KR20240048593A - Compound for organic electric element, organic electric element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a compound represented by Formula 1, an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric device. do. By including the compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered and the luminous efficiency and lifespan can be improved.

Description

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

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

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic electric devices that utilize the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic electric device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as organic layers in organic electric devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. there is. In addition, light-emitting materials can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to realize better natural colors.

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

Currently, the portable display market is increasing in size toward large-area displays, which requires greater power consumption than that required for existing portable displays. Therefore, power consumption has become a very important factor for portable displays that have a limited power source such as batteries, and issues of efficiency and lifespan 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 materials due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T ₁ 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, and electron injection materials, must be supported by stable and efficient materials. This must take precedence, and in particular, the development of a host material for the light-emitting layer is necessary.

The purpose of the present invention is to provide a compound for an organic electric device that can lower the driving voltage of the device and improve the luminous efficiency 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:

(Ar ³ is lim)

In another aspect, the present invention provides a method for recovering a reusable compound represented by the above chemical formula by recovering the compound represented by the above chemical formula after deposition.

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

In another aspect, the present invention provides an organic electric device and an electronic device thereof including a compound represented by the above formula and a compound represented by one of the following formulas.

By using the compound according to the embodiment of the present invention, the driving voltage of the device can be lowered, the luminous efficiency and lifespan can be improved, and the compound used in the deposition process can be recovered and reused.

1 to 3 are exemplary diagrams of organic electroluminescent devices according to embodiments of the present invention.

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or arylene group may include a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc.

As used in the present invention, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, and the term "fluorenylene group" refers to a substituted or unsubstituted fluorenylene group, and the fluorenyl group or The fluorenylene group includes spiro compounds formed by R and R' bonded to each other in the structure below, and also includes compounds formed by adjacent R" bonded to each other to form a ring. "Substituted fluorenyl group", "substituted The fluorenylene group" means that at least one of R, R', and R" in the structure below is a substituent other than hydrogen, and in the formula below, R" may be 1 to 8. In the present specification, regardless of the valence, Fluorenyl group, fluorenylene group, etc. may be referred to as fluorene group or fluorene.

The term "spiro compound" used in the present invention has a 'spiro connection', and the spiro connection means 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 the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also 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. Unless otherwise specified, the term "heteroatom" used in this specification refers to an element other than carbon, such as N, O, S, P or Si, and instead of carbon forming a ring, SO ₂ , P= It may also contain heteroatom groups such as O. In the present specification, heterocyclic groups include single rings containing heteroatoms, ring aggregates, multiple fused ring systems, spiro compounds, etc.

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

In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent, may be written as the 'name of the 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 name of the group may be written by distinguishing the valence, such as the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene', but the valence and Regardless, it can also be written as the parent compound name, ‘phenanthrene’. Similarly, in the case of pyrimidine, it can be written as 'pyrimidine' regardless of the valence, or it can be written as the 'name of the group' of the valence, such as pyrimidineyl group in the case of monovalent group, pyrimidineylene in the case of divalent group, etc. there is.

Additionally, in this specification, when describing compound names or substituent names, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu. Orene can be described as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless explicitly stated otherwise, the chemical formula used in the present invention applies the same as the substituent definition according to the exponent definition of the following chemical formula.

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

In addition, unless otherwise specified in the specification, a ring refers to an aryl ring, heteroaryl ring, fluorene ring, aliphatic ring, etc., a number-ring refers to a condensed ring, and a number-atom ring refers to the form of a ring. It can mean. For example, naphthalene corresponds to a 2-ring condensed ring, anthracene to a 3-ring condensed ring, thiophene or furan corresponds to a 5-membered heterocycle, and benzene or pyridine corresponds to a 6-membered aromatic ring.

In addition, unless otherwise specified in the specification, the ring formed by combining adjacent groups is an aromatic ring group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and an aliphatic ring group of C ₃ to C ₆₀ . Here, the aromatic ring group may include an aryl ring, and the heterocyclic group may include a heteroaryl ring.

Unless otherwise specified in the specification, 'neighboring groups' refers to groups R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , and R ₅ using the following chemical formula as an example. and R ₆ , as well as R ₇ and R ₈ that share one carbon, and ring configurations that are not immediately adjacent, such as between R ₁ and R ₇ , between R ₁ and R ₈ , or between R ₄ and R ₅ , etc. Substituents bonded to elements (such as carbon or nitrogen) may also be included. In other words, if there are substituents on immediately adjacent ring elements such as carbon or nitrogen, they can become neighboring groups, but if no substituents are bonded to the immediately adjacent ring elements, they can be bonded to the next ring element. It can be a group adjacent to a substituent, and substituents bonded to carbons of the same ring can also be said to be neighboring groups. In the formula below, when substituents bonded to the same carbon, such as R ₇ and R ₈ , combine to form a ring, a compound containing a spiro moiety may be formed.

,

In addition, in this specification, the expression 'neighboring groups can combine with each other to form a ring' is used in the same meaning as 'neighboring groups can selectively form a ring by combining with each other', and at least one pair of This refers to a case where neighboring groups combine with each other to form a ring.

In addition, unless otherwise specified in the specification, an aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkylcy group. Substituents such as arylthio groups, arylthio groups, etc., rings formed by bonding adjacent groups, etc. are each deuterium; halogen; Cyano group; nitro group; siloxane group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₃₀ aliphatic ring group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; C ₁ -C ₂₀ alkylthio group; C ₆ -C ₂₀ arylthio group; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; and a phosphine oxide group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group.

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

In adding reference numerals to components in each drawing, it should be noted that identical components are given the same reference numerals as much as possible even if they are shown in different drawings. Additionally, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only used to distinguish the component from other components, and the essence, order, or order of the component is not limited by the term. When a component is described as being “connected,” “coupled,” or “connected” to another component, that component may be directly connected or connected to that other component, but 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, this means not only when it is "directly above" the other component, but also when 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.

1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.

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 material layer formed between the second electrode 170, and an inorganic material layer may be included between the first electrode 110 and the second electrode 120.

For example, the first electrode 110 may be an anode, and the second electrode 170 may be a cathode. In the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode. .

The organic material layer refers to a layer containing at least one organic material. For example, 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. However, the electron injection layer 160 may be an inorganic material layer that does not contain organic materials.

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

Preferably, the luminous efficiency improvement layer 180 may be formed on one side of both sides of the first electrode 110 or both sides of the second electrode 170 that is not in contact with the organic material layer or the inorganic material layer, and the luminous efficiency improvement layer 180 ) is formed, the light efficiency of the organic electric device can be improved.

For example, the luminous efficiency improvement layer 180 may be formed on the second electrode 170. In the case of a top emission organic light emitting device, the luminous efficiency improvement layer 180 is formed to form the second electrode 170. ) can reduce optical energy loss due to SPPs (surface plasmon polaritons), and in the case of bottom emission organic light emitting devices, the light efficiency improvement layer 180 serves as a buffer for the second electrode 170. can do.

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

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

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

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

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

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

The first stack (ST1) is an organic material layer formed on the first electrode 110, which includes a first hole injection layer 320, a first hole transport layer 330, a first light emitting layer 340, and a first electron transport layer 350. ) may include, and the second stack (ST2) may include a second hole injection layer 420, a second hole transport layer 430, a second light emitting layer 440, and a second electron transport layer 450. . In this way, the first stack and the second stack may be organic material layers with the same stacked structure, or they may be organic material layers with different stacked structures.

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

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

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

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

The compound represented by Formula 1 of the present invention may be included in the organic layer. For example, the compound represented by Formula 1 of the present invention includes a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), an auxiliary light emitting layer (220), an electron transport layer (150, It can be used as a material for the light emitting layer (140, 340, 440), the light emitting layer (140, 340, 440), or the light efficiency improvement layer (180), but is preferably used as a material for the light emitting layer (140, 340, 440) or/and the light efficiency improvement layer (180), More preferably, it can be used as a host for the light emitting layer (140, 340, 440).

Even if the core is identical, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so research on the selection of the core and the combination of sub-substituents attached to it is required, and in particular, when the energy level and T ₁ value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using the compound represented by Formula 1 as a material for the light emitting layer (140, 340, 440), the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interface properties, etc.) By optimizing it, the lifespan and efficiency of organic electric devices can be improved simultaneously.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, an anode 110 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120 is formed thereon. , It can be manufactured by forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160, and then depositing a material that can be used as the cathode 170 thereon. there is. In addition, a light-emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) may be further formed between the light-emitting layer 140 and the electron transport layer 150. As shown, it can also be formed in a stack structure.

In addition, the organic material layer uses a variety of polymer materials, such as a solution process or solvent process rather than a deposition method, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, and doctor bleed process. It can be manufactured with fewer layers by methods such as a printing process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

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

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

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

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

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

<Formula 1> <Formula A>

In Formula 1, each symbol is defined as follows.

X and Y are independently O, S or N, one of which is N and the other is O or S.

^In a pentagonal ring containing X and ^Y , the bond between XCY is indicated when means bonded by a single bond, ^and when X is O or S and Y is N, the carbon to which Ar ¹ is bonded and It means to do.

L ¹ to L ³ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; 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 C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P, and Ar ³ is of formula A. Ar ¹ may include one or more deuterium, and Ar ¹ may be an aryl group substituted with deuterium.

Ring A is an aryl ring with C ₁₀ or more. However, when the A ring is a naphthyl C ₁₀ aryl ring, the case where 2,3-naphthyl is condensed to the Z ring is excluded. That is, when the A ring is naphthyl, only 1,2-naphthyl or 3,4-naphthyl condensed to the Z ring is possible.

Ring A may be substituted with one or more R that are the same or different from each other.

Z is O or S.

R ¹ , R ² and R are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₂₀ alkoxy group; and aryloxy groups of C ₆ to C ₆₀ , and adjacent R ² groups may be bonded to each other to form a benzene ring.

a is an integer from 0 to 7, and b is an integer from 0 to 3. When these are integers of 2 or more, the plurality of R ¹ is the same as or different from each other, and the plurality of R ² are the same as or different from each other.

When at least one of Ar ¹ , Ar ² , R ¹ , R ² and R is an aryl group, the aryl group is, for example, C ₆ ~C ₃₀ , C ₆ ~C ₂₉ , C ₆ ~C ₂₈ , C ₆ ~C ₂₇ , C ₆ ~C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~ It may be an aryl group such as C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenyl, biphenyl, naphthyl, terphenyl, It may be phenanthrene, triphenylene, etc.

When at least one of L ¹ to L ³ is an arylene group, the arylene group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ to C _26. , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , It may be an arylene group such as C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, tri. It may be phenylene, etc.

When at least one of Ar ¹ , Ar ² , R ¹ , R ² , R, L ¹ to L ³ is a heterocyclic group, the heterocyclic group is, for example, C ₂ to C ₃₀ , C ₂ to C ₂₉ , C ₂ to C ₂₈ , C ₂ ~C ₂₇ , C ₂ ~C ₂₆ , C ₂ ~C ₂₅ , C ₂ ~C ₂₄ , C ₂ ~C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~ C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ , etc., specifically, pyridine, pyridine, etc. Mydine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoline. Quinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzo Thiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzo. Furopyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzooxazole , benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl It may be -9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc.

When at least one of Ar ¹ , Ar ² , R ¹ , R ² , R, L ¹ to L ³ is an aliphatic ring group, the aliphatic ring group is, for example, C ₃ to C ₃₀ , C ₃ to C ₂₉ , C ₃ to C ₂₈ , C ₃ ~C ₂₇ , C ₃ ~C ₂₆ , C ₃ ~C ₂₅ , C ₃ ~C ₂₄ , C ₃ ~C ₂₃ , C ₃ ~C ₂₂ , C ₃ ~C ₂₁ , C ₃ ~C ₂₀ , C ₃ ~C ₁₉ , C ₃ ~C ₁₈ , C ₃ ~C ₁₇ , C ₃ ~C ₁₆ , C ₃ ~C ₁₅ , C ₃ ~C ₁₄ , C ₃ ~C ₁₃ , C ₃ ~C ₁₂ , C ₃ ~C ₁₁ , C ₃ ~C ₁₀ , C ₃ ~C ₈ , C ₃ ~C ₆ , C ₆ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , It may be an aliphatic ring group such as C ₁₈ , and specifically, it may be a cyclopentanyl group, a cyclohexanyl group, a norbornyl group, or an adamantyl group.

The aryl group, arylene group, fluorenyl group, fluorenylene group, hetero ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and benzene ring formed by bonding adjacent R ³ groups to each other. are each deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent R ³ groups with each other When at least one of the benzene rings formed by bonding is substituted with an aryl group, the aryl group is, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₉ , C ₆ ~ C ₂₈ , C ₆ ~ C ₂₇ , C ₆ ~ C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~ C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , etc. may be an aryl group.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent groups are bonded to each other. When at least one of the rings formed is substituted with a heterocyclic group, the heterocyclic group is, for example, C ₂ ~ C ₃₀ , C ₂ ~ C ₂₉ , C ₂ ~ C ₂₈ , C ₂ ~ C ₂₇ , C ₂ ~ C ₂₆ , C ₂ ~C ₂₅ , C ₂ ~C ₂₄ , C ₂ ~C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~ C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C _{14, C 15 ,} C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , It may be a heterocyclic group such as C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ , etc.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent R ³ groups with each other When at least one of the benzene rings formed by bonding is substituted with an aliphatic ring group, the aliphatic ring group is, for example, C ₃ ~ C ₃₀ , C ₃ ~ C ₂₉ , C ₃ ~ C ₂₈ , C ₃ ~ C ₂₇ , C ₃ ~ C ₂₆ , C ₃ ~C ₂₅ , C ₃ ~C ₂₄ , C ₃ ~C ₂₃ , C ₃ ~C ₂₂ , C ₃ ~C ₂₁ , C ₃ ~C ₂₀ , C ₃ ~C ₁₉ , C ₃ ~C ₁₈ , C ₃ ~C ₁₇ , C ₃ ~C ₁₆ , C ₃ ~C ₁₅ , C ₃ ~C ₁₄ , C ₃ ~C ₁₃ , C ₃ ~C ₁₂ , C ₃ ~C ₁₁ , C ₃ ~C ₁₀ , C ₃ ~ Aliphatic ring groups such as C ₈ , C ₃ ~ C ₆ , C ₆ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , specifically, cyclopentanyl group , cyclohexanyl group, norbornyl group, adamantyl group, etc.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent R ³ groups with each other When at least one of the benzene rings formed by bonding is substituted with an alkyl group, the alkyl group is, for example, C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , C ₄ , etc. It may be an alkyl group, for example, a methyl group, an ethyl group, a t-butyl group, etc.

Formula 1 may be represented by one of the following Formulas 1-1 to 1-4.

<Formula 1-1> <Formula 1-2> <Formula 1-3> <Formula 1-4>

In Formulas 1-1 to 1-4, X, Y, R ¹ , L ¹ to L ³ , Ar ¹ to Ar ³ and a are as defined in Formula 1.

Formula A may be represented by Formula A-1 or Formula A-2 below.

<Formula A-1> <Formula A-2>

In Formula A-1 and Formula A-2, R ² , Z, and b are as defined in Formula A, R ³ is defined as R in Formula A, and c is an integer from 0 to 6, When c is an integer of 2 or more, multiple R ³ 's are the same or different from each other, and * indicates the bonding position.

The above Chemical Formula A-1 may be represented by one of the following Chemical Formulas A-1-1 to Chemical Formulas A-1-4.

<Formula A-1-1> <Formula A-1-2> <Formula A-1-3> <Formula A-1-4>

In Formulas A-1-1 to A-1-4, R ² , R ³ , Z, b, and c are as defined in Formula A-1.

The formula A-2 may be represented by one of the following formulas A-2-1 to A-2-4.

<Formula A-2-1> <Formula A-2-2> <Formula A-2-3> <Formula A-2-4>

In Formulas A-2-1 to A-2-4, R ² , R ³ , Z, b, and c are as defined in Formula A-2.

At least one of L ¹ to L ³ may be selected from the group consisting of the following formulas L1 to L3.

<Formula L1> <Formula L2> <Formula L3>

In the above chemical formulas L1 to L3, * represents the bonding position.

R ⁴ and R ⁵ are independently 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; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups, and adjacent groups may be bonded to each other to form a ring.

d is an integer from 0 to 4, e is an integer from 0 to 6, and when these are integers of 2 or more, the plurality of R ⁴ is the same as or different from each other, the plurality of R ⁵ are the same as or different from each other, and adjacent groups They can combine with each other to form a ring.

The formula L1 may be one of the following formulas L1-1 to L1-3, the formula L2 may be one of the following formulas L2-1 to L2-6, and the formula L3 may be one of the following formulas L3-1 to L2-6. It may be one of formula L3-4.

<Formula L1-1> <Formula L1-2> <Formula L1-3>

<Formula L2-1> <Formula L2-2> <Formula L2-3>

<Formula L2-4> <Formula L2-5> <Formula L2-6>

<Formula L3-1> <Formula L3-2> <Formula L3-3> <Formula L3-4>

In Formula L1-1 to Formula L1-3, Formula L2-1 to Formula L2-6, and Formula L3-1 to Formula L3-4, R ⁴ , R ⁵ , d and e are as defined above.

Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

.

The Reorganization Energy (RE) value of the compound represented by Formula 1 is 0.12 to 0.30, preferably 0.15 to 0.29.

Hereinafter, relocation energy will be described.

Reorganization energy refers to the energy lost due to changes in the molecular structure arrangement when charges (electrons, holes) move. It depends on molecular geometry and has the characteristic that the smaller the difference between the PES (Potential Energy Surface) in the neutral state and the PES in the charged state, the smaller the value. The RE value can be obtained by the calculation formula below.

NONE: Neutral geometry of Neutral molecules (= NO opt.)

NOAE: Anion geometry of neutral molecules

NOCE: Cation geometry of neutral molecules

AONE: Neutral geometry of anion molecules

AOAE: Anion geometry of anion molecules (= AO opt.)

CONE: Neutral geometry of Cation molecules

COCE: Cation geometry of Cation molecules (= CO opt.)

Relocation energy value and charge mobility are inversely proportional, and under the condition of having the same r and T values, the RE value of each material directly affects mobility.

The relationship between RE value and mobility is expressed as follows and is explained as a charge transfer matrix element.

λ : Reorganization energy

μ : mobility

r: dimer displacement

t: intermolecular

According to the above equation, it can be seen that the smaller the RE value, the faster the mobility of charges.

To obtain the rearrangement energy value, a simulation tool that can calculate the potential energy according to the molecular structure is needed. For example, Gaussian09 (hereinafter referred to as G09) and Schrodinger Materials Science's Jaguar (hereinafter referred to as JG) modules can be used. Both G09 and JG are tools that analyze the characteristics of molecules through quantum mechanical (QM) calculations, and have the function of optimizing the molecular structure or calculating the energy (single-point energy) for a given molecular structure.

The process of performing QM calculations on molecular structures requires large computational resources, for example, two cluster servers could be used for these calculations. Each cluster server consists of four node workstations and one master workstation, and each node uses a CPU of 36 cores or more to perform parallel computing through symmetric multi-processing (SMP). Molecular QM calculations can be performed.

Using G09, calculate the optimized molecular structure and its potential energy (NONE / COCE) in the neutral/charged state required for rearrangement energy. By changing only the charges in the two optimized structures, the charge state potential energy (NOCE) of the structure optimized for the neutral state and the neutral state potential energy (CONE) of the structure optimized for the charge state are calculated. Afterwards, the relocation energy is calculated according to the relationship below.

Since Schrödinger provides a function to automatically proceed with this calculation process, the potential energy for each state can be sequentially calculated and the RE value through the JG module simply by providing the basic state molecular structure (NO). .

According to another embodiment of the present invention, the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, wherein the organic material layer is a compound represented by Formula 1 It provides an organic electric device containing a.

The organic material layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer provides an organic electric device including the compound of claim 1 and a compound represented by Formula 2 or Formula 3 below.

<Formula 2> <Formula 3>

In Formula 2 and Formula 3, each symbol is defined as follows.

Ar ³ to Ar ⁵ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

Ar ⁶ is an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and -L'-N(R _a )(R _b ).

L ⁴ to L ⁷ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

W is O, S, C(R')(R") or N(R ₁ ).

Ring B is an aryl ring of C ₆ to C ₂₀ . For example, ring B is C ₆ ~C ₂₀ , C ₆ ~C ₁₈ , C ₆ ~C ₁₆ , C ₆ ~C ₁₄ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₄ , C ₁₆ , C It may be an aryl ring such as ₁₈ , and specifically, it may be phenylene, naphthylene, phenanthrene, triphenylene, etc.

Ring B may be substituted with one or more R ₁₁ that are the same or different from each other.

R ⁸ , R ⁹ , R', R" and R ₁₁ are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si _{and a} C ₂ to C ₆₀ aliphatic ring group containing at least one heteroatom among _P ; _{a C 2 to} C ₂₀ alkyl group _{; ~} C ₂₀ alkynyl group; C ₆ ~C ₂₀ aryloxy group and -L'-N(R _a )(R _b ) _; They can combine with each other to form a ring, R' and R" can combine with each other to form a ring, and n and o are each integers from 0 to 4. When R' and R" combine with each other to form a ring, a spiro compound can be formed.

L' is a single bond; C ₆ -C ₃₀ arylene group; fluorenylene group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups.

R _a , R _b and R ₁ are each independently an aryl group of C ₆ -C ₃₀ ; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups.

When at least one of Ar ³ to Ar ⁶ , R ⁸ , R ⁹ , R', R", R ₁₁ , R _a , R _b and R ₁ is an aryl group, the aryl group is, for example, C ₆ to C ₃₀ , C ₆ ~C ₂₉ , C ₆ ~C ₂₈ , C ₆ ~C ₂₇ , C ₆ ~C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~ C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , etc. Specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

When at least one of L ⁴ to L ⁷ and L' is an arylene group, the arylene group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ ~C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , It may be an arylene group such as C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenylene, biphenyl, naphthylene, terphenyl, and phenene. It may be tren, triphenylene, etc.

When at least one of the Ar ³ to Ar ⁶ , R ⁸ , R ⁹ , R', R", R ₁₁ , R _a , R _b , R ₁ , L ⁴ to L ⁷ , L' is a heterocyclic group, Heterocyclic groups are, for example, C ₂ to C ₃₀ , C ₂ to C ₂₉ , C ₂ to C ₂₈ , C ₂ to C ₂₇ , C ₂ to C ₂₆ , C ₂ to C ₂₅ , C ₂ to C ₂₄ , C ₂ to C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C 17 , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , C ₂₃ , C ₂₄ , C _{25 , C 26 ,} C ₂₇ , C ₂₈ , C ₂₉ , etc., and may be heterocyclic groups, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, Pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphtho Benzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarba Sol, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, benzothione Enopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine , dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[ fluorene-9,9'-xanthene], etc.

At least one of Ar ³ to Ar ⁶ , R ⁸ , R ⁹ , R', R", R ₁₁ , R _a , R _b , and R ₁ is a fluorenyl group, or at least one of L ⁴ to L ⁷ and L' When is a fluorenylene group, the fluorenyl group or fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene , Spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9-(naphthalene-2 -1) It may be 9-phenyl-9 H -fluorene, etc.

The aryl group, arylene group, fluorenyl group, fluorenylene group, hetero ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the rings formed by bonding adjacent groups are each 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; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent groups are bonded to each other. When at least one of the rings formed is substituted with an aryl group, the aryl group is, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₉ , C ₆ ~ C ₂₈ , C ₆ ~ C ₂₇ , C ₆ ~ C ₂₆ , C ₆ ~ C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C It may be an aryl group such as ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , or C ₁₈ .

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent groups are bonded to each other. When at least one of the rings formed is substituted with a heterocyclic group, the heterocyclic group is, for example, C ₂ ~ C ₃₀ , C ₂ ~ C ₂₉ , C ₂ ~ C ₂₈ , C ₂ ~ C ₂₇ , C ₂ ~ C ₂₆ , C ₂ ~C ₂₅ , C ₂ ~C ₂₄ , C ₂ ~C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~ C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C _{14, C 15 ,} C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , It may be a heterocyclic group such as C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , or C ₂₉ .

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent groups are bonded to each other. When at least one of the rings formed is substituted with a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spy Robifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9- It may be (naphthalen-2-yl)9-phenyl- 9H -fluorene, etc.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and adjacent groups are bonded to each other. When at least one of the rings formed is substituted with an alkyl group, the alkyl group is, for example, an alkyl group such as C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , C ₄ , etc. It may be, for example, a methyl group, an ethyl group, a t-butyl group, etc.

Formula 2 may be represented by one of the following Formulas 2-1 to 2-3.

<Formula 2-1> <Formula 2-2> <Formula 2-3>

In Formulas 2-1 to 2-3, Ar ⁴ , Ar ⁵ , L ⁴ to L ⁶ are the same as defined in Formula 2.

X ¹ to X ³ are each independently O, S, C(R ₂ )(R ₃ ) or N(R ₄ ).

R ¹⁰ to R ¹⁵ , R ₂ and R ₃ are independently 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; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups, and adjacent groups may be bonded to each other to form a ring. R ₂ and R ₃ may combine with each other to form a ring, and in this case, a spiro compound may be formed.

p, r, and t are each integers from 0 to 4, and q, s, and u are each integers from 0 to 3. When these are integers of 2 or more, each of the plurality of R ¹⁰ to the plurality of R ¹⁵ is the same or different from each other.

The ring formed by combining adjacent groups is an aromatic ring group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and C ₃ to C ₆₀ aliphatic ring groups. Here, the aromatic ring group may include an aryl ring, and the heterocyclic group may include a heteroaryl ring.

When neighboring groups combine to form an aromatic ring, the aromatic ring may be, for example, C ₆ to C ₂₀ , C ₆ to C ₁₈ , C ₆ to C ₁₆ , C ₆ to C ₁₄ , C ₆ to C ₁₃ , It may be an aromatic ring such as C ₆ ~C ₁₂ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₈ , specifically, benzene, naphthalene, anthracene, and phenene. It may be an aryl ring such as tren, pyrene, etc.

R ₄ is an aryl group of C ₆ -C ₃₀ ; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups.

Formula 3 may be represented by one of the following Formulas 3-1 to 3-19.

<Formula 3-1> <Formula 3-2> <Formula 3-3>

<Formula 3-4> <Formula 3-5> <Formula 3-6>

<Formula 3-7> <Formula 3-8> <Formula 3-9>

<Formula 3-10> <Formula 3-11> <Formula 3-12>

<Formula 3-13> <Formula 3-14> <Formula 3-15>

<Formula 3-16> <Formula 3-17> <Formula 3-18>

<Formula 3-19>

In Formulas 3-1 to 3-19, W, R ⁸ , R ⁹ , Ar ⁶ , L ⁷ , B ring, n, and o are as defined in Formula 3.

R ¹⁶ to R ¹⁸ are independently 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; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups, and adjacent groups may be bonded to each other to form a ring.

w and x are each an integer of 0 to 6, and v is an integer of 0 to 2. When these are integers of 2 or more, each of a plurality of R ¹⁶ to a plurality of R ¹⁸ is the same or different from each other.

Specifically, the compound represented by Formula 2 may be one of the following compounds, but is not limited thereto.

.

Specifically, the compound represented by Formula 3 may be one of the following compounds, but is not limited thereto.

.

In another aspect, the present invention provides an electronic device including a display device including an organic electric element and a control unit for driving the display device, wherein the organic electric element includes the compound represented by Formula 1 above.

In another aspect, the present invention provides a compound represented by Formula 1, which is obtained by depositing an organic layer in the manufacturing process of an organic electric device, then recovering and purifying the material of the organic layer from deposition equipment. The purity of the compound obtained through recovery and purification is more than 99.9%.

In another aspect, the present invention includes the steps of depositing an organic layer material containing a compound represented by Formula 1, recovering the organic layer material attached to deposition equipment, and purifying the recovered organic layer material to produce the organic layer material having a purity of 99.9% or more. A method for recovering the compound represented by Formula 1 is provided, which includes the step of obtaining the compound represented by Formula 1.

The purification step may include recrystallizing the recovered organic layer material using a recrystallization solvent, adsorption separation using an adsorbent, and sublimation purification.

The recrystallization step may include a preliminary purification process to obtain the compound represented by Formula 1 with a purity of 98% using a recrystallization solvent.

As a recrystallization solvent, a polar solvent with a polarity index (PI) of 5.5 to 7.2 may be used, or a mixture of a polar solvent with a polarity index (PI) of 5.5 to 7.2 and a non-polar solvent with a polarity index of 2.0 to 4.7 may be used.

When using a mixture of polar and non-polar solvents as a recrystallization solvent, the non-polar solvent may be used in a ratio of 15% (v/v) or less compared to the polar solvent.

In addition, the recrystallization solvent is preferably a single solvent of methylpyrrolidone (N-methylpyrrolidone: NMP); Or the methyl pyrrolidone, dimethyl imidazolidinone (1,3-dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethyl formamide (N, N-dimethyl formamide), dimethyl acetate A mixed polar solvent containing any one selected from the group consisting of amide (dimethyl acetamide) and dimethyl sulfoxide, or toluene, DCM (Dichloromethane), DCE (dichloroethane), THF (tetrahydrofuran), chloroform ( A single or mixed non-polar solvent selected from the group consisting of chloroform, ethyl acetate and butanone, or a mixture of polar and non-polar solvents can be used.

The preliminary purification process may include dissolving the crude organic light-emitting material recovered from the deposition equipment in a polar solvent at 90°C to 120°C and then cooling to 0°C to 5°C to precipitate crystals.

In the preliminary purification process, the crude organic light-emitting material recovered from the deposition equipment is dissolved in a polar solvent at 90°C to 120°C, then cooled to 35°C to 40°C, a non-polar solvent is added, and then the temperature is heated to 0°C to 5°C. It may include cooling to precipitate crystals.

The preliminary purification process may include dissolving the crude organic light-emitting material recovered from the deposition equipment in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

The preliminary purification process may include first recrystallizing from a polar solvent and then recrystallizing again from a non-polar solvent.

In the adsorption separation step using the adsorbent, activated carbon, silica gel, alumina, or known materials for adsorption may be used as the adsorbent.

Hereinafter, examples of synthesis of compounds represented by Formula 1, Formula 2, and Formula 3 according to the present invention and examples of manufacturing organic electric devices will be described in detail through examples, but the present invention is not limited to the following examples. no.

[Synthesis Example 1] Compound of Formula 1

The compound (final products) represented by Formula 1 according to the present invention can be synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

I. Exemplary Compounds of Sub1

Sub1 in Scheme 1 was synthesized as disclosed in Korean Patent No. 10-2112786 (registration notice on May 13, 2020), and compounds belonging to Sub1 may be the following compounds, but are not limited thereto.

The FD-MS (Field Desorption-Mass Spectrometry) values of the above compounds are shown in Table 1 below.

compound FD-MS compound FD-MS Sub1-1 m/z=421.18(C ₂₇ H ₂₄ BNO ₃ =421.3) Sub1-2 m/z=426.22(C ₂₇ H ₁₉ D ₅ BNO ₃ =426.33) Sub1-3 m/z=471.2(C ₃₁ H ₂₆ BNO ₃ =471.36) Sub1-4 m/z=421.18(C ₂₇ H ₂₄ BNO ₃ =421.3) Sub1-5 m/z=511.14(C ₂₇ H ₁₉ BF ₅ NO ₃ =511.26) Sub1-6 m/z=421.18(C ₂₇ H ₂₄ BNO ₃ =421.3) Sub1-7 m/z=426.22(C ₂₇ H ₁₉ D ₅ BNO ₃ =426.33) Sub1-8 m/z=497.22(C ₃₃ H ₂₈ BNO ₃ =497.4) Sub1-9 m/z=497.22(C ₃₃ H ₂₈ BNO ₃ =497.4) Sub1-10 m/z=547.23(C ₃₇ H ₃₀ BNO ₃ =547.46) Sub1-11 m/z=497.22(C ₃₃ H ₂₈ BNO ₃ =497.4) Sub1-12 m/z=421.18(C ₂₇ H ₂₄ BNO ₃ =421.3) Sub1-13 m/z=511.14(C ₂₇ H ₁₉ BF ₅ NO ₃ =511.26) Sub1-14 m/z=497.22(C ₃₃ H ₂₈ BNO ₃ =497.4) Sub1-15 m/z=421.18(C ₂₇ H ₂₄ BNO ₃ =421.3) Sub1-16 m/z=421.18(C ₂₇ H ₂₄ BNO ₃ =421.3) Sub1-17 m/z=497.22(C ₃₃ H ₂₈ BNO ₃ =497.4) Sub1-18 m/z=547.23(C ₃₇ H ₃₀ BNO ₃ =547.46) Sub1-19 m/z=437.16(C ₂₇ H ₂₄ BNO ₂ S=437.36) Sub1-20 m/z=487.18(C ₃₁ H ₂₆ BNO ₂ S=487.42) Sub1-21 m/z=487.18(C ₃₁ H ₂₆ BNO ₂ S=487.42) Sub1-22 m/z=437.16(C ₂₇ H ₂₄ BNO ₂ S=437.36) Sub1-23 m/z=513.19(C ₃₃ H ₂₈ BNO ₂ S=513.46) Sub1-24 m/z=437.16(C ₂₇ H ₂₄ BNO ₂ S=437.36) Sub1-25 m/z=442.19(C ₂₇ H ₁₉ D ₅ BNO ₂ S=442.39) Sub1-26 m/z=513.19(C ₃₃ H ₂₈ BNO ₂ S=513.46) Sub1-27 m/z=519.24(C ₃₃ H ₃₄ BNO ₂ S=519.51) Sub1-28 m/z=437.16(C ₂₇ H ₂₄ BNO ₂ S=437.36) Sub1-29 m/z=437.16(C ₂₇ H ₂₄ BNO ₂ S=437.36) Sub1-30 m/z=493.22(C ₃₁ H ₃₂ BNO ₂ S=493.47) Sub1-31 m/z=437.16(C ₂₇ H ₂₄ BNO ₂ S=437.36) Sub1-32 m/z=513.19(C ₃₃ H ₂₈ BNO ₂ S=513.46) Sub1-33 m/z=513.19(C ₃₃ H ₂₈ BNO ₂ S=513.46)

II. Synthesis example of Sub2

Sub2 of Scheme 1 may be synthesized through the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2>

1. Sub2-1 synthesis example

After dissolving Sub2-1-a (20.0 g, 58.1 mmol) in THF (Tetrahydrofuran) (291 mL), Sub2-1-b (13.1 g, 58.1 mmol), NaOH (7.0 g, 174 mmol), Pd(PPh) ₃ ) ₄ (4.03 g, 3.49 mmol) and water (145 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 17.1 g of product (yield 72%).

2. Sub2-8 synthesis example

After dissolving Sub2-8-a (20.0 g, 58.1 mmol) in THF (291 mL), Sub2-1-b (13.1 g, 58.1 mmol), NaOH (7.0 g, 174 mmol), Pd(PPh ₃ ) ₄ (4.03 g, 3.49 mmol) and water (145 mL) were added and the synthesis was performed in the same manner as in the synthesis example of Sub2-1 to obtain 17.8 g of product (yield 75%).

3. Sub2-15 synthesis example

After dissolving Sub2-15-a (10.0 g, 27.8 mmol) in THF (139 mL), Sub2-15-b (8.4 g, 27.8 mmol), NaOH (3.3 g, 83.3 mmol), Pd(PPh ₃ ) ₄ (1.92 g, 1.67 mmol) and water (69 mL) were added and the synthesis was performed in the same manner as in the synthesis example of Sub2-1 to obtain 8.9 g of product (yield 64%).

4. Sub2-21 synthesis example

After dissolving Sub2-21-a (10.0 g, 23.8 mmol) in THF (119 mL), Sub2-1-b (5.4 g, 23.8 mmol), NaOH (2.9 g, 71.4 mmol), Pd(PPh ₃ ) ₄ (1.65 g, 1.43 mmol) and water (59 mL) were added and the synthesis was performed in the same manner as in the synthesis example of Sub2-1 to obtain 8.4 g of product (yield 73%).

5. Sub2-25 synthesis example

After dissolving Sub2-25-a (20.0 g, 58.1 mmol) in THF (291 mL), Sub2-1-b (13.1 g, 58.1 mmol), NaOH (7.0 g, 174 mmol), Pd(PPh ₃ ) ₄ (4.03 g, 3.49 mmol) and water (145 mL) were added and the synthesis was performed in the same manner as in the synthesis example of Sub2-1 to obtain 16.6 g of product (yield 70%).

Compounds belonging to Sub2 may be, but are not limited to, the following compounds, and the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 2.

.

compound FD-MS compound FD-MS Sub2-1 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-2 m/z=463.15(C ₂₉ H ₂₂ ClN ₃ O=463.97) Sub2-3 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-4 m/z=457.1(C ₂₉ H ₁₆ ClN ₃ O=457.92) Sub2-5 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-6 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-7 m/z=559.15(C ₃₇ H ₂₂ ClN ₃ O=560.05) Sub2-8 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-9 m/z=412.11(C ₂₅ H ₉ D ₅ ClN ₃ O=412.89) Sub2-10 m/z=507.11(C ₃₃ H ₁₈ ClN ₃ O=507.98) Sub2-11 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-12 m/z=499.09(C ₃₁ H ₁₈ ClN ₃ S=500.02) Sub2-13 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-14 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-15 m/z=499.09(C ₃₁ H ₁₈ ClN ₃ S=500.02) Sub2-16 m/z=517.14(C ₃₂ H ₂₄ ClN ₃ S=518.08) Sub2-17 m/z=499.09(C ₃₁ H ₁₈ ClN ₃ S=500.02) Sub2-18 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-19 m/z=499.09(C ₃₁ H ₁₈ ClN ₃ S=500.02) Sub2-20 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-21 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-22 m/z=575.12(C ₃₇ H ₂₂ ClN ₃ S=576.11) Sub2-23 m/z=499.09(C ₃₁ H ₁₈ ClN ₃ S=500.02) Sub2-24 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-25 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-26 m/z=412.11(C ₂₅ H ₉ D ₅ ClN ₃ O=412.89) Sub2-27 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-28 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-29 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-30 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-31 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-32 m/z=575.12(C ₃₇ H ₂₂ ClN ₃ S=576.11) Sub2-33 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-34 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-35 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-36 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-37 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96)

III. Example of synthesis of final compound (compound of formula 1)

1. P-1 synthesis example

After dissolving Sub1-1 (5.0 g, 11.9 mmol) in THF (Tetrahydrofuran) (59 mL), Sub2-1 (4.8 g, 11.9 mmol), NaOH (1.4 g, 35.6 mmol), Pd(PPh ₃ ) ₄ ( 0.82 g, 0.71 mmol) and water (30 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 6.2 g of product (yield 78%).

2. P-6 synthesis example

After dissolving Sub1-2 (5.0 g, 11.7 mmol) in THF (59 mL), Sub2-18 (5.0 g, 11.7 mmol), NaOH (1.4 g, 35.2 mmol), Pd(PPh ₃ ) ₄ (0.81 g, 0.70 mmol) and water (30 mL) were added, and the synthesis was performed in the same manner as in the synthesis example of P-1, to obtain 6.1 g of product (yield 75%).

3. P-11 synthesis example

Sub1-19 (5.0 g, 11.4 mmol) was dissolved in THF (57 mL), then Sub2-15 (5.7 g, 11.4 mmol), NaOH (1.4 g, 34.3 mmol), Pd(PPh ₃ ) ₄ (0.79 g, 0.69 mmol) and water (29 mL) were added and the synthesis was performed in the same manner as in the synthesis example of P-1, to obtain 6.3 g of product (yield 71%).

4. P-36 synthesis example

Sub1-6 (5.0 g, 11.9 mmol) was dissolved in THF (59 mL), then Sub2-8 (4.8 g, 11.9 mmol), NaOH (1.4 g, 35.6 mmol), Pd(PPh ₃ ) ₄ (0.82 g, 0.71 mmol) and water (30 mL) were added and the synthesis was performed in the same manner as in the synthesis example of P-1 to obtain 6.3 g of product (yield 79%).

5. P-51 synthesis example

After dissolving Sub1-22 (5.0 g, 11.4 mmol) in THF (57 mL), Sub2-21 (5.5 g, 11.4 mmol), NaOH (1.4 g, 34.3 mmol), Pd(PPh ₃ ) ₄ (0.79 g, 0.69 mmol) and water (29 mL) were added and the synthesis was performed in the same manner as in the synthesis example of P-1 to obtain 6.6 g of product (yield 76%).

6. P-77 synthesis example

After dissolving Sub1-15 (5.0 g, 11.9 mmol) in THF (59 mL), Sub2-25 (4.8 g, 11.9 mmol), NaOH (1.4 g, 35.6 mmol), Pd(PPh ₃ ) ₄ (0.82 g, 0.71 mmol) and water (30 mL) were added and the synthesis was performed in the same manner as in the synthesis example of P-1 to obtain 6.2 g of product (yield 78%).

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.

compound FD-MS compound FD-MS P-1 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-2 m/z=716.22(C ₅₀ H ₂₈ N ₄ O ₂ =716.8) P-3 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-4 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-5 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.9) P-6 m/z=687.21(C ₄₆ H ₂₁ D ₅ N ₄ OS=687.83) P-7 m/z=732.2(C ₅₀ H ₂₈ N ₄ OS=732.86) P-8 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.9) P-9 m/z=732.2(C ₅₀ H ₂₈ N ₄ OS=732.86) P-10 m/z=748.18(C ₅₀ H ₂₈ N ₄ S ₂ =748.92) P-11 m/z=774.19(C ₅₂ H ₃₀ N ₄ S ₂ =774.96) P-12 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-13 m/z=766.24(C ₅₄ H ₃₀ N ₄ O ₂ =766.86) P-14 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-15 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.9) P-16 m/z=774.19(C ₅₂ H ₃₀ N ₄ S ₂ =774.96) P-17 m/z=722.27(C ₅₀ H ₃₄ N ₄ O ₂ =722.85) P-18 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-19 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-20 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-21 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-22 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-23 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-24 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-25 m/z=772.14(C ₄₆ H ₂₁ F ₅ N ₄ OS=772.75) P-26 m/z=671.24(C ₄₆ H ₂₁ D ₅ N ₄ O ₂ =671.77) P-27 m/z=774.19(C ₅₂ H ₃₀ N ₄ S ₂ =774.96) P-28 m/z=834.25(C ₅₈ H ₃₄ N ₄ OS=835) P-29 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-30 m/z=738.25(C ₅₀ H ₃₄ N ₄ OS=738.91) P-31 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-32 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-33 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-34 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-35 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-36 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-37 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-38 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-39 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-40 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-41 m/z=671.24(C ₄₆ H ₂₁ D ₅ N ₄ O ₂ =671.77) P-42 m/z=776.26(C ₅₃ H ₃₆ N ₄ OS=776.96) P-43 m/z=780.24(C ₅₂ H ₃₆ N ₄ S ₂ =781.01) P-44 m/z=774.19(C ₅₂ H ₃₀ N ₄ S ₂ =774.96) P-45 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-46 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-47 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-48 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-49 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.9) P-50 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-51 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.9) P-52 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-53 m/z=774.19(C ₅₂ H ₃₀ N ₄ S ₂ =774.96) P-54 m/z=834.25(C ₅₈ H ₃₄ N ₄ OS=835) P-55 m/z=792.25(C ₅₆ H ₃₂ N ₄ O ₂ =792.9) P-56 m/z=834.25(C ₅₈ H ₃₄ N ₄ OS=835) P-57 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-58 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-59 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-60 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-61 m/z=687.21(C ₄₆ H ₂₁ D ₅ N ₄ OS=687.83) P-62 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-63 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-64 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-65 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-66 m/z=772.14(C ₄₆ H ₂₁ F ₅ N ₄ OS=772.75) P-67 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-68 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-69 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-70 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-71 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-72 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-73 m/z=850.22(C ₅₈ H ₃₄ N ₄ S ₂ =851.06) P-74 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-75 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-76 m/z=687.21(C ₄₆ H ₂₁ D ₅ N ₄ OS=687.83) P-77 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-78 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-79 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-80 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-81 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-82 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-83 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-84 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-85 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-86 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-87 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-88 m/z=703.19(C ₄₆ H ₂₁ D ₅ N ₄ S ₂ =703.89) P-89 m/z=666.21(C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-90 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-91 m/z=682.18(C ₄₆ H ₂₆ N ₄ OS=682.8) P-92 m/z=698.16(C ₄₆ H ₂₆ N ₄ S ₂ =698.86) P-93 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-94 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-95 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-96 m/z=818.27(C ₅₈ H ₃₄ N ₄ O ₂ =818.94) P-97 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-98 m/z=792.25(C ₅₆ H ₃₂ N ₄ O ₂ =792.9) P-99 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84) P-100 m/z=742.24(C ₅₂ H ₃₀ N ₄ O ₂ =742.84)

[Synthesis Example 2] Compounds of Formula 3 and Formula 4

1. N-12 synthesis example

N-12a (30 g, 0.08 mol), N-12b (34.8 g, 0.08 mol), Pd ₂ (dba) ₃ (2.3 g, 0.003 mol), NaOt-Bu (24.5 g, 0.25 mol), P(t -Bu) ₃ (2.1 g, 0.005 mol) and Toluene (170mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 53 g (85.8%) of product N-12.

2. N-19 synthesis example

To N-19a (50 g, 0.13 mol), N-19b (35 g, 0.13 mol), Pd ₂ (dba) ₃ (3.6 g, 0.004 mol), NaOt-Bu (37.6 g, 0.40 mol), P(t -Bu) ₃ (3.2 g, 0.008 mol) and Toluene (260 mL) were added, and the synthesis was performed in the same manner as in the synthesis example of compound N-12, to obtain 67 g (83.4%) of product N-19.

3. S-32 synthesis example

In S-32a (10 g, 0.04 mol), S-32b (15.6 g, 0.04 mol), Pd ₂ (dba) ₃ (1.1 g, 0.001 mol), NaOt-Bu (11.7 g, 0.12 mol), P(t -Bu) ₃ (1.0 g, 0.002 mol) and Toluene (80 mL) were added, and the synthesis was performed in the same manner as in the synthesis example of compound N-12, to obtain 18 g (80.8%) of product S-32.

4. S-74 synthesis example

In S-74a (15 g, 0.06 mol), S-74b (20.9 g, 0.06 mol), Pd ₂ (dba) ₃ (1.6 g, 0.002 mol), NaOt-Bu (16.9 g, 0.18 mol), P(t -Bu) ₃ (1.4 g, 0.004 mol) and Toluene (120 mL) were added, and the synthesis was performed in the same manner as in the synthesis example of compound N-12 to obtain 27 g (86.4%) of product S-74.

5. S-104 synthesis example

S-104a (30 g, 0.13 mol), S-104b (48.2.9 g, 0.13 mol), Pd ₂ (dba) ₃ (3.5 g, 0.004 mol), NaOt-Bu (36.4 g, 0.38 mol), P (t-Bu) ₃ (3.1 g, 0.008 mol) and Toluene (250 mL) were added, and the synthesis was performed in the same manner as in the synthesis example of compound N-12, to obtain 60 g (81.5%) of product S-104. .

Compounds N-1 to N-96 of the present invention prepared according to the above synthesis examples are shown in Table 4, and the FD-MS values of compounds S-1 to S-108 are shown in Table 5 below.

compound FD-MS compound FD-MS N-1 m/z=487.19(C ₃₆ H ₂₅ NO=487.6) N-2 m/z=553.19(C ₄₀ H ₂₇ NS=553.72) N-3 m/z=563.26(C ₄₃ H ₃₃ N=563.74) N-4 m/z=602.27(C ₄₅ H ₃₄ N ₂ =602.78) N-5 m/z=517.15(C ₃₆ H ₂₃ NOS=517.65) N-6 m/z=603.2(C ₄₄ H ₂₉ NS=603.78) N-7 m/z=735.29(C ₅₇ H ₃₇ N=735.93) N-8 m/z=562.24(C ₄₂ H ₃₀ N ₂ =562.72) N-9 m/z=565.17(C ₄₀ H ₂₃ NO ₃ =565.63) N-10 m/z=581.14(C ₄₀ H ₂₃ NO ₂ S=581.69) N-11 m/z=823.24(C ₅₉ H ₃₇ NS ₂ =824.07) N-12 m/z=727.3(C ₅₄ H ₃₇ N ₃ =727.91) N-13 m/z=627.22(C ₄₆ H ₂₉ NO ₂ =627.74) N-14 m/z=633.16(C ₄₄ H ₂₇ NS ₂ =633.83) N-15 m/z=675.29(C ₅₂ H ₃₇ N=675.88) N-16 m/z=678.3(C ₅₁ H ₃₈ N ₂ =678.88) N-17 m/z=669.21(C ₄₈ H ₃₁ NOS=669.84) N-18 m/z=785.22(C ₅₆ H ₃₅ NS ₂ =786.02) N-19 m/z=617.18(C ₄₄ H ₂₇ NOS=617.77) N-20 m/z=601.2(C ₄₄ H ₂₇ NO ₂ =601.71) N-21 m/z=779.32(C ₅₉ H ₄₁ NO=779.98) N-22 m/z=583.23(C ₄₂ H ₃₃ NS=583.79) N-23 m/z=679.32(C ₅₂ H ₄₁ N=679.91) N-24 m/z=726.27(C ₅₄ H ₃₄ N ₂ O=726.88) N-25 m/z=593.18(C ₄₂ H ₂₇ NOS=593.74) N-26 m/z=774.22(C ₅₄ H ₃₄ N ₂ S ₂ =775) N-27 m/z=557.24(C ₄₀ H ₃₁ NO ₂ =557.69) N-28 m/z=652.25(C ₄₈ H ₃₂ N ₂ O=652.8) N-29 m/z=619.29(C ₄₆ H ₃₇ NO=619.81) N-30 m/z=603.2(C ₄₄ H ₂₉ NS=603.78) N-31 m/z=813.3(C ₆₂ H ₃₉ NO=814) N-32 m/z=784.29(C ₅₇ H ₄₀ N ₂ S=785.02) N-33 m/z=577.2(C ₄₂ H ₂₇ NO ₂ =577.68) N-34 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.79) N-35 m/z=801.34(C ₆₂ H ₄₃ N=802.03) N-36 m/z=575.24(C ₄₂ H ₂₉ N ₃ =575.72) N-37 m/z=577.2(C ₄₂ H ₂₇ NO ₂ =577.68) N-38 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.79) N-39 m/z=801.34(C ₆₂ H ₄₃ N=802.03) N-40 m/z=575.24(C ₄₂ H ₂₉ N ₃ =575.72) N-41 m/z=601.2(C ₄₄ H ₂₇ NO ₂ =601.71) N-42 m/z=471.11(C ₃₁ H ₂₁ NS ₂ =471.64) N-43 m/z=675.29(C ₅₂ H ₃₇ N=675.88) N-44 m/z=727.3(C ₅₄ H ₃₇ N ₃ =727.91) N-45 m/z=603.2(C ₄₄ H ₂₉ NS=603.78) N-46 m/z=561.16(C ₃₈ H ₂₇ NS ₂ =561.76) N-47 m/z=799.32(C ₆₂ H ₄₁ N=800.02) N-48 m/z=702.27(C ₅₂ H ₃₄ N ₂ O=702.86) N-49 m/z=729.27(C ₅₄ H ₃₅ NO ₂ =729.88) N-50 m/z=785.22(C ₅₆ H ₃₅ NS ₂ =786.02) N-51 m/z=812.32(C ₆₂ H ₄₀ N ₂ =813.02) N-52 m/z=681.22(C ₄₈ H ₃₁ N ₃ S=681.86) N-53 m/z=615.18(C ₄₄ H ₂₅ NO ₃ =615.69) N-54 m/z=763.15(C ₅₂ H ₂₉ NS ₃ =763.99) N-55 m/z=593.31(C ₄₅ H ₃₉ N=593.81) N-56 m/z=840.33(C ₆₂ H ₄₀ N ₄ =841.03) N-57 m/z=657.18(C ₄₆ H ₂₇ NO ₂ S=657.79) N-58 m/z=824.23(C ₅₈ H ₃₆ N ₂ S ₂ =825.06) N-59 m/z=1195.42(C ₉₁ H ₅₇ NS=1196.52) N-60 m/z=656.19(C ₄₆ H ₂₈ N ₂ OS=656.8) N-61 m/z=607.16(C ₄₂ H ₂₅ NO ₂ S=607.73) N-62 m/z=773.2(C ₅₄ H ₃₁ NO ₃ S=773.91) N-63 m/z=1013.4(C ₇₉ H ₅₁ N=1014.28) N-64 m/z=758.24(C ₅₄ H ₃₄ N ₂ OS=758.94) N-65 m/z=623.14(C ₄₂ H ₂₅ NOS ₂ =623.79) N-66 m/z=763.16(C ₅₂ H ₂₉ NO ₂ S ₂ =763.93) N-67 m/z=799.2(C ₅₆ H ₃₃ NOS ₂ =800.01) N-68 m/z=743.23(C ₅₄ H ₃₃ NOS=743.92) N-69 m/z=872.25(C ₆₂ H ₃₆ N ₂ O ₂ S=873.04) N-70 m/z=772.22(C ₅₄ H ₃₂ N ₂ O ₂ S=772.92) N-71 m/z=830.28(C ₆₁ H ₃₈ N ₂ S=831.05) N-72 m/z=808.25(C ₅₈ H ₃₃ FN ₂ O ₂ =808.91) N-73 m/z=929.21(C ₆₄ H ₃₅ NO ₃ S ₂ =930.11) N-74 m/z=963.27(C ₆₈ H ₄₁ N ₃ S ₂ =964.22) N-75 m/z=809.24(C ₅₈ H ₃₅ NO ₂ S=809.98) N-76 m/z=893.29(C ₆₆ H ₃₉ NO ₃ =894.04) N-77 m/z=794.28(C ₅₈ H ₃₈ N ₂ S=795.02) N-78 m/z=900.26(C ₆₄ H ₄₀ N ₂ S ₂ =901.16) N-79 m/z=758.28(C ₅₅ H ₃₈ N ₂ S=758.98) N-80 m/z=1082.37(C ₈₁ H ₅₀ N ₂ S=1083.37) N-81 m/z=573.25(C ₄₄ H ₃₁ N=573.74) N-82 m/z=649.28(C ₅₀ H ₃₅ N=649.84) N-83 m/z=699.29(C ₅₄ H ₃₇ N=699.9) N-84 m/z=699.29(C ₅₄ H ₃₇ N=699.9) N-85 m/z=673.28(C ₅₂ H ₃₅ N=673.86) N-86 m/z=649.28(C ₅₀ H ₃₅ N=649.84) N-87 m/z=625.28(C ₄₈ H ₃₅ N=625.82) N-88 m/z=673.28(C ₅₂ H ₃₅ N=673.86) N-89 m/z=773.31(C ₆₀ H ₃₉ N=773.98) N-90 m/z=749.31(C ₅₈ H ₃₉ N=749.96) N-91 m/z=699.29(C ₅₄ H ₃₇ N=699.9) N-92 m/z=599.26(C ₄₆ H ₃₃ N=599.78) N-93 m/z=639.26(C ₄₈ H ₃₃ NO=639.8) N-94 m/z=765.25(C ₅₇ H ₃₅ NS=765.97) N-95 m/z=677.31(C ₅₂ H ₃₉ N=677.89) N-96 m/z=727.3(C ₅₄ H ₃₇ N ₃ =727.91)

compound FD-MS compound FD-MS S-1 m/z=408.16(C ₃₀ H ₂₀ N ₂ =408.5) S-2 m/z=534.21(C ₄₀ H ₂₆ N ₂ =534.66) S-3 m/z=560.23(C ₄₂ H ₂₈ N ₂ =560.7) S-4 m/z=584.23(C ₄₄ H ₂₈ N ₂ =584.72) S-5 m/z=560.23(C ₄₂ H ₂₈ N ₂ =560.7) S-6 m/z=634.24(C ₄₈ H ₃₀ N ₂ =634.78) S-7 m/z=610.24(C ₄₆ H ₃₀ N ₂ =610.76) S-8 m/z=498.17(C ₃₆ H ₂₂ N ₂ O=498.59) S-9 m/z=574.2(C ₄₂ H ₂₆ N ₂ O=574.68) S-10 m/z=660.26(C ₅₀ H ₃₂ N ₂ =660.82) S-11 m/z=686.27(C ₅₂ H ₃₄ N ₂ =686.86) S-12 m/z=620.14(C ₄₂ H ₂₄ N ₂ S ₂ =620.79) S-13 m/z=640.2(C ₄₆ H ₂₈ N ₂ S=640.8) S-14 m/z=560.23(C ₄₂ H ₂₈ N ₂ =560.7) S-15 m/z=558.21(C ₄₂ H ₂₆ N ₂ =558.68) S-16 m/z=548.19(C ₄₀ H ₂₄ N ₂ O=548.65) S-17 m/z=573.22(C ₄₂ H ₂₇ N ₃ =573.7) S-18 m/z=564.17(C ₄₀ H ₂₄ N ₂ S=564.71) S-19 m/z=574.2(C ₄₂ H ₂₆ N ₂ O=574.68) S-20 m/z=564.17(C ₄₀ H ₂₄ N ₂ S=564.71) S-21 m/z=564.17(C ₄₀ H ₂₄ N ₂ S=564.71) S-22 m/z=813.31(C ₆₁ H ₃₉ N ₃ =814) S-23 m/z=696.26(C ₅₃ H ₃₂ N ₂ =696.85) S-24 m/z=691.23(C ₄₉ H ₂₉ N ₃ O ₂ =691.79) S-25 m/z=710.27(C ₅₄ H ₃₄ N ₂ =710.88) S-26 m/z=610.24(C ₄₆ H ₃₀ N ₂ =610.76) S-27 m/z=670.15(C ₄₆ H ₂₆ N ₂ S ₂ =670.85) S-28 m/z=640.29(C ₄₈ H ₃₆ N ₂ =640.83) S-29 m/z=598.2(C ₄₄ H ₂₆ N ₂ O=598.71) S-30 m/z=623.24(C ₄₆ H ₂₉ N ₃ =623.76) S-31 m/z=458.18(C ₃₄ H ₂₂ N ₂ =458.56) S-32 m/z=548.19(C ₄₀ H ₂₄ N ₂ O=548.65) S-33 m/z=508.19(C ₃₈ H ₂₄ N ₂ =508.62) S-34 m/z=508.19(C ₃₈ H ₂₄ N ₂ =508.62) S-35 m/z=623.24(C ₄₆ H ₂₉ N ₃ =623.76) S-36 m/z=564.17(C ₄₀ H ₂₄ N ₂ S=564.71) S-37 m/z=627.2(C ₄₆ H ₂₉ NS=627.81) S-38 m/z=505.1(C ₃₄ H ₁₉ NS ₂ =505.65) S-39 m/z=514.15(C ₃₆ H ₂₂ N ₂ S=514.65) S-40 m/z=575.17(C ₄₂ H ₂₅ NS=575.73) S-41 m/z=642.21(C ₄₆ H ₃₀ N ₂ S=642.82) S-42 m/z=575.17(C ₄₂ H ₂₅ NS=575.73) S-43 m/z=606.18(C ₄₂ H ₂₆ N ₂ OS=606.74) S-44 m/z=575.17(C ₄₂ H ₂₅ NS=575.73) S-45 m/z=551.17(C ₄₀ H ₂₅ NS=551.71) S-46 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.79) S-47 m/z=525.16(C ₃₈ H ₂₃ NS=525.67) S-48 m/z=642.21(C ₄₆ H ₃₀ N ₂ S=642.82) S-49 m/z=548.19(C ₄₀ H ₂₄ N ₂ O=548.65) S-50 m/z=473.14(C ₃₄ H ₁₉ NO ₂ =473.53) S-51 m/z=566.15(C ₃₉ H ₂₂ N ₂ OS=566.68) S-52 m/z=459.16(C ₃₄ H ₂₁ NO=459.55) S-53 m/z=473.14(C ₃₄ H ₁₉ NO ₂ =473.53) S-54 m/z=523.16(C ₃₈ H ₂₁ NO ₂ =523.59) S-55 m/z=539.13(C ₃₈ H ₂₁ NOS=539.65) S-56 m/z=548.19(C ₄₀ H ₂₄ N ₂ O=548.65) S-57 m/z=489.12(C ₃₄ H ₁₉ NOS=489.59) S-58 m/z=545.09(C ₃₆ H ₁₉ NOS ₂ =545.67) S-59 m/z=549.17(C ₄₀ H ₂₃ NO ₂ =549.63) S-60 m/z=565.15(C ₄₀ H ₂₃ NOS=565.69) S-61 m/z=523.16(C ₃₈ H ₂₁ NO ₂ =523.59) S-62 m/z=598.2(C ₄₄ H ₂₆ N ₂ O=598.71) S-63 m/z=539.13(C ₃₈ H ₂₁ NOS=539.65) S-64 m/z=589.15(C ₄₂ H ₂₃ NOS=589.71) S-65 m/z=498.17(C ₃₆ H ₂₂ N ₂ O=498.59) S-66 m/z=509.18(C ₃₈ H ₂₃ NO=509.61) S-67 m/z=548.19(C ₄₀ H ₂₄ N ₂ O=548.65) S-68 m/z=549.17(C ₄₀ H ₂₃ NO ₂ =549.63) S-69 m/z=449.12(C ₃₂ H ₁₉ NS=449.57) S-70 m/z=439.1(C ₃₀ H ₁₇ NOS=439.53) S-71 m/z=647.22(C ₄₉ H ₂₉ NO=647.78) S-72 m/z=717.28(C ₅₂ H ₃₅ N ₃ O=717.87) S-73 m/z=459.16(C ₃₄ H ₂₁ NO=459.55) S-74 m/z=533.18(C ₄₀ H ₂₃ NO=533.63) S-75 m/z=525.16(C ₃₈ H ₂₃ NS=525.67) S-76 m/z=564.17(C ₄₀ H ₂₄ N ₂ S=564.71) S-77 m/z=575.19(C ₄₂ H ₂₅ NO ₂ =575.67) S-78 m/z=663.22(C ₄₉ H ₂₉ NO ₂ =663.78) S-79 m/z=647.22(C ₄₉ H ₂₉ NO=647.78) S-80 m/z=496.16(C ₃₆ H ₂₀ N ₂ O=496.57) S-81 m/z=565.15(C ₄₀ H ₂₃ NOS=565.69) S-82 m/z=505.1(C ₃₄ H ₁₉ NS ₂ =505.65) S-83 m/z=765.25(C ₅₆ H ₃₅ NOSi=765.99) S-84 m/z=615.17(C ₄₄ H ₂₅ NOS=615.75) S-85 m/z=603.17(C ₄₃ H ₂₅ NOS=603.74) S-86 m/z=772.29(C ₅₉ H ₃₆ N ₂ =772.95) S-87 m/z=802.33(C ₆₁ H ₄₂ N ₂ =803.02) S-88 m/z=607.23(C ₄₇ H ₂₉ N=607.76) S-89 m/z=524.23(C ₃₉ H ₂₈ N ₂ =524.67) S-90 m/z=665.22(C ₄₉ H ₃₁ NS=665.85) S-91 m/z=633.25(C ₄₉ H ₃₁ N=633.79) S-92 m/z=775.29(C ₅₉ H ₃₇ NO=775.95) S-93 m/z=535.23(C ₄₁ H ₂₉ N=535.69) S-94 m/z=623.22(C ₄₇ H ₂₉ NO=623.76) S-95 m/z=687.2(C ₅₁ H ₂₉ NS=687.86) S-96 m/z=735.29(C ₅₇ H ₃₇ N=735.93) S-97 m/z=611.26(C ₄₇ H ₃₃ N=611.79) S-98 m/z=679.23(C ₅₀ H ₃₃ NS=679.88) S-99 m/z=787.32(C ₆₁ H ₄₁ N=788.01) S-100 m/z=743.33(C ₅₅ H ₄₁ N ₃ =743.95) S-101 m/z=485.21(C ₃₇ H ₂₇ N=485.63) S-102 m/z=471.2(C ₃₆ H ₂₅ N=471.6) S-103 m/z=571.19(C ₄₃ H ₂₅ NO=571.68) S-104 m/z=584.23(C ₄₄ H ₂₈ N ₂ =584.72) S-105 m/z=539.24(C ₄₀ H ₂₁ D ₅ N ₂ =539.69) S-106 m/z=453.15(C ₃₂ H ₁₅ NS=471.6) S-107 m/z=563.26(C ₄₃ H ₂₆ D ₄ NO=563.74) S-108 m/z=589.26(C ₄₄ H ₂₃ D ₅ N ₂ =584.72)

Manufacturing and evaluation of organic electric devices

[Example 1] to [Example 36] Red organic light emitting device (phosphorescent host)

N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter referred to as , 2-TNATA) film was vacuum deposited to form a 60 nm thick hole injection layer, and then 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPD) was deposited on the hole injection layer. ) A hole transport layer was formed by vacuum deposition to a thickness of 50 nm.

Next, tris(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter, TCTA) was vacuum deposited on the hole transport layer to a thickness of 10 nm to form an auxiliary light emitting layer.

Then, as a host on the light-emitting auxiliary layer, the first compound included in Formula 1 of the present invention and the second compound included in Formula 2 or Formula 3 of the present invention were applied at a weight ratio of 5:5 as shown in Table 6 below. The mixed mixture is used, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as '(piq) ₂ Ir(acac)') is used as the dopant, and the weight ratio of host and dopant is 95:5. A 30 nm thick light emitting layer was formed by doping with a dopant so that .

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited on the emitting layer to form a 10 nm thick hole blocking layer. Then, bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) was vacuum deposited to a thickness of 45 nm on the hole blocking layer to form an electron transport layer. Afterwards, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[Comparative Example 1]

An organic electroluminescent device was manufactured in the same manner as in the above example, except that a 5:5 mixture of Comparative Compound A below and Compound N-12 of the present invention was used as a host material for the light emitting layer.

<Comparative Compound A>

A forward bias direct current voltage was applied to the organic electroluminescent device manufactured according to the Examples and Comparative Examples of the present invention, and the electroluminescence (EL) characteristics were measured using Photo Research's PR-650, based on 2500 cd/m ² In terms of luminance, the T95 lifespan was measured using a lifespan measuring device manufactured by McScience. The measurement results are shown in Table 6 below.

first compound Second compound driving voltage
(V) electric current
density
(mA/ ^cm2 ) radiation
efficiency
(cd/A) T(95) CIE x y Comparative Example 1 Comparative compound A Compound (N-12) 5.6 9.8 25.6 98.4 0.632 0.323 Example 1 Compound (P-1) Compound (N-12) 5.5 8.3 30.3 108.6 0.642 0.324 Example 2 Compound (P-2) Compound (N-12) 5.6 8.4 29.7 104.3 0.640 0.339 Example 3 Compound (P-3) Compound (N-12) 5.4 7.7 32.4 111.6 0.643 0.327 Example 4 Compound (P-4) Compound (N-12) 5.5 7.9 31.6 114.6 0.646 0.331 Example 5 Compound (P-6) Compound (N-12) 5.4 8.1 31.0 112.6 0.641 0.349 Example 6 Compound (P-11) Compound (N-12) 5.2 8.0 31.4 108.5 0.643 0.337 Example 7 Compound (P-15) Compound (N-12) 5.6 8.7 28.6 100.5 0.648 0.338 Example 8 Compound (P-20) Compound (N-12) 5.4 7.8 32.2 117.9 0.646 0.341 Example 9 Compound (P-31) Compound (N-12) 5.4 8.7 28.9 102.5 0.646 0.337 Example 10 Compound (P-32) Compound (N-12) 5.4 7.9 31.5 115.5 0.648 0.344 Example 11 Compound (P-36) Compound (N-12) 5.3 7.7 32.4 119.4 0.643 0.342 Example 12 Compound (P-41) Compound (N-12) 5.3 7.6 32.9 123.9 0.646 0.335 Example 13 Compound (P-51) Compound (N-12) 5.4 7.8 32.1 119.3 0.647 0.336 Example 14 Compound (P-57) Compound (N-12) 5.6 8.4 29.6 110.7 0.646 0.348 Example 15 Compound (P-63) Compound (N-12) 5.5 8.7 28.7 107.5 0.647 0.347 Example 16 Compound (P-65) Compound (N-12) 5.6 8.6 28.9 108.3 0.647 0.335 Example 17 Compound (P-70) Compound (N-12) 5.5 8.5 29.5 109.3 0.649 0.337 Example 18 Compound (P-80) Compound (N-12) 5.5 8.9 28.1 104.1 0.642 0.333 Example 19 Compound (P-82) Compound (N-12) 5.4 7.9 31.7 121.6 0.641 0.350 Example 20 Compound (P-95) Compound (N-12) 5.5 8.1 30.8 117.0 0.641 0.339 Example 21 Compound (P-3) Compound (N-17) 5.1 7.4 34.0 117.9 0.649 0.348 Example 22 Compound (P-3) Compound (N-82) 5.2 7.6 32.7 115.7 0.644 0.327 Example 23 Compound (P-3) Compound (S-32) 5.3 7.4 33.7 122.9 0.647 0.321 Example 24 Compound (P-3) Compound (S-108) 5.2 7.1 35.0 125.7 0.645 0.341 Example 25 Compound (P-20) Compound (N-17) 5.1 7.4 33.8 125.2 0.650 0.321 Example 26 Compound (P-20) Compound (N-82) 5.2 7.7 32.4 122.7 0.648 0.337 Example 27 Compound (P-20) Compound (S-32) 5.2 7.5 33.5 129.6 0.645 0.349 Example 28 Compound (P-20) Compound (S-108) 5.1 7.2 34.7 133.4 0.642 0.321 Example 29 Compound (P-41) Compound (N-17) 5.1 7.2 34.5 131.1 0.643 0.350 Example 30 Compound (P-41) Compound (N-82) 5.2 7.6 33.1 128.8 0.650 0.337 Example 31 Compound (P-41) Compound (S-32) 5.2 7.3 34.1 136.2 0.644 0.343 Example 32 Compound (P-41) Compound (S-108) 5.1 7.1 35.4 139.7 0.648 0.338 Example 33 Compound (P-82) Compound (N-17) 5.1 7.5 33.2 128.4 0.644 0.345 Example 34 Compound (P-82) Compound (N-82) 5.2 7.8 32.0 126.2 0.643 0.344 Example 35 Compound (P-82) Compound (S-32) 5.2 7.6 32.9 133.8 0.643 0.326 Example 36 Compound (P-82) Compound (S-108) 5.1 7.3 34.2 137.3 0.644 0.333

From Table 6, it can be seen that when the compound of the present invention is used as the light emitting layer host material, the driving voltage is generally lowered and both efficiency and lifespan are improved compared to the case where comparative compound A is used.

As can be seen above, when multiple compounds are mixed to form the host of the light emitting layer, the characteristics are different depending on the type of the first compound and the second compound, and when the same compound is applied to the second compound, the properties are different depending on the type of the first compound. It can be seen that there is a significant difference in characteristics. Likewise, there are differences in driving voltage, efficiency, and lifespan depending on the type of the second compound.

Comparing Comparative Compound A and the compound of the present invention, as can be seen in Table 6 above, the overall performance of the device is improved when the compound of the present invention is used as a host. In the case of comparative compound A, 2,3-naphthobenzothiophene is substituted for triazine, which is a structure excluded from Chemical Formula 1 of the present invention. The compound of the present invention has a structure in which 1,2-naphthobenzofuran, 1,2-naphthobenzothiophene, 3,4-naphthobenzofuran, and 3,4-naphthobenzothiophene are substituted by triazine. .

Therefore, it can be seen that even if the same substituent is substituted, the performance of the device varies when a compound with a different condensation position of the substituent is used as a host.

Table 7 below shows the energy levels of Comparative Compound A and Compounds P-31 and P-80 of the present invention measured using the DFT Method (B3LYP/6-31g(D)) of the Gaussian program.

Comparative compound A P-31 P-80 HOMO(eV) -5.343 -5.537 -5.604 LUMO(eV) -2.078 -2.039 -2.048

Looking at Table 7 above, it can be seen that the compounds of the present invention, P-31 and P-80, have deeper (smaller) HOMO values than comparative compound A. Therefore, because the HOMO energy level is lower, holes moving from the light-emitting layer to the hole transport layer can be effectively blocked, and as a result, the light-emitting area within the light-emitting layer is narrowed when forming exciton, and the efficiency appears to have increased significantly.

This suggests that even if a similar type of substituent is substituted on the same skeleton, the energy properties vary depending on the condensation position of the substituent, and as a result, the characteristics of the device change.

In addition, in the case of the compound of the present invention, the x value of CIE (color index) slightly increased compared to the comparative compound, so it appears that the color of the device is affected when the compound of the present invention is used as a host. That is, when phenanthrooxazole and specific forms of naphthobenzofuran and naphthobenzothiophene are simultaneously substituted with triazine substituents as in the present invention, the effect appears to be maximized due to their synergistic action.

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. The scope of protection of the present invention should be interpreted in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

100, 200, 300: Organic electric element 110: First electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: Light efficiency improvement layer 210: Buffer layer
220: Light-emitting auxiliary layer 320: First hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: Second electron transport layer CGL: Charge generation layer
ST1: first stack ST2: second stack

Claims (18)

Compound represented by Formula 1:
<Formula 1><FormulaA>

In Formula 1,
X and Y are independently O, S or N, one of which is N and the other is O or S,
L ¹ to L ³ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; 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 C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P,
Ar ³ is formula A,
Ring A is an aryl ring of C ₁₀ or more that is unsubstituted or substituted with one or more R, except when ring A is naphthyl and 2, 3-naphthyl is condensed to ring Z;
Z is O or S,
R ¹ , R ² and R are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₂₀ alkoxy group; and aryloxy groups of C ₆ to C ₆₀ , and adjacent R ² groups may combine with each other to form a benzene ring.
a is an integer from 0 to 7, b is an integer from 0 to 3,
The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and a benzene ring formed by bonding adjacent R ³ groups to each other. are each deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups. According to clause 1,
A compound characterized in that the above Chemical Formula 1 is represented by the following Chemical Formula 1-1:
<Formula 1-1>

In Formula 1-1, X, Y, R ¹ , L ¹ to L ³ , Ar ¹ to Ar ³ and a are as defined in claim 1. According to clause 1,
The above Chemical Formula 1 is a compound characterized in that it is represented by one of the following Chemical Formulas 1-2 to 1-4:
<Formula 1-2><Formula1-3><Formula1-4>

In Formulas 1-2 to 1-4, X, Y, R ¹ , L ¹ to L ³ , Ar ¹ to Ar ³ and a are as defined in claim 1. According to clause 1,
A compound characterized in that Ar ¹ contains one or more deuterium. According to clause 1,
The compound represented by Formula 1 is one of the following compounds:
. In an organic electric device comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode,
The organic material layer is an organic electric device containing the compound of any one of claims 1 to 5. According to clause 6,
The organic material layer includes a phosphorescent light-emitting layer,
The phosphorescent light-emitting layer is an organic electric device comprising the compound of claim 1 and a compound represented by the following Formula 2 or Formula 3:
<Formula 2><Formula3>

In Formula 2 and Formula 3,
Ar ³ to Ar ⁵ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P,
Ar ⁶ is an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; and -L'-N(R _a )(R _b ),
L ⁴ to L ⁷ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P,
W is O, S, C(R')(R") or N(R ₁ ),
The B ring is an aryl ring of C ₆ to C ₂₀ , and the B ring can be substituted with one or more of the same or different R ₁₁ ,
R ⁸ , R ⁹ , R', R" and R ₁₁ are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si _{and a} C ₂ to C ₆₀ aliphatic ring group containing at least one heteroatom among _P ; _{a C 2 to} C ₂₀ alkyl group _{; ~} C ₂₀ alkynyl group; C ₆ ~C ₂₀ aryloxy group and -L'-N(R _a )(R _b ) _; They can combine with each other to form a ring, R' and R" can combine with each other to form a ring, n and o are each integers from 0 to 4,
L' is a single bond; C ₆ -C ₃₀ arylene group; fluorenylene group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups,
R _a , R _b and R ₁ are each independently an aryl group of C ₆ -C ₃₀ ; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups,
The aryl group, arylene group, fluorenyl group, fluorenylene group, hetero ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the rings formed by bonding adjacent groups are each 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; Phosphine oxide substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₃₀ aryloxy group; C ₆ -C ₃₀ arylthio group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₃₀ aliphatic ring groups. According to clause 7,
The compound represented by Formula 2 is an organic electric device that is one of the following compounds:























. According to clause 7,
The compound represented by Formula 3 is one of the following compounds:


























. According to clause 6,
The organic material layer is an organic electric device characterized in that it includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. According to clause 10,
The organic material layer is an organic electric device, characterized in that it further includes a charge generation layer formed between the two or more stacks. According to clause 6,
The organic electric device further includes a light efficiency improvement layer, wherein the light efficiency improvement layer is formed on a layer that is not in contact with the organic material layer among both surfaces of the first electrode or the second electrode. A display device including the organic electric element of claim 6; and
An electronic device comprising a control unit that drives the display device. According to clause 13,
The organic electric device is an electronic device characterized in that it is selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices. A compound obtained by depositing an organic layer in the manufacturing process of an organic electric device, then recovering and purifying the material of the organic layer from deposition equipment,
The compound is characterized in that it is a compound represented by Formula 1 of claim 1. According to clause 15,
A compound characterized in that the purity of the compound is 99.9% or more. Depositing an organic layer material containing the compound represented by Formula 1 of claim 1;
Recovering the organic layer material attached to deposition equipment; and
A method for recovering a compound represented by Formula 1, comprising the step of purifying the recovered organic layer material to obtain a compound represented by Formula 1 with a purity of 99.9% or more. According to clause 17,
The purification step includes the steps of recrystallizing the recovered organic layer material using a recrystallization solvent, adsorption separation using an adsorbent, and sublimation purification.