KR102663762B1 - 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 device, an organic electric device using the same, and an electronic device including the organic electric device. According to the present invention, an organic electric device having high luminous efficiency, low driving voltage, and high heat resistance can be provided. and can improve the color purity and lifespan of organic electric devices.

Description

Compounds for organic electric devices, organic electric devices using the same, and their electronic devices {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic electric devices that utilize the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic electric device, and may be composed 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 organic layers in organic electric devices 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, depending on their function. In addition, the light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. there is. In addition, light-emitting materials can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to realize better natural colors.

On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interactions, and color purity is reduced or the efficiency of the device is reduced due to the luminescence attenuation effect. This causes an increase in color purity and energy transfer. In order to increase luminous efficiency through , a host/dopant system can be used as a luminescent material. The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

Currently, the portable display market is increasing in size toward large-area displays, which requires greater power consumption than that required by existing portable displays. Therefore, power consumption has become an important factor for portable displays that have a limited power source such as batteries, and issues of efficiency and lifespan are also important factors that must be resolved.

Efficiency, lifespan, driving voltage, etc. are related to each other. As efficiency increases, driving voltage relatively decreases, and as driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

In addition, recently, in order to solve the problem of light emission from 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 has been studied, and the method of using a light emitting auxiliary layer between the hole transport layer and the light emitting layer has been studied. Since the material properties are different, it is necessary to develop a light-emitting auxiliary layer according to 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, and excitons are generated through recombination.

However, since the material used in the hole transport layer must have a low HOMO value, most of them have a low T1 value. This causes the exciton generated in the light-emitting layer to pass over to the hole transport layer interface or the hole transport layer, resulting in a low T1 value. Light is emitted from or at the interface of the hole transport layer due to charge unbalance within the light emitting layer.

When light is emitted from the hole transport layer interface, the color purity and efficiency of the organic electric device are reduced and the lifespan is shortened. Therefore, it must be a material with a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the emitting layer, have a high T1 value, and have hole mobility within an appropriate driving voltage range (within the blue device driving voltage range of the full device). The development of a light-emitting auxiliary layer with mobility is urgently needed.

However, this cannot be achieved simply by 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 appropriate combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer must be achieved. When this is achieved, high-efficiency and long-life devices can be implemented.

Meanwhile, there is also a need to develop light-emitting layer and auxiliary light-emitting layer materials with stable characteristics, that is, high glass transition temperature, in response to Joule heating generated when driving the device. It is reported that the low glass transition temperature of the light-emitting layer and light-emitting auxiliary layer materials reduces the uniformity of the thin film surface when driving the device, and the material may be deformed due to the heat generated during device driving, which has a significant impact on device lifespan.

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

The purpose of the present invention is to provide a compound that has high heat resistance, can reduce the driving voltage of the device, and improve 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. Do it as

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

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 the color purity and lifespan of the device can be improved.

1 to 3 schematically show organic electric devices according to embodiments of the present invention.

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

In order to explain the present embodiments, it should be noted that when adding reference numerals to components in each drawing, the same components are given the same reference numerals as much as possible even if they are shown in different drawings. Additionally, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted. In the drawings referenced below, the scale ratio does not apply.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, 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 there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

Additionally, when a component, such as a layer, membrane, region, plate, etc., is said to be "on" or "on" another component, it means not only that it is "directly above" the other component, but also that there is another component in between. It should be understood that it can also include cases. Conversely, when an element is said to be "right on top" of another part, it should be understood to mean that there is no other part in between.

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

As used in this application, the term “halo” or “halogen” includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise specified.

As used in this application, the term "alkyl" or "alkyl group", unless otherwise specified, has 1 to 60 carbons connected by a single bond, and includes a straight chain alkyl group, branched chain alkyl group, cycloalkyl (cycloaliphatic) group, and alkyl-substituted group. It refers to radicals of saturated aliphatic functional groups, including cycloalkyl groups and cycloalkyl-substituted alkyl groups.

The term “haloalkyl group” or “halogenalkyl group” used in this application refers to an alkyl group in which halogen is substituted, unless otherwise specified.

As used in this application, the term "alkenyl" or "alkynyl", unless otherwise specified, has a double bond or triple bond, includes a straight or branched chain group, and has a carbon number of 2 to 60, but is limited thereto. It doesn't work.

The term “cycloalkyl” used in this application refers to alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.

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

As used in this application, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means 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 to this.

The terms “aryl group” and “arylene group” used in this application each have 6 to 60 carbon atoms unless otherwise specified, but are not limited thereto. In the present application, an aryl group or arylene group includes a single ring, a ring aggregate, a multiple ring system fused, a compound, etc. For example, the aryl group may include a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group, and the arylene group may include a fluorenylene group or a substituted fluorenylene group. It may include a group.

As used in this application, the term "ring assemblies" refers to two or more ring systems (single rings or fused ring systems) directly connected to each other through single or double bonds, and the It means that the number of direct connections is one less than the total number of ring systems in the compound. In ring aggregates, the same or different ring systems may be directly connected to each other through single or double bonds.

In the present application, since the aryl group includes a ring assembly, the aryl group includes biphenyl and terphenyl in which a benzene ring, which is a single aromatic ring, is linked by a single bond. In addition, the aryl group also includes compounds in which an aromatic ring system bonded to an aromatic single ring is linked by a single bond, so, for example, it also includes compounds in which a benzene ring, a single aromatic ring, and fluorene, a bonded aromatic ring system, are linked by a single bond. do.

The term "fused multiple ring system" used in this application refers to a fused ring form sharing at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. This includes forms in which at least one heterocyclic ring is fused. This fused multiple ring system may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.

The term "spiro compound" used in this application has a 'spiro union', and the spiro union refers to a connection made by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms in one compound, they are 'monospiro-', 'dispiro-', and 'trispiro-' respectively. 'It is called a compound.

As used in this application, the terms "fluorenyl group", "fluorenylene group", and "fluorenetriyl group" mean that R, R', R", and R'" in the following structures are all hydrogen, respectively, unless otherwise specified. It refers to a monovalent, divalent or trivalent functional group, and "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl group" refers to substituents R, R', R", R' "Means that at least one of them is a substituent other than hydrogen, and includes cases where R and R' are bonded to each other to form a spiro compound with the carbon to which they are bonded. In this specification, fluorenyl group, fluorenylene group, and fluorenetriyl group may all be referred to as fluorene groups regardless of valence such as monovalent, divalent, trivalent, etc.

In addition, R, R', R" and R'" are each independently selected from an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. 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, It may be a triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline. For example, the substituted fluorenyl group and fluorenylene group are monovalent groups 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 this application includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and unless otherwise specified, each carbon number containing one or more heteroatoms. It means a ring of 2 to 60, but is not limited thereto. As used in this application, the term "heteroatom" refers to N, O, S, P, or Si, unless otherwise specified, and the heterocyclic group refers to a single ring containing heteroatoms, a ring aggregate, a fused multiple ring system, or a ring group. refers to compounds, etc.

For example, “heterocyclic group” may also include compounds containing heteroatoms such as SO ₂ , P=O, etc., such as the compounds below, instead of carbon forming a ring.

As used in this application, the term “ring” includes single and polycyclic rings, includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" as used in this application includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems, and spiro compounds, and includes aromatics as well as non-aromatics, and hydrocarbons. Rings of course include heterocycles containing at least one heteroatom.

The term "aliphatic ring" used in this application refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes single rings, ring aggregates, fused multiple ring systems, spiro compounds, etc., and has the number of carbon atoms unless otherwise specified. It refers to a ring of 3 to 60, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it is an aliphatic ring.

Additionally, when prefixes are named consecutively, it means that the substituents are listed in the order they are listed first. For example, an arylalkoxy group refers to an alkoxy group substituted with an aryl group, an alkoxycarbonyl group refers to a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group refers to an alkenyl group substituted with an arylcarbonyl group. Arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in this application, "substituted" means 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 group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, silane group, Substituted with one or more substituents selected from the group consisting of a boron group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P. meaning, and is not limited to these substituents.

In this application, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent, may be written as the 'name of the functional group reflecting the valence', but is described as the 'parent compound name'. You may. For example, in the case of 'phenanthrene', a type of aryl group, the monovalent 'group' is 'phenanthryl (group)', the divalent group is 'phenanthrylene (group)', etc., and the names of the groups are separated by valence. However, it can also be written as 'phenanthrene', which is the name of the parent compound, regardless of the valence.

Similarly, in the case of pyrimidine, it is written as 'pyrimidine' regardless of the valence, or in the case of monovalent, as pyrimidinyl (group), in the case of divalent, as pyrimidinylene (group), etc. It can also be written as ‘name of’. Therefore, in the present application, when the type of substituent is described as the name of the parent compound, it may mean an n-valent 'group' formed by detachment of a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.

Additionally, in this specification, when describing compound names or substituent names, 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, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless explicitly stated, the chemical formula used in this application applies the same as the substituent definition according to the index definition in the following chemical formula.

Here, when a is an integer of 0, it means that the substituent R1 is absent. That is, when a is 0, it means that hydrogen is bonded to all carbons forming the benzene ring. In this case, the indication of hydrogen bonded to carbon is omitted. and chemical formulas or compounds can be written. In addition, when a is an integer of 1, one substituent R1 is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can be bonded, for example, as follows, and a is 4 to 6 Even when it is an integer, it is bonded to the carbon of the benzene ring in a similar way, and when a is an integer of 2 or more, R1 may be the same or different.

In the present application, substituents bonding to each other to form a ring means that a plurality of substituents bonded to each other share an arbitrary atom, for example, a carbon atom, or at least one atom of heteroatoms O, N, S, Si, and P. This means forming a saturated or unsaturated ring. For example, in the case of naphthalene, the adjacent methyl group butadienyl group substituted on one of the benzene rings shares one carbon to form an unsaturated ring, or the vinyl group and propyleneyl group share one carbon to form an unsaturated ring. It can be seen as forming a ring. Additionally, in the case of fluorene, it can be viewed as an aryl group with 13 carbon atoms, but it can also be viewed as two methyl groups substituted for a biphenyl group bonded to each other to share one carbon to form a ring.

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

Referring to FIG. 1, the 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). It includes an organic layer containing a compound according to the present invention between the second electrodes 170.

The first electrode 110 may be an anode, and the second electrode 170 may be a cathode. 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, 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 may be formed sequentially on the first electrode 110.

Preferably, the capping layer 180 may be formed on one side of the first electrode 110 or the second electrode 170 that is not in contact with the organic layer. When the capping layer 180 is formed, the organic electricity The optical 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 to separate the second electrode 170 from the second electrode 170. Optical energy loss due to SPPs (surface plasmon polaritons) can be reduced, and in the case of bottom emission organic light emitting devices, the capping layer 180 can serve as a buffer for the second electrode 170. .

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

Referring to FIG. 2, the 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, and a hole injection layer 120 sequentially formed on the first electrode 110. It may include a light emitting auxiliary layer 220, a light emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170, and a capping layer 180 may be formed on the second electrode. You 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.

Additionally, according to another embodiment of the present invention, the organic layer may be formed in a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer. This will be explained with reference to FIG. 3 .

Referring to Figure 3, the organic electric device 300 according to another embodiment of the present invention has two stacks (ST1, ST2) of multi-layered organic material layers between the first electrode 110 and the second electrode 170. More than a set may be formed, and a charge generation layer (CGL) may be formed between the stacks of the organic material layers.

Specifically, the organic electric device according to an 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. It may include (170) and a capping layer (180).

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

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

In this way, the first stack and the second stack may be organic material layers with the same stacked structure, or they may be organic material layers with different stacked 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. This charge generation layer (CGL) is formed between the first light-emitting layer 340 and the second light-emitting layer 440 to increase the current efficiency generated in each light-emitting layer and to smoothly distribute charges.

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

At this time, the second hole transport layer 430 includes a second stack (ST2) whose energy level is set higher than the triplet excited state energy level of the second light emitting layer 440.

Since the energy level of the second hole transport layer 430 is higher than that of the second light emitting layer 440, triplet exciton of the second light emitting layer 440 flows to the second hole transport layer 430, resulting in lower light emission efficiency. can be prevented. That is, the second hole transport layer 430 functions to transport holes from the inherent second light-emitting layer 440 and at the same time functions as an exciton blocking layer that prevents triplet excitons from crossing over. .

Additionally, in order to function as an exciton blocking layer, the first hole transport layer 330 may also be set to an energy level higher than the triplet excitation energy level of the first light emitting layer 340. In addition, the first electron transport layer 350 is also set to an energy level higher than the energy level of the triplet excitation state of the first light-emitting layer 340, and the second electron transport layer 450 is also set to a higher energy level than the triplet excitation state of the second light-emitting layer 440. It is desirable to set the energy level to a higher energy level than the state energy level.

In FIG. 3, n may be an integer between 1 and 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 light-emitting layers are formed using a multi-layer stack structure as shown in Figure 3, it is possible to manufacture an organic electroluminescent device that not only emits white light due to the mixing effect of the light emitted from each light-emitting layer, but also emits light of various colors. Organic electroluminescent devices that emit light can also be manufactured.

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

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

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

The encapsulation layer can play a role in preventing external oxygen and moisture from penetrating into the organic electric device.

Meanwhile, even if the core is similar to the same, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so the selection of the core and the combination of sub-substituents attached to it are important. Research is needed, and in particular, when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

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

An 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, an 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 is formed thereon. After forming an organic material layer including 320, 420, a hole transport layer (130, 330, 430), a light emitting layer (130, 330, 430), an electron transport layer (150, 350, 450), and an electron injection layer (160), It can be manufactured by depositing a material that can be used as the cathode 170 thereon. In addition, an auxiliary light emitting layer 220 is formed between the hole transport layers 130, 330, 430 and the light emitting layers 130, 330, 430, and an auxiliary electron transport layer (not shown) is formed 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 uses a variety of polymer materials, such as a solution process or solvent process rather than a deposition method, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, and doctor bleed process. It can be manufactured with fewer layers by methods such as a printing process, screen printing process, or 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 formation method.

The organic electric device according to an embodiment of the present invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

The organic electric device according to an embodiment of the present invention may be selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices.

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 that controls 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 one aspect of the present invention will be described.

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

<Formula 1>

In Formula 1, each symbol can be defined as follows.

1) T is NR''', S, O or CR'R".

2) a+b, c+d, and e+f are 1, and when a to f are each 0, it means a single bond.

3) n and m are 0 or 1, and n+m is 1 or more.

4) X ¹ , X ² , Y ¹ , Y ² , Z ¹ and Z ² are NR''', S, O or CR'R".

5) R ¹ to R ¹² are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and adjacent R ¹ to R ¹² may be bonded to each other to form a ring.

L' is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of.

R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

delete

6) R', R" and R''' are independently hydrogen, C ₁ ~ C ₅₀ alkyl group; C ₆ ~ C ₆₀ aryl group; C ₃ ~ C ₆₀ aliphatic ring group; O, N, S , Si, and P, and is selected from the group consisting of a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom, and R' and R" may be combined with each other to form a spiro compound.

Preferably, Formula 1 may be represented by Formula 2 below.

<Formula 2>

^{In Formula 2 , T , ​ ​}

More preferably, Formula 1 may be represented by Formula 3 or Formula 4 below.

<Formula 3>

<Formula 4>

^{In Formulas 3 and 4 , T ,}

Specifically, the compound represented by Formula 1 may be one of the following Formulas P-1 to Formula P-176, but the compound represented by Formula 1 is not limited thereto.

As another specific example of the present invention, the present invention includes a first electrode; second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Formula 1 alone or in combination.

As another specific example of the present invention, the present invention includes a first electrode; 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 side of both sides of the first electrode and the second electrode that is not in contact with the organic layer, and the organic layer or capping layer is represented by Formula 1 Includes the compounds singly or in combination.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an auxiliary electron transport layer, an electron transport layer, and an electron injection layer.

Preferably, the organic material layer includes the light-emitting layer or the light-emitting auxiliary layer.

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

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

As another specific example of the present invention, the present invention provides an electronic device including a display device including an organic electric element containing the compound represented by Chemical Chamber 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 compounds, or the compound may be included in a combination of two or more types of other compounds.

Hereinafter, the synthesis example of the compound represented by Formula 1 and the manufacturing example of the organic electric device according to the present invention will be described in detail through examples, but the present invention is not limited to the following examples.

< Synthesis example 1>

Final compounds 1 to 12 (final products 1 to 12) represented by Formula 1 according to the present invention can be synthesized through the method (1) from Sub A, B, and C as shown in Scheme 1 below, and are limited thereto. That is not the case.

<Scheme 1>

Sub A synthesis example

Sub A of Scheme 1 can be synthesized from Sub 1 through the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2>

Below, a specific example of Scheme 2 will be described.

Example of synthesis of Sub A-4

(1) Synthesis of Sub 1-2

After dissolving Sub 1-1 (60 g, 172.59 mmol) in DMF (860 ml) in a round bottom flask, Bis(pinacolato)diboron (48.21 g, 189.85 mmol), Pd(dppf)Cl ₂ (12.63 g, 17.26 mmol) ), KOAc (50.81 g, 517.76 mmol) were added and stirred at 100°C. When the reaction was completed, DMF was removed through distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 51.1 g of product (yield: 75%).

(2) Sub 1- 4 of synthesis

After dissolving Sub 1-2 (45 g, 114.0 mmol) obtained in the above synthesis with THF (570 ml) in a round bottom flask, Sub 1-3 (51.05 g, 114.0 mmol), Pd(PPh ₃ ) ₄ (6.59 g) , 5.7 mmol), NaOH (13.68 g, 342.01 mmol), and water (285 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 50.72 g of product (yield: 70%).

(3) Synthesis of Sub 1-5

Sub 1-4 (50 g, 78.66 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (3.60 g, 3.93 mmol), t-BuONa (22.68 g, 235.99 mmol), 50wt% P(t-Bu) ₃ (3.18 g, 7.87 mmol, toluene (400 ml) was added and stirred at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was purified on silica gel. Column and recrystallization gave 30.16 g of product (yield: 64%).

(4) Synthesis of Sub A-4

Sub 1-5 (30 g, 50.07 mmol) obtained in the above synthesis, Sub 1-6 (10.21 g, 50.07 mmol), Pd ₂ (dba) ₃ (2.29 g, 2.50 mmol), t-BuONa (14.44 g, 150.21 mmol), 50wt% P(t-Bu) ₃ (2.03 g, 5.01 mmol), toluene (250 ml) was added and stirred at 110°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, and the organic layer was washed with MgSO ₄ After drying and concentration, the resulting compound was recrystallized using a silica gel column to obtain 24.34 g of product (yield: 72%).

Synthesis example of Sub A-13

(1) Synthesis of Sub 2-2

After dissolving Sub 2-1 (60 g, 147.53 mmol) in DMF (740 ml) in a round bottom flask, Bis(pinacolato)diboron (41.21 g, 162.28 mmol), Pd(dppf)Cl ₂ (10.79 g, 14.75 mmol) ), KOAc (43.43 g, 442.58 mmol) was added and 52.21 g of product (yield: 78%) was obtained using the Sub A-4 synthesis method.

(2) Sub 2- 4 of synthesis

After dissolving Sub 2-2 (50 g, 110.19 mmol) obtained in the above synthesis with THF (550 ml) in a round bottom flask, Sub 2-3 (44.04 g, 110.19 mmol), Pd(PPh ₃ ) ₄ (6.37 g) , 5.51 mmol), NaOH (13.22 g, 330.56 mmol), and water (275 ml) were added, and 44.89 g of product (yield: 63%) was obtained using the Sub A-4 synthesis method.

(3) Synthesis of Sub A-13

Sub 2-4 (40 g, 61.86 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.83 g, 3.09 mmol), t-BuONa (17.84 g, 185.58 mmol), 50wt% P(t-Bu) ₃ (2.50 g, 6.19 mmol, toluene (310 ml) was added and 26.42 g of product (yield: 70%) was obtained using the above Sub A-4 synthesis method.

Synthesis example of Sub A-25

(1) Synthesis of Sub 3-2

After dissolving Sub 3-1 (50 g, 177.60 mmol) in DMF (890 ml) in a round bottom flask, Bis(pinacolato)diboron (49.61 g, 195.36 mmol), Pd(dppf)Cl ₂ (13.00 g, 17.76 mmol) ), KOAc (52.29 g, 532.80 mmol) was added and 48.43 g of product (yield: 83%) was obtained using the Sub A-4 synthesis method.

(2) Synthesis of Sub 3-4

After dissolving Sub 3-2 (45 g, 136.94 mmol) obtained in the above synthesis with THF (690 ml) in a round bottom flask, Sub 3-3 (74.07 g, 136.94 mmol), Pd(PPh ₃ ) ₄ (7.92 g , 6.85 mmol), NaOH (16.43 g, 410.83 mmol), and water (350 ml) were added, and 48.09 g of product (yield: 53%) was obtained using the Sub A-4 synthesis method.

(3) Synthesis of Sub A-25

Sub 3-4 (40 g, 60.37 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.76 g, 3.02 mmol), t-BuONa (17.41 g, 181.10 mmol), 50wt% P(t-Bu) ₃ (2.44 g, 6.04 mmol, toluene (310 ml) was added and 24.94 g of product (yield: 66%) was obtained using the above Sub A-4 synthesis method.

Synthesis example of Sub A-39

(1) Synthesis of Sub 1-2

After dissolving Sub 1-1 (50 g, 143.82 mmol) in DMF (720 ml) in a round bottom flask, Bis(pinacolato)diboron (40.17 g, 158.21 mmol), Pd(dppf)Cl ₂ (10.52 g, 14.38 mmol) ), KOAc (42.34 g, 431.47 mmol) was added and 42.57 g of product (yield: 75%) was obtained using the above Sub A-4 synthesis method.

(2) Synthesis of Sub 4-2

After dissolving Sub 1-2 (40 g, 101.34 mmol) obtained in the above synthesis with THF (500 ml) in a round bottom flask, Sub 4-1 (51.16 g, 101.34 mmol), Pd(PPh ₃ ) ₄ (5.86 g) , 5.07 mmol), NaOH (12.16 g, 304.01 mmol), and water (250 ml) were added, and 53.35 g of product (yield: 76%) was obtained using the Sub A-4 synthesis method.

(3) Synthesis of Sub A-39

Sub 4-2 (53 g, 76.51 mmol) obtained in the above synthesis was added with Pd ₂ (dba) ₃ (3.50 g, 3.83 mmol), t-BuONa (22.06 g, 229.54 mmol), 50wt% P(t-Bu) ₃ (3.10 g, 7.65 mmol, toluene (380 ml) was added and 28.74 g of product (yield: 60%) was obtained using the above Sub A-4 synthesis method.

Meanwhile, compounds belonging to Sub A may be the following compounds, but are not limited thereto.

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

compound FD-MS compound FD-MS Sub A-1 m/z=658.18(C ₄₆ H ₂₇ ClN ₂ O=659.19) Sub A-2 m/z=700.17(C ₄₈ H ₂₉ ClN ₂ S=701.28) Sub A-3 m/z=624.14(C ₄₂ H ₂₅ ClN ₂ S=625.19) Sub A-4 m/z=674.16(C ₄₆ H ₂₇ ClN ₂ S=675.25) Sub A-5 m/z=624.14(C ₄₂ H ₂₅ ClN ₂ S=625.19) Sub A-6 m/z=699.18(C ₄₉ H ₃₀ ClNS=700.30) Sub A-7 m/z=658.18(C ₄₆ H ₂₇ ClN ₂ O=659.19) Sub A-8 m/z=559.17(C ₃₉ H ₂₆ ClNO=560.09) Sub A-9 m/z=658.18(C ₄₆ H ₂₇ ClN ₂ O=659.19) Sub A-10 m/z=699.18 (C ₄₉ H ₃₀ ClNS=700.30) Sub A-11 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub A-12 m/z=624.14(C ₄₂ H ₂₅ ClN ₂ S=625.19) Sub A-13 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub A-14 m/z=658.17(C ₄₇ H ₂₇ ClO ₂ =659.18) Sub A-15 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub A-16 m/z=683.20(C ₄₉ H ₃₀ ClNO=684.24) Sub A-17 m/z=624.13(C ₄₃ H ₂₅ ClOS=625.18) Sub A-18 m/z=534.14(C ₃₇ H ₂₃ ClO ₂ =535.04) Sub A-19 m/z=599.11(C ₄₉ H ₃₀ ClNS=700.30) Sub A-20 m/z=484.12(C ₃₃ H ₂₁ ClO ₂ =484.98) Sub A-21 m/z=624.13(C ₄₃ H ₂₅ ClOS=625.18) Sub A-22 m/z=474.05(C ₃₀ H ₁₅ ClO ₂ S=474.96) Sub A-23 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub A-24 m/z=549.10(C ₃₆ H ₂₀ ClNOS=550.07) Sub A-25 m/z=625.13(C ₄₂ H ₂₄ ClNOS=626.17) Sub A-26 m/z=625.16(C ₄₃ H ₂₈ ClNS=626.21) Sub A-27 m/z=699.18(C ₄₉ H ₃₀ ClNS=700.30) Sub A-28 m/z=699.18(C ₄₉ H ₃₀ ClNS=700.30) Sub A-29 m/z=615.09(C ₄₀ H ₂₂ ClNS ₂ =616.19) Sub A-30 m/z=550.12(C ₃₇ H ₂₃ ClOS=551.10) Sub A-31 m/z=540.04(C ₃₄ H ₁₇ ClOS ₂ =541.08) Sub A-32 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub A-33 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub A-34 m/z=599.11 (C ₄₀ H ₂₂ ClNOS=600.13) Sub A-35 m/z=625.16(C ₄₃ H ₂₈ ClNS=626.21) Sub A-36 m/z=565.07(C ₃₆ H ₂₀ ClNS ₂ =566.13) Sub A-37 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub A-38 m/z=635.20(C ₄₅ H ₃₀ ClNO=636.19) Sub A-39 m/z=625.16(C ₄₃ H ₂₈ ClNS=626.21) Sub A-40 m/z=709.25(C ₅₂ H ₃₆ ClN=710.32) Sub A-41 m/z=625.16(C ₄₃ H ₂₈ ClNS=626.21) Sub A-42 m/z=624.13(C ₄₃ H ₂₅ ClOS=625.18) Sub A-43 m/z=624.13(C ₄₃ H ₂₅ ClOS=625.18) Sub A-44 m/z=684.22(C ₅₀ H ₃₃ ClO=685.26) Sub A-45 m/z=650.18(C ₄₆ H ₃₁ ClS=651.26) Sub A-46 m/z=634.21(C ₄₆ H ₃₁ ClO=635.20) Sub A-47 m/z=624.13(C ₄₃ H ₂₅ ClOS=625.18) Sub A-48 m/z=683.20(C ₄₉ H ₃₀ ClNO=684.24)

Sub B synthesis example

Sub B of Scheme 1 can be synthesized from Sub 1 through the reaction route of Scheme 3 below, but is not limited thereto.

<Scheme 3>

Below, a specific example of Scheme 3 will be described.

Example of synthesis of Sub B-8

(1) Synthesis of Sub 5-2

After dissolving Sub 5-1 (50 g, 162.54 mmol) in DMF (820 ml) in a round bottom flask, Bis(pinacolato)diboron (45.40 g, 178.79 mmol), Pd(dppf)Cl ₂ (11.89 g, 16.25 mmol) ), KOAc (47.85 g, 487.61 mmol) was added and stirred at 100°C. When the reaction was completed, DMF was removed through distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 47.27 g of product (yield: 82%).

(2) Synthesis of Sub 5-4

After dissolving Sub 5-2 (47 g, 132.51 mmol) obtained in the above synthesis with THF (660 ml) in a round bottom flask, Sub 5-3 (37.44 g, 132.51 mmol), Pd(PPh ₃ ) ₄ (7.66 g) , 6.63 mmol), NaOH (15.90 g, 397.54 mmol), and water (330 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 43.91 g of product (yield: 77%).

(3) Synthesis of Sub 5-5

Sub 5-4 (43 g, 99.91 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (4.57 g, 5.00 mmol), t-BuONa (28.81 g, 299.74 mmol), 50wt% P(t-Bu) ₃ (4.04 g, 9.99 mmol, toluene (500 ml) was added and stirred at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was passed through a silica gel column and Recrystallized to obtain 31.48 g of product (yield: 80%).

(4) Synthesis of Sub B-8

Sub 5-5 (30 g, 76.16 mmol) obtained in the above synthesis, Sub 5-6 (26.21 g, 76.16 mmol), Pd ₂ (dba) ₃ (3.49 g, 3.81 mmol), t-BuONa (21.96 g, 228.48 mmol), 50wt% P(t-Bu) ₃ (3.08 g, 7.62 mmol) and toluene (380 ml) were added and stirred at 110°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, and the organic layer was extracted with MgSO ₄ After drying and concentration, the resulting compound was recrystallized using a silica gel column to obtain 23.70 g of product (yield: 51%).

Synthesis example of Sub B-22

(1) Synthesis of Sub 6-2

After dissolving Sub 6-1 (50 g, 143.82 mmol) in DMF (720 ml) in a round bottom flask, Bis(pinacolato)diboron (40.17 g, 158.21 mmol), Pd(dppf)Cl ₂ (10.52 g, 14.38 mmol) ), KOAc (42.34 g, 431.47 mmol) was added and 40.30 g of product (yield: 71%) was obtained using the above Sub B-8 synthesis method.

(2) Synthesis of Sub 6-4

After dissolving Sub 6-2 (40 g, 101.34 mmol) obtained in the above synthesis with THF (500 ml) in a round bottom flask, Sub 6-3 (28.73 g, 101.34 mmol), Pd(PPh ₃ ) ₄ (5.86 g) , 5.07 mmol), NaOH (12.16 g, 304.01 mmol), and water (250 ml) were added, and 38.69 g of product (yield: 81%) was obtained using the Sub B-8 synthesis method.

(3) Synthesis of Sub B-22

Sub 6-4 (38 g, 80.61 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (3.69 g, 4.03 mmol), t-BuONa (23.24 g, 241.83 mmol), 50wt% P(t-Bu) ₃ (3.26 g, 8.06 mmol, toluene (400 ml) was added and 26.64 g of product (yield: 76%) was obtained using the above Sub B-8 synthesis method.

Synthesis example of Sub B-29

(1) Synthesis of Sub 7-2

After dissolving Sub 7-1 (50 g, 122.94 mmol) in DMF (620 ml) in a round bottom flask, Bis(pinacolato)diboron (34.34 g, 135.23 mmol), Pd(dppf)Cl ₂ (9.0 g, 12.29 mmol) ), KOAc (36.20 g, 368.81 mmol) was added and 45.74 g of product (yield: 82%) was obtained using the above Sub B-8 synthesis method.

(2) Synthesis of Sub 7-4

After dissolving Sub 7-2 (45 g, 99.17 mmol) obtained in the above synthesis with THF (500 ml) in a round bottom flask, Sub 7-3 (29.71 g, 99.17 mmol), Pd(PPh ₃ ) ₄ (5.73 g) , 4.96 mmol), NaOH (11.90 g, 297.51 mmol), and water (250 ml) were added, and 35.23 g of product (yield: 65%) was obtained using the Sub B-8 synthesis method.

(3) Synthesis of Sub B-29

Sub 7-4 (35 g, 64.04 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.93 g, 3.20 mmol), t-BuONa (18.47 g, 192.13 mmol), 50wt% P(t-Bu) ₃ (2.59 g, 6.40 mmol, toluene (320 ml) was added and 23.19 g of product (yield: 71%) was obtained using the above Sub B-8 synthesis method.

Synthesis example of Sub B-37

(1) Synthesis of Sub 8-2

After dissolving Sub 8-1 (50 g, 150.79 mmol) in DMF (750 ml) in a round bottom flask, Bis(pinacolato)diboron (42.12 g, 165.87 mmol), Pd(dppf)Cl ₂ (11.03 g, 15.08 mmol) ), KOAc (44.4 g, 452.37 mmol) was added and 47.96 g of product (yield: 84%) was obtained using the above Sub B-8 synthesis method.

(2) Synthesis of Sub 8-4

After dissolving Sub 8-2 (47 g, 124.12 mmol) obtained in the above synthesis with THF (620 ml) in a round bottom flask, Sub 8-3 (42.16 g, 124.12 mmol), Pd(PPh ₃ ) ₄ (7.17 g) , 6.21 mmol), NaOH (14.89 g, 372.37 mmol), and water (310 ml) were added, and 45.71 g of product (yield: 72%) was obtained using the Sub B-8 synthesis method.

(3) Synthesis of Sub B-37

Sub 8-4 (45 g, 87.99 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (4.03 g, 4.40 mmol), t-BuONa (25.37 g, 263.96 mmol), 50wt% P(t-Bu) ₃ (3.56 g, 8.80 mmol, toluene (440 ml) was added and 29.75 g of product (yield: 76%) was obtained using the above Sub B-8 synthesis method.

Meanwhile, compounds belonging to Sub B may be the following compounds, but are not limited thereto.

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

compound FD-MS compound FD-MS Sub B-1 m/z=493.12(C ₃₄ H ₂₀ ClNO=493.99) Sub B-2 m/z=459.08(C ₃₀ H ₁₈ ClNS=459.99) Sub B-3 m/z=509.10(C ₃₄ H ₂₀ ClNS=510.05) Sub B-4 m/z=568.17(C ₄₀ H ₂₅ ClN ₂ =569.10) Sub B-5 m/z=459.08(C ₃₀ H ₁₈ ClNS=459.99) Sub B-6 m/z=568.17(C ₄₀ H ₂₅ ClN ₂ =569.10) Sub B-7 m/z=569.15(C ₄₀ H ₂₄ ClNO=570.09) Sub B-8 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub B-9 m/z=644.20 (C ₄₆ H ₂₉ ClN ₂ =645.20) Sub B-10 m/z=549.10 (C ₃₆ H ₂₀ ClNOS=550.07) Sub B-11 m/z=575.15(C ₃₉ H ₂₆ ClNS=576.15) Sub B-12 m/z=518.15(C ₃₆ H ₂₃ ClN ₂ =519.04) Sub B-13 m/z=518.14(C ₃₇ H ₂₃ ClO=519.04) Sub B-14 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-15 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-16 m/z=583.13(C ₄₀ H ₂₂ ClNO ₂ =584.07) Sub B-17 m/z=493.12(C ₃₄ H ₂₀ ClNO=493.99) Sub B-18 m/z=549.10(C ₃₆ H ₂₀ ClNOS=550.07) Sub B-19 m/z=443.11(C ₃₀ H ₁₈ ClNO=443.93) Sub B-20 m/z=583.13(C ₄₀ H ₂₂ ClNO ₂ =584.07) Sub B-21 m/z=418.08(C ₂₈ H ₁₅ ClO ₂ =418.88) Sub B-22 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-23 m/z=519.14(C ₃₆ H ₂₂ ClNO=520.03) Sub B-24 m/z=549.10(C ₃₆ H ₂₀ ClNOS=550.07) Sub B-25 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-26 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-27 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub B-28 m/z=534.12(C ₃₇ H ₂₃ ClS=535.10) Sub B-29 m/z=509.10(C ₃₄ H ₂₀ ClNS=510.05) Sub B-30 m/z=575.15(C ₃₉ H ₂₆ ClNS=576.15) Sub B-31 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-32 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-33 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub B-34 m/z=534.12 (C ₃₇ H ₂₃ ClS=535.10) Sub B-35 m/z=535.12(C ₃₆ H ₂₂ ClNS=536.09) Sub B-36 m/z=565.07(C ₃₆ H ₂₀ ClNS ₂ =566.13) Sub B-37 m/z=444.13(C ₃₁ H ₂₁ ClO=444.96) Sub B-38 m/z=460.11(C ₃₁ H ₂₁ ClS=461.02) Sub B-39 m/z=444.13(C ₃₁ H ₂₁ ClO=444.96) Sub B-40 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub B-41 m/z=519.18(C ₃₇ H ₂₆ ClN=520.07) Sub B-42 m/z=469.16(C ₃₃ H ₂₄ ClN=470.01) Sub B-43 m/z=444.13(C ₃₁ H ₂₁ ClO=444.96) Sub B-44 m/z=575.15(C ₃₉ H ₂₆ ClNS=576.15) Sub B-45 m/z=534.12(C ₃₇ H ₂₃ ClS=535.10) Sub B-46 m/z=518.14(C ₃₇ H ₂₃ ClO=519.04) Sub B-47 m/z=584.14(C ₄₁ H ₂₅ ClS=585.16) Sub B-48 m/z=593.19(C ₄₃ H ₂₈ ClN=594.15)

Sub C synthesis example

Sub C of Scheme 1 can be synthesized from Sub 1 through the reaction route of Scheme 4 below, but is not limited thereto.

<Scheme 4>

Below, a specific example of Scheme 4 will be described.

Synthesis example of Sub C-11

(1) Synthesis of Sub 9-2

After dissolving Sub 9-1 (50 g, 168.02 mmol) in DMF (840 ml) in a round bottom flask, Bis(pinacolato)diboron (46.93 g, 184.82 mmol), Pd(dppf)Cl ₂ (12.29 g, 16.80 mmol) ), KOAc (49.47 g, 504.05 mmol) was added and stirred at 100°C. When the reaction was completed, DMF was removed through distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 40.53 g of product (yield: 70%).

(2) Synthesis of Sub 9-4

After dissolving Sub 9-2 (40 g, 116.06 mmol) obtained in the above synthesis with THF (580 ml) in a round bottom flask, Sub 9-3 (32.79 g, 116.06 mmol), Pd(PPh ₃ ) ₄ (6.71 g) , 5.8 mmol), NaOH (13.93 g, 348.17 mmol), and water (290 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 33.17 g of product (yield: 68%).

(3) Synthesis of Sub 9-5

Sub 9-4 (33 g, 78.51 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (3.59 g, 3.93 mmol), t-BuONa (22.64 g, 235.52 mmol), 50wt% P(t-Bu) ₃ (3.18 g, 7.85 mmol, toluene (400 ml) was added and stirred at 100°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated, and the resulting compound was passed through a silica gel column and Recrystallized to obtain 22.60 g of product (yield: 75%).

(4) Synthesis of Sub C-11

Sub 9-5 (22 g, 57.31 mmol) obtained in the above synthesis, Sub 9-6 (16.05 g, 57.31 mmol), Pd ₂ (dba) ₃ (2.62 g, 2.87 mmol), t-BuONa (16.52 g, 171.92 mmol), 50wt% P(t-Bu) ₃ (2.32 g, 5.73 mmol) and toluene (290 ml) were added and stirred at 110°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, and the organic layer was extracted with MgSO ₄ After drying and concentration, the resulting compound was recrystallized using a silica gel column to obtain 25.19 g of product (yield: 0.82%).

Synthesis example of Sub C-17

(1) Synthesis of Sub 10-2

After dissolving Sub 10-1 (50 g, 100.65 mmol) in DMF (500 ml) in a round bottom flask, Bis(pinacolato)diboron (28.11 g, 110.71 mmol), Pd(dppf)Cl ₂ (7.36 g, 10.06 mmol) ), KOAc (29.63 g, 301.94 mmol) was added and 39.41 g of product (yield: 72%) was obtained using the Sub C-11 synthesis method.

(2) Synthesis of Sub 10-4

After dissolving Sub 10-2 (39 g, 71.71 mmol) obtained in the above synthesis with THF (360 ml) in a round bottom flask, Sub 10-3 (20.33 g, 71.71 mmol), Pd(PPh ₃ ) ₄ (4.14 g) , 3.59 mmol), NaOH (8.61 g, 215.13 mmol), and water (180 ml) were added, and 36.49 g of product (yield: 82%) was obtained using the Sub C-11 synthesis method.

(3) Synthesis of Sub C-17

Sub 10-4 (36 g, 58.01 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.66 g, 2.90 mmol), t-BuONa (16.73 g, 174.04 mmol), 50wt% P(t-Bu) ₃ (2.35 g, 5.80 mmol, toluene (290 ml) was added and 26.09 g of product (yield: 77%) was obtained using the Sub C-11 synthesis method above.

Synthesis example of Sub C-27

(1) Synthesis of Sub 11-2

After dissolving Sub 11-1 (50 g, 115.54 mmol) in DMF (580 ml) in a round bottom flask, Bis(pinacolato)diboron (32.27 g, 127.09 mmol), Pd(dppf)Cl ₂ (8.45 g, 11.55 mmol) ), KOAc (34.02 g, 346.62 mmol) was added and 41.57 g of product (yield: 75%) was obtained using the Sub C-11 synthesis method.

(2) Synthesis of Sub 11-4

After dissolving Sub 11-2 (40 g, 83.37 mmol) obtained in the above synthesis with THF (420 ml) in a round bottom flask, Sub 11-3 (24.98 g, 83.37 mmol), Pd(PPh ₃ ) ₄ (4.82 g , 4.17 mmol), NaOH (10.0 g, 250.10 mmol), and water (210 ml) were added, and 32.93 g of product (yield: 69%) was obtained using the Sub C-11 synthesis method.

(3) Synthesis of Sub C-27

Sub 11-4 (32 g, 55.89 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.56 g, 2.79 mmol), t-BuONa (16.11 g, 167.67 mmol), 50wt% P(t-Bu) ₃ (2.26 g, 5.59 mmol, toluene (280 ml) was added and 21.87 g of product (yield: 73%) was obtained using the above Sub C-11 synthesis method.

Synthesis example of Sub C-42

(1) Synthesis of Sub 12-2

After dissolving Sub 12-1 (50 g, 115.81 mmol) in DMF (580 ml) in a round bottom flask, Bis(pinacolato)diboron (32.35 g, 127.39 mmol), Pd(dppf)Cl ₂ (8.47 g, 11.58 mmol) ), KOAc (34.10 g, 347.42 mmol) was added and 43.25 g of product (yield: 78%) was obtained using the Sub C-11 synthesis method.

(2) Synthesis of Sub 12-4

After dissolving Sub 12-2 (43 g, 89.8 mmol) obtained in the above synthesis with THF (450 ml) in a round bottom flask, Sub 12-3 (30.5 g, 89.8 mmol), Pd(PPh ₃ ) ₄ (5.19 g) , 4.49 mmol), NaOH (10.78 g, 269.41 mmol), and water (225 ml) were added, and 39.55 g of product (yield: 72%) was obtained using the Sub C-11 synthesis method.

(3) Synthesis of Sub C-42

Sub 12-4 (39 g, 63.77 mmol) obtained in the above synthesis, Pd ₂ (dba) ₃ (2.92 g, 3.19 mmol), t-BuONa (18.39 g, 191.30 mmol), 50wt% P(t-Bu) ₃ (2.58 g, 6.38 mmol, toluene (320 ml) was added and 26.41 g of product (yield: 76%) was obtained using the above Sub C-11 synthesis method.

Meanwhile, compounds belonging to Sub C may be the following compounds, but are not limited thereto.

Table 3 below shows the FD-MS values of compounds belonging to Sub C.

compound FD-MS compound FD-MS Sub C-1 m/z=493.12(C ₃₄ H ₂₀ ClNO=493.99) Sub C-2 m/z=509.10(C ₃₄ H ₂₀ ClNS=510.05) Sub C-3 m/z=518.15(C ₃₆ H ₂₃ ClN ₂ =519.04) Sub C-4 m/z=509.10(C ₃₄ H ₂₀ ClNS=510.05) Sub C-5 m/z=608.17(C ₄₂ H ₂₅ ClN ₂ O=609.13) Sub C-6 m/z=459.08(C ₃₀ H ₁₈ ClNS=459.99) Sub C-7 m/z=459.08(C ₃₀ H ₁₈ ClNS=459.99) Sub C-8 m/z=443.11(C ₃₀ H ₁₈ ClNO=443.93) Sub C-9 m/z=518.15 (C ₃₆ H ₂₃ ClN ₂ =519.04) Sub C-10 m/z=493.12 (C ₃₄ H ₂₀ ClNO=493.99) Sub C-11 m/z=535.12(C ₃₆ H ₂₂ ClNS=536.09) Sub C-12 m/z=625.16(C ₄₃ H ₂₈ ClNS=626.21) Sub C-13 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub C-14 m/z=569.15(C ₄₀ H ₂₄ ClNO=570.09) Sub C-15 m/z=519.14(C ₃₆ H ₂₂ ClNO=520.03) Sub C-16 m/z=418.08(C ₂₈ H ₁₅ ClO ₂ =418.88) Sub C-17 m/z=583.13(C ₄₀ H ₂₂ ClNO ₂ =584.07) Sub C-18 m/z=518.14(C ₃₇ H ₂₃ ClO=519.04) Sub C-19 m/z=583.13(C ₄₀ H ₂₂ ClNO ₂ =584.07) Sub C-20 m/z=368.06(C ₂₄ H ₁₃ ClO ₂ =368.82) Sub C-21 m/z=443.11(C ₃₀ H ₁₈ ClNO=443.93) Sub C-22 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub C-23 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub C-24 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub C-25 m/z=434.05(C ₂₈ H ₁₅ ClOS=434.94) Sub C-26 m/z=585.13(C ₄₀ H ₂₄ ClNS=586.15) Sub C-27 m/z=535.12(C ₃₆ H ₂₂ ClNS=536.09) Sub C-28 m/z=450.03(C ₂₈ H ₁₅ ClS ₂ =451.00) Sub C-29 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub C-30 m/z=509.10(C ₃₄ H ₂₀ ClNS=510.05) Sub C-31 m/z=599.11(C ₄₀ H ₂₂ ClNOS=600.13) Sub C-32 m/z=534.12(C ₃₇ H ₂₃ ClS=535.10) Sub C-33 m/z=459.08(C ₃₀ H ₁₈ ClNS=459.99) Sub C-34 m/z=450.03 (C ₂₈ H ₁₅ ClS ₂ =451.00) Sub C-35 m/z=410.09(C ₂₇ H ₁₉ ClS=410.96) Sub C-36 m/z=450.03(C ₂₈ H ₁₅ ClS ₂ =451.00) Sub C-37 m/z=460.11(C ₃₁ H ₂₁ ClS=461.02) Sub C-38 m/z=420.16(C ₃₀ H ₂₅ Cl=420.98) Sub C-39 m/z=545.19(C ₃₉ H ₂₈ ClN=546.11) Sub C-40 m/z=460.11(C ₃₁ H ₂₁ ClS=461.02) Sub C-41 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub C-42 m/z=544.20(C ₄₀ H ₂₉ Cl=545.12) Sub C-43 m/z=609.19(C ₄₃ H ₂₈ ClNO=610.15) Sub C-44 m/z=544.20(C ₄₀ H ₂₉ Cl=545.12) Sub C-45 m/z=593.19(C ₄₃ H ₂₈ ClN=594.15) Sub C-46 m/z=584.14(C ₄₁ H ₂₅ ClS=585.16) Sub C-47 m/z=460.11(C ₃₁ H ₂₁ ClS=461.02) Sub C-48 m/z=635.24(C ₄₆ H ₃₄ ClN=636.24)

[Example of synthesis of final compound 1]

Final products 1, 5, and 9 of Scheme 1 can be synthesized from Sub A through the reaction route of Scheme 5, but are not limited thereto.

<Scheme 5>

Below, a specific example of Scheme 5 will be described.

Synthesis example of P-70

(1) Synthesis of Sub B-22-1

After dissolving Sub B-22 (20 g, 53.36 mmol) in THF (230 ml) in a round bottom flask, Sub 6-5 (9.98 g, 45.98 mmol), Pd(PPh ₃ ) ₄ (2.66 g, 2.30 mmol) , NaOH (5.52 g, 137.95 mmol) and water (115 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 21.29 g of product (yield: 81%).

(2) Synthesis of Sub B-22-2

Sub B-22-1 (21 g, 36.74 mmol) and Triphenylphosphine (28.91 g, 110.21 mmol) obtained in the above synthesis were dissolved in o-Dichlorobenzene (180 ml) and refluxed for 24 hours. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 13.48 g of product (yield: 68%).

(3) Synthesis of P-70

Add Sub B-22-2 (13 g, 24.09 mmol) and Sub 6-6 (5.41 g, 26.50 mmol) obtained in the above synthesis to a round bottom flask, and add Pd ₂ (dba) ₃ (1.10 g, 1.20 mmol) and NaOt. -Bu (6.95 g, 72.27 mmol), 50wt% P(t-Bu) ₃ (0.97 g, 2.41 mmol), and toluene (120 mL) were added, respectively, and stirred at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 7.71 g of product (yield: 52%).

Synthesis example of P-77

(1) Synthesis of Sub B-29-1

After dissolving Sub B-29 (20 g, 39.21 mmol) in THF (200 ml) in a round bottom flask, Sub 7-5 (6.55 g, 39.21 mmol), Pd(PPh ₃ ) ₄ (2.27 g, 1.96 mmol) , NaOH (4.71 g, 117.64 mmol) and water (100 ml) were added and 17.31 g of product (yield: 74%) was obtained using the P-70 synthesis method.

(2) Synthesis of Sub B-29-2

Sub B-29-1 (17 g, 28.49 mmol) and Triphenylphosphine (22.42 g, 85.47 mmol) obtained in the above synthesis were dissolved in o-Dichlorobenzene (145 ml), and 9.33 g of product (9.33 g) was obtained using the P-70 synthesis method. Yield: 58%) was obtained.

(3) Synthesis of P-77

Add Sub B-29-2 (9 g, 15.94 mmol) and Sub 6-6 (3.58 g, 17.53 mmol) obtained in the above synthesis to a round bottom flask, add Pd ₂ (dba) ₃ (0.73 g, 0.80 mmol), NaOt -Bu (4.60 g, 47.81 mmol), 50wt% P(t-Bu) ₃ (0.64 g, 1.59 mmol), and toluene (80 mL) were added, respectively, and then 6.63 g of product was obtained using the P-70 synthesis method. (yield: 65%) was obtained.

Synthesis example of P-85

(1) Synthesis of Sub B-37-1

After dissolving Sub B-37 (20 g, 44.95 mmol) in THF (225 ml) in a round bottom flask, Sub 8-5 (9.75 g, 44.95 mmol), Pd(PPh ₃ ) ₄ (2.60 g, 2.25 mmol) , NaOH (5.39 g, 134.84 mmol) and water (112 ml) were added and 19.08 g of product (yield: 73%) was obtained using the P-70 synthesis method.

(2) Synthesis of Sub B-37-2

Sub B-37-1 (19 g, 32.66 mmol) and Triphenylphosphine (25.70 g, 97.99 mmol) obtained in the above synthesis were dissolved in o-Dichlorobenzene (165 ml), and 10.95 g of product (10.95 g) was obtained using the P-70 synthesis method. Yield: 61%) was obtained.

(3) Synthesis of P-85

Add Sub B-37-2 (10 g, 18.19 mmol) and Sub 6-6 (4.08 g, 20.01 mmol) obtained in the above synthesis to a round bottom flask, and add Pd ₂ (dba) ₃ (0.83 g, 0.91 mmol) and NaOt. -Bu (5.25 g, 54.58 mmol), 50wt% P(t-Bu) ₃ (0.74 g, 1.82 mmol), and toluene (90 mL) were added, respectively, and then 7.28 g of product was obtained using the P-70 synthesis method. (yield: 64%) was obtained.

[Example of synthesis of final compound 2]

The final compounds 2, 6, and 11 of Scheme 1 can be synthesized from Sub A through the reaction route of Scheme 6 below, but are not limited thereto.

<Scheme 6>

Below, a specific example of Scheme 6 will be described.

Example of synthesis of P-4

(1) Synthesis of Sub A-4-1

After dissolving Sub A-4 (20 g, 29.62 mmol) in THF (150 ml) in a round bottom flask, Sub 1-7 (4.09 g, 29.62 mmol), Pd(PPh ₃ ) ₄ (1.71 g, 1.48 mmol) , NaOH (3.55 g, 88.86 mmol) and water (75 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 11.72 g of product (yield: 54%).

(2) Synthesis of P-4

Sub A-4-1 (11 g, 15.01 mmol) obtained in the above synthesis was added to a round bottom flask along with Pd(OAc) ₂ (0.34 g, 1.50 mmol) and 3-nitropyridine (0.19 g, 1.50 mmol) and C ₆ After dissolving in F ₆ (44 ml) and DMI (22 ml), tert-butyl peroxybenzoate (5.83 g, 30.02 mmol) was added and stirred at 90°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 6.25 g of product (yield: 57%).

Synthesis example of P-13

(1) Synthesis of Sub A-13-1

After dissolving Sub A-13 (20 g, 32.78 mmol) in THF (165 ml) in a round bottom flask, Sub 2-5 (6.16 g, 32.78 mmol), Pd(PPh ₃ ) ₄ (1.89 g, 1.64 mmol) , NaOH (3.93 g, 98.34 mmol) and water (82 ml) were added, and 15.05 g of product (yield: 64%) was obtained using the P-4 synthesis method.

(2) Synthesis of P-13

Sub A-13-1 (15 g, 20.90 mmol) obtained in the above synthesis was added to a round bottom flask along with Pd(OAc) ₂ (0.47 g, 2.09 mmol) and 3-nitropyridine (0.26 g, 2.09 mmol) and C ₆ After dissolving in F ₆ (60 ml) and DMI (30 ml), tert-butyl peroxybenzoate (8.12 g, 41.79 mmol) was added and 7.18 g of product (yield: 48%) was obtained using the above P-4 synthesis method. .

Synthesis example of P-39

(1) Synthesis of Sub A-39-1

After dissolving Sub A-39 (20 g, 31.94 mmol) in THF (160 ml) in a round bottom flask, Sub 1-7 (4.41 g, 31.94 mmol), Pd(PPh ₃ ) ₄ (1.85 g, 1.60 mmol) , NaOH (3.83 g, 95.81 mmol) and water (80 ml) were added, and 13.54 g of product (yield: 62%) was obtained using the P-4 synthesis method.

(2) Synthesis of P-39

Sub A-39-1 (13 g, 19.01 mmol) obtained in the above synthesis was added to a round bottom flask along with Pd(OAc) ₂ (0.43 g, 1.90 mmol) and 3-nitropyridine (0.24 g, 1.90 mmol) and C ₆ After dissolving in F ₆ (52 ml) and DMI (26 ml), tert-butyl peroxybenzoate (7.38 g, 38.02 mmol) was added and 5.98 g of product (yield: 43%) was obtained using the above P-4 synthesis method. .

Synthesis example of P-107

(1) Synthesis of Sub C-11-1

After dissolving Sub C-11 (20 g, 37.31 mmol) in THF (186 ml) in a round bottom flask, Sub 2-5 (7.01 g, 37.31 mmol), Pd(PPh ₃ ) ₄ (2.16 g, 1.87 mmol) , NaOH (4.48 g, 111.92 mmol) and water (93 ml) were added, and 15.85 g of product (yield: 66%) was obtained using the above P-4 synthesis method.

(2) Synthesis of P-107

Sub C-11-1 (15 g, 23.30 mmol) obtained in the above synthesis was added to a round bottom flask along with Pd(OAc) ₂ (0.52 g, 2.33 mmol) and 3-nitropyridine (0.29 g, 2.33 mmol) and C ₆ After dissolving in F ₆ (60 ml) and DMI (30 ml), tert-butyl peroxybenzoate (9.05 g, 46.60 mmol) was added and 9.12 g of product (yield: 61%) was obtained using the above P-4 synthesis method. .

Synthesis example of P-123

(1) Synthesis of Sub C-27-1

After dissolving Sub C-27 (20 g, 37.31 mmol) in THF (186 ml) in a round bottom flask, Sub 2-5 (7.01 g, 37.31 mmol), Pd(PPh ₃ ) ₄ (2.16 g, 1.87 mmol) , NaOH (4.48 g, 111.92 mmol) and water (93 ml) were added, and 13.93 g of product (yield: 58%) was obtained using the above P-4 synthesis method.

(2) Synthesis of P-123

Sub C-27-1 (13 g, 20.19 mmol) obtained in the above synthesis was added to a round bottom flask along with Pd(OAc) ₂ (0.45 g, 2.02 mmol) and 3-nitropyridine (0.25 g, 2.02 mmol) and C ₆ After dissolving in F ₆ (52 ml) and DMI (26 ml), tert-butyl peroxybenzoate (7.84 g, 40.39 mmol) was added and 6.09 g of product (yield: 47%) was obtained using the above P-4 synthesis method. .

Synthesis example of P-138

(1) Synthesis of Sub C-42-1

After dissolving Sub C-42 (20 g, 36.69 mmol) in THF (183 ml) in a round bottom flask, Sub 12-5 (6.90 g, 36.69 mmol), Pd(PPh ₃ ) ₄ (2.12 g, 1.83 mmol) , NaOH (4.40 g, 110.07 mmol) and water (91 ml) were added, and 12.93 g of product (yield: 54%) was obtained using the above P-4 synthesis method.

(2) Synthesis of P-138

Sub C-42-1 (12 g, 18.38 mmol) obtained in the above synthesis was added to a round bottom flask along with Pd(OAc) ₂ (0.41 g, 1.84 mmol) and 3-nitropyridine (0.23 g, 1.84 mmol) and C ₆ After dissolving in F ₆ (48 ml) and DMI (24 ml), tert-butyl peroxybenzoate (7.14 g, 36.76 mmol) was added and 5.86 g of product (yield: 49%) was obtained using the above P-4 synthesis method. .

[Example of synthesis of final compound 3]

The final compounds 3, 7, and 10 of Scheme 1 can be synthesized from Sub A through the reaction route of Scheme 7 below, but are not limited thereto.

<Scheme 7>

Below, a specific example of Scheme 7 will be described.

Synthesis example of P-56

(1) Synthesis of Sub B-8-1

After dissolving Sub B-8 (20 g, 32.78 mmol) in THF (165 ml) in a round bottom flask, Sub 5-7 (6.03 g, 32.78 mmol), Pd(PPh ₃ ) ₄ (1.89 g, 1.64 mmol) , NaOH (3.93 g, 98.34 mmol) and water (82 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 16.14 g of product (yield: 69%).

(2) Synthesis of P-56

Sub B-8-1 (16 g, 22.41 mmol) obtained in the above synthesis was added to an excess of trifluoromethanesulfonic acid and stirred at room temperature for 24 hours, then water and pyridine (8:1) were slowly added and stirred. did. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 6.42 g of product (yield: 42%).

Synthesis example of P-113

(1) Synthesis of Sub C-17-1

After dissolving Sub C-17 (20 g, 34.24 mmol) in THF (170 ml) in a round bottom flask, Sub 5-7 (6.30 g, 34.24 mmol), Pd(PPh ₃ ) ₄ (1.98 g, 1.71 mmol) , NaOH (4.11 g, 102.73 mmol) and water (85 ml) were added and 15.30 g of product (yield: 65%) was obtained using the P-56 synthesis method.

(2) Synthesis of P-113

Sub C-17-1 (15 g, 21.81 mmol) obtained in the above synthesis was added to an excess of trifluoromethanesulfonic acid and stirred at room temperature for 24 hours, then water and pyridine (8:1) were slowly added thereto. 7.29 g of product (yield: 51%) was obtained using the P-56 synthesis method.

[Example of synthesis of final compound 4]

The final compounds 4, 8, and 12 of Scheme 1 can be synthesized from Sub A through the reaction route of Scheme 8 below, but are not limited thereto.

<Scheme 8>

Below, a specific example of Scheme 8 will be described.

Synthesis example of P-25

(1) Synthesis of Sub A-25-1

After dissolving Sub A-25 (20 g, 31.94 mmol) in THF (160 ml) in a round bottom flask, Sub 3-5 (5.75 g, 31.94 mmol), Pd(PPh ₃ ) ₄ (1.85 g, 1.60 mmol) , NaOH (3.83 g, 95.82 mmol), water (80 ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 12.05 g of product (yield: 52%).

(2) Synthesis of P-25

After dissolving Sub A-25-1 (12 g, 16.53 mmol) obtained in the above synthesis with THF (85 ml) in a round bottom flask, THF (66.12 ml, 66.13 mmol) in which 1.0M methylmagnesium bromide was dissolved was slowly added dropwise. Afterwards, it was stirred at room temperature. When the reaction was completed, extraction was performed with diethyl ether and water, and the organic layer was dried with MgSO ₄ and concentrated to obtain an intermediate product. This intermediate product was dissolved in acetic acid solution (96 ml), HCl (2 ml) was added, and refluxed. When the reaction was completed, water was added and stirred, and the resulting solid was filtered under reduced pressure and washed with water and methanol to obtain 5.27 g of the product as a white powder (yield: 45%).

Table 4 below shows the FD-MS values of compounds P-1 to P-176 synthesized according to the above synthesis method.

compound FD-MS compound FD-MS P-1 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-2 m/z=782.28(C ₅₇ H ₃₈ N ₂ S=783.01) P-3 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-4 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-5 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-6 m/z=805.24(C ₅₉ H ₃₅ NOS=806.00) P-7 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-8 m/z=690.27(C ₅₁ H ₃₄ N ₂ O=690.85) P-9 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-10 m/z=755.23(C ₅₅ H ₃₃ NOS=755.94) P-11 m/z=815.32(C ₆₂ H ₄₁ NO=816.02) P-12 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-13 m/z=715.25(C ₅₃ H ₃₃ NO ₂ =715.85) P-14 m/z=730.20(C ₅₃ H ₃₀ O ₂ S=730.88) P-15 m/z=705.18 (C ₅₀ H ₂₇ NO ₂ S=705.83) P-16 m/z=755.23(C ₅₅ H ₃₃ NOS=755.94) P-17 m/z=805.24(C ₅₉ H ₃₅ NOS=806.00) P-18 m/z=606.17(C ₄₃ H ₂₆ O ₂ S=606.74) P-19 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-20 m/z=615.22(C ₄₅ H ₂₉ NO ₂ =615.73) P-21 m/z=680.18(C ₄₉ H ₂₈ O ₂ S=680.82) P-22 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-23 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-24 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-25 m/z=707.23(C ₅₁ H ₃₃ NOS=707.89) P-26 m/z=731.23(C ₅₃ H ₃₃ NOS=731.91) P-27 m/z=755.23(C ₅₅ H ₃₃ NOS=755.94) P-28 m/z=805.24(C ₅₉ H ₃₅ NOS=806.00) P-29 m/z=721.15(C ₅₀ H ₂₇ NOS ₂ =721.89) P-30 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-31 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-32 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-33 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-34 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-35 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-36 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-37 m/z=731.23(C ₅₃ H ₃₃ NOS=731.91) P-38 m/z=707.23(C ₅₁ H ₃₃ NOS=707.89) P-39 m/z=731.23(C ₅₃ H ₃₃ NOS=731.91) P-40 m/z=815.32(C ₆₂ H ₄₁ NO=816.02) P-41 m/z=731.23(C ₅₃ H ₃₃ NOS=731.91) P-42 m/z=755.23(C ₅₅ H ₃₃ NOS=755.94) P-43 m/z=755.23(C ₅₅ H ₃₃ NOS=755.94) P-44 m/z=815.32(C ₆₂ H ₄₁ NO=816.02) P-45 m/z=756.25(C ₅₆ H ₃₆ OS=756.96) P-46 m/z=815.32(C ₆₂ H ₄₁ NO=816.02) P-47 m/z=706.23(C ₅₂ H ₃₄ OS=706.90) P-48 m/z=755.23(C ₅₅ H ₃₃ NOS=755.94) P-49 m/z=700.25(C ₅₂ H ₃₂ N ₂ O=700.84) P-50 m/z=565.15(C ₄₀ H ₂₃ NOS=565.59) P-51 m/z=715.23(C ₅₃ H ₃₃ NS=715.91) P-52 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-53 m/z=665.22(C ₄₉ H ₃₁ NS=665.85) P-54 m/z=749.28(C ₅₆ H ₃₅ N ₃ =749.92) P-55 m/z=691.20(C ₅₀ H ₂₉ NOS=691.85) P-56 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-57 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.90) P-58 m/z=730.21(C ₅₂ H ₃₀ N ₂ OS=730.89) P-59 m/z=631.20(C ₄₅ H ₂₉ NOS=631.79) P-60 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-61 m/z=640.19(C ₄₇ H ₂₈ OS=640.80) P-62 m/z=615.17(C ₄₄ H ₂₅ NOS=615.75) P-63 m/z=640.19(C ₄₇ H ₂₈ OS=640.80) P-64 m/z=665.24(C ₄₉ H ₃₁ NO ₂ =665.79) P-65 m/z=674.24(C ₅₀ H ₃₀ N ₂ O=674.80) P-66 m/z=605.14(C ₄₂ H ₂₃ NO ₂ S=605.71) P-67 m/z=649.24(C ₄₉ H ₃₁ NO=649.79) P-68 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-69 m/z=665.24(C ₄₉ H ₃₁ NO ₂ =665.79) P-70 m/z=615.17(C ₄₄ H ₂₅ NOS=615.75) P-71 m/z=725.27(C ₅₅ H ₃₅ NO=725.89) P-72 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-73 m/z=615.17(C ₄₄ H ₂₅ NOS=615.75) P-74 m/z=615.17(C ₄₄ H ₂₅ NOS=615.75) P-75 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-76 m/z=715.23(C ₅₃ H ₃₃ NS=715.91) P-77 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.80) P-78 m/z=631.20(C ₄₅ H ₂₉ NOS=631.79) P-79 m/z=641.18(C ₄₆ H ₂₇ NOS=641.79) P-80 m/z=565.15(C ₄₀ H ₂₃ NOS=565.69) P-81 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-82 m/z=640.19(C ₄₇ H ₂₈ OS=640.80) P-83 m/z=741.25(C ₅₅ H ₃₅ NS=741.95) P-84 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-85 m/z=625.24(C ₄₇ H ₃₁ NO=625.77) P-86 m/z=641.22(C ₄₇ H ₃₁ NS=641.83) P-87 m/z=625.24(C ₄₇ H ₃₁ NO=625.77) P-88 m/z=691.29(C ₅₂ H ₃₇ NO=691.87) P-89 m/z=625.24(C ₄₇ H ₃₁ NO=625.77) P-90 m/z=675.29(C ₅₂ H ₃₇ N=675.88) P-91 m/z=651.26(C ₄₉ H ₃₃ NO=651.81) P-92 m/z=631.20(C ₄₅ H ₂₉ NOS=631.79) P-93 m/z=665.22(C ₄₉ H ₃₁ NS=665.85) P-94 m/z=649.24(C ₄₉ H ₃₁ NO=649.79) P-95 m/z=666.24(C ₅₀ H ₃₄ S=666.88) P-96 m/z=665.22(C ₄₉ H ₃₁ NS=665.85) P-97 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-98 m/z=641.22(C ₄₇ H ₃₁ NS=641.83) P-99 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-100 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.80) P-101 m/z=680.19(C ₄₈ H ₂₈ N ₂ OS=680.83) P-102 m/z=665.22(C ₄₉ H ₃₁ NS=665.85) P-103 m/z=565.15(C ₄₀ H ₂₃ NOS=565.69) P-104 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-105 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-106 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.74) P-107 m/z=641.18(C ₄₆ H ₂₇ NOS=641.79) P-108 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-109 m/z=566.17(C ₄₁ H ₂₆ OS=566.72) P-110 m/z=641.18(C ₄₆ H ₂₇ NOS=641.79) P-111 m/z=625.20(C ₄₆ H ₂₇ NO ₂ =625.73) P-112 m/z=624.21(C ₄₇ H ₂₈ O ₂ =624.74) P-113 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-114 m/z=650.26(C ₅₀ H ₃₄ O=650.82) P-115 m/z=655.16(C ₄₆ H ₂₅ NO ₂ S=655.77) P-116 m/z=665.24(C ₄₉ H ₃₁ NO ₂ =665.79) P-117 m/z=549.17(C ₄₀ H ₂₃ NO ₂ =549.63) P-118 m/z=540.12(C ₃₈ H ₂₀ O ₂ S=540.64) P-119 m/z=615.17(C ₄₄ H ₂₅ NOS=615.75) P-120 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-121 m/z=691.20(C ₅₀ H ₂₉ NOS=691.85) P-122 m/z=657.16(C ₄₆ H ₂₇ NS ₂ =657.85) P-123 m/z=641.18(C ₄₆ H ₂₇ NOS=641.79) P-124 m/z=657.16(C ₄₆ H ₂₇ NS ₂ =657.85) P-125 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-126 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.86) P-127 m/z=671.14(C ₄₆ H ₂₅ NOS ₂ =671.83) P-128 m/z=640.19(C ₄₇ H ₂₈ OS=640.80) P-129 m/z=565.15(C ₄₀ H ₂₃ NOS=565.69) P-130 m/z=556.10(C ₃₈ H ₂₀ OS ₂ =556.70) P-131 m/z=697.19(C ₄₉ H ₃₁ NS ₂ =697.91) P-132 m/z=556.10(C ₃₈ H ₂₀ OS ₂ =556.70) P-133 m/z=592.22(C ₄₄ H ₃₂ S=592.80) P-134 m/z=691.29(C ₅₂ H ₃₇ NO=691.87) P-135 m/z=651.26(C ₄₉ H ₃₃ NO=651.81) P-136 m/z=667.23(C ₄₉ H ₃₃ NS=667.87) P-137 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-138 m/z=650.26(C ₅₀ H ₃₄ O=650.82) P-139 m/z=681.21(C ₄₉ H ₃₁ NOS=681.85) P-140 m/z=650.26(C ₅₀ H ₃₄ O=650.82) P-141 m/z=699.26(C ₅₃ H ₃₃ NO=699.85) P-142 m/z=640.19(C ₄₇ H ₂₈ OS=640.80) P-143 m/z=641.22(C ₄₇ H ₃₁ NS=641.83) P-144 m/z=707.26(C ₅₂ H ₃₇ NS=707.94) P-145 m/z=695.28(C ₄₉ H ₂₉ D ₃ N ₄ O=695.84) P-146 m/z=919.34(C ₆₃ H ₂₉ D ₉ N ₆ S=920.15) P-147 m/z=873.35(C ₆₃ H ₃₅ D ₅ N ₄ O=874.07) P-148 m/z=878.30(C ₆₁ H ₃₄ D ₄ N ₄ OS=879.09) P-149 m/z=826.19(C ₅₅ H ₃₀ N ₄ OS ₂ =826.99) P-150 m/z=953.35(C ₆₇ H ₃₉ D ₄ N ₅ S=954.20) P-151 m/z=760.24(C ₅₃ H ₂₈ D ₃ N ₃ OS=760.93) P-152 m/z=830.35(C ₅₈ H ₂₆ D ₁₀ N ₄ O ₂ =831.01) P-153 m/z=770.27(C ₅₄ H ₃₄ N ₄ O ₂ =770.89) P-154 m/z=889.34(C ₆₃ H ₃₅ D ₅ N ₄ S=890.13) P-155 m/z=745.29(C ₅₃ H ₃₁ D ₃ N ₄ O=745.90) P-156 m/z=959.36(C ₆₉ H ₄₅ N ₅ O=960.15) P-157 m/z=779.27(C ₅₅ H ₃₃ N ₅ O=779.90) P-158 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.80) P-159 m/z=601.18(C ₄₂ H ₂₃ N ₃ O ₂ =601.67) P-160 m/z=835.24(C ₅₇ H ₃₃ N ₅ OS=835.99) P-161 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.90) P-162 m/z=895.32(C ₆₁ H ₂₅ D ₁₀ N ₅ OS=896.11) P-163 m/z=820.27(C ₅₈ H ₃₆ N ₄ S=821.01) P-164 m/z=743.24(C ₅₃ H ₃₃ N ₃ S=743.93) P-165 m/z=873.35(C ₆₃ H ₃₅ D ₅ N ₄ O=874.07) P-166 m/z=697.16(C ₄₇ H ₂₇ N ₃ S ₂ =697.87) P-167 m/z=788.29(C ₅₅ H ₃₂ D ₄ N ₄ S=789.01) P-168 m/z=701.25(C ₅₁ H ₃₁ N ₃ O=701.83) P-169 m/z=791.35(C ₅₅ H ₂₅ D ₁₀ N ₅ O=791.98) P-170 m/z=817.28(C ₅₈ H ₃₅ N ₅ O=817.95) P-171 m/z=821.31(C ₅₈ H ₃₁ D ₄ N ₅ O=821.98) P-172 m/z=821.26(C ₅₇ H ₃₅ N ₅ S=822.00) P-173 m/z=570.16(C ₃₈ H ₁₈ D ₃ N ₃ OS=570.68) P-174 m/z=923.27(C ₆₄ H ₃₇ N ₅ OS=924.09) P-175 m/z=756.31(C ₅₂ H ₂₄ D ₁₀ N ₄ S=756.99) P-176 m/z=879.34(C ₆₄ H ₄₁ N ₅ =880.07)

Manufacturing evaluation of organic electric devices

( Example ) Red Fabrication and testing of organic light emitting devices

First, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)- as a hole injection layer on the ITO layer (anode) formed on the glass substrate. A N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a 60 nm thick film.

Next, 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 this film to form a hole transport layer. was formed.

The above invention compound represented by Chemical Formula 1 was used as a host on the upper part of the hole transport layer, and as a dopant, (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate] was doped with 95:5 weight. By doing so, a 30 nm thick light emitting layer was deposited on the hole transport layer.

As a hole blocking layer, (1,1'-bisphenyl)-4-oleito)bis(2-methyl-8-quinoline oleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm.

As an electron transport layer, tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed to a thickness of 40 nm.

Afterwards, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

A forward bias direct current voltage was applied to the organic electroluminescent devices of the Examples and Comparative Examples manufactured in this way, and the electroluminescence (EL) characteristics were measured using Photoresearch's PR-650, and the measurement results showed a luminance of 2500 cd/m ^2. The T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience. Table 5 below shows the device fabrication and evaluation results.

( Comparative example 1~3)

An organic electroluminescent device was manufactured in the same manner as Example 1, except that comparative compounds A, B, and C were used as hosts.

Comparative compound A Comparative compound B Comparative compound C

The physical properties measured according to the above examples and comparative examples are shown in Table 3 below.

compound Driving
Voltage electric current
(mA/cm2) Luminance
(cd/m2) efficiency
(cd/A) T(95) CIE x y Comparative example (1) Comparative compound (A) 7.0 21.2 2500.0 11.8 80.7 0.62 0.34 Comparative example (2) Comparative compound (B) 7.2 21.7 2500.0 11.5 88.2 0.63 0.35 Comparative example (3) Comparative compound (C) 7.3 21.9 2500.0 11.4 80.1 0.63 0.31 Example (1) P-2 6.8 16.3 2500.0 15.3 97.4 0.63 0.34 Example (2) P-8 6.8 16.0 2500.0 15.6 96.3 0.63 0.32 Example (3) P-10 6.7 16.1 2500.0 15.5 99.0 0.61 0.33 Example (4) P-16 6.8 17.1 2500.0 14.6 100.9 0.62 0.34 Example (5) P-18 6.8 16.9 2500.0 14.8 100.7 0.65 0.34 Example (6) P-23 6.8 16.7 2500.0 14.9 101.6 0.63 0.30 Example (7) P-25 6.6 17.4 2500.0 14.4 96.9 0.60 0.30 Example (8) P-31 6.5 17.4 2500.0 14.3 99.6 0.62 0.34 Example (9) P-33 6.5 16.9 2500.0 14.8 98.9 0.65 0.31 Example (10) P-39 6.7 16.7 2500.0 15.0 96.0 0.61 0.31 Example (11) P-44 6.8 17.6 2500.0 14.2 96.6 0.62 0.32 Example (12) P-45 6.7 17.5 2500.0 14.3 96.2 0.61 0.34 Example (13) P-52 6.7 16.1 2500.0 15.5 95.3 0.64 0.30 Example (14) P-53 6.7 16.5 2500.0 15.1 99.7 0.61 0.32 Example (15) P-60 6.8 16.5 2500.0 15.1 95.3 0.62 0.35 Example (16) P-61 6.8 17.4 2500.0 14.3 101.4 0.64 0.31 Example (17) P-66 6.7 17.4 2500.0 14.3 100.9 0.64 0.32 Example (18) P-71 6.8 16.7 2500.0 14.9 101.6 0.64 0.32 Example (19) P-74 6.5 17.0 2500.0 14.7 97.6 0.63 0.32 Example (20) P-79 6.6 17.7 2500.0 14.1 96.7 0.63 0.31 Example (21) P-82 6.6 17.7 2500.0 14.1 95.9 0.65 0.32 Example (22) P-87 6.8 17.7 2500.0 14.1 97.7 0.65 0.31 Example (23) P-92 6.8 17.2 2500.0 14.6 96.1 0.64 0.33 Example (24) P-117 6.8 17.8 2500.0 14.1 101.4 0.60 0.31 Example (25) P-149 6.6 16.7 2500.0 15.0 95.2 0.64 0.30 Example (26) P-172 6.8 16.4 2500.0 15.2 97.9 0.60 0.32

As can be seen from the results in Table 5, when a red organic electroluminescent device was manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, the organic electroluminescent device was produced more efficiently than the comparative examples using Comparative Compounds A to Comparative Compound C. It can be seen that not only can the driving voltage of the light emitting device be lowered, but also the luminous efficiency and lifespan can be significantly improved.

In order to examine the effect of the compounds of the present invention, compounds with relatively high structural similarity were set as comparison groups. However, in conclusion, Comparative Compounds A to C are structurally different from the compounds of the present invention, so the chemical and physical properties of the compounds This is significantly different, and as a result, the compound of the present invention produces significantly superior device results that those skilled in the art could not have predicted at all.

In addition, in the above-described device manufacturing evaluation results, the device characteristics were described by applying the compound of the present invention only to the light-emitting layer, but the compound of the present invention can be applied to one or more layers among the light-emitting layer, hole transport layer, and light-emitting auxiliary layer.

The above description is merely an illustrative description of the present invention, and those skilled in the art will know how to improve performance by including other compounds in the emitting layer without departing from the essential characteristics of the present invention. Various variations will be possible, such as:

Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting 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 in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

100, 200, 300: Organic electric element 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-emitting auxiliary layer 320: First hole injection layer
330: first hole transport layer 340: first light emitting 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 light emitting layer
450: Second electron transport layer CGL: Charge generation layer
ST1: first stack ST2: second stack

Claims (12)

Compound represented by Formula 1:
<Formula 1>

In Formula 1,
T is NR''', S, O or CR'R",
a+b, c+d, and e+f are each 1, and when a to f are each 0, it means a single bond,
n, m are 0 or 1, n+m is 1 or more,
^{X 1 , ​ ​ ​}
R ¹ to R ¹² are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); and at least one pair of adjacent R ¹ to adjacent R ¹² may be bonded to each other to form a ring,
L' is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of,
R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
R', R" and R''' are independently of each other hydrogen, an alkyl group of C ₁ to C ₅₀ ; an aryl group of C ₆ to C ₆₀ ; an aliphatic ring group of C ₃ to C ₆₀ ; and O, N, S, It is selected from the group consisting of a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom among Si and P, and R' and R" may be combined with each other to form a spiro compound. The compound according to claim 1, wherein Formula 1 is represented by Formula 2:
<Formula 2>

^{In Formula 2 , T , ​ ​} The compound according to claim 1, wherein Formula 1 is represented by Formula 3 or Formula 4:
<Formula 3>

<Formula 4>

^{In Formulas 3 and 4 , T ,} The compound according to claim 1, wherein the compound represented by Formula 1 is one of the following compounds:























first electrode; 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 characterized in that it contains a compound represented by the formula (1) of claim 1. first electrode; second electrode; an organic material layer formed between the first electrode and the second electrode; And in the organic electric device including a capping layer,
The capping layer is formed on one side of both sides of the first electrode and the second electrode that is not in contact with the organic layer,
The organic material layer or capping layer is an organic electric device characterized in that it contains a compound represented by the formula (1) of claim 1. The method of claim 5 or 6,
The organic material layer is an organic electric device characterized in that it includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. According to claim 7,
An organic electric device, wherein the organic material layer includes the light-emitting layer or the light-emitting auxiliary layer. The method of claim 5 or 6,
The organic material layer is an organic electric device characterized in that it includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. According to clause 9,
The organic material layer is an organic electric device, characterized in that it further includes a charge generation layer formed between the two or more stacks. A display device including the organic electric element of claim 5 or 6; and a control unit that drives the display device. According to claim 11,
The organic electric device is an electronic device characterized in that it is selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices.