KR20210020211A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention relates to a compound for an organic electric element, the organic electric element using the same, and an electronic device comprising the organic electric element. According to the present invention, it is possible to provide the organic electric element having high luminous efficiency, low driving voltage, and high heat resistance, and it is possible to improve the color purity and lifespan of the organic electric element.

Description

Compound for organic electric element, organic electric element using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emission phenomenon 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 may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron have. In addition, the light-emitting material 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 emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the increase in color purity and energy transfer 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 light with high efficiency. 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, and for this reason, power consumption that is greater than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for portable displays that have a limited power supply source, such as a battery, and efficiency and life problems are also important factors that must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan. 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 energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.

In addition, in recent years, in order to solve the problem of light emission in the hole transport layer in organic electroluminescent devices, a method of using a light emitting auxiliary layer between the hole transport layer and the light emitting layer is being studied, and desired according to each light emitting layer (R, G, B). Since material properties are different, it is time to develop a light emitting auxiliary layer for each light emitting layer.

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, in the case of the material used for the hole transport layer, since it must have a low HOMO value, most have a low T1 value, and as a result, excitons generated in the light-emitting layer pass to the hole transport layer interface or the hole transport layer, resulting in the hole transport layer interface. Light emission in the light emitting layer or charge unbalance in the light emitting layer is caused to emit light at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electronic device are deteriorated, and the lifespan is shortened. Therefore, it must be a material having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, has a high T1 value, and has a suitable driving voltage range (within the range of the driving voltage of the blue device of the full device). There is an urgent need to develop a light-emitting auxiliary layer having mobility).

However, this cannot be achieved simply with the structural characteristics of the core of the light-emitting auxiliary layer material, and the characteristics of the core and sub-substituents of the light-emitting auxiliary layer material, and the proper combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer are made. When it is lost, a high-efficiency and long-life device can be implemented.

Meanwhile, development of materials for a light-emitting layer and a light-emitting auxiliary layer having a stable characteristic, that is, a high glass transition temperature, against Joule heating generated when the device is driven is also required. The low glass transition temperature of the light-emitting layer and the light-emitting auxiliary layer material decreases the uniformity of the thin film surface when the device is driven, and the material may be deformed due to heat generated when the device is driven, which is reported to have a great effect on the life of the device.

Therefore, it is necessary to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance, and materials that form the organic material layer in the device, such as hole injection material, hole transport material, and light emission, are required to fully exhibit the excellent characteristics of organic electronic devices. Materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials must be supported by stable and efficient materials. In particular, development of materials used for light-emitting auxiliary layers and light-emitting layers is urgently required.

An object of the present invention is to provide a compound having high heat resistance, lowering the driving voltage of the device, and improving the luminous efficiency, color purity, and lifespan of the device, an organic electric device using the same, and an electronic device including the organic electric device To do.

In one aspect, the present invention provides a compound represented by the following formula.

<Formula 1> <Formula 1-1>

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

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and lifespan of the device can be improved.

1 to 3 schematically illustrate organic electric devices according to embodiments of the present invention.
4 shows a chemical formula according to an aspect of the present invention.

Hereinafter, preferred embodiments of the present invention will be described with reference to the accompanying drawings.

In order to describe the present embodiments, in adding reference numerals to elements of each drawing, it should be noted that the same elements are assigned the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, if 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 will be omitted. In the drawings referred to below, the accumulation ratio is not applied.

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 used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term.

When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected or connected to that other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.

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.

Terms used in the present specification and the appended claims are as follows, unless otherwise stated, without departing from the spirit of the present invention.

The term "halo" or "halogen" as used in this 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 means a radical of a saturated aliphatic functional group including a cycloalkyl group and a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present application means 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 have a carbon number of 2 to 60, but are limited thereto. It does not become.

The term "cycloalkyl" as used in the present application means an alkyl forming a ring having 3 to 60 carbon atoms unless otherwise specified, and is not limited thereto.

The term "alkoxy group" or "alkyloxy group" used in the present application refers to an alkyl group to which an oxygen radical is bonded, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

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 It has a carbon number of, but is not limited thereto.

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 includes a single cyclic type, a ring aggregate, and several cyclic compounds conjugated. For example, the aryl group may include a phenyl group, a biphenyl monovalent functional group, a naphthalene monovalent functional group, a fluorenyl group, and a substituted fluorenyl group, and the arylene group may include a fluorenylene group, a substituted fluorenylene group It may contain a group.

The term "ring assemblies" as used herein refers to two or more ring systems (single ring or fused ring system) being directly connected to each other through a single bond or a double bond, and between such rings It means that the number of direct linkages is one less than the total number of ring systems in the compound. In the ring aggregate, the same or different ring systems may be directly linked to each other through a single bond or a double bond.

In the present application, since the aryl group includes a ring aggregate, the aryl group includes biphenyl and terphenyl in which the benzene ring, which is a single aromatic ring, is connected by a single bond. In addition, since the aryl group also includes a compound in which the aromatic ring system conjugated with an aromatic single ring is connected by a single bond, for example, a compound in which fluorene, an aromatic ring system conjugated with an aromatic single ring benzene ring, is connected by a single bond. do.

The term "conjugated multiple ring systems" as used in the present application refers to a fused ring form that shares at least two atoms, and includes a form in which a ring system of two or more hydrocarbons is fused and at least one heteroatom And at least one conjugated heterocyclic system. Several such fused ring systems may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings. For example, the aryl group may be a naphthalenyl group, a phenanthrenyl group, or a fluorenyl group, but is not limited thereto.

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 is called a compound.

The terms "fluorenyl group", "fluorenylene group", and "fluorentriyl group" as used in the present application refer to R, R', R" and R'" in the following structures, respectively, unless otherwise stated. It refers to a monovalent, divalent or trivalent functional group, and "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorentriyl group" is a substituent R, R', R", R' It means that at least one of "is a substituent other than hydrogen, and includes the case where R and R'are bonded to each other to form a spy compound with the carbon to which they are bonded. In the present specification, a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of valence such as monovalent, divalent, or trivalent.

In addition, the R, R', R" and R'" are each independently an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 1 to 20, an aryl group having a carbon number of 6 to 30, 3 to It may be a heterocyclic group having 30 carbon atoms, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, imidazole, Triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline. For example, the substituted fluorenyl group and fluorenylene group are monovalent of 9,9-dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spirobi[9H-fluorene], respectively. It may be a functional group or a divalent functional group.

The term "heterocyclic group" 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, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" used in the present application represents N, O, S, P or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.

For example, the “heterocyclic group” may also include a compound including a heteroatom group such as _{SO 2} , P=O, and the like, as in the following compounds instead of carbon forming a ring.

The term "ring" as used in the present application includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" as used in the present application includes ring assemblies such as biphenyl, terphenyl, etc., several fused ring systems and spiro compounds, and includes not only aromatic but also non-aromatic, hydrocarbon Rings of course include heterocycles containing at least one heteroatom.

The term "aliphatic ring group" used in the present application refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic types, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring and cyclohexane, which is a non-aromatic ring, are fused, it is an aliphatic ring.

In addition, when the prefixes are named consecutively, it means 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 means an alkenyl group substituted with an arylcarbonyl group, where The arylcarbonyl group is 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 And, it 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', which is a kind of aryl group, the monovalent'group' is'phenanthryl (group)', and the divalent group is named by dividing the valence such as'phenanthrylene (group)', etc. Although it may be described, it can also be described with the parent compound name'phenanthrene' 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, it is referred to as pyrimidinyl (group), and in the case of divalent, the'group of the corresponding valency is expressed as pyrimidinylene (group). It can also be written as'name of'. 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, in the present specification, when describing the name of the compound or the name of the substituent, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in this application is applied in the same way as the definition of the substituent 　 in the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that the substituent R 1 does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6 In the case of an integer of, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different from each other.

Unless otherwise stated in the present application, to form a ring means that adjacent groups are bonded to each other to form a single ring or several conjugated rings, and a single ring and a plurality of conjugated rings formed are hydrocarbon rings as well as at least one It includes a heterocycle including a heteroatom, and may include aromatic and non-aromatic rings.

In addition, unless otherwise specified in the present specification, when indicating a condensed ring, a number in'number-condensed ring' indicates the number of condensed rings. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., can be expressed as a 3-condensed ring.

Meanwhile, the term "bridged bicyclic compound" used in the present application refers to a compound in which two rings share 3 or more atoms to form a ring unless otherwise specified. At this time, the shared atom may include carbon or heteroatom.

Hereinafter, a stacked structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.

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 is included between the second electrodes 170.

The first electrode 110 may be an anode (anode), 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 formed on the first electrode 110.

Preferably, the capping layer 180 may be formed on one surface of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the capping layer 180 is formed, organic electricity The light efficiency of the device can be improved.

For example, the capping layer 180 may be formed on the second electrode 170. In the case of a top emission organic light emitting device, the capping layer 180 is formed so that the capping layer 180 is formed on the second electrode 170. Optical energy loss due to SPPs (surface plasmon polaritons) of can be reduced, and in the case of a bottom emission organic light emitting device, the capping layer 180 can function as a buffer for the second electrode 170 .

Meanwhile, a buffer layer 210 or a light emission auxiliary layer 220 may be further formed between the hole transport layer 130 and the emission layer 140, which will be described with reference to FIG. 2.

Referring to FIG. 2, an organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, A light emission auxiliary layer 220, a light emission layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a capping layer 180 may be formed on the second electrode. I can.

Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.

In addition, according to another embodiment of the present invention, the organic material layer may have a plurality of stacks including a hole transport layer, an emission layer, and an electron transport layer. This will be described with reference to FIG. 3.

Referring to FIG. 3, in an organic electric device 300 according to another embodiment of the present invention, two stacks ST1 and ST2 formed of a multi-layered organic material layer are formed between the first electrode 110 and the second electrode 170. A set or more may be formed, and a charge generation layer CGL may be formed between the stack of organic material layers.

Specifically, the organic electric device according to the embodiment of the present invention includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a capping layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer ( 350) may be included.

The second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450.

As described above, the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.

A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2. The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361. The charge generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase the current efficiency generated in each emission layer and smoothly distribute electric charges.

The first emission layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 is a material doped with a greenish yellow dopant and a red dopant in a green host. May be included, but the materials of the first emission layer 340 and the second emission layer 440 according to the exemplary embodiment of the present invention are not limited thereto.

In this case, the second hole transport layer 430 includes a second stack ST2 in which the energy level is set higher than the triplet excitation energy level of the second emission layer 440.

Since the energy level of the second hole transport layer 430 is higher than that of the second light emitting layer 440, the triplet exciton of the second light emitting layer 440 passes to the second hole transport layer 430, resulting in lower luminous efficiency. Can be prevented. That is, the second hole transport layer 430 may function as an exciton blocking layer that prevents the tripping of triplet excitons while transporting holes from the inherent second emission layer 440. .

In addition, the first hole transport layer 330 may also be set to an energy level higher than the triplet excitation energy level of the first emission layer 340 for the function of the exciton blocking layer. In addition, the first electron transport layer 350 is also set to an energy level higher than that of the triplet excited state of the first emission layer 340, and the second electron transport layer 450 is also triplet excitation of the second emission layer 440. It is preferable to set the energy level higher than the energy level of the state.

In FIG. 3, n may be an integer of 1-5. When n is 2, a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.

When a plurality of emission layers are formed by the multilayer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electroluminescent device in which white light is emitted by the mixing effect of light emitted from each emission layer, as well as various colors of light. An organic electroluminescent device that emits light can also be manufactured.

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material of the capping layer 180, but preferably, the hole transport layer 130, 330, 430, the light emission auxiliary layer 220 ), the light emitting layers 140, 340, and 440, and/or the capping layer 180 may be used as a material.

The organic electric device according to FIGS. 1 to 3 may further include a protective layer (not shown) and an encapsulation layer (not shown). The protective layer may be located on the capping layer, the encapsulation layer is located on the capping layer, and at least one side portion of the first electrode, the second electrode, and the organic material layer to protect the first electrode, the second electrode, and the organic material layer It can be formed to cover.

The protective layer may provide a flattened surface so that the encapsulation layer can be uniformly formed, and may serve to protect the first electrode, the second electrode, and the organic material layer in the manufacturing process of the encapsulation layer.

The encapsulation layer may play a role of preventing external oxygen and moisture from penetrating into the organic electronic device.

On the other hand, even with the same and similar core, the band gap, electrical characteristics, and interface characteristics 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 In particular, long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved.

Accordingly, in the present invention, by using the compound represented by Chemical Formula 1 as a material for the light emission auxiliary layer 220, the light emission layers 140, 340, and 440, and/or the capping layer 180, the energy level and T1 value between each organic material layer, By optimizing the intrinsic properties of the material (mobility, interfacial properties, etc.), it was possible to simultaneously improve the lifespan and efficiency of the organic electric device.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, the anode 110 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120 thereon. 320, 420), hole transport layers (130, 330, 430), light emitting layers (140, 340, 440), electron transport layers (150, 350, 450), and after forming an organic material layer including the electron injection layer 160, It can be manufactured by depositing a material that can be used as the cathode 170 thereon. In addition, a light emission auxiliary layer 220 between the hole transport layer (130, 330, 430) and the light emitting layer (140, 340, 440), an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 May be further formed or may be formed in a stack structure as described above.

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 blaze. It can be manufactured with fewer layers by a method such as a printing 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.

The organic electric device according to an embodiment of the present invention may include an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

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).

<Formula 1> <Formula 1-1>

In Formula 1,

1) X is NL ^a -Ar ^a , O, S or CR'R”,

2) L and L ^a are 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; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; Or a combination thereof,

3) Ar ^a , Ar ¹ and Ar ² are each independently a 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; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; Or a combination thereof; Or neighboring groups can be bonded to each other to form a ring,

4) R ₁ to R ₃ , R'and R” are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro 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; 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 ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C _20; An alkoxyl group of C ₁ to C _30; C ₆ ~ C ₃₀ aryloxy group; C ₆ ~ C ₃₀ arylthio group; Formula 1-1; Or neighboring groups can be bonded to each other to form a ring,

5) a is an integer of 0-3; b is an integer of 0-4; c is an integer of 0-5; However, a+b+c ≥ 1, and at this time, at least one of _{R 1} to R _{3 is Formula 1-1,}

6) n is 1 or 2,

7) The R ₁ ~ R ₃ , Ar ^a , R', R”, Ar ¹ ~ Ar ² and the rings formed by bonding with each other and neighboring groups are deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; 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; _{O, N, S, Si, and C 2} -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof.

Preferably, Formula 1 may be represented by any one of Formulas 2 to 4 below, but is not limited thereto.

In Formulas 2 to 4, X, R ₁ to R ₃ , a to c, L and Ar ¹ to Ar ² are the same as defined in Formula 1.

More preferably, Formula 1 may be represented by any one of Formulas 5 to 16 below, but is not limited thereto.

In Formulas 5 to 16, R', R”, L, L ^a , Ar ^a and Ar ¹ to Ar ² are the same as defined in Formula 1 above.

In addition, Formula 1 may be represented by any one of Formulas 17 to 22 below, but is not limited thereto.

In Formulas 17 to 22, X, n, L, and Ar ¹ to Ar ² are the same as defined in Formula 1.

Even more preferably ^{, at least one of Ar 1} and Ar ² may be the following Formula A, but is not limited thereto.

In Formula A,

1) d is an integer of 0-3; e is an integer from 0 to 4

2) Y is the same as the definition of X in Formula 1 of claim 1,

3) R ₄ to R ₅ are the same as the definitions _{of R 1} to R ₃ in Formula 1 of claim 1.

Meanwhile, the compound of Formula 1 is any one of the following P-1 to P-120, but is not limited thereto.

In another embodiment of the present invention, the present invention provides a first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a compound represented by Formula 1 alone or in combination.

In another embodiment of the present invention, the present invention provides a first electrode; A second electrode; An organic material layer formed between the first electrode and the second electrode; And a capping layer, wherein the capping layer is formed on one surface not in contact with the organic material layer among both surfaces of the first electrode and the second electrode, and the organic material layer or the capping layer is represented by Formula 1 The compound to be used alone or as a mixture is included.

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. That is, 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 may include a compound represented by Formula (1). .

Preferably, the organic material layer includes at least one of the hole transport layer, an emission auxiliary layer, and an emission layer. That is, the compound may be included in at least one of the hole transport layer, the light emitting auxiliary layer, and the light emitting layer.

The organic material layer includes two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode.

Preferably, the organic material layer further includes a charge generation layer formed between the two or more stacks.

As yet another specific embodiment of the present invention, the present invention provides an electronic device including a display device including an organic electric device including the compound represented by Formula 1 and a control unit for driving the display device.

In an embodiment of the present invention, the compound of Formula 1 may be included alone, the compound may be included in a combination of two or more different from each other, or the compound may be included in a combination of two or more with another compound.

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

< Synthesis example >

The final product represented by Formula 1 according to the present invention may be synthesized as shown in Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

(The X, R ₁ to R ₃ , a to c, L and Ar ^{1 to 2} are the same as defined in Formula 1.)

I. Synthesis of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction paths of Schemes 2-1 to 2-3 below, but is not limited thereto.

<Reaction Scheme 2-1>

<Reaction Scheme 2-2>

<Reaction Scheme 2-3>

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

Sub 1- I of Synthesis example

Dissolve 1-bromo-2,4-dichlorobenzene (50.0 g, 221.35 mmol) in 1000 mL of THF in a round bottom flask and then (7-phenyl-7H-benzo[c]carbazol-1-yl)boronic acid (74.64 g, 221.35mmol), Pd(PPh ₃ ) ₄ (7.67 g, 6.64 mmol), NaOH (26.56 g, 664.04 mmol), and 330 mL of water were added, followed by stirring at 80°C. When the reaction was completed, CH ₂ Cl ₂ and water were extracted, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 72.0 g (yield: 74.2%) of the product.

Synthesis example of Sub 1-1

Sub 1-I (72.0 g, 164.25 mmol) obtained in the above synthesis was dissolved in 300 mL of DMSO in a round bottom flask, tri-tert-phenylphosphine (3.3 g, 16.4 mmol) and Pd(OAc) ₂ (1.1 g, 4.9 mmol), K ₂ CO ₃ (68.1 g, 492.7 mmol) was added and stirred at 165 °C. When the reaction was completed _{, the resultant 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 using a silica gel column to obtain 44.5 g (yield: 66%) of the product.

Synthesis example of Sub 1-5

Sub 1-II (55.0 g, 125.4 mmol) was obtained by using the synthesis method of Sub 1-I as the product 35.6 g (yield: 70%).

Synthesis example of Sub 1-12

Sub 1-III (42.0 g, 95.8 mmol) was used to obtain 27.5 g (yield: 71%) of the product using the synthesis method of Sub 1-I.

Synthesis example of Sub 1-19

Sub 1-IV (40.0 g, 105.46 mmol) was obtained by using the synthesis method of Sub 1-I to obtain 25.5 g (yield: 70%) of the product.

Synthesis example of Sub 1-38

Sub 1-V (25.0 g, 46.34 mmol) was obtained by using the synthesis method of Sub 1-I as the product 16.2 g (yield: 69%).

Examples of Sub 1 are as follows, but are not limited thereto.

Table 1 below shows the FD-MS values of compounds belonging to Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-2 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-3 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-4 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-5 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-6 m/z=477.13 (C ₃₄ H ₂₀ ClN=477.99) Sub 1-7 m/z=501.13 (C ₃₆ H ₂₀ ClN=502.01) Sub 1-8 m/z=527.14 (C ₃₈ H ₂₂ ClN=528.05) Sub 1-9 m/z=451.11 (C ₃₂ H ₁₈ ClN=451.95) Sub 1-10 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-11 m/z=401.10 (C ₂₈ H ₁₆ ClN=401.89) Sub 1-12 m/z=402.09 (C ₂₇ H ₁₅ ClN ₂ =402.88) Sub 1-13 m/z=501.13 (C ₃₆ H ₂₀ ClN=502.01) Sub 1-14 m/z=577.16 (C ₄₂ H ₂₄ ClN=578.11) Sub 1-15 m/z=507.08 (C ₃₄ H ₁₈ ClNS=508.04) Sub 1-16 m/z=491.11 (C ₃₄ H ₁₈ ClNO=491.97) Sub 1-17 m/z=406.13 (C ₂₈ H ₁₁ D ₅ lN=406.92) Sub 1-18 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-19 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-20 m/z=418.06 (C ₂₈ H ₁₅ ClS=418.94) Sub 1-21 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-22 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-23 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-24 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-25 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-26 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-27 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-28 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-29 m/z=342.03 (C ₂₂ H ₁₁ ClS=342.84) Sub 1-30 m/z=326.05 (C ₂₂ H ₁₁ ClO=326.78) Sub 1-31 m/z=326.05 (C ₂₂ H ₁₁ ClO=326.78) Sub 1-32 m/z=326.05 (C ₂₂ H ₁₁ ClO=326.78) Sub 1-33 m/z=493.12 (C ₃₄ H ₂₀ ClNO=493.99) Sub 1-34 m/z=493.12 (C ₃₄ H ₂₀ ClNO=493.99) Sub 1-35 m/z=493.12 (C ₃₄ H ₂₀ ClNO=493.99) Sub 1-36 m/z=493.12 (C ₃₄ H ₂₀ ClNO=493.99) Sub 1-37 m/z=493.12 (C ₃₄ H ₂₀ ClNO=493.99) Sub 1-38 m/z=452.10 (C ₃₂ H ₁₇ ClO=452.94) Sub 1-39 m/z=426.08 (C ₃₀ H ₁₅ ClO=426.90) Sub 1-40 m/z=470.09 (C ₃₂ H ₁₆ ClFO=470.93) Sub 1-41 m/z=508.07 (C ₃₄ H ₁₇ ClOS=509.02) Sub 1-42 m/z=351.10 (C ₂₃ H ₁₀ ClNO=351.79) Sub 1-43 m/z=352.10 (C ₂₅ H ₁₇ Cl=352.86) Sub 1-44 m/z=352.10 (C ₂₅ H ₁₇ Cl=352.86) Sub 1-45 m/z=352.10 (C ₂₅ H ₁₇ Cl=352.86) Sub 1-46 m/z=507.08 (C ₃₄ H ₁₈ ClNS=508.04) Sub 1-47 m/z=491.11 (C ₃₄ H ₁₈ ClNO=491.97) Sub 1-48 m/z=566.15 (C ₄₀ H ₂₃ ClN ₂ =567.09) Sub 1-49 m/z=448.01 (C ₂₈ H _{13 ClS 2} =448.98) Sub 1-50 m/z=432.04 (C ₂₈ H ₁₃ ClOS=432.92) Sub 1-51 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 1-52 m/z=468.16 (C ₃₄ H ₂₅ Cl=469.02) Sub 1-53 m/z=477.13 (C ₃₄ H ₂₀ ClN=477.99) Sub 1-54 m/z=568.16 (C ₄₁ H ₂₅ ClO=569.10) Sub 1-55 m/z=567.14 (C ₄₀ H ₂₂ ClNO=568.07) Sub 1-56 m/z=518.14 (C ₃₇ H ₂₃ ClO=519.04) Sub 1-57 m/z=660.26 (C ₄₉ H ₃₇ Cl=661.29)

II. Sub 2 example

Sub 2 of Scheme 1 is the same as Scheme 3 below, but is not limited thereto.

<Reaction Scheme 3>

Since Reaction Scheme 3 is obvious to those skilled in the art, a detailed description will be omitted below.

Examples of Sub 2 are as follows, but are not limited thereto.

Table 2 below shows the FD-MS values of compounds belonging to Sub 2.

compound FD-MS compound FD-MS Sub 2-1 m/z=169.09 (C ₁₂ H ₁₁ N=169.22) Sub 2-2 m/z=245.12 (C ₁₈ H ₁₅ N=245.32) Sub 2-3 m/z=245.12 (C ₁₈ H ₁₅ N=245.32) Sub 2-4 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 2-5 m/z=219.10 (C ₁₆ H ₁₃ N=219.29) Sub 2-6 m/z=295.14 (C ₂₂ H ₁₇ N=295.38) Sub 2-7 m/z=345.15 (C ₂₆ H ₁₉ N=345.45) Sub 2-8 m/z=269.12 (C ₂₀ H ₁₅ N=269.35) Sub 2-9 m/z=319.14 (C ₂₄ H ₁₇ N=319.41) Sub 2-10 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 2-11 m/z=293.12 (C ₂₂ H ₁₅ N=293.37) Sub 2-12 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-13 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-14 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-15 m/z=325.09 (C ₂₂ H ₁₅ NS=325.43) Sub 2-16 m/z=259.10 (C ₁₈ H ₁₃ NO=259.31) Sub 2-17 m/z=259.10 (C ₁₈ H ₁₃ NO=259.31) Sub 2-18 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-19 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-20 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.41) Sub 2-21 m/z=359.13 (C ₂₆ H ₁₇ NO=359.43) Sub 2-22 m/z=375.11 (C ₂₆ H ₁₇ NS=375.49) Sub 2-23 m/z=285.15 (C ₂₁ H ₂₉ N=285.39) Sub 2-24 m/z=285.15 (C ₂₁ H ₂₉ N=285.39) Sub 2-25 m/z=409.18 (C ₃₁ H ₂₃ N=409.53) Sub 2-26 m/z=409.18 (C ₃₁ H ₂₃ N=409.53) Sub 2-27 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 2-28 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 2-29 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.41) Sub 2-30 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.41) Sub 2-31 m/z=310.11 (C ₂₁ H ₁₄ N ₂ O=310.36) Sub 2-32 m/z=386.14 (C ₂₇ H ₁₈ N ₂ O=386.45) Sub 2-33 m/z=170.08 (C ₁₁ H ₁₀ N ₂ =170.22) Sub 2-34 m/z=220.10 (C ₁₅ H ₁₂ N ₂ =220.28) Sub 2-35 m/z=200.14 (C ₁₄ H ₈ D ₅ N=187.08) Sub 2-36 m/z=200.14 (C ₁₂ H ₁₀ FN=187.22) Sub 2-37 m/z=194.08 (C ₁₃ H ₁₀ N ₂ =194.24)

Synthesis example of final compound

Synthesis example of P-1

Sub 1-1 (22.0 g, 54.7 mmol) was put in a round bottom flask and dissolved with toluene (300 mL), then Sub 2-1 (9.2 g, 54.7 mmol), Pd ₂ (dba) ₃ (1.5 g, 1.64 mmol) ), P(t-Bu) ₃ (0.66 g, 3.28 mmol), NaOt-Bu (16.1 g, 164.22 mmol) was added and stirred at 100°C. When the reaction was completed _{, the resultant 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 through a silica gel column to obtain 24.2 g (yield: 87%) of the product.

Synthesis example of P-13

Sub 1-2 (17.5 g, 43.54 mmol) and Sub 2-12 (11.9 g, 43.54 mmol) were obtained by using the synthesis method of P-1 to obtain 21.2 g (yield: 75%) of the product.

Synthesis example of P-30

Sub 1-5 (13.4 g, 33.34 mmol) and Sub 2-19 (10.3 g, 33.34 mmol) were used to obtain 17.6 g (yield: 82%) of the product using the synthesis method of P-1.

Synthesis example of P-64

Sub 1-19 (18.2 g, 53.09 mmol) and Sub 2-17 (13.7 g, 53.09 mmol) were obtained by using the synthesis method of P-1 to obtain 25.5 g (yield: 84%) of the product.

Synthesis example of P-96

Sub 1-33 (10.2 g, 20.65 mmol) and Sub 2-2 (5.07 g, 20.65 mmol) were prepared by using the synthesis method of P-1 to obtain 11.6 g (yield: 79%) of the product.

Meanwhile, the FD-MS values of the compounds P-1 to P-120 of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=534.21 (C ₄₀ H ₂₆ N ₂ =534.66) P-2 m/z=610.24 (C ₄₆ H ₃₀ N ₂ =610.76) P-3 m/z=640.20 (C ₄₆ H ₂₈ N ₂ S=640.80) P-4 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) P-5 m/z=674.24 (C ₅₀ H ₃₀ N ₂ O=674.80) P-6 m/z=650.27 (C ₄₉ H ₃₄ N ₂ =650.83) P-7 m/z=774.30 (C ₅₉ H ₃₈ N ₂ =774.97) P-8 m/z=772.29 (C ₅₉ H ₃₆ N ₂ =772.95) P-9 m/z=699.27 (C ₅₂ H ₃₃ N ₃ =699.86) P-10 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) P-11 m/z=534.21 (C ₄₀ H ₂₆ N ₂ =534.66) P-12 m/z=610.24 (C ₄₆ H ₃₀ N ₂ =610.76) P-13 m/z=640.20 (C ₄₆ H ₂₈ N ₂ S=640.80) P-14 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) P-15 m/z=674.24 (C ₅₀ H ₃₀ N ₂ O=674.80) P-16 m/z=650.27 (C ₄₉ H ₃₄ N ₂ =650.83) P-17 m/z=774.30 (C ₅₉ H ₃₈ N ₂ =774.97) P-18 m/z=772.29 (C ₅₉ H ₃₆ N ₂ =772.95) P-19 m/z=699.27 (C ₅₂ H ₃₃ N ₃ =699.86) P-20 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) P-21 m/z=634.24 (C ₄₈ H ₃₀ N ₂ =634.78) P-22 m/z=710.27 (C ₅₄ H ₃₄ N ₂ =710.88) P-23 m/z=690.21 (C ₅₀ H ₃₀ N ₂ S=690.86) P-24 m/z=675.23 (C ₄₉ H ₂₉ N ₂ O=675.79) P-25 m/z=552.20 (C ₄₀ H ₂₅ FN ₂ =552.65) P-26 m/z=534.21 (C ₄₀ H ₂₆ N ₂ =534.66) P-27 m/z=610.24 (C ₄₆ H ₃₀ N ₂ =610.76) P-28 m/z=640.20 (C ₄₆ H ₂₈ N ₂ S=640.80) P-29 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) P-30 m/z=674.24 (C ₅₀ H ₃₀ N ₂ O=674.80) P-31 m/z=660.26 (C ₅₀ H ₃₂ N ₂ =660.82) P-32 m/z=610.24 (C ₄₆ H ₃₀ N ₂ =610.76) P-33 m/z=740.23 (C ₅₄ H ₃₂ N ₂ S=740.92) P-34 m/z=750.27 (C ₅₆ H ₃₄ N ₂ O=750.90) P-35 m/z=724.25 (C ₅₄ H ₃₂ N ₂ O=724.86) P-36 m/z=634.24 (C ₄₈ H ₃₀ N ₂ =634.78) P-37 m/z=710.27 (C ₅₄ H ₃₄ N ₂ =710.88) P-38 m/z=690.21 (C ₅₀ H ₃₀ N ₂ S=690.86) P-39 m/z=751.26 (C ₅₅ H ₃₃ N ₃ O=751.89) P-40 m/z=559.20 (C ₄₁ H ₂₅ N ₃ =559.67) P-41 m/z=534.21 (C ₄₀ H ₂₆ N ₂ =534.66) P-42 m/z=610.24 (C ₄₆ H ₃₀ N ₂ =610.76) P-43 m/z=640.20 (C ₄₆ H ₂₈ N ₂ S=640.80) P-44 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) P-45 m/z=674.24 (C ₅₀ H ₃₀ N ₂ O=674.80) P-46 m/z=650.27 (C ₄₉ H ₃₄ N ₂ =650.83) P-47 m/z=774.30 (C ₅₉ H ₃₈ N ₂ =774.97) P-48 m/z=772.29 (C ₅₉ H ₃₆ N ₂ =772.95) P-49 m/z=699.27 (C ₅₂ H ₃₃ N ₃ =699.86) P-50 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) P-51 m/z=634.24 (C ₄₈ H ₃₀ N ₂ =634.78) P-52 m/z=710.27 (C ₅₄ H ₃₄ N ₂ =710.88) P-53 m/z=690.21 (C ₅₀ H ₃₀ N ₂ S=690.86) P-54 m/z=675.23 (C ₄₉ H ₂₉ N ₂ O=675.79) P-55 m/z=570.29 (C ₄₂ H ₁₈ D ₁₀ N ₂ =570.76) P-56 m/z=475.14 (C ₃₄ H ₂₁ NS=475.61) P-57 m/z=551.17 (C ₄₀ H ₂₅ NS=551.71) P-58 m/z=581.13 (C ₄₀ H ₂₃ NS ₂ =581.75) P-59 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-60 m/z=615.17 (C ₄₄ H ₂₅ NOS=615.75) P-61 m/z=475.14 (C ₃₄ H ₂₁ NS=475.61) P-62 m/z=551.17 (C ₄₀ H ₂₅ NS=551.71) P-63 m/z=581.13 (C ₄₀ H ₂₃ NS ₂ =581.75) P-64 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-65 m/z=615.17 (C ₄₄ H ₂₅ NOS=615.75) P-66 m/z=475.14 (C ₃₄ H ₂₁ NS=475.61) P-67 m/z=551.17 (C ₄₀ H ₂₅ NS=551.71) P-68 m/z=581.13 (C ₄₀ H ₂₃ NS ₂ =581.75) P-69 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-70 m/z=615.17 (C ₄₄ H ₂₅ NOS=615.75) P-71 m/z=551.17 (C ₄₀ H ₂₅ NS=551.71) P-72 m/z=615.17 (C ₄₄ H ₂₅ NOS=615.75) P-73 m/z=591.20 (C ₄₃ H ₂₉ NS=591.77) P-74 m/z=715.23 (C ₅₅ H ₃₃ NS=715.91) P-75 m/z=713.22 (C ₅₃ H ₃₁ NS=713.90) P-76 m/z=575.17 (C ₄₂ H ₂₅ NS=575.73) P-77 m/z=551.17 (C ₄₀ H ₂₅ NS=551.71) P-78 m/z=631.14 (C ₄₄ H ₂₅ NS ₂ =634.81) P-79 m/z=616.16 (C ₄₃ H ₂₄ N ₂ OS=616.74) P-80 m/z=493.13 (C ₃₄ H ₂₀ FNS=493.60) P-81 m/z=459.16 (C ₃₄ H ₂₁ NO=459.55) P-82 m/z=535.19 (C ₄₀ H ₂₅ NO=535.65) P-83 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-84 m/z=549.17 (C ₄₀ H ₂₃ NO ₂ =549.63) P-85 m/z=599.19 (C ₄₄ H ₂₅ NO ₂ =599.69) P-86 m/z=459.16 (C ₃₄ H ₂₁ NO=459.55) P-87 m/z=535.19 (C ₄₀ H ₂₅ NO=535.65) P-88 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-89 m/z=549.17 (C ₄₀ H ₂₃ NO ₂ =549.63) P-90 m/z=599.19 (C ₄₄ H ₂₅ NO ₂ =599.69) P-91 m/z=459.16 (C ₃₄ H ₂₁ NO=459.55) P-92 m/z=535.19 (C ₄₀ H ₂₅ NO=535.65) P-93 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-94 m/z=549.17 (C ₄₀ H ₂₃ NO ₂ =549.63) P-95 m/z=599.19 (C ₄₄ H ₂₅ NO ₂ =599.69) P-96 m/z=702.27 (C ₅₂ H ₃₄ N ₂ O=702.86) P-97 m/z=766.26 (C ₅₆ H ₃₄ N ₂ O ₂ =766.90) P-98 m/z=742.30 (C ₅₅ H ₃₈ N ₂ O=742.92) P-99 m/z=866.33 (C ₆₅ H ₄₂ N ₂ O=867.06) P-100 m/z=864.31 (C ₆₅ H ₄₀ N ₂ O=865.05) P-101 m/z=735.26 (C ₅₆ H ₃₃ NO=735.89) P-102 m/z=683.22 (C ₅₂ H ₂₉ NO=683.81) P-103 m/z=727.23 (C ₅₄ H ₃₀ FNO=727.84) P-104 m/z=692.19 (C ₄₉ H ₂₈ N ₂ OS=692.84) P-105 m/z=515.20 (C ₃₇ H ₁₇ D ₅ N ₂ O=515.63) P-106 m/z=485.21 (C ₃₇ H ₂₇ N=485.63) P-107 m/z=591.20 (C ₄₃ H ₂₉ NS=591.77) P-108 m/z=486.21 (C ₃₆ H ₂₆ N ₂ =486.62) P-109 m/z=640.20 (C ₄₆ H ₂₈ N ₂ S=640.80) P-110 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) P-111 m/z=699.27 (C ₅₂ H ₃₃ N ₃ =699.86) P-112 m/z=581.13 (C ₄₀ H ₂₃ NS ₂ =581.75) P-113 m/z=565.15 (C ₄₀ H ₂₃ NOS=565.69) P-114 m/z=575.22 (C ₄₃ H ₂₉ NO=575.71) P-115 m/z=601.28 (C ₄₆ H ₃₅ N=601.79) P-116 m/z=716.23 (C ₅₂ H ₃₂ N ₂ S=716.90) P-117 m/z=701.27 (C ₅₃ H ₃₅ NO=701.87) P-118 m/z=700.25 (C ₅₂ H ₃₂ N ₂ O=700.84) P-119 m/z=651.26 (C ₄₉ H ₃₃ NO=651.81) P-120 m/z=797.37 (C ₆₁ H ₄₇ N=794.05)

Manufacturing evaluation of organic electric devices

( Example 1) Red organic electroluminescent device ( Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured according to a conventional method by using the compound of the present invention as a light emitting auxiliary layer material.

First, on the ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ After vacuum deposition of -phenylbenzene-1,4-diamine (hereinafter, 2-TNATA) to a thickness of 60 nm to form a hole injection layer, 4,4-bis[N-(1) as a hole transport compound on the hole injection layer -Naphthyl)-N-phenylamino]biphenyl (hereinafter, abbreviated as -NPD) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.

Subsequently, after vacuum-depositing the compound P-2 of the present invention to a thickness of 20 nm on the hole transport layer to form an emission auxiliary layer, CBP as a host material on the emission auxiliary layer, bis-(1-phenylisoquinolyl)iridium ( Ⅲ) acetylacetonate (hereinafter, (piq) ₂ Ir(acac)) was used as a dopant material, doped at a weight ratio of 95:5, and vacuum deposited to a thickness of 30 nm to form a light emitting layer.

Subsequently, BAlq was vacuum deposited on the emission layer to a thickness of 5 nm to form a hole blocking layer, and Bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, BeBq ₂ ) was added to a thickness of 40 nm on the hole blocking layer. The electron transport layer was formed by vacuum deposition.

Thereafter, LiF, a halogenated alkali metal, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

( Example 2) to ( Example 28)

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

( Comparative example One)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light emission auxiliary layer of Example 1 was not formed.

( Comparative example 2)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used as the light emitting auxiliary layer material of Example 1 above.

<Comparative compound 1>

Electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 28 and Comparative Examples 1 to 2, and the measurement As a result, the T95 life was measured using a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m ^2. Table 4 below shows the results of device fabrication and evaluation.

compound Driving voltage electric current
(mA/cm2) Luminance
(cd/m2) efficiency
(cd/A) T(95) CIE X Y Comparative Example (1) - 6.1 33.3 2500 7.5 62.7 0.66 0.32 Comparative Example (2) Comparative compound 1 5.8 13.7 2500 18.2 97.3 0.66 0.33 Example (1) Compound P-2 4.8 9.2 2500 27.2 113.8 0.66 0.33 Example (2) Compound P-3 4.8 9.1 2500 27.6 114.9 0.66 0.32 Example (3) Compound P-4 4.8 9.0 2500 27.9 114.5 0.66 0.33 Example (4) Compound P-6 4.8 9.1 2500 27.5 113.1 0.66 0.32 Example (5) Compound P-10 5.3 11.0 2500 22.7 103.7 0.66 0.33 Example (6) Compound P-28 4.7 8.8 2500 28.4 112.6 0.66 0.32 Example (7) Compound P-34 4.9 9.3 2500 27.0 108.5 0.66 0.33 Example (8) Compound P-38 4.9 9.4 2500 26.6 110.7 0.66 0.32 Example (9) Compound P-40 5.3 10.7 2500 23.3 103.0 0.66 0.32 Example (10) Compound P-44 4.7 8.9 2500 28.1 111.8 0.66 0.32 Example (11) Compound P-49 5.3 10.9 2500 22.9 101.9 0.66 0.32 Example (12) Compound P-50 5.3 10.9 2500 23.0 102.6 0.66 0.33 Example (13) Compound P-53 5.1 9.9 2500 25.2 105.9 0.66 0.33 Example (14) Compound P-58 5.0 9.7 2500 25.9 111.6 0.66 0.33 Example (15) Compound P-62 5.2 10.0 2500 25.0 108.1 0.66 0.33 Example (16) Compound P-73 5.2 10.2 2500 24.5 106.7 0.66 0.33 Example (17) Compound P-77 5.2 10.3 2500 24.3 107.3 0.66 0.33 Example (18) Compound P-80 5.1 9.8 2500 25.5 105.4 0.66 0.33 Example (19) Compound P-82 5.0 9.7 2500 25.8 111.1 0.66 0.33 Example (20) Compound P-95 4.9 9.4 2500 26.7 109.4 0.66 0.32 Example (21) Compound P-96 5.4 10.4 2500 24.0 104.1 0.66 0.33 Example (22) Compound P-97 5.5 11.1 2500 22.6 101.5 0.66 0.32 Example (23) Compound P-98 5.5 11.2 2500 22.3 100.4 0.66 0.33 Example (24) Compound P-105 5.5 11.5 2500 21.8 99.9 0.66 0.33 Example (25) Compound P-106 5.4 10.6 2500 23.5 104.8 0.66 0.32 Example (26) Compound P-115 5.5 11.6 2500 21.5 99.1 0.66 0.33 Example (27) Compound P-116 5.0 9.5 2500 26.2 109.9 0.66 0.32 Example (28) Compound P-120 5.5 11.8 2500 21.2 98.5 0.66 0.32

As can be seen from the results of Table 4, when a red organic electroluminescent device was manufactured using the material for an organic electroluminescent device of the present invention as a light emitting auxiliary layer material, Comparative Example 1 and Comparative Compound without using the light emitting auxiliary layer Compared to Comparative Example 2 in which 1 was used as the light emitting auxiliary layer material, the driving voltage of the organic electroluminescent device could be lowered, and the luminous efficiency and lifespan were significantly improved.

In more detail, the device results of Comparative Example 2 using Comparative Compound 1 having a similar basic skeleton to the compound of the present invention were improved than Comparative Example 1 in which the light-emitting auxiliary layer material was not used.

On the other hand, the compound of the present invention has the same core skeleton as Comparative Compound 1, but Comparative Compound 1 has an amino group substituted for the N element of the pentagonal ring constituting the core (that is, the N element of the carbazole constituting the core). The compounds of the invention differ in that the amino group is substituted with the hexagonal ring of the core (ie, the C element of benzene constituting the core).

Accordingly, looking at the device results of Comparative Examples and Examples, it can be seen that even though Comparative Compound 1 and the compounds of the present invention are the same core, the physical properties of the compound are significantly different depending on the substitution position of the amino group. By replacing the amino group in each ring, the properties of the compound such as hole characteristics, light efficiency characteristics, energy level (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, and electron blocking characteristics are more suitable for the red light-emitting auxiliary layer. This suggests that the device results of Examples 1 to 28, which are completely different from the device characteristics of Comparative Example 1, can be derived.

In addition, in the evaluation results of the above-described device fabrication, the device characteristics in which the compound of the present invention is applied to the light-emitting auxiliary layer are described, but the compound of the present invention can be applied to one or more of the light-emitting layer, the hole transport layer, and the light-emitting auxiliary layer.

The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains, various methods such as a method of improving performance including other compounds within the range not departing from the essential characteristics of the present invention. Transformation will be possible.

Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to describe the present invention, and the scope of the spirit of the present invention is not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: capping layer 210: buffer layer
220: light emission auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first emission layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second emission layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (13)

Compound represented by the following formula (1):
<Formula 1><Formula1-1>

In Formula 1,
1) X is NL ^a -Ar ^a , O, S or CR'R”,
2) L and L ^a are 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; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; Or a combination thereof,
3) Ar ^a , Ar ¹ and Ar ² are each independently a 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; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; Or a combination thereof; Or neighboring groups can be bonded to each other to form a ring,
4) R ₁ to R ₃ , R'and R” are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro 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; 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 ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C _20; An alkoxyl group of C ₁ to C _30; C ₆ ~ C ₃₀ aryloxy group; C ₆ ~ C ₃₀ arylthio group; Formula 1-1; Or neighboring groups can be bonded to each other to form a ring,
5) a is an integer of 0-3; b is an integer of 0-4; c is an integer of 0-5; However, a+b+c ≥ 1, and at this time, at least one of _{R 1} to R _{3 is Formula 1-1,}
6) n is 1 or 2,
7) The R ₁ ~ R ₃ , Ar ^a , R', R”, Ar ¹ ~ Ar ² and the rings formed by bonding with each other and neighboring groups are deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; 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; _{O, N, S, Si, and C 2} -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof. The compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 2 to 4:

In Formulas 2 to 4, X, R ₁ to R ₃ , a to c, L and Ar ¹ to Ar ² are the same as defined in Formula 1 of claim 1. The compound of claim 1, wherein Formula 1 is represented by any one of Formulas 5 to 16 below:

In Formulas 5 to 16, R', R”, L, L ^a , Ar ^a and Ar ¹ to Ar ² are the same as defined in Formula 1 of claim 1. The compound of claim 1, wherein at least one of ^{Ar 1} and Ar ^{2 is Formula A:}

In Formula A,
1) d is an integer of 0-3; e is an integer from 0 to 4
2) Y is the same as the definition of X in Formula 1 of claim 1,
3) R ₄ to R ₅ are the same as the definitions _{of R 1} to R ₃ in Formula 1 of claim 1. The compound of claim 1, wherein the compound represented by Formula 1 is one of the following P-1 to P-120:

A first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound represented by the formula (1) of claim 1 alone or in combination. A first electrode; A second electrode; An organic material layer formed between the first electrode and the second electrode; And in the organic electric device comprising a capping layer,
The capping layer is formed on one surface of both surfaces of the first electrode and the second electrode not in contact with the organic material layer,
The organic electroluminescent device, characterized in that the organic material layer or the capping layer comprises a compound represented by Formula 1 of claim 1 alone or in combination. The method according to claim 6 or 7,
The organic material layer comprises 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. The method of claim 8,
The organic material layer is an organic electric device comprising at least one of the hole transport layer, the light emitting auxiliary layer and the light emitting layer. The method according to claim 6 or 7,
The organic material layer comprises at least two stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode. The method of claim 10,
The organic material layer further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 6 or 7; And a control unit for driving the display device. The method of claim 12,
The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

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