, 163 mmol), (2-bromo-5-chlorophenyl) diphenylmethanol (61.0 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd(PPh ₃ ) ₄ obtained in the above synthesis (11.3 g, 9.80 mmol) was obtained as a product 60.2 g (yield: 78%) using the synthesis method of Sub1-2-c.

(2) Synthesis example of Sub1-102

Sub1-102-f (60.2 g, 127 mmol), acetic acid (320 mL), sulfuric acid (50 mL) obtained in the synthesis was 11.8 g (yield: 20%) of the product using the synthesis method of Sub1-75 Got it.

8. Sub2-1, Sub2-5 synthesis example

(1) Synthesis example of Sub2-1-g

Sub1-1-b (50.0 g, 163 mmol), 1-bromo-2-nitrobenzene (33.0 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd(PPh ₃ ) ₄ (11.3 g) obtained in the above synthesis , 9.80 mmol) was obtained as a product 41.3 g (yield: 84%) using the synthesis method of Sub1-2-c.

(2) Sub2-1, Sub2-5 synthesis example

Sub2-1-g (41.3 g, 137 mmol) obtained in the above synthesis was added to a round bottom flask, and PPh ₃ (90.0 g, 343 mmol) and o- Dichlorobenzene (690 mL) were additionally added. After that, reflux at 180 ^o C for 24 hours. When the reaction is complete, the product was extracted with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ , concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 18.4 g (yield 50%) of the product Sub2-1 and 12.3 of the product Sub2-5. g (yield 33%) was obtained.

9. Sub2-6 synthesis example

(1) Synthesis example of Sub2-6-g

Sub1-1-b (50.0 g, 163 mmol), 2-bromo-1-nitronaphthalene (41.2 g, 163 mmol), NaOH (19.6 g, 490 mmol), Pd(PPh ₃ ) ₄ (11.3 g) obtained in the above synthesis , 9.80 mmol) was obtained as a product 48.2 g (yield: 84%) using the synthesis method of Sub1-2-c.

(2) Example of Sub2-6 synthesis

Sub2-6-g (48.2 g, 137 mmol), PPh ₃ (90.0 g, 343 mmol), o- Dichlorobenzene (690 mL) obtained in the above synthesis was added to the product 13.5 g (yield 31%).

The compound belonging to Sub1 or Sub2 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub1 or Sub2.

II. Synthesis of Sub3 and Sub4

The compound belonging to Sub3 or Sub4 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub3 or Sub4.

III. Final Product Synthesis

1. Synthesis Example of P-6

(1) Inter-6 synthesis example

After dissolving Sub1-6 (13.1 g, 33.0 mmol) obtained in the above synthesis in DMF (165 mL), bis(pinacolato)diboron (9.2 g, 36.3 mmol), KOAc (9.7 g, 99.0 mmol), PdCl ₂ (dppf ) (0.72 g, 0.99 mmol) was added and stirred at 120 ^o C. When the reaction was completed, DMF was removed through distillation, and extraction was performed with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized with a Silicagel column to obtain 11.8 g (yield: 73%) of the product.

(2) Synthesis example of P-6

After dissolving Inter-6 (11.8 g, 24.2 mmol) obtained in the above synthesis in THF (120 mL), Sub3-46 (7.0 g, 24.2 mmol), NaOH (2.9 g, 72.5 mmol), Pd(PPh ₃ ) ₄ (1.68 g, 1.45 mmol) and water (60 mL) were added and stirred at 80 ^o C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a Silicagel column to obtain 12.5 g (yield: 84%) of the product.

2. Synthesis Example of P-16

(1) Inter-16 synthesis example

Sub1-16 (11.8 g, 36.8 mmol), bis(pinacolato) diboron (10.3 g, 40.5 mmol), KOAc (10.8 g, 110 mmol), PdCl ₂ (dppf) (0.81 g, 1.10 mmol) obtained in the above synthesis The product 11.5 g (yield: 76%) was obtained using the synthesis method of Inter-6.

(2) Synthesis example of P-6

Inter-16 (11.5 g, 28.0 mmol), Sub3-12 (7.5 g, 28.0 mmol), NaOH (3.4 g, 83.9 mmol), Pd(PPh ₃ ) ₄ (1.94 g, 1.68 mmol) obtained in the above synthesis above Using the synthesis method of P-6, the product 11.7 g (yield: 81%) was obtained.

3. Synthesis Example of P-45

(1) Synthesis example of Inter-45

Sub1-32 (16.6 g, 54.5 mmol), bis(pinacolato) diboron (15.2 g, 59.9 mmol), KOAc (16.0 g, 163 mmol), PdCl ₂ (dppf) (1.20 g, 1.63 mmol) obtained in the above synthesis was prepared. The product 16.0 g (yield: 74%) was obtained using the synthesis method of Inter-6.

(2) Synthesis example of P-45

Inter-45 (16.0 g, 40.3 mmol), Sub3-19 (14.4 g, 40.3 mmol), NaOH (4.8 g, 121 mmol), Pd(PPh ₃ ) ₄ (2.79 g, 2.42 mmol) obtained in the above synthesis were described above. Using the synthesis method of P-6, the product 20.3 g (yield: 85%) was obtained.

4. Synthesis Example of P-63

(1) Synthesis example of Inter-63

Sub1-55 (10.5 g, 29.6 mmol), bis(pinacolato) diboron (8.3 g, 32.6 mmol), KOAc (8.7 g, 88.8 mmol), PdCl ₂ (dppf) (0.65 g, 0.89 mmol) obtained in the above synthesis The product 10.0 g (yield: 76%) was obtained using the synthesis method of Inter-6.

(2) Synthesis example of P-63

Inter-63 (10.0 g, 22.5 mmol), Sub3-52 (4.8 g, 22.5 mmol), NaOH (2.7 g, 67.5 mmol), Pd(PPh ₃ ) ₄ (1.56 g, 1.35 mmol) obtained in the synthesis above Using the synthesis method of P-6, the product 9.1 g (yield: 81%) was obtained.

5. Synthesis Example of P-70

(1) Inter-70-1 synthesis example

Sub1-17 (12.0 g, 37.4 mmol), bis(pinacolato) diboron (10.4 g, 41.1 mmol), KOAc (11.0 g, 112 mmol), PdCl ₂ (dppf) (0.82 g, 1.12 mmol) obtained in the above synthesis The product 11.4 g (yield: 74%) was obtained using the synthesis method of Inter-6.

(2) Synthesis example of Inter-70-2

Sub1-44 (11.1 g, 36.4 mmol), bis(pinacolato) diboron (10.2 g, 40.1 mmol), KOAc (10.7 g, 109 mmol), PdCl ₂ (dppf) (0.80 g, 1.09 mmol) obtained in the above synthesis Using the synthesis method of Inter-6, the product 18.5 g (yield: 78%) was obtained.

(3) Synthesis example of Inter-70-3

Inter-70-1 (11.4 g, 27.7 mmol), Sub4-2 (8.6 g, 30.4 mmol), NaOH (3.3 g, 83.0 mmol), Pd(PPh ₃ ) ₄ (1.92 g, 1.66 mmol) obtained in the above synthesis The product 10.8 g (yield: 88%) was obtained using the synthesis method of P-6.

(4) Synthesis example of P-70

Inter-70-3 (10.8 g, 24.4 mmol), Inter70-2 (9.7 g, 24.4 mmol), NaOH (2.9 g, 73.1 mmol), Pd(PPh ₃ ) ₄ (1.69 g, 1.46 mmol) obtained in the above synthesis The product 12.6 g (yield: 82%) was obtained using the synthesis method of P-6.

6. Synthesis Example of P-76

(1) Synthesis example of P-76

Sub2-1 (18.4 g, 68.3 mmol), Toluene (340 mL), Sub3-12 (18.3 g, 68.3 mmol), Pd ₂ (dba) ₃ (1.88 g, 2.05 mmol) obtained in the above synthesis, P(t- Bu) ₃ (0.83 g, 4.10 mmol), NaOt-Bu (13.1 g, 137 mmol) was added and stirred at 100 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 25.3 g (yield: 74%) of the product.

7. Synthesis Example of P-100

(1) Synthesis example of P-76

Sub2-6 (13.5 g, 42.3 mmol), Sub3-12 (11.3 g, 42.3 mmol), Pd ₂ (dba) ₃ (1.16 g, 1.27 mmol), P(t-Bu) ₃ (0.51 g) obtained in the above synthesis , 2.54 mmol), NaOt-Bu (8.1 g, 84.5 mmol) was obtained by using the synthesis method of P-76 as the product 16.5 g (yield: 71%).

8. Synthesis Example of P-107

(1) Synthesis example of Inter-107

Sub1-75 (14.8 g, 44.7 mmol), bis(pinacolato) diboron (12.5 g, 49.2 mmol), KOAc (13.2 g, 134 mmol), PdCl ₂ (dppf) (0.98 g, 1.34 mmol) obtained in the above synthesis Using the synthesis method of Inter-6, the product 14.9 g (yield: 79%) was obtained.

(2) Synthesis example of P-107

Inter-107 (14.9 g, 35.3 mmol), Sub3-20 (13.2 g, 35.3 mmol), NaOH (4.2 g, 106 mmol), Pd(PPh ₃ ) ₄ (2.45 g, 2.12 mmol) obtained in the synthesis above Using the synthesis method of P-6, the product 18.6 g (yield: 83%) was obtained.

9. Synthesis Example of P-139

(2) Synthesis example of Inter-139-1

Sub1-102 (11.8 g, 25.9 mmol), bis(pinacolato) diboron (7.2 g, 28.5 mmol), KOAc (7.6 g, 77.8 mmol), PdCl ₂ (dppf) (0.57 g, 0.78 mmol) obtained in the above synthesis Using the synthesis method of Inter-6, the product 21.8 g (yield: 65%) was obtained.

(3) Synthesis example of Inter-139-2

Inter-70-1 (10.0 g, 24.3 mmol), Sub4-8 (7.6 g, 26.7 mmol), NaOH (2.9 g, 72.8 mmol), Pd(PPh ₃ ) ₄ (1.68 g, 1.46 mmol) obtained in the above synthesis Using the synthesis method of P-6, the product 9.1 g (yield: 85%) was obtained.

(4) Synthesis example of P-139

Inter-139-1 (11.3 g, 20.6 mmol), Inter139-2 (9.1 g, 20.6 mmol), NaOH (2.5 g, 61.8 mmol), Pd(PPh ₃ ) ₄ (1.43 g, 1.24 mmol) obtained in the above synthesis Using the synthesis method of P-6, the product 12.1 g (yield: 75%) was obtained.

Meanwhile, the FD-MS values of the compounds P-1 to P-140 of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.

[Synthesis Example 2]

The compound represented by Chemical Formula 51 according to the present invention (final product 3) is the applicant's Korean Patent No. 10-1786749 (registered on October 11, 2017), Korean Patent Application 2014-0152779 (filed on November 5, 2014), and Korea It was prepared by the synthesis method disclosed in the application patent 2014-0161275 (filed on November 19, 2014). Ar ¹ to Ar ³ are the same as defined in Formula 51.

<Reaction Scheme 4>

[Synthesis Example 3]

The compound represented by Chemical Formula 52 according to the present invention (final product 4) is disclosed in Korean Patent Registration No. 10-1786749 (registered on October 11, 2017) and Korean Patent Application 2014-0152779 (filed on November 5, 2014). It was prepared by a synthetic method. Ar ⁴ to Ar ⁷ and L ¹ are the same as defined in Formula 52

<Reaction Scheme 5>

[Synthesis Example 4]

The compound represented by Chemical Formula 53 (final product 5) according to the present invention was prepared by the synthesis method disclosed in Korean Patent Registration No. 10-1857632 (registration dated May 8, 2018). Ar ⁸ , R ¹ to R ⁴ , t to w, X ³ , L ² are the same as defined in Formula 53

<Reaction Scheme 6>

Manufacturing evaluation of organic electric devices

[Experimental Example 1] Green organic electric device (electron transport layer)

An organic electric device was manufactured according to a conventional method using the compound of the present invention as an electron transport layer material. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer first A -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. Then, CBP[4,4'-N,N'-dicarbazole-biphenyl] as a host and Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant were doped with 95:5 weight on the top of the hole transport layer. By doing so, a light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and the holes An electron transport layer was formed by vacuum depositing the compound of the invention represented by Formula (1) on the blocking layer to a thickness of 40 nm. Thereafter, as an electron injection layer, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to be used as a cathode, thereby manufacturing an organic electric device.

[Comparative Example 1] to [Comparative Example 3]

An organic electric device was manufactured in the same manner as in Experimental Example 1, except that Comparative Compounds A to C were used instead of the compounds of the present invention as the electron transport layer material.

<Comparative Compound A> <Comparative Compound B> <Comparative Compound C>

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch by applying a forward bias DC voltage to the organic electric devices of Examples and Comparative Examples thus prepared, and the result of the measurement was at 5000 cd/m ² standard luminance. The T95 life was measured through a life measurement equipment manufactured by McScience. Table 4 below shows the results of device fabrication and evaluation.

As can be seen from the results of Table 4, when a green organic electric device was manufactured using the material for an organic electric device of the present invention as an electron transport material, the organic electric device was compared with the comparative example using Comparative Compound A to Comparative Compound C. The driving voltage can be remarkably improved.

In other words, the results of Comparative Example 2 or 3 using Comparative Compound B or Comparative Compound C were relatively superior to Comparative Example 1 using Comparative Compound A, and the core was similar to Comparative Compound B or Comparative Compound C, but quinazoline, Examples 1 to 34 of the compounds of the present invention substituted with heterocycles such as quinoxaline, phenanthroline, and triazine showed remarkably excellent results in driving voltage.

In addition, compared to Comparative Compound C formed with a pentagonal ring, Comparative Compound B formed with a hexagonal ring showed improved driving voltage and lifespan, which was judged to have improved performance due to the difference in physical properties of the compound (especially, LUMO difference). , It can be seen that even in the compound of the present invention, the result of the driving voltage of the hexagonal ring compound is remarkable compared to the pentagonal ring compound.

In particular, compared to Comparative Compound B or Comparative Compound C, the compound of the present invention has a structure in which at least one heterocycle including N is bonded, and the physical properties (especially, LUMO) of the compound change as the heterocycle is bonded.

Table 5 below shows the physical property values of Compound P-2 and Comparative Compound C of the present invention.

Referring to Table 5, compared to Comparative Compound C, as the LUMO of Compound P-2 of the present invention decreases, electron injection from the electron injection layer to the electron transport layer in which the compound is formed becomes easier, and the movement to the host becomes easier, and thus fast driving. It is judged to show voltage.

[Experimental Example 2] Red organic electric device (Mixed host)

The compound of the present invention was used as a green host material to fabricate an organic electric device according to a conventional method. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer first A -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. Next, as a host on the hole transport layer, a mixture of the present invention compound represented by Formula (1) and the inventive compound represented by Formulas (51) to (53) in 3:7 was used, and as a dopant (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate] was doped with a weight of 95:5 to deposit a light emitting layer having a thickness of 30 nm on the light emitting auxiliary layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and an electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm. Then, LiF, an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, followed by Al 150 An organic electric device was manufactured by depositing to a thickness of nm and using it as a cathode.

[Comparative Example 4] and [Comparative Example 5]

An organic electric device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound B or Comparative Compound C was used alone as a host.

[Comparative Example 6] and [Comparative Example 7]

An organic electric device was manufactured in the same manner as in Experimental Example 2, except that Inventive Compound 1-23 and Comparative Compound B or Comparative Compound C were used as a mixture as a host.

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company by applying a forward bias DC voltage to the organic electric devices of the Examples and Comparative Examples thus prepared, and the measurement result was at a reference luminance of 2500 cd/m ² . The T95 life was measured through a life measurement equipment manufactured by McScience. Table 6 below shows the results of device fabrication and evaluation.

[Experimental Example 3] Green Organic Device (Mixed Host)

An organic electric device was manufactured according to a conventional method by using the compound of the present invention as a green host material. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer first A -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. Next, as a host on the hole transport layer, a mixture of the inventive compound represented by Formula (1) and the inventive compound represented by Formulas (51) to (53) at 6:4 was used, and as a dopant, Ir (ppy ) ₃ [tris(2-phenylpyridine)-iridium] was doped with a weight of 95:5 to deposit a light emitting layer having a thickness of 30 nm on the light emitting auxiliary layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and an electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm. Then, LiF, an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, followed by Al 150 An organic electric device was manufactured by depositing to a thickness of nm and using it as a cathode.

[Comparative Example 8] and [Comparative Example 9]

An organic electric device was manufactured in the same manner as in Experimental Example 3, except that Comparative Compound B or Comparative Compound C was used alone as a host.

[Comparative Example 10] and [Comparative Example 11]

An organic electric device was manufactured in the same manner as in Experimental Example 3, except that Inventive Compound 1-23 and Comparative Compound B or Comparative Compound C were used as a mixture as a host.

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch by applying a forward bias DC voltage to the organic electric devices of Examples and Comparative Examples thus prepared, and the result of the measurement was at 5000 cd/m ² standard luminance. The T95 life was measured through a life measurement equipment manufactured by McScience. Table 7 below shows the results of device fabrication and evaluation.

As can be seen from the results of Tables 6 and 7 above, in the case of manufacturing a red organic electric device and a green organic electric device using the material for an organic electric device of the present invention as a host material, comparison using the comparative compound B or the comparative compound C It is possible to significantly improve the driving voltage, luminous efficiency, and lifespan of the organic electric device than before.

In other words, compared to Comparative Examples using Comparative Compound B or Comparative Compound C alone in Tables 6 and 7 (Comparative Example 4, Comparative Example 5, Comparative Example 8, Comparative Example 9), Comparative Example using Compound 1-23 by mixing (Comparative Example 6, Comparative Example 7, Comparative Example 10, Comparative Example 11) was improved in luminous efficiency and lifetime, and the invention compound represented by Formulas (51) to (53) and the present invention represented by Formula (1) Examples 35 to 109 in which the compound was mixed were remarkably improved in driving voltage, luminous efficiency and lifetime.

Comparative Examples 4 and 5 in which Comparative Compound B and Comparative Compound C were used alone as hosts, or Comparative Examples 6 and 7 or Comparative Examples 10 and 11 used as a mixture compared to Comparative Examples 8 and 9 showed improved luminous efficiency and lifetime. It can be seen that this can improve the hole characteristics that are insufficient in Comparative Compound B and Comparative Compound C with Inventive Compound 1-23 as an additional host.

Based on these characteristics, when using the compound of the present invention, which has a faster electron injection than Comparative Compound B or Comparative Compound C, it was expected to show a fast driving voltage and high luminous efficiency. Looking at the device measurement results, it was compared with Comparative Compound B and Comparative Compound C. Thus, it can be seen that the driving voltage, efficiency and life of the compound of the present invention are remarkably improved.

In addition, since it has a fast electron injection property, when a compound with good hole injection is mixed, charge balance between holes and electrons can be achieved in the light emitting layer, and Inventive Compound 2-14 with good hole injection has high efficiency. You can confirm that you have. On the other hand, it can be confirmed that Inventive Compound 3-24, which is not good for hole injection, has low efficiency. However, Invention Compound 2-14 has low electron stability, and Invention Compound 3-24 is judged to have good electron stability, and it can be seen that it affects the lifespan.

Table 8 below shows the physical property values of Compound P-76 of the present invention and Compound P-93 of the present invention.

Referring to Table 8, in the case of the red organic electric device, it is determined that the triplet electron transfer to the red dopant is not easy because the compound P-76 of the present invention formed in a pentagonal shape has a too high T1. On the other hand, the compound P-93 of the present invention formed in a hexagonal shape has T1 suitable as a red host, and compared to the pentagonal compound, the triplet electron transfer of the hexagonal compound transferred to the red dopant becomes very easy. It is judged to be more suitable as a host of.

However, in the case of a green organic electric device, T1 of the green dopant is formed higher than T1 of the red dopant.

Therefore, since the compound P-76 of the present invention, which is a pentagonal compound as a host, has a higher T1 than the compound P-93 of the present invention, which is a hexagonal compound, it facilitates the transfer of triplet electrons transferred to the green dopant. In comparison, it is judged that the pentagonal compounds are more suitable as green organic electric devices.

If such a change in the mother nucleus plays a decisive role in the difference in physical properties of the compound, this suggests that results that cannot be inferred by those skilled in the art can be derived.

[Experimental Example 4] Blue Organic Electric Device (Capping Layer)

An organic electric device was manufactured according to a conventional method using the compound of the present invention as a capping layer material. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer first A -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. Subsequently, 9,10-di(naphthalen-2-yl)anthracene was used as a host and BD-052X (Idemitsu kosan) was used as a dopant on the top of the hole transport layer, but these were doped with a weight of 93:7 to deposit a light emitting layer having a thickness of 30 nm. . Next, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato) aluminum (hereinafter, abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm on the emission layer. Thus, a hole blocking layer was formed, and tris(8-quinolinol) aluminum (hereinafter, abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm to form an electron transport layer. On the electron transport layer, LiF, which is an alkali metal halide, is deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al is deposited to a thickness of 150 nm to be used as a cathode, and the present invention represented by Formula (1) An organic electric device was manufactured by forming a capping layer of the compound to a thickness of 60 nm.

[Comparative Example 12]

An organic electric device was manufactured in the same manner as in Experimental Example 4, except that the capping layer was not used.

[Comparative Example 13]

An organic electric device was manufactured in the same manner as in Experimental Example 4, except that Comparative Compound A was used instead of the inventive compound represented by Formula (1) as the capping layer material.

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company by applying a forward bias DC voltage to the organic electric devices of Examples and Comparative Examples thus prepared, and the result of the measurement was at 500 cd/m ² standard luminance. The T95 life was measured through a life measurement equipment manufactured by McScience. Table 9 below shows the results of device fabrication and evaluation.

[Experimental Example 5] Green Organic Electric Device (Capping Layer)

The compound of the present invention was used as a capping layer material to fabricate an organic electric device according to a conventional method. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer first A -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. Then, CBP[4,4'-N,N'-dicarbazole-biphenyl] as a host and Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant were doped with 95:5 weight on the top of the hole transport layer. By doing so, a light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and tris( 8-quinolinol) aluminum (hereinafter, abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm to form an electron transport layer. On the electron transport layer, LiF, which is an alkali metal halide, is deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al is deposited to a thickness of 150 nm to be used as a cathode, and the present invention represented by Formula (1) An organic electric device was manufactured by forming a capping layer of the compound to a thickness of 60 nm.

[Comparative Example 14]

An organic electric device was manufactured in the same manner as in Experimental Example 5, except that the capping layer was not used.

[Comparative Example 15]

An organic electric device was manufactured in the same manner as in Experimental Example 5, except that Comparative Compound A was used instead of the inventive compound represented by Formula (1) as the capping layer material.

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch by applying a forward bias DC voltage to the organic electric devices of Examples and Comparative Examples thus prepared, and the result of the measurement was at 5000 cd/m ² standard luminance. The T95 life was measured through a life measurement equipment manufactured by McScience. Table 10 below shows the results of device fabrication and evaluation.

[Experimental Example 6] Red Organic Electric Device (Capping Layer )

An organic electric device was manufactured according to a conventional method using the compound of the present invention as a capping layer material. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer first A -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. Subsequently, CBP[4,4'-N,N'-dicarbazole-biphenyl] as a host and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] as a dopant on the top of the hole transport layer By doping with 95:5 weight, a light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and tris( 8-quinolinol) aluminum (hereinafter, abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm to form an electron transport layer. On the electron transport layer, LiF, which is an alkali metal halide, is deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al is deposited to a thickness of 150 nm to be used as a cathode, and the present invention represented by Formula (1) An organic electric device was manufactured by forming a capping layer of the compound to a thickness of 60 nm.

[Comparative Example 16]

An organic electric device was manufactured in the same manner as in Experimental Example 6, except that the capping layer was not used.

[Comparative Example 17]

An organic electric device was manufactured in the same manner as in Experimental Example 6, except that Comparative Compound A was used instead of the Inventive Compound represented by Formula (1) as the capping layer material.

The electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company by applying a forward bias DC voltage to the organic electric devices of the Examples and Comparative Examples thus prepared, and the measurement result was at a reference luminance of 2500 cd/m ² . The T95 life was measured through a life measurement equipment manufactured by McScience. Table 11 below shows the results of device fabrication and evaluation.

As can be seen from the results of Tables 9 to 11, high color purity and luminous efficiency can be remarkably improved when an organic electric device including the compound of the present invention is configured as a capping layer.

In addition, comparing the results of the device with and without the capping layer, it can be seen that the color purity and efficiency increase with the capping layer, and the efficiency is significantly improved when the compound of the present invention is used than when the capping layer is Comparative Compound A. Is showing that.

In the case of using the capping layer, SPPs (Surface plasmon polaritons) are generated at the interface between the Al electrode and the organic material with high refractive index, and among them, TE (transverse electric) polarized light is generated from the capping layer in a vertical direction by evanescent waves. Transverse magnetic (TM) polarized light that disappears and moves along the cathode and the light efficiency improvement layer is considered to be due to the amplification of the wavelength due to surface plasmon resonance, enabling high efficiency and effective color purity control. .

As described above, in the visible light wavelength band (range of 430 nm to 780 nm), the compound of the present invention has a high refractive index of 1.8 to 2.1, and thus, light generated in the organic layer is an organic light-emitting device according to the principle of constructive interference. As the efficiency of extraction to the outside is increased, it greatly contributes to the improvement of the light efficiency of the organic electric device.

The above description is merely illustrative of the technical idea of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications and variations without departing from the essential characteristics of the present invention. In addition, since the embodiments disclosed in the present invention are not intended to limit the technical idea of the present invention, but are intended to describe the technical idea, the scope of the technical idea of the present invention is not limited by these embodiments. The scope of protection of the present invention should be interpreted by the claims below, and all technical ideas within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric device
110, 110, 310: first electrode
120, 220, 320: hole injection layer
321: first hole injection layer
130, 230: hole transport layer
331: first hole transport layer
332: second hole transport layer
243: buffer layer
253: light emission auxiliary layer
140, 240: light emitting layer
341: first light-emitting layer
342: second light-emitting layer
150, 250: electron transport layer
351: first electron transport layer
352: second electron transport layer
160, 260, 360: electron injection layer
170, 270, 370: second electrode
180, 280, 380: capping layer
390: first charge generation layer
391: second charge generation layer
ST1: 1st stack
ST2: 2nd stack
CGL: charge generation layer

Claims (11)

A compound represented by the following formula (1):
Formula (1)

In the above formula (1),
a is an integer of 1 or 2, b is an integer of 0 to 3,
When a is 1, Y is each independently deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₃₀ aryloxy group; -L'-N(R ^a ) (R ^b ); And -L ^a -Ar ^a is selected from the group consisting of, and when a is 1 and b is 2 or 3, adjacent Ys may be bonded to each other to form a ring,
When a is 2, b is an integer of 1, and Y is, each independently, a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₁ ~ C ₅₀ alkylene group; C ₃ ~ C ₆₀ aliphatic ring group; And it is selected from the group consisting of a fused ring of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60,
X ¹ and X ² are each independently selected from the group consisting of CR'R", NR ^c , O and S,
R′ and R” are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ to C ₅₀ alkyl group; C ₁ to C ₃₀ alkoxy group; C ₆ to C ₆₀ aryl group; flu Orenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, R'and R" may be bonded to each other to form a ring,
R ^c is, each independently, deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₃₀ aryloxy group; -L'-N(R ^a ) (R ^b ); And -L ^a -Ar ^a is selected from the group consisting of,
m and n are integers of 0 or 1, when m or n is 0, it means that no bridge bond exists, and o is an integer of 0 to 5,
Z is, each independently, deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N(R ^a ) (R ^b ); And -L ^a -Ar ^a is selected from the group consisting of, adjacent Z to each other can form a ring,
When a is 1, at least one of R ^c , Y and Z is -L ^a -Ar ^a ,
L ^a is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom,
Ar ^a is a C ₂ ~ C ₆₀ heterocyclic group containing at least one N,
L'is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom,
R ^a and R ^b are deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group,
In the above Y, R ^a , R ^b , Ar ^a , R', R", R ^c , Z and L ^a , L', the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group , Alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkylene group, arylene group, fluorenylene group, respectively deuterium; nitro group; nitrile group; halogen group; amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ substituted with deuterium C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group; C ₃ to C ₂₀ cycloalkyl group; C ₇ to C ₂₀ arylalkyl group and C ₈ to C ₂₀ arylalkenyl group One or more substituents selected from may be further substituted, and the additionally substituted substituents may be bonded to each other to form a ring, and the additionally substituted substituents are each deuterium, a nitro group, a nitrile group, a halogen group; amino; C ₁ ~ Import alkylthio of C _20; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl; C ₂ ~ C ₂₀ alkenyl group a; C ₂ ~ C ₂₀ alkynyl of; C ₆ ~ C ₂₀ aryl group; C ₆ to C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ to C ₂₀ heterocyclic group; C ₃ to C ₂₀ cycloalkyl group; C ₇ to C ₂₀ arylalkyl group ; And one or more substituents selected from the group consisting of C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and these substituents may be bonded to each other to form a ring. The method of claim 1,
When a is 1, Y is, each independently, a C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom,
When a is 2, Y is, each independently, a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And it is selected from the group consisting of an alkylene group of C ₁ ~ C ₅₀ ,
The R′ and R” are each independently hydrogen; C ₁ to C ₅₀ alkyl group; C ₆ to C ₆₀ aryl group; fluorenyl group; And at least one hetero from O, N, S, Si and P It is selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing an atom,
R ^c and Z are each independently a C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; And O, N, S, Si, and a compound characterized in that selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P. The method of claim 1,
A compound, characterized in that the compound represented by the formula (1) is represented by any one of the following formulas (2) to (6):
Formula (2) Formula (3)

Formula (4) Formula (5)

Formula (6)

In the above formulas (2) to (6), X ¹ , X ² , Z, Y, b, n, m and o are the same as defined in claim 1. The method of claim 1,
A compound, characterized in that the compound represented by the formula (1) is represented by any one of the following formulas (7) to (50):
Formula (7) Formula (8) Formula (9) Formula (10)

Formula (11) Formula (12) Formula (13) Formula (14)

Formula (15) Formula (16) Formula (17) Formula (18)

Formula (19) Formula (20) Formula (21) Formula (22)

Formula (23) Formula (24)

Formula (25) Formula (26)

Formula (27) Formula (28)

Formula (29) Formula (30)

Formula (31) Formula (32)

Formula (33) Formula (34)

Formula (35) Formula (36)

Formula (37) Formula (38)

Formula (39) Formula (40)

Formula (41) Formula (42)

Formula (43) Formula (44)

Formula (45) Formula (46)

Formula (47) Formula (48)

Formula (49) Formula (50)

In the above formulas (7) to (50), X ¹ , X ² , Z, Y, R ^c , R', R", b and o are the same as defined in claim 1. A first electrode;
A second electrode; And
Including; an organic material layer positioned between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound of claim 1. A first electrode;
A second electrode;
An organic material layer positioned between the first electrode and the second electrode; And
A capping layer disposed on one or more of one surface of the first electrode opposite to the organic material layer and one surface of the second electrode opposite to the organic material layer; and
The organic material layer or the capping layer is an organic electric device comprising the compound of claim 1. The method according to claim 5 or 6,
The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer,
At least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, or an electron injection layer included in the organic material layer comprises the compound of claim 1. The method according to claim 5 or 6,
The organic material layer includes at least one of an electron transport auxiliary layer, an electron transport layer, and an electron injection layer,
An organic electric device in which at least one of the electron transport auxiliary layer, the electron transport layer, and the electron injection layer included in the organic material layer includes the compound of claim 1. The method according to claim 5 or 6,
An organic electric device in which the emission layer included in the organic material layer comprises the compound of claim 1. The method of claim 6,
An organic electric device in which the capping layer comprises the compound of claim 1. The method of claim 9,
The light emitting layer is an organic electric device further comprising at least one compound represented by any one of the following formulas (51) to (53):
Formula (51) Formula (52) Formula (53)

In the above formulas (51) to (53),
X ³ is NAr ⁹ , CR ⁵ R ⁶ , O or S,
Ar ¹ to Ar ⁹ are each independently deuterium; halogen; Cyano group; C ₁ ~ C ₂₀ alkyl group; C ₁ ~ C ₂₀ alkoxy group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And C ₈ ~ C ₂₀ is selected from the group consisting of arylalkenyl group,
L ¹ is a C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group,
L ² is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group,
R ¹ to R ⁴ are each independently deuterium; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, adjacent R ¹ to R ⁴ may be bonded to each other to form a ring,
R ⁵ and R ⁶ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ ~ C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring 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 ; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, R ⁵ and R ⁶ may be bonded to each other to form a ring,
t and w are integers from 0 to 4, u and v are integers from 0 to 3,
In the above Ar ¹ to Ar ⁹ , L ¹ , L ² and R ¹ to R ⁶ , the aryl group, fluorenyl group, heterocyclic group, alicyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, cycloalkyl group , Arylalkyl group, arylalkenyl group, arylene group, and fluorenylene group are each deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and the additionally substituted substituents may be bonded to each other to form a ring. And each of the additionally substituted substituents is deuterium; Nitro group; Nitrile group; Halogen group; Amino group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₆ ~ C ₂₀ aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And one or more substituents selected from the group consisting of C ₈ ~ C ₂₀ arylalkenyl group may be further substituted, and these substituents may be bonded to each other to form a ring.

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