KR102611191B1 - Compound for organic electric element and organic electric device comprising the same - Google Patents

Abstract

The present invention relates to a compound for an organic electric device and an organic electric device using the same. According to the present invention, it is possible to provide an organic electric device with high luminous efficiency, low driving voltage, and high heat resistance, and the color purity and lifespan of the organic electric device. can be improved.

Description

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

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

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 in the organic material layer 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 luminescence mechanism. You can. 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 moves to a longer wavelength due to intermolecular interactions, and problems arise such as a decrease in color purity or a decrease in the efficiency of the device due to the emission attenuation effect, thereby increasing 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. Since portable displays have batteries that provide limited power, more efficient power consumption is required than that required by existing portable displays. In addition, in addition to efficient power consumption, luminous efficiency and lifespan issues must also be resolved.

Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. It indicates a tendency for lifespan 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. Therefore, there is a need to develop a light-emitting material that has high thermal stability and can efficiently achieve charge balance within the light-emitting layer.

In other words, in order to fully demonstrate the excellent characteristics of organic electric devices, the materials that make up the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials, must be stable and efficient. Support by materials must be a priority, but the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently developed.

The purpose of the present invention is to provide a compound that can improve the high luminous efficiency, low driving voltage, high heat resistance, color purity and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

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

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 are diagrams schematically showing organic electric devices according to embodiments of the present invention.

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

In adding reference numerals to components in each drawing, it should be noted that the same reference numerals are assigned to the same components 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 thereof will be omitted.

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, 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.

The terms used in this specification and in the appended claims are as follows, unless otherwise noted.

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" has a double bond or triple bond, respectively, includes a straight or branched chain group, and has a carbon number of 2 to 60, unless otherwise specified. It is not limited.

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.

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 type, a ring aggregate, a multiple ring system fused, a compound, etc. For example, the aryl group may refer to a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group.

As used in this application, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group of fluorene, respectively, unless otherwise specified, and "substituted fluorenyl group" or "substituted fluorenyl group" "Orenylene group" refers to a monovalent or divalent functional group of substituted fluorene, and "substituted fluorene" refers to a group in which at least one of the following substituents R, R', R", and R''' is a functional group other than hydrogen. This means that R and R' are combined with each other to form a spiro compound with the carbon to which they are connected.

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, 3 It may be a heterocyclic group having a carbon number of 30 to 30. For example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene, or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, or imidazole. , triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline. For example, the substituted fluorenyl group and fluorenylene group are 9,9, respectively. -It may be a monovalent or divalent functional group of dimethylfluorene, 9,9-diphenylfluorene, and 9,9'-spirobi[9H-fluorene].

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 direct connection between such rings. This means that the number of connections is one less than the total number of ring systems in this 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" as 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.

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 refers to a ring numbered from 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.

Additionally, the “heterocyclic group” may also include a ring containing SO ₂ instead of carbon forming the ring. For example, “heterocyclic group” includes the following compounds:

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.

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.

Also, 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, boron means substituted with one or more substituents selected from the group consisting of a 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. and is not limited to these substituents.

In this application, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., exemplified by each symbol and its substituent, may be written as the 'name of the functional group reflecting the valence', but is written 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 name of the group is written by dividing the 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 may be written as 'pyrimidine' regardless of the valence, or the 'group' of the corresponding valence, such as pyrimidinyl (group) in the case of monovalent, pyrimidinylene (group) in the case of divalent, etc. It can also be written as ‘name’. 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.

Also, unless explicitly stated otherwise, 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 0, the substituent R ¹ is absent, when a is 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is 2 or 3, each is as follows They are bonded together, and in this case, R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, and the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted. .

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 and butadienyl groups substituted on one of the benzene rings share one carbon to form an unsaturated ring, or the vinyl and propylenyl groups 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.

In this application, the organic electric device may narrowly refer to an organic light-emitting diode including an anode, a cathode, and an organic material layer located between the anode and the cathode, and more broadly, may refer to the organic light-emitting diode and the device that drives the organic light-emitting diode. It may also refer to electronic devices such as display devices, lighting devices, and solar cells that include electronic circuits for the following purposes.

The electronic device may be, for example, a current or future wired or wireless communication terminal, and may include all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers. It can be included.

Organic electric device Figures 1 to 3 are illustrative diagrams of organic electric devices according to embodiments of the present invention.

First, 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). and an organic layer containing a compound according to the present invention between the second electrode 170 and the second electrode 170.

At this time, the first electrode 110 may be an anode and the second electrode 170 may be a cathode. In the case of the 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 sequentially disposed on the first electrode 110.

A capping layer may be located on one or more of one side of the first electrode 110 opposite the organic layer and one side of the second electrode 170 opposite the organic layer. The side opposite to the organic material layer may refer to the side opposite to the side adjacent to the organic material layer. The capping layer may contain a compound according to the invention. When the capping layer contains the compound according to the present invention, the luminous efficiency of the organic electric device can be improved.

For example, the capping layer 180 may be located on the second electrode 170. In the case of a top emission organic light emitting device, the capping layer 180 may serve to reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode 170. In the case of a bottom emission organic light emitting device, the capping layer 180 may serve as a buffer for the second electrode 170.

In addition, referring to Figure 2, the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 220, a hole transport layer 230, and a buffer layer ( 233), a light emitting auxiliary layer 243, a light emitting layer 240, an electron transport layer 250, an electron injection layer 260, and a second electrode 270.

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

A capping layer 280 may be positioned on the second electrode 270. In the case of a top emission organic light emitting device, the capping layer 280 may serve to reduce optical energy loss due to surface plasmon polaritons (SPPs) in the second electrode 270. In the case of a bottom emission organic light emitting device, the capping layer 280 may serve as a buffer for the second electrode 270.

In addition, referring to Figure 3, the organic electric device 300 according to another embodiment of the present invention includes a first stack ( ST1), a second stack (ST2), and a charge generation layer (CGL: Charge Generation Layer). Here, a charge generation layer (CGL) may be disposed at the boundary between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer 380 and a second charge generation layer 381. This charge generation layer (CGL) can serve to increase the efficiency of current generated in each light-emitting layer and to smoothly distribute charges between the first and second light-emitting layers 341 and 342.

In addition, the first stack (ST1) includes a first hole injection layer 321, a first hole transport layer 331, a first light emitting layer 341, and a first electron transport layer ( 351) may be included.

The second stack ST2 may include a second hole transport layer 332, a second light emitting layer 342, a second electron transport layer 352, and an electron injection layer 360. The second hole transport layer 332, the second light emitting layer 342, the second electron transport layer 352, and the electron injection layer 360 may be sequentially disposed on the second charge generation layer 381.

The first light-emitting layer 341 may include a light-emitting material containing a blue fluorescent dopant in a blue host, and the second light-emitting layer 342 may contain a material doped with a greenish yellow dopant and a red dopant in a green host. However, the materials included in each of the first and second light emitting layers 341 and 342 according to the embodiment of the present invention are not limited thereto.

Here, the second hole transport layer 332 includes a second stack (ST2) whose energy level is set higher than the triplet excited state energy level of the second light emitting layer 342.

At this time, since the energy level of the second hole transport layer 332 is higher than that of the second light emitting layer 342, the triplet exciton of the second light emitting layer 342 flows to the second hole transport layer 332, thereby increasing the luminous efficiency. This can prevent it from falling. That is, the second hole transport layer 332 functions to transport holes from the inherent second light-emitting layer 342 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 331 may also be set to an energy level higher than the triplet excitation energy level of the first light emitting layer 341. In addition, the first electron transport layer 351 is also set to an energy level higher than the energy level of the triplet excitation state of the first light-emitting layer 341, and the second electron transport layer 352 is also set to a higher energy level than the triplet excitation state of the second light-emitting layer 342. It is desirable to set the energy level to a higher energy level than the state energy level.

The charge generation layer (CGL) and the second stack (ST2) may be repeatedly positioned n times, which is a positive integer. For example, when n is 2, the charge generation layer (CGL) is located on the first stack (ST1), the second stack (ST2) is located on the charge generation layer (CGL), and the second stack An additional charge generation layer may be located in (ST2), and an additional stack may be located on the additional charge generation layer.

A capping layer 380 may be positioned on the second electrode 370. In the case of a top emission organic light emitting device, the capping layer 380 may serve to reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode 370. In the case of a bottom emission organic light emitting device, the capping layer 380 may serve as a buffer for the second electrode 370.

Meanwhile, the organic electric device 300 of FIG. 3 may be an organic electric device 300 that emits white light due to a mixing effect of light emitted from the first light-emitting layer 341 and the second light-emitting layer 342, but according to the present invention The embodiment is not limited to this.

The compound according to the present invention is a hole injection layer (120, 220), a hole transport layer (130, 230), a buffer layer (233), a light emitting auxiliary layer (243), an electron transport layer (150, 250), and an electron transport layer (150, 250) of Figure 1 or 2. It may be used as a material for the injection layers 160 and 260, or as a host or dopant material for the light emitting layers 140 and 240. For example, the compound of the present invention can be used as a material for the light emitting auxiliary layer 243 in FIG. 2.

In addition, the compound according to the present invention includes the first hole injection layer 321, the first hole transport layer 331, the first light-emitting layer 341, the first electron transport layer 351, and the first charge generation layer 380 in FIG. ), it may be used as a material for the second charge transport layer 381, the second hole transport layer 332, the second light emitting layer 342, the second electron transport layer 352, and the electron injection layer 360. For example, the compound of the present invention can be used as a material for the first hole transport layer 331, and in some cases, it can also be used as the second charge generation layer 381.

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 may cover one or more side surfaces of the first electrode, the second electrode, and the organic material layer to protect the first electrode, the second electrode, and the organic material layer. It can be formed to cover.

The protective layer 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.

On the other hand, even if it is the same core, 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, 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.

Organic electroluminescent devices according to embodiments of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD (Physical Vapor Deposition) or CVD (Chemical Vapor Deposition). For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode (110, 210, 310) is formed thereon, and a hole injection layer (120, 220, 320), a hole transport layer (130, 230, 330), a light emitting layer (140, 240, 341, 342), and an electron transport layer (150, 250, 351, 352) are formed thereon. ) and an electron injection layer (160, 260, 360) and then depositing a material that can be used as a cathode (170, 270, 370) thereon.

In addition, the organic material layer uses a variety of polymer materials and is made using 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 blading. It can be manufactured with fewer layers by methods such as processing, 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.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to achieve high resolution and having excellent fairness, while being manufactured using the color filter technology of existing LCDs. Various structures for white organic electric devices, mainly used as backlight devices, are being proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in parallel with each other in a plane, and a stacking method in which R, G, and B light emitting layers are stacked top and bottom. There is a color conversion material (CCM) method that uses electroluminescence by a blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom, and the present invention. can be applied to these WOLEDs as well.

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>

^{Hereinafter ,} R ¹ , R ^{2 , X 1 ,}

R ¹ and R ² are, independently of each other, hydrogen; heavy hydrogen; halogen; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ; 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(Ra)(Rb);

When R ¹ or R ² is an aryl group, R ¹ and R ² may independently be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group, For example, R ¹ and R ² may each independently be benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, or terphenyl.

When R ¹ or R ² is an alkyl group, R ¹ and R ² may independently be a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₂₀ alkyl group, or a C ₁ to C ₁₀ alkyl group.

When R ¹ or R ² is a heterocyclic group, R ¹ and R ² may independently be a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group, for example, pyrrole, It may be pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

X ¹ and X ² are independently selected from the group consisting of a single bond, O, S, and NR ³ , and at least one of X ¹ and X ² may not be a single bond.

When X ¹ or X ^{2 is} a single bond ^{, the two carbons connected to X 1 or} A ring containing X ¹ can form a pentagonal ring.

R ³ is, independently of each other, an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ₁ to C ₅₀ alkyl group.

When R ³ is an aryl group, R ³ may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group. For example, R ³ is benzene, naphthalene, It may be anthracene, phenanthrene, tetracene, benzoanthracene or terphenyl.

When R ³ is a heterocyclic group, R ³ may be a heterocyclic group of C ₂ to C ₃₀ or a heterocyclic group of C ₂ to C _15. For example, R ³ is pyrrole, pyrazole, imidazole, or triazole. , furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

When R ³ is an alkyl group, R ³ may be a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₂₀ alkyl group, or a C ₁ to C ₁₀ alkyl group.

L ¹ and L ² are, independently of each other, a single bond; C ₆ ~ C ₆₀ arylene group; It may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group and a C ₃ ~ C ₆₀ aliphatic ring group containing at least one hetero atom among O, N, S, Si, and P.

When L ¹ and L ² are aryl groups, L ¹ and L ² may independently be a C ₆ to C ₄₀ arylene group, a C ₆ to C ₃₀ arylene group, or a C ₆ to C ₂₀ arylene group. For example, L ¹ and L ² may each independently be a divalent functional group of benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, or terphenyl.

When L ¹ and L ² are heterocyclic groups, L ¹ and L ² may independently be a divalent functional group of a C ₂ to C ₃₀ heterocyclic ring or a divalent functional group of a C ₂ to C ₁₅ heterocyclic ring. , for example, pyrrole, pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran. 2 may be a functional group.

Ar ¹ and Ar ² are, independently of each other, an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ; 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; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; and -L'-N(Ra)(Rb).

When Ar ¹ and Ar ² are aryl groups, Ar ¹ and Ar ² may independently be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group, For example, Ar ¹ and Ar ² may independently be benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, or terphenyl.

When Ar ¹ and Ar ² are heterocyclic groups, Ar ¹ and Ar ² may independently be a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group, for example, Ar ¹ and Ar ² are, independently of each other, pyrrole, pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene. Or it may be dibenzofuran.

When Ar ¹ and Ar ² are alkyl groups, Ar ¹ and Ar ² may independently be a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₂₀ alkyl group, or a C ₁ to C ₁₀ alkyl group.

In R ¹ , R ² , Ar ¹ and Ar ² , Ra and Rb are each independently an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ₁ to C ₅₀ alkyl group.

When Ra and Rb are aryl groups, Ra and Rb may independently be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group, for example, Ra and Rb, independently of each other, may be benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene or terphenyl.

When Ra and Rb are heterocyclic groups, Ra and Rb may be, independently of each other, a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group. For example, Ra and Rb are each other. Independently, it can be pyrrole, pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran. there is.

When Ra and Rb are alkyl groups, Ra and Rb may independently be a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₂₀ alkyl group, or a C ₁ to C ₁₀ alkyl group.

In R ¹ , R ² , Ar ¹ and Ar ² , L' is independently a single bond; C ₆ ~ C ₆₀ arylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and C ₃ to C ₆₀ aliphatic ring groups.

When L' is an aryl group, L' may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group. For example, L' may be benzene, naphthalene, It may be anthracene, phenanthrene, tetracene, benzoanthracene or terphenyl.

When L' is a heterocyclic group, L' may be a heterocyclic group of C ₂ to C ₃₀ or a heterocyclic group of C ₂ to C _15. For example, L' may be pyrrole, pyrazole, imidazole, or triazole. , furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

When L' is an alkyl group, L' may be a C ₁ -C ₄₀ alkylene group, a C ₁ -C ₂₀ alkylene group, or a C ₁ -C ₁₀ alkylene group.

o1 and o2 may be integers of 0 or 1, respectively, and o1+o2 may be an integer of 1 or more. That is, the compound represented by Formula 1 includes one or more of -L ¹ -Ar ¹ and -L ² -Ar ² .

n may be an integer from 0 to 3, and m may be an integer from 0 to 4.

In R ^{1 ,} R ² , L ^{1 ,} L ² , ^{X 1} , Each aryloxy group is deuterium; nitro group; Nitrile group; halogen group; amino group; A silane group unsubstituted or substituted with a C ₁ to C ₂₀ alkyl group or a C ₆ to C ₂₀ aryl group; siloxane group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group may be substituted, and these substituents may be combined with each other to form a ring.

In Formula 1, at least one of Ar ¹ and Ar ² may be represented by the following Formula A-1 or A-2.

[Formula A-1] [Formula A-2]

Q ¹ to Q ⁹ may be independently N or CR ^e .

R ^e are, independently of each other, hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl groups.

When R ^e is an aryl group, for example, R ^e may be benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, or terphenyl.

When R ^e is a heterocyclic group, R ^e may be a C ₂ to C ₁₅ heterocyclic group. For example, R ^e is pyrrole, pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridine. It may be minced, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

When R ^e is an alkyl group, R ^e may be a C ₁ to C ₂₀ alkyl group or a C ₁ to C ₁₀ alkyl group.

Z may be selected from the following formulas Z-1 to Z-15.

Formula Z-1 Formula Z-2 Formula Z-3 Formula Z-4 Formula Z-5

Formula Z-6 Formula Z-7 Formula Z-8 Formula Z-9 Formula Z-10

Formula Z-11 Formula Z-12 Formula Z-13 Formula Z-14 Formula Z-15

The * may represent a position where each of Formulas Z-1 to Z-15 is condensed with a ring containing Q ¹ to Q ⁴ .

W ¹ and W ² may, independently of each other, be a single bond, NL ³ -Ar ³ , S, O or C(R ^f )(R ^g ).

V may be, independently of each other, N or CR ^h .

In Formula Z-1 to Formula Z-15, L ³ is a single bond; C ₆ -C ₆₀ arylene group; A divalent functional group of a C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A divalent functional group of the fused ring group of the aliphatic ring of C ₃ -C ₆₀ and the aromatic ring of C ₆ -C ₆₀ ; C ₁ ~ C ₅₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; and C ₂ to C ₂₀ alkynylene groups.

When L ³ is an aryl group, L ³ may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group. For example, L ³ is benzene, naphthalene, It may be anthracene, phenanthrene, tetracene, benzoanthracene or terphenyl.

When L ³ is a heterocyclic group, L ³ may be a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group. For example, L ³ is pyrrole, pyrazole, imidazole, or triazole. , furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

When L ³ is an alkyl group, L ³ may be a C ₁ to C ₄₀ alkylene group, a C ₁ to C ₂₀ alkylene group, or a C ₁ to C ₁₀ alkylene group.

In Formulas Z-1 to Z-15, Ar ³ , R ^f and R ^g are, independently of each other, a C ₆ to C ₆₀ aryl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -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; and C ₆ -C ₃₀ aryloxy groups.

R ^h is, independently of each other, hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -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; and C ₆ -C ₃₀ aryloxy groups.

R ^h is selected independently from each other, meaning that when a plurality of v among the v included in the formulas Z-1 to Z-15 is CR ^h , the plurality of R ^h are selected independently from each other and are the same or different from each other. It means you can do it.

R ^f and R ^g may be bonded to each other to form a spiro compound together with the carbon to which R ^f and R ^g are bonded.

In Formula 1, Ar ¹ and Ar ² may be represented by one of the following formulas B-1 to B-4.

[Formula B-1] [Formula B-2]

[Formula B-3] [Formula B-4]

Y ¹ and Y ² may be, independently of each other, NL ⁴ -Ar ⁴ , O, S or C(R ⁱ )(R ^j ).

In Formula B-1 to Formula B-4, L ⁴ is a single bond; C ₆ -C ₆₀ arylene group; A divalent functional group of a C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A divalent functional group of the fused ring group of the aliphatic ring of C ₃ -C ₆₀ and the aromatic ring of C ₆ -C ₆₀ ; C ₁ ~ C ₅₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; and C ₂ to C ₂₀ alkynylene groups.

When L ⁴ is an arylene group, L ⁴ may be a C ₆ to C ₄₀ arylene group, a C ₆ to C ₃₀ arylene group, or a C ₆ to C ₂₀ arylene group. For example, L ⁴ may be benzene, It may be a divalent functional group of naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene or terphenyl.

When L ⁴ is a divalent functional group of a heterocyclic group, L ⁴ may be a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group. For example, L ⁴ is pyrrole, pyrazole, It may be a divalent functional group of imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

When L ⁴ is an alkylene group, L ⁴ may be a C ₁ to C ₄₀ alkylene group, a C ₁ to C ₂₀ alkylene group, or a C ₁ to C ₁₀ alkylene group.

In Formulas B-1 to B-4, Ar ⁴ , ^Ri and R ^j are, independently of each other, a C ₆ to C ₆₀ aryl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -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; and C ₆ -C ₃₀ aryloxy groups.

R ⁴ to R ⁸ are, independently of each other, hydrogen; heavy hydrogen; halogen; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ; 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 ⁵ -N(R ^k )(R ^l ); and R ⁴ to R ⁸ may each be combined with each other to form a ring.

R ^k and R ^l are, independently of each other, an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ₁ to C ₅₀ alkyl group.

L ⁵ is a single bond independently of each other; C ₆ ~ C ₆₀ arylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and C ₃ to C ₆₀ aliphatic ring groups.

a, b, q and s may be integers from 0 to 4.

r may be an integer from 0 to 2.

When the compound of Formula 1 is used in the organic material layer of an organic electric device, an organic electric device with excellent luminous efficiency and lifespan can be manufactured.

The compound represented by Formula 1 may be represented by Formula 2 or Formula 3 below.

[Formula 2] [Formula 3]

In Formula 2 and Formula 3, R ¹ , R ² , X ¹ , X ² , L ¹ , Ar ¹ , m and n are the same as defined in Formula 1.

When the compound represented by Formula 2 or Formula 3 is used in the organic material layer of an organic electric device, an organic electric device with excellent luminous efficiency and lifespan can be manufactured.

The compound represented by Formula 1 may be represented by any one of Formulas 4 to 7 below.

[Formula 4] [Formula 5]

[Formula 6] [Formula 7]

In Formulas 4 to 7, R ¹ , R ² , X ¹ , X ² , L ² , Ar ¹ , Ar ² , m and n are the same as defined in Formula 1.

When a compound represented by any one of Formulas 4 to 7 is used in the organic material layer of an organic electric device, an organic electric device with excellent luminous efficiency and lifespan can be manufactured.

The compound represented by Formula 1 may be represented by any one of Formulas 8 to 10 below.

[Formula 8] [Formula 9]

[Formula 10]

In Formulas 8 to 10, R ¹ , R ² , R ³ , L ¹ , L ² , Ar ¹ , Ar ² , m, n, o1 and o2 are the same as defined in Formula 1.

When a compound represented by any one of Formulas 8 to 10 is used in the organic material layer of an organic electric device, an organic electric device with excellent luminous efficiency and lifespan can be manufactured.

The compound represented by Formula 1 may be represented by any one of Formulas 11 to 13 below.

[Formula 11] [Formula 12]

[Formula 13]

In Formulas 11 to 13, R ¹ , R ² , R ³ , L ¹ , L ² , Ar ¹ , Ar ² , m, n, o1 and o2 are the same as defined in Formula 1.

When a compound represented by any one of Formulas 11 to 13 is used in the organic material layer of an organic electric device, an organic electric device with excellent luminous efficiency and lifespan can be manufactured.

The compound represented by Formula 1 may be one of the following Formulas P-1 to Formula P-106, but the compound represented by Formula 1 is not limited thereto.

As another example, the present invention provides an organic electric device containing the compound represented by Formula 1 above.

The organic electric device includes a first electrode; second electrode; and an organic material layer located between the first electrode and the second electrode, wherein the organic material layer may include a compound represented by Formula 1, and the compound represented by Formula 1 is a hole injection layer of the organic material layer, a hole injection layer, and a hole injection layer of the organic material layer. It may be included in at least one of a transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In particular, the compound represented by Formula 1 may be included in the light-emitting layer.

Specifically, an organic electric device is provided in which the organic material layer includes one of the compounds represented by Formula 1, and more specifically, the organic material layer includes a compound represented by the individual chemical formulas (P-1 to P-106). Provides an organic electric device that

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

In another embodiment, a layer containing the compound alone, in a combination of two or more different compounds, or in a combination of two or more compounds with other compounds may be an auxiliary light emitting layer.

In other words, each layer may contain a compound corresponding to Formula 1 alone, a mixture of two or more compounds of Formula 1, or a mixture of a compound of Formula 1 and a compound that does not correspond to the present invention. This may be included. Here, the compound that does not fall under the present invention may be a single compound, or may be two or more types of compounds. At this time, when the compound is included in a combination of two or more types of other compounds, the other compounds may be already known compounds of each organic layer, or may be compounds to be developed in the future. At this time, the compound included in the organic layer may be composed of only the same type of compound, but may also be a mixture of two or more different types of compounds represented by Chemical Formula 1.

For example, the organic layer may be a mixture of two compounds with different structures at a molar ratio of 99:1 to 1:99.

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

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]

The compound (final products) represented by Formula 1 according to the present invention can be synthesized by reacting any one of Core 1 to 4 with Sub 1 as shown in Scheme 1 below, but the method of synthesizing the compound represented by Formula 1 is limited to this. It doesn't work.

<Scheme 1>

^In Scheme ^{1 ,} R ^{1 ,} R ^{2 ,} X ¹ , It is the same as that, and Hal ¹ is Br or Cl.

I. Synthesis of Core 1 to 4

Cores 1 to 4 of Scheme 1 may be synthesized through the reaction route of the following Scheme, but are not limited thereto.

1. Core1 synthesis example

(1) Core 1-1 synthesis

<Scheme 2>

(1-1) Core 1-II-1 synthesis

8-bromo-6-chloro-2-iodoimidazo[1,2-b]pyridazine (200 g, 558.10 mmol), (2-aminophenyl)boronic acid (91.72 g, 669.72 mmol), Pd(PPh ₃ ) ₄ (32.25 g, 27.90 mmol), K ₂ CO ₃ (231.40 g, 1,674.29 mmol) into the reactor, add 4,000 mL Toluene, and add 2,000 mL of water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 96.95 g of product (yield: 71%). got it

(1-2) Core 1-I-1 synthesis

Core 1-II-1 (96.95 g, 299.63 mmol) obtained in the above synthesis was placed in a round bottom flask, 500mL of water was added, and 177mL of 12M HCl was added. Afterwards, dissolve sodium nitrite (31.01 g, 449.45 mmol) in 100 mL of water and set the reactor temperature to 0°C. CH ₃ CO ₂ Na (221.21 g, 2,696.67 mmol) and NaN ₃ (42.85 g, 659.19 mmol) are dissolved in 1,700 mL of water and added dropwise. After the reaction time was 3 hours, when the reaction was completed, extraction was performed with methylene dichloride, the organic layer was dried with NaSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 30.93 g of product (yield: 38%).

(1-3) Core 1-1 synthesis

Core 1-I-1 (30.93 g 88.23 mmol) obtained in the above synthesis was placed in a round bottom flask, and 154 mL of 1,2,4-trichlorobenzen was added. Afterwards, nitrogen substitution is performed and the temperature of the reactor is set to 185°C. After the reaction time was 30 minutes, when the reaction was completed, it was concentrated and the resulting compound was recrystallized using a silicagel column to obtain 14.23 g of product (yield: 50%).

(2) Core 1-2 synthesis

<Scheme 3>

(2-1) Core 1-II-2 synthesis

8-bromo-6-chloro-2-iodoimidazo[1,2-b]pyridazine (50g, 139.52 mmol), (2-(methylthio)phenyl)boronic acid (28.13 g, 167.43 mmol), Pd(PPh ₃ ) ₄ (8.06 g, 6.98 mmol) and K ₂ CO ₃ (57.85 g, 418.57 mmol) into a round bottom flask, add 1,000 mL Toluene, and add 500 mL of water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 35.13 g of product (yield: 71%). got it

(2-2) Core 1-I-2 synthesis

Core 1-II-2 (35.13 g, 99.06 mmol) and H ₂ O ₂ (3.54 g, 104.02 mmol) obtained in the above synthesis were placed in a round bottom flask, and 1,000 mL Acetic acid was added. Afterwards, nitrogen substitution is performed and the reactor temperature is set to 60°C. After the reaction time was overnight, when the reaction was completed, the reactant was concentrated under reduced pressure to obtain 33.05 g of product (yield: 90%).

(2-3) Core 1-2 synthesis

Add 27.5 g of sulfuric acid to Core 1-I-2 (33.05 g, 93.18 mmol) obtained in the above synthesis. Afterwards, nitrogen substitution is performed and the reactor temperature is set to 60°C. After the reaction time was overnight, when the reaction was completed, it was neutralized with 1,000 mL of water and 11.18 g of NaOH to precipitate as a solid to obtain 29.66 g of product (yield: 94%).

(3) Core 1-3 synthesis

<Scheme 4>

(3-1) Core 1-II-3 synthesis

8-bromo-6-chloro-2-iodoimidazo[1,2-b]pyridazine (100 g, 279.05 mmol), (2-nitrophenyl)boronic acid (55.90 g, 334.86 mmol), Pd(PPh ₃ ) ₄ (16.12 g, 13.95 mmol), K ₂ CO ₃ (115.70 g, 837.15 mmol) into the reactor, add 2000 mL Toluene, and add 1,000 mL of water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 70.05 g of product (yield: 71%). got it

(3-2) Core 1-I-3 synthesis

Core 1-II-4 (70.05 g, 198.12 mmol) obtained in the above synthesis was placed in a round bottom flask, triphenylphosphine (129.92 g, 495.31 mmol) was added, and 1,2-dichlorobenzene (1,400 mL) was heated to 220°C. The reactants were dissolved and stirred for 16 hours. When the reaction is completed, the reactant is concentrated under reduced pressure and quenched by adding water. The reactant that has become a solid is obtained by filtering. The reactant that came out as a filtrate is obtained by removing water, filtered under reduced pressure, dried over MgSO ₄ and concentrated. The resulting compound was recrystallized using a silicagel column to obtain 28.67 g of product (yield: 45%).

(3-3) Core 1-3 synthesis

Core 1-I-4 (28.67 g, 89.16 mmol) obtained in the above synthesis was placed in a round bottom flask, and iodobenzene (18.20 g, 89.16 mmol), Copper (0.57 g, 8.92 mmol) and 18-Crown-6 (1.18 g) , 4.46 mmol), and K ₂ CO ₃ (36.96 g, 267.47 mmol) were added, the temperature was raised to 220°C with nitrobenzene (300 mL), and the reactants were dissolved and stirred for 6 hours. When the reaction is completed, the reactant is concentrated under reduced pressure and quenched by adding water. The reactant that has become a solid is obtained by filtering. The reactant that came out as a filtrate is obtained by removing water, filtered under reduced pressure, dried over MgSO ₄ and concentrated. The resulting compound was recrystallized using a silicagel column to obtain 27.30 g of product (yield: 77%).

2. Core 2 synthesis example

(1) Core 2-1 synthesis

<Scheme 5>

(1-1) Sub 1-I-2 synthesis

Sub 1-1 (70.00g, 227.75 mmol) was added to a round bottom flask, 1-bromo-4-chlorobenzene (50.14 g, 2261.92 mmol), Sodium tert-butoxide (65.66 g, 683.26 mmol) and Pd ₂ (dba) ₃ (10.43 g, 11.39 mmol), and add 750mL of Toluene. Afterwards, nitrogen substitution was performed, the reactor temperature was adjusted to 80°C, and Tri-tert-butylphosphine (4.61 g, 22.78 mmol) was added. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 69.48 g of product (yield: 73%). got it

(1-2) Sub 1-2 synthesis

Sub 1-I-2 (69.48 g, 166.26 mmol), Bis(pinacolato)diboron (63.33 g, 249.39 mmol), Pd ₂ (dba) ₃ (7.61 g, 8.31 mmol) and potassium acetate (48.96 g) obtained from the above synthesis. , 498.78 mmol), and When the reaction was completed, water was added to the reactant and quenched. The water in the reactant was removed. After filtering under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated to obtain 55.90 g of product (yield: 66%).

(1-3) Core 2-IV-1 synthesis

Sub 1-2 (55.90 g, 109.73 mmol) obtained in the above synthesis was placed in a round bottom flask, and 3-bromo-2-chloroaniline (27.19 g, 131.68 mmol) and Pd ₂ (PPh ₃ ) ₄ (6.34 g, 5.49 mmol) ), and K ₂ CO ₃ (45.50 g, 329.19 mmol) were added, the temperature was raised to 120°C with 1,000 mL of toluene and 500 mL of water, and the reactants were dissolved and stirred for 6 hours. When the reaction is completed, the reactant is concentrated under reduced pressure and quenched by adding water. The reactant that has become a solid is obtained by filtering. The reactant that came out as a filtrate is obtained by removing water, filtered under reduced pressure, dried over MgSO ₄ and concentrated. The resulting compound was recrystallized using a silicagel column to obtain 39.66 g of product (yield: 71%).

(1-4) Core 2-III-1 synthesis

Core 2-IV-1 (39.66 g, 77.91 mmol), Bis(pinacolato)diboron (29.68 g, 116.86 mmol), Pd ₂ (dba) ₃ (3.57 g, 3.90 mmol) and potassium acetate (22.94 g) obtained from the above synthesis. , 233.73 mmol), and When the reaction was completed, water was added to the reactant and quenched. The water in the reactant was removed. After filtering under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated to obtain 30.41 g of product (yield: 65%).

(1-5) Core 2-II-1 synthesis

Core 2-III-1 (30.41 g, 50.64 mmol), 8-bromo-6-chloro-2-iodoimidazo[1,2-b]pyridazine (21.78 g, 60.77 mmol), Pd(PPh ₃ ) obtained from the above synthesis. _{Add 4} (2.93 g, 2.53 mmol) and K ₂ CO ₃ (21.00 g, 151.92 mmol) into the reactor, add 600mL Toluene, and add 300mL water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 25.71 g of product (yield: 72%). got it

(1-6) Core 2-I-1 synthesis

Core 2-II-1 (25.71 g, 36.46 mmol) obtained in the above synthesis was placed in a round bottom flask, 150mL of water was added, and 47mL of 12M HCl was added. Afterwards, dissolve sodium nitrite (3.77 g, 54.69 mmol) in 13 mL of water and set the reactor temperature to 0°C. CH ₃ CO ₂ Na (26.92 g, 328.15 mmol) and NaN ₃ (5.21 g, 80.22 mmol) are dissolved in 200 mL of water and added dropwise. After the reaction time was 3 hours, when the reaction was completed, extraction was performed with methylene dichloride, the organic layer was dried with NaSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.61 g of product (yield: 36%).

(1-7) Core 2-1 synthesis

Core 2-I-1 (9.61 g 13.13 mmol) obtained in the above synthesis was placed in a round bottom flask, and 50 mL of 1,2,4-trichlorobenzen was added. Afterwards, nitrogen substitution is performed and the temperature of the reactor is set to 185°C. After the reaction time was 30 minutes, when the reaction was completed, it was concentrated and the resulting compound was recrystallized using a silicagel column to obtain 4.71 g of product (yield: 51%).

(2) Core 2-2 synthesis

<Scheme 6>

(2-1) Core 2-IV-2 synthesis

14H-benzo[c]benzofuro[2,3-a]carbazole (20.00 g, 65.07 mmol), (2-bromo-6-chlorophenyl)(methyl)sulfane (17.78 g, 74.83 mmol), Pd ₂ (dba) ₃ Add 210mL of (2.98 g, 3.25 mmol), Sodium tert-butoxide (18.76 g, 195.22 mmol), and Toluene. Afterwards, nitrogen substitution was performed, the reactor temperature was adjusted to reflux at 80°C, and Tri-tert-butylphosphine (1.32 g, 6.51 mmol) was added. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 20.83 g of product (yield: 69%). got it

(2-2) Core 2-III-2 synthesis

Core 2-IV-2 (20.83 g, 44.90 mmol), Bis(pinacolato)diboron (17.10 g, 67.35 mmol), Pd ₂ (dba) ₃ (2.06 g, 2.24 mmol) and potassium acetate (13.22 g) obtained from the above synthesis. , 134.70 mmol), and When the reaction was completed, water was added to the reactant and quenched. The water in the reactant was removed. After filtering under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated to obtain 16.46 g of product (yield: 66%).

(2-3) Core 2-II-2 synthesis

Core 2-III-2 (16.46 g, 29.63 mmol), 8-bromo-6-chloro-2-iodoimidazo[1,2-b]pyridazine (11.68 g, 32.60 mmol), Pd(PPh ₃ ) obtained from the above synthesis. _{Add 4} (1.71 g, 1.48 mmol) and K ₂ CO ₃ (12.29 g, 88.90 mmol) into the reactor, add 320 mL Toluene, and add 160 mL of water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 13.69 g of product (yield: 70%). got it

(2-4) Core 2-I-2 synthesis

Core 2-II-2 (13.69 g, 20.74 mmol) and H ₂ O ₂ (0.74 g, 21.78 mmol) obtained in the above synthesis were placed in a round bottom flask, and 400 mL Acetic acid was added. Afterwards, nitrogen substitution is performed and the reactor temperature is set to 60°C. After the reaction time was overnight, when the reaction was completed, the reactant was concentrated under reduced pressure to obtain 12.62 g of product (yield: 90%).

(2-5) Core 2-2 synthesis

Add 5.5 g of sulfuric acid to Core 2-I-2 (12.62 g, 18.67 mmol) obtained in the above synthesis. Afterwards, nitrogen substitution is performed and the reactor temperature is set to 60°C. After the reaction time was overnight, when the reaction was completed, it was neutralized with 400 mL of water and 2.24 g of NaOH to precipitate as a solid to obtain 11.06 g of product (yield: 92%).

(3) Core 2-3 synthesis

<Scheme 7>

(3-1) Core 2-IV-3 synthesis

5-phenyl-5,7-dihydroindolo[2,3-b]carbazole (30.00 g, 90.25 mmol), 4-bromo-2-chloro-1-nitrobenzene (24.54 g, 103.79 mmol), Pd ₂ (dba) ₃ (4.13 g, 4.51 mmol), Sodium tert-butoxide (26.02 g, 270.75 mmol), and Toluene 300mL are added. Afterwards, nitrogen substitution was performed, the reactor temperature was adjusted to reflux at 80°C, and Tri-tert-butylphosphine (1.83 g, 9.02 mmol) was added. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 30.83 g of product (yield: 70%). got it

(3-2) Core 2-III-3 synthesis

Core 2-IV-3 (30.83 g, 63.17 mmol), Bis(pinacolato)diboron (24.06 g, 94.76 mmol), Pd ₂ (dba) ₃ (2.89 g, 3.16 mmol) and potassium acetate (18.60 g) obtained from the above synthesis. , 189.52 mmol), and When the reaction was completed, water was added to the reactant and quenched. The water in the reactant was removed. After filtering under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated to obtain 23.79 g of product (yield: 65%).

(3-3) Core 2-II-3 synthesis

Core 2-III-3 (23.79 g, 41.06 mmol), 8-bromo-6-chloro-2-iodoimidazo[1,2-b]pyridazine (16.19 g, 45.17 mmol), Pd(PPh ₃ ) obtained from the above synthesis. _{Add 4} (2.37 g, 2.05 mmol) and K ₂ CO ₃ (17.03 g, 123.19 mmol) into a round bottom flask, add 400 mL Toluene, and add 200 mL of water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 19.66 g of product (yield: 70%). got it

(3-4) Core 2-I-3 synthesis

Core 2-II-3 (19.66 g, 28.74 mmol) obtained in the above synthesis was placed in a round bottom flask, triphenylphosphine (18.85 g, 71.86 mmol) was added, and 400 mL of 1,2-dichlorobenzene was used to prepare Core 1-I- 8.62 g (yield: 46%) of Core 2-I-3 was obtained using the same method as synthesis method 3.

(3-5) Core 2-3 synthesis

Core 2-I-3 (28.82g, 89.63 mmol), iodobenzene (18.29 g, 89.63 mmol), Copper (0.57 g, 8.96 mmol), and 18-Crown-6 (1.18 g, 4.48 mmol) obtained from the above synthesis, and 26.38 g of Core 3-3 (yield: 74%) was obtained in the same manner as the above Core 1-3 synthesis using K ₂ CO ₃ (37.16 g, 268.89 mmol).

3. Core 3 synthesis example

(1) Core 3-1 synthesis

<Scheme 8>

(1-1) Core 3-II-1 synthesis

8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (200 g, 558.10 mmol), (2-aminophenyl)boronic acid (91.72 g, 669.72 mmol), Pd(PPh ₃ ) ₄ (32.25 g, 27.90 mmol), K ₂ CO ₃ (231.40 g, 1,674.29 mmol), 4,000 mL of Toluene, and 2,000 mL of water to obtain 95.59 g of Core 3-II-1 (yield: : 70%) was obtained.

(1-2) Core 3-I-1 synthesis

Core 3-II-1 (95.59 g, 295.41 mmol), 12M HCl 170mL, Sodium nitrite (30.57 g, 443.12 mmol), CH ₃ CO ₂ Na (218.09 g, 2,658.69 mmol), NaN ₃ (42.25 g) obtained from the above synthesis. , 649.90 mmol), 31.30 g of Core 3-I-1 (yield: 39%) was obtained in the same manner as the Core 1-I-1 synthesis method above using 2,300 mL of water.

(1-3) Core 3-1 synthesis

Core 3-I-1 (31.30 g 89.28 mmol) obtained in the above synthesis, using 156 mL of 1,2,4-trichlorobenzen, was used to obtain 13.82 g of Core 3-1 (yield: 48%) in the same manner as the above Core 1-1 synthesis method. ) was obtained.

(2) Core 3-2 synthesis

<Scheme 9>

(2-1) Core 3-II-2 synthesis

8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (50g, 139.52 mmol), (2-(methylthio)phenyl)boronic acid (28.13 g, 167.43 mmol), Pd(PPh ₃ ) _{4 35.63 g} ( Yield: 72%) was obtained.

(2-2) Core 3-I-2 synthesis

Using Core 3-II-2 (35.63 g, 100.46 mmol), H ₂ O ₂ (3.59 g, 105.48 mmol), and 1,000 mL of Acetic acid obtained in the above synthesis, Core was prepared in the same manner as the Core 1-I-2 synthesis method. 31.65 g (yield: 85%) of 3-I-2 was obtained.

(2-3) Core 3-2 synthesis

28.10 g of Core 3-2 (yield : 93%) was obtained.

(3) Core 3-3 synthesis

<Scheme 10>

(3-1) Core 3-II-3 synthesis

8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (100 g, 279.05 mmol), (2-nitrophenyl)boronic acid (55.90 g, 334.86 mmol), Pd(PPh ₃ ) ₄ (16.12 _{72.02 g} of Core 3-II-3 (yield: 73%) was obtained.

(3-2) Core 3-I-3 synthesis

Core 3-II-3 (72.02 g, 203.71 mmol) and triphenylphosphine (133.57 g, 509.26 mmol) obtained in the above synthesis were added, and 1,2-dichlorobenzene (1,400 mL) was used to synthesize Core 1-I-3 and In the same way, 28.82 g of Core 3-I-3 (yield: 44%) was obtained.

(3-3) Core 3-3 synthesis

Core 3-I-3 (28.82g, 89.63 mmol), iodobenzene (18.29 g, 89.63 mmol), Copper (0.57 g, 8.96 mmol), and 18-Crown-6 (1.18 g, 4.48 mmol) obtained from the above synthesis, and 26.38 g of Core 3-3 (yield: 74%) was obtained in the same manner as the above Core 1-3 synthesis using K ₂ CO ₃ (37.16 g, 268.89 mmol).

4. Core 4 synthesis example

(1) Core 4-1 synthesis

<Scheme 11>

(1-1) Core 4-IV-1 synthesis method

2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100.00 g, 339.95 mmol), 2-bromo-6-chloroaniline (84.23 g, 407.94 mmol), Pd ₂ (PPh ₃ ) ₄ (19.64 g, 17.00 mmol), K ₂ CO ₃ (140.95 g, 1,019.85 mmol), Toluene 2,000 mL, and water 1,000 mL using Core 2-IV-1. 64.91 g (yield: 65%) of Core 4-IV-1 was obtained using the same method as the synthesis method.

(1-2) Core 4-III-1 synthesis

Core 4-IV-1 (64.91 g, 220.97 mmol), Bis(pinacolato)diboron (84.17 g, 331.45 mmol), Pd ₂ (dba) ₃ (10.12 g, 11.05 mmol), potassium acetate (65.06 g) obtained from the above synthesis. , 662.90 mmol), .

(1-3) Core 4-II-1 synthesis

Core 4-III-1 (57.89 g, 150.26 mmol), 8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (64.62 g, 180.31 mmol), Pd(PPh ₃ ) obtained from the above synthesis. 52.99 g of Core 4-II-1 using the same method as the above Core 2-II-1 synthesis method using ₄ (8.68 g, 7.51 mmol), K ₂ CO ₃ (62.30 g, 450.78 mmol), Toluene 1,100mL, and water 550mL. (yield: 72%) was obtained.

(1-4) Core 4-I-1 synthesis

Core 4-II-1 (52.99 g, 108.19 mmol) obtained from the above synthesis, 950mL of water, 97mL of 12M HCl, Sodium nitrite (11.20 g, 162.28 mmol), CH ₃ CO ₂ Na (79.87 g, 973.67 mmol), NaN ₃ (15.47 g, 238.01 mmol) was used to obtain 21.80 g of Core 4-I-1 (yield: 39%) using the same method as the Core 2-II-1 synthesis method.

(1-5) Core 4-1 synthesis

Core 4-I-1 (21.80 g 42.19 mmol) obtained in the above synthesis, using 110 mL of 1,2,4-trichlorobenzen, was used to obtain 10.52 g of Core 4-1 (yield: 51%) in the same manner as the above Core 2-1 synthesis method. ) was obtained.

(2) Core 4-2 synthesis

<Scheme 12>

(2-1) Core 4-IV-2 synthesis

11H-benzo[a]carbazole (20.00 g, 92.05 mmol), (2-bromo-6-chlorophenyl)(methyl)sulfane (25.15 g, 105.86 mmol), Pd ₂ (dba) ₃ (4.21 g, 4.60 mmol), Core 4-IV-2 24.09 using the same method as the above Core 2-IV-2 synthesis using Sodium tert-butoxide (26.54 g, 276.15 mmol), Toluene 300mL, and Tri-tert-butylphosphine (1.86 g, 9.21 mmol). g (yield: 70%) was obtained.

(2-2) Core 4-III-2 synthesis

Core 4-IV-2 (24.09 g, 64.44 mmol), Bis(pinacolato)diboron (24.54 g, 96.65 mmol), Pd ₂ (dba) ₃ (2.95 g, 3.22 mmol), potassium acetate (18.97 g) obtained from the above synthesis. , 193.31 mmol), X-phos (7.14 g, 9.67 mmol), and 480 mL of dioxane were used to obtain 20.29 g of Core 4-III-2 (yield: 69%) in the same manner as the Core 2-III-2 synthesis method above. .

(2-3) Core 4-II-2 synthesis

Core 4-III-2 (20.29 g, 44.46 mmol), 8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (17.53 g, 48.91 mmol), Pd(PPh ₃ ) obtained from the above synthesis. _{17.74 g} of Core 4 _- II-2 ( Yield: 70%) was obtained.

(3-4) Core 4-I-2 synthesis

Core 4-II-2 (17.74 g, 31.12 mmol), H ₂ O ₂ (1.11 g, 32.68 mmol), and 530 mL of Acetic acid obtained in the above synthesis were used to prepare Core 4 in the same manner as the Core 2-I-2 synthesis method. 16.59 g (yield: 91%) of -I-2 was obtained.

(3-5) Core 4-2 synthesis

14.43 g of Core 4-2 (yield: 92%) was obtained.

(3) Core 4-3 synthesis

<Scheme 13>

(3-1) Core 4-IV-3 synthesis

Add 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (50.00 g, 135.40 mmol) into a round bottom flask, 1- Bromo-2-chloro-3-nitrobenzene (38.42 g, 162.48 mmol), Pd ₂ (PPh ₃ ) ₄ (7.82 g, 6.77 mmol), and K ₂ CO ₃ (56.14 g, 406.21 mmol) were added, and 1,000 mL of Toluene was added. Raise the temperature to 80°C with 500 mL of water and stir for 6 hours with the reactant dissolved. When the reaction is completed, the reactant is concentrated under reduced pressure and quenched by adding water. The reactant that has become a solid is obtained by filtering. The reactant that came out as a filtrate is obtained by removing water, filtered under reduced pressure, dried over MgSO ₄ and concentrated. The resulting compound was recrystallized using a silicagel column to obtain 37.80 g of product (yield: 70%).

(3-2) Core 4-III-3 synthesis

Core 4-IV-3 (37.89 g, 94.78 mmol), Bis(pinacolato)diboron (36.10 g, 142.17 mmol), Pd ₂ (dba) ₃ (4.34 g, 4.74 mmol), and potassium acetate (27.91 g) obtained from the above synthesis. , 284.34 mmol), X-phos (10.50 g, 14.22 mmol), and 750 mL of dioxane were used to obtain 30.68 g of Core 4-III-3 (yield: 66%) in the same manner as the Core 2-III-3 synthesis method above. .

(3-3) Core 4-II-3 synthesis

Core 4-III-3 (30.68 g, 62.56 mmol), 8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (24.66 g, 68.81 mmol), Pd(PPh ₃ ) obtained from the above synthesis. 26.79 _g (26.79 g) of Core 4-II _- 3 ₍ Yield: 72%) was obtained.

(3-4) Core 4-I-3 synthesis

Core 4-II-3 (26.79 g, 45.04 mmol) and triphenylphosphine (29.53 g, 112.60 mmol) obtained in the above synthesis were added, and 530 mL of 1,2-dichlorobenzene was used in the same manner as the Core 2-I-3 synthesis method. 12.42 g of Core 4-I-3 (yield: 49%) was obtained.

(3-5) Core 4-3 synthesis

Core 4-I-3 (12.42 g, 22.07 mmol), iodobenzene (4.50 g, 22.07 mmol), Copper (0.14 g, 2.21 mmol), 18-Crown-6 (0.29 g, 1.10 mmol), K obtained from the above synthesis 11.00 g of Core 4-3 (yield: 78%) was obtained in the same manner as the above Core 2-3 synthesis using CO ₃ (9.15 g, 66.21 mmol ₎ and 70mL of nitrobenzene.

Meanwhile, compounds belonging to Core 1 to Core 4 may be the following compounds, but are not limited thereto. Table 1 below shows the FD-MS values of the following compounds belonging to Core 1 to Core 4.

Ⅱ. Synthesis of Sub 1

Sub 1 of Schemes 1 to 4 may be synthesized through the reaction routes of Schemes 14 to 18, but is not limited thereto.

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

1. Synthesis example of Sub 1-1

<Scheme 14>

(1) Sub 1-I-1 synthesis

4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-5-yl)-1,3,2-dioxaborolane (100.00 g, 290.51 mmol), 1-bromo-2-nitrobenzene Add (70.42 g, 348.61 mmol), Pd(PPh ₃ ) ₄ (16.79 g, 14.53 mmol), K ₂ CO ₃ (120.45 g, 871.54 mmol), Toluene 2,000mL, and water 1,000mL. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 73.94 g of product (yield: 75%). got it

(2) Sub 1-1 synthesis

Add Sub 1-I-1 (73.94 g, 217.88 mmol), triphenylphosphine (142.87 g, 544.71 mmol), and 1,500 mL of 1,2-dichlorobenzene obtained in the above synthesis, raise the temperature to 220°C, and stir for 16 hours with the reactants dissolved. I order it. When the reaction is completed, the reactant is concentrated under reduced pressure and quenched by adding water. The reactant that has become a solid is obtained by filtering. The reactant that came out as a filtrate is obtained by removing water, filtered under reduced pressure, dried over MgSO ₄ and concentrated. The resulting compound was recrystallized using a silicagel column to obtain 40.18 g of product (yield: 60%).

2. Synthesis example of Sub 1-16

<Scheme 15>

(1) Sub 1-I-16 synthesis

2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (80.00 g, 249.81 mmol), 1-bromo-2-nitrobenzene (60.56 g, 299.78 mmol), Pd(PPh ₃ ) ₄ (14.43 g, 12.49 mmol), K ₂ CO ₃ (103.58 g, 749.44 mmol), Toluene 1,600mL, and water 800mL are added. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 58.30 g of product (yield: 74%). got it

(2) Sub 1-16 synthesis

Sub 1-I-16 (58.30 g, 184.86 mmol) obtained in the above synthesis was placed in a round bottom flask, triphenylphosphine (121.22 g, 462.15 mmol) was added, and 1,100 mL of 1,2-dichlorobenzene was heated to 220°C to dissolve the reactant. Stir in a dissolved state for 16 hours. When the reaction is completed, the reactant is concentrated under reduced pressure and quenched by adding water. The reactant that has become a solid is obtained by filtering. The reactant that came out as a filtrate is obtained by removing water, filtered under reduced pressure, dried over MgSO ₄ and concentrated. The resulting compound was subjected to a silicagel column, and the spot under TLC (Methylene chloride: hexane=1:3) was separated and recrystallized to obtain 22.00 g of the product (yield: 42%).

3. Synthesis example of Sub 1-21

<Scheme 16>

(1) Sub 1-I-21 synthesis

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H- carbazole (80.00 g, 216.64 mmol), 1-bromo-2-nitrobenzene ( 52.52 g, 259.97 mmol), Pd(PPh ₃ ) ₄ (12.52 g, 10.83 mmol), K ₂ CO ₃ (89.82 g, 649.93 mmol), 1,600 mL of Toluene, and 800 mL of water were used to synthesize Sub 1-I-16. 56.69 g (yield: 72%) of Sub 1-I-21 was obtained in the same manner.

(2) Sub 1-21 synthesis

Sub 1-I-21 (56.69 g, 155.98 mmol), triphenylphosphine (102.28 g, 389.96 mmol), and 1,100 mL of 1,2-dichlorobenzene obtained in the above synthesis were used to synthesize Sub 1-16 in the same manner as above. 21 22.23 g (yield: 743%) was obtained.

4. Synthesis example of Sub 1-29

<Scheme 17>

(1) Sub 1-I-29 synthesis

4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane (80.00 g, 314.79 mmol), 1-bromo-2-nitrobenzene (76.31 g, 377.74 mmol), Sub 1- was synthesized in the same manner as the Sub 1-I-16 synthesis method above using Pd(PPh ₃ ) ₄ (18.19 g, 15.74 mmol), K ₂ CO ₃ (130.52 g, 944.36 mmol), 1,600 mL of Toluene, and 800 mL of water. 60.42 g of I-29 (yield: 77%) was obtained.

(2) Sub 1-29 synthesis

Sub 1-I-29 (60.42 g, 242.39 mmol), triphenylphosphine (158.94 g, 605.97 mmol), and 1,200 mL of 1,2-dichlorobenzene obtained in the above synthesis were used to synthesize Sub 1-16 in the same manner as above. 29 23.17 g (yield: 44%) was obtained.

5. Synthesis example of Sub 1-32

<Scheme 18>

(1) Sub 1-III-32 synthesis

4,4,5,5-tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane (80.00 g, 314.79 mmol), 1-bromo-2-nitrobenzene (76.31 g, 377.74 mmol), Sub 1- was synthesized in the same manner as the Sub 1-I-16 synthesis method above using Pd(PPh ₃ ) ₄ (18.19 g, 15.74 mmol), K ₂ CO ₃ (130.52 g, 944.36 mmol), 1,600 mL of Toluene, and 800 mL of water. 58.85 g (yield: 75%) of III-32 was obtained.

(2) Sub 1-II-32 synthesis

Sub 1-III-32 (58.85 g, 236.09 mmol), triphenylphosphine (154.81 g, 590.23 mmol), and 1,200 mL of 1,2-dichlorobenzene obtained in the above synthesis were used to synthesize Sub 1-16 in the same manner as above. 28.21 g of II-32 (yield: 55%) was obtained.

(3) Sub 1-I-32 synthesis

Sub 1-II-32 (28.21 g, 129.85 mmol) obtained in the above synthesis was placed in a round bottom flask, and 2,7-dibromo-9,9-diphenyl-9 H -fluorene (92.75 g, 194.77 mmol) and Sodium tert were added. -Add butoxide (37.44 g, 389.55 mmol), Pd ₂ (dba) ₃ (5.95 g, 6.49 mmol), and 430mL of toluene. Afterwards, nitrogen substitution was performed, the reactor temperature was adjusted to 80°C, and Tri-tert-butylphosphine (2.63 g, 12.98 mmol) was added. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 58.86 g of product (yield: 74%). got it

(4) Sub 1-32 synthesis

Sub 1-I-32 (58.86 g, 96.09 mmol), Bis(pinacolato)diboron (31.72 g, 124.92 mmol), PdCl ₂ (dppf) ₃ (3.52 g, 4.80 mmol) and potassium acetate (28.29 g) obtained from the above synthesis. , 288.27 mmol) was placed in a round bottom flask, 1200 mL of DMF was added and stirred at 100°C for 6 hours. When the reaction was completed, water was added to the reactant and quenched. The water in the reactant was removed. After filtering under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated to obtain 45.64 g of product (yield: 72%).

Meanwhile, the compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows the FD-MS values of the compounds belonging to Sub 1.

Ⅲ. Product synthesis

1. P-6 synthesis example

<Scheme 19>

(1) P-I-6 synthesis

Add Core 2-1 (4.7 g, 7.30 mmol) and 140mL of THF. Afterwards, nitrogen substitution is performed and the reactor temperature is set to -70°C. Add 0.60mL of n -BuLi 2.5M. After 2 hours, water is added to terminate the reaction. When the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 3.38 g of product (yield: 82%).

(2) P-6 synthesis

PI-6 (3.38 g, 5.99 mmol), phenylboronic acid (0.73 g, 5.99 mmol), Pd(PPh ₃ ) ₄ (0.35 g, 0.30 mmol), K ₂ CO ₃ (2.48 g, 17.96 mmol) obtained from the above synthesis. , Add 60mL of Toluene and 30mL of water. Afterwards, nitrogen substitution is performed and the reactor temperature is adjusted to reflux at 120°C. After the reaction time was overnight, when the reaction was completed, water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 2.51 g of product (yield: 69%). got it

2. P-19 synthesis example

<Scheme 20>

(1) P-I-19 synthesis

Core 1-1 (7.20 g, 21.26 mmol), phenylboronic acid (2.59 g, 21.26 mmol), Pd(PPh ₃ ) ₄ (1.23 g, 1.06 mmol), K ₂ CO ₃ (8.82 g, 63.79 mmol), Toluene 140mL , 4.78 g of PI-19 (yield: 67%) was obtained in the same manner as the P-6 synthesis method above using 70 mL of water.

(2) P-19 synthesis

PI-19 (4.78 g, 14.25 mmol), Sub 1-8 (7.13 g, 21.37 mmol), Pd ₂ (dba) ₃ (0.65 g, 0.71 mmol), Sodium tert-butoxide (4.11 g, 42.74 mmol) obtained from the above synthesis. mmol), add 50mL of Toluene. Afterwards, nitrogen substitution is performed, the reactor temperature is adjusted to reflux at 120°C, and Tri-tert-butylphosphine (0.29 g, 1.42 mmol) is added. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 6.40 g of product (yield: 71%). got it

3. P-20 synthesis example

<Scheme 21>

(1) P-IV-20 synthesis

Sub 1-9 (20.00 g, 31.17 mmol), (2-bromo-6-chlorophenyl)(methyl)sulfane (7.40 g, 31.17 mmol), Pd(PPh ₃ ) ₄ (1.80 g, 1.56 mmol), K ₂ CO 13.62 g (yield: 65%) of P-IV-20 was obtained in the same manner as the P-6 synthesis method above using ₃ (12.92 g, 93.51 mmol), 400 mL of toluene, and 200 mL of water.

(2) P-III-20 synthesis

P-IV-20 (13.62 g, 20.26 mmol), Bis(pinacolato)diboron (7.72 g, 30.39 mmol), Pd ₂ (dba) ₃ (0.93 g, 1.01 mmol), potassium acetate (5.97 g, 10.52 g (yield: 68%) of P-III-20 was obtained in the same manner as the above Core 2-III-2 synthesis using 60.78 mmol),

(3) P-II-20 synthesis

P-III-20 (10.52 g, 13.78 mmol), 2-bromoimidazo[1,2- b ]pyridazine (3.00 g, 15.15 mmol), Pd(PPh ₃ ) ₄ (0.80 g, 0.69 mmol) obtained from the above synthesis, 8.25 g (yield: 69%) of P-II-20 was obtained in the same manner as the above Core 2-II-2 synthesis using K ₂ CO ₃ (5.71 g, 41.33 mmol), 210 mL Toluene, and 105 mL water.

(4) P-I-20 synthesis

PI-20 was prepared in the same manner as the Core 2-I-2 synthesis using P-II-20 (8.25 g, 9.51 mmol), H ₂ O ₂ (0.34 g, 9.98 mmol), and 250mL Acetic acid obtained in the above synthesis. 6.60 g (yield: 90%) was obtained.

(5) P-20 synthesis

Using P-I-20 (6.60 g, 8.56 mmol) obtained in the above synthesis, 1.03 g of sulfuric acid, 200 mL of water, and 1.03 g of NaOH, 5.88 g of P-20 (yield: 93%) was obtained in the same manner as the Core 2-2 synthesis. got it

4. P-85 synthesis example

<Scheme 22>

(1) P-I-85 synthesis

Core 3-4 (8.00 g, 24.83 mmol), Sub 1-23 (12.38 g, 37.24 mmol), Pd ₂ (dba) ₃ (1.14 g, 1.24 mmol), Sodium tert-butoxide (7.16 g, 74.48 mmol), Add 80mL of toluene. Afterwards, nitrogen substitution is performed, the reactor temperature is adjusted to reflux at 80°C, and Tri-tert-butylphosphine (0.50 g, 2.48 mmol) is added. After the reaction time was overnight, when the reaction was completed, the water in the reactant was removed, filtered under reduced pressure, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.98 g of product (yield: 70%). got it

(2) P-85 synthesis

The PI-6 was prepared using PI-85 (9.98 g, 17.38 mmol) obtained in the above synthesis, 300mL of THF, and 1.42mL of n -BuLi 2.5M. 7.88 g of P-85 (yield: 84%) was obtained using the same method as the synthesis method.

5. P-92 synthesis example

<Scheme 23>

<Scheme 23>

(1) P-IV-92 synthesis

Sub 1-29 (20.00 g, 92.05 mmol), (2-bromo-6-chlorophenyl)(methyl)sulfane (24.05 g, 101.26 mmol), Pd ₂ (dba) ₃ (4.21 g, 4.60 mmol), Sodium tert- 23.75 g of P-IV-92 (yield: 69%) was produced in the same manner as the above PI-85 synthesis using butoxide (26.54 g, 276.15 mmol), Toluene 300mL, and Tri-tert-butylphosphine (1.86 g, 9.21 mmol). got it

(2) P-III-92 synthesis

P-IV-92 (23.75 g, 63.52 mmol), Bis(pinacolato)diboron (24.19 g, 95.27 mmol), Pd ₂ (dba) ₃ (2.91 g, 3.18 mmol), potassium acetate (18.70 g, 19.51 g (yield: 66%) of P-III-92 was obtained in the same manner as the PI-85 synthesis using 470 mL of dioxane (190.55 mmol),

(3) P-II-92 synthesis

P-III-92 (19.51 g, 41.92 mmol), 2-bromoimidazo[1,2- b ]pyridazine (9.13 g, 46.11 mmol), Pd(PPh ₃ ) ₄ (2.42 g, 2.10 mmol) obtained from the above synthesis, 13.21 g (yield: 69%) of P-II-92 was obtained in the same manner as the above P-II-20 synthesis using K ₂ CO ₃ (17.38 g, 125.76 mmol), 380 mL Toluene, and 190 mL water.

(4) P-I-92 synthesis

Using the same method as _the PI-20 synthesis method, _12.30 g of PI-92 ( Yield: 90%) was obtained.

(5) P-92 synthesis

10.55 g of P-92 (yield: 92%) was obtained in the same manner as the P-20 synthesis using P-I-92 (12.30 g, 26.03 mmol), 7.66 g of sulfuric acid, 370 mL of water, and 3.12 g of NaOH obtained in the above synthesis. .

Meanwhile, the FD-MS values of compounds P-1 to P-100 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

The synthesis examples are for some of the exemplary compounds represented by Formula 1, and the reactions include BuchwaldHartwig cross coupling reaction, Suzuki cross-coupling reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, and intramolecular acid-induced cyclization reaction. (J. mater. Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005 , 70, 5014.), based on Lithium-halogen exchange reaction, Grignard reaction, and Cyclic Dehydration reaction. Those skilled in the art will easily understand that the reaction proceeds even if other substituents defined in Formula 1 are combined in addition to the substituents specified in the specific synthesis example.

Manufacturing evaluation of organic electric devices

[Example 1] Red organic light emitting device (phosphorescent host)

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. )-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a 60 nm thick film. Next, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was added to a thickness of 60 nm. A hole transport layer was formed by vacuum deposition. The above invention compound (compound P-3) represented by Chemical Formula 1 was used as a host on the upper part of the hole transport layer, and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate] was used as a dopant. A 30 nm thick light emitting layer was deposited on the hole transport layer by doping at a weight of 95:5. (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinoline oleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole-blocking layer, and the electron transport layer Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a 40 nm thick film. 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.

[Example 2] to [Example 25]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that the compounds of the present invention shown in Table 4 below were used as the phosphorescent host material instead of the compound P-3 of the present invention.

[Comparative Example 1] and [Comparative Example 2]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that Comparative Compound A and Comparative Compound B below were used instead of Compound P-3 of the present invention as the phosphorescent host material.

[Comparative Compound A] [Comparative Compound B]

A forward bias direct current voltage was applied to the organic electroluminescent devices of Examples and Comparative Examples manufactured in this way, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch. As a result of the measurement, the electroluminescence (EL) characteristics were measured at a standard luminance of 2500 cd/m2. The T95 lifespan was measured using a lifespan measuring device manufactured by McScience. Table 4 below shows the results of device fabrication and evaluation.

[Table 4]

As can be seen from the results in Table 4, the device using the compound according to an embodiment of the present invention as the phosphorescent host material of the light-emitting layer has a lower driving voltage, There has been a significant improvement in luminous efficiency and lifespan.

When using polycyclic compound type Comparative Compound B and the compound of the present invention rather than CBP (Comparative Compound A), which is widely used as a host material, the driving voltage, efficiency, and lifespan of the organic electric device were improved. In addition, Comparative Compound B and the compounds used in Examples 1 to 20 of the present invention have similar structures, but the substituents bonded to N of carbazole are different. Due to these differences, it can be seen that the electrical properties of the organic electroluminescent device are further improved in the case of the present invention.

This is because the compound of the present invention has a relatively lower LUMO level than Comparative Compound 1, which facilitates the injection of electrons from the ETL into the light-emitting layer, improving the charge balance within the light-emitting layer, ultimately improving the driving voltage and lifespan of the device. In addition, when a specific substituent is introduced as in the compound of the present invention rather than a triazine being introduced into the N portion of carbazole as in Comparative Example 2, the conjugation length of the compound becomes longer, allowing for the transition from the host to the dopant. It is believed that the efficiency of organic electroluminescent devices has improved because charge transfer becomes easier.

In addition, in the above-described device fabrication 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 be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting the present invention, and the spirit and scope of the present invention are 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 device
110, 110, 310: first electrode
120, 220, 320: Hole injection layer
321: First hole injection layer
130, 230, 330: Hole transport layer
331: first hole transport layer
332: Second hole transport layer
233: buffer layer
140, 240: light emitting layer
341: first light emitting layer
342: second light emitting layer
243: Light-emitting auxiliary layer
150: Electron transport layer
351: first electron transport layer
352: second electron transport layer
160, 360: Electron injection layer
170, 270, 370: second electrode
380: first charge generation layer
381: second charge generation layer
ST1: first stack
ST2: Second Stack
CGL: Charge generation layer

Claims (13)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
1) R ¹ and R ² are, independently of each other, hydrogen; heavy hydrogen; halogen; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ; 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(Ra)(Rb);
^{2 ) X 1 and _ _} One is selected from the group consisting of O, S and NR ³ , and the other is a single bond,
3) L ¹ and L ² are, independently of each other, a single bond; C ₆ ~ C ₆₀ arylene group; It is selected from the group consisting of a C ₂ to C ₆₀ heterocyclic group and a C ₃ to C ₆₀ aliphatic ring group containing at least one heteroatom among O, N, S, Si and P,
4) R ³ is, independently of each other, an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ₁ ~ C ₅₀ alkyl group; selected from the group consisting of,
5) Ar ¹ and Ar ² are, independently of each other, an aryl group of C ₆ to C ₆₀ ; It is selected from the group consisting of C ₂ to C ₆₀ heterocyclic groups containing at least one hetero atom among O, N, S, Si and P,
6) Ra and Rb are, independently of each other, an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ₁ ~ C ₅₀ alkyl group; selected from the group consisting of,
7) L' is a single bond independently of each other; C ₆ ~ C ₆₀ arylene group; A divalent functional group of a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and is selected from the group consisting of divalent functional groups of C ₃ to C ₆₀ aliphatic ring groups,
8) o1 and o2 are integers of 0 or 1, respectively, and o1+o2 is an integer of 1 or more,
9) n is an integer from 0 to 3, m is an integer from 0 to 4,
10) In R ¹ , R ² , L ^{1 ,} L ² , ^{X 1 ,} group and aryloxy group are each deuterium; nitro group; Nitrile group; halogen group; amino group; A silane group unsubstituted or substituted with a C ₁ to C ₂₀ alkyl group or a C ₆ to C ₂₀ aryl group; siloxane group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; One or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group may be substituted, and these substituents may be combined with each other to form a ring.
According to clause 1,
R ¹ and R ² are, independently of each other, hydrogen; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and C ₁ to C ₅₀ alkyl group; C ₁ ~ C ₃₀ alkoxy group; is selected from the group consisting of,
X ¹ and X ² are independently selected from the group consisting of a single bond, O, ^{S ,} and NR ³ , and at least one of
L ¹ and L ² are, independently of each other, a single bond; C ₆ ~ C ₆₀ arylene group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P,
R ³ is, independently of each other, an aryl group of 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;
Ar ¹ and Ar ² are, independently of each other, an aryl group of 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.
According to clause 1,
The compound represented by Formula 1 is a compound characterized by being represented by the following Formula 2 or Formula 3:
[Formula 2] [Formula 3]

In Formula 2 and Formula 3, R ¹ , R ² , X ¹ , X ² , L ¹ , Ar ¹ , m and n are the same as defined in claim 1.
According to clause 1,
The compound represented by Formula 1 is a compound characterized in that it is represented by any one of the following Formulas 4 to 7:
[Formula 4] [Formula 5]

[Formula 6] [Formula 7]

In Formulas 4 to 7, R ¹ , R ² , X ¹ , X ² , L ² , Ar ¹ , Ar ² , m and n are the same as defined in claim 1.
According to clause 1,
The compound represented by Formula 1 is a compound characterized in that it is represented by any one of the following Formulas 8 to 10:
[Formula 8] [Formula 9]

[Formula 10]

In Formulas 8 to 10, R ¹ , R ² , R ³ , L ¹ , L ² , Ar ¹ , Ar ² , m, n, o1 and o2 are the same as defined in claim 1.
According to clause 1,
The compound represented by Formula 1 is a compound characterized in that it is represented by any one of the following Formulas 11 to 13:
[Formula 11] [Formula 12]

[Formula 13]

In Formulas 11 to 13, R ¹ , R ² , R ³ , L ¹ , L ² , Ar ¹ , Ar ² , m, n, o1 and o2 are the same as defined in claim 1.
According to clause 1,
A compound characterized in that at least one of Ar ¹ and Ar ² is represented by the following formula A-1 or A-2:
[Formula A-1] [Formula A-2]

In the above formulas A-1 and A-2,
Q ¹ to Q ⁹ are, independently of each other, N or CR ^e ,
R ^e are, independently of each other, hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group,
Z is selected from Formula Z-1 to Formula Z-15:
Formula Z-1 Formula Z-2 Formula Z-3 Formula Z-4 Formula Z-5

Formula Z-6 Formula Z-7 Formula Z-8 Formula Z-9 Formula Z-10

Formula Z-11 Formula Z-12 Formula Z-13 Formula Z-14 Formula Z-15

In Formula Z-1 to Formula Z-15,
The * represents the position where each of Formulas Z-1 to Z-15 is condensed with a ring containing Q ¹ to Q ⁴ ,
W ¹ and W ² are, independently of each other, a single bond, NL ³ -Ar ³ , S, O or C(R ^f )(R ^g ),
V is, independently of each other, N or CR ^h ,
L ³ is a single bond; C ₆ -C ₆₀ arylene group; A divalent functional group of a C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A divalent functional group of the fused ring group of the aliphatic ring of C ₃ -C ₆₀ and the aromatic ring of C ₆ -C ₆₀ ; C ₁ ~ C ₅₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; and C ₂ to C ₂₀ alkynylene groups,
Ar ³ , R ^f , and R ^g are, independently of each other, a C ₆ to C ₆₀ aryl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -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; and an aryloxy group of C ₆ -C ₃₀ ,
R ^h is, independently of each other, hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -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; and an aryloxy group of C ₆ -C ₃₀ ,
R ^f and R ^g may be bonded to each other to form a spiro compound together with the carbon to which R ^f and R ^g are bonded.
According to clause 1,
A compound characterized in that Ar ¹ and Ar ² are represented by one of the following formulas B-1 to B-4:
[Formula B-1] [Formula B-2]

[Formula B-3] [Formula B-4]

In Formula B-1 to Formula B-4,
Y ¹ and Y ² are, independently of each other, NL ⁴ -Ar ⁴ , O, S or C(R ⁱ )(R ^j ),
L ⁴ is a single bond; C ₆ -C ₆₀ arylene group; A divalent functional group of a C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A divalent functional group of the fused ring group of the aliphatic ring of C ₃ -C ₆₀ and the aromatic ring of C ₆ -C ₆₀ ; C ₁ ~ C ₅₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; and C ₂ to C ₂₀ alkynylene groups,
Ar ⁴ , R ⁱ and R ^j are, independently of each other, a C ₆ to C ₆₀ aryl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -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; and an aryloxy group of C ₆ -C ₃₀ ,
R ⁴ to R ⁸ are, independently of each other, hydrogen; heavy hydrogen; halogen; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ; 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 ⁵ -N(R ^k )(R ^l ); wherein R ⁴ to R ⁸ may each be combined with each other to form a ring,
R ^k and R ^l are, independently of each other, an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring 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 ₁ ~ C ₅₀ alkyl group; selected from the group consisting of,
L ⁵ is a single bond independently of each other; C ₆ ~ C ₆₀ arylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and C ₃ to C ₆₀ aliphatic ring groups,
a, b, q and s are integers from 0 to 4,
r is an integer from 0 to 2.
According to clause 1,
The compound represented by Formula 1 is characterized in that it is one of the following Formulas P-1 to Formula P-106.




















first electrode; second electrode; And an organic material layer located between the first electrode and the second electrode,
The organic material layer is an organic electric device containing the compound of claim 1.
According to clause 10,
The organic 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,
The compound is an organic electric device wherein at least one layer 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 includes the compound of claim 1.
According to clause 10,
The organic material layer includes a first stack, a second stack, and a charge generation layer at the boundary of the first stack and the second stack,
The first stack includes at least one layer of a first hole injection layer, a first hole transport layer, a first light emitting layer, and a first electron transport layer,
The second stack includes at least one layer of a second hole injection layer, a second hole transport layer, a second light emitting layer, a second electron transport layer, and an electron injection layer,
The charge generation layer includes at least one of a first charge generation layer and a second charge generation layer,
Included in the organic layer are a first hole injection layer, a first hole transport layer, a first light-emitting layer, a first electron transport layer, a second hole injection layer, a second hole transport layer, a second light-emitting layer, a second electron transport layer, an electron injection layer, An organic electric device wherein at least one of the first charge generation layer and the second charge generation layer includes the compound of claim 1.
first electrode;
second electrode;
an organic material layer located between the first electrode and the second electrode; and
It includes a capping layer located on at least one of one side of the first electrode opposite to the organic material layer and one side of the second electrode opposite to the organic material layer,
The capping layer is an organic electric device comprising the compound of claim 1.

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