WO2024010280A1 - Compound for organic electric element, organic electric element using same, and electronic device thereof - Google Patents

Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode; and an electronic device comprising the organic electric element. By including the compound represented by chemical formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered and the light emission efficiency and lifespan thereof can be improved.

Description

Compounds for organic electric devices, organic electric devices using them, and electronic devices thereof

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

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

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

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

Currently, the portable display market is increasing in size toward large-area displays, 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 substances 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 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:

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

By using the compound according to the embodiment of the present invention, the driving voltage of the device can be lowered and the luminous efficiency and lifespan can be improved.

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

[Explanation of symbols]

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

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.

The term "fluorenyl group" used in the present invention 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 elements 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.

The term 'silyl group' used in the present invention refers to a substituted or unsubstituted silyl group and a substituent represented by -Si(R) ₃ '. The unsubstituted silyl group is -SiH ₃ , and the substituted silyl group includes at least one of the H substituents other than H, such as deuterium, an alkyl group, an aryl group, a heterocyclic group, a fluorenyl group, an aliphatic ring, an aromatic ring, and an aliphatic ring. It means that it has been replaced with a substituent such as a fused ring group.

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 is applied identically to 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 the 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, anthracene corresponds 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 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 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.

When 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 nature, sequence, or order of the component is not limited by the term. When a component is described as being “connected,” “coupled,” or “connected” to another component, that component may be directly connected or connected to that other component, but there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

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

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 electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.

Additionally, according to another embodiment of the present invention, the organic 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 efficiency of current generated in each light-emitting layer and 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, the intrinsic properties of the material (mobility, interface properties, etc.), 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 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>

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

Z ¹ to Z ³ are C(R') or N, and at least one of Z ¹ to Z ³ is N.

R' is 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 a C ₆ to C ₂₀ aryloxy group.

X ¹ to X ⁵ are independently C(R _a ) or C(R _b ).

The R _a are the same or different from each other and are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; A C ₂ to C ₁₆ 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 ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne group; C ₁ ~ C ₃₀ alkoxy group; and aryloxy groups of C ₆ to C ₃₀ , and adjacent groups may be bonded to each other to form a ring.

The R _b are the same or different from each other and are independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A C ₂ to C ₁₆ 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 ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne group; C ₁ ~ C ₃₀ alkoxy group; and aryloxy groups of C ₆ to C ₃₀ , and adjacent groups may be bonded to each other to form a ring.

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 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 a silyl group.

However, in Formula 1, compounds in which Ar ¹ and R _b both contain a 9-carbazolyl group are excluded. Here, the 9-carbazolyl group refers to a substituted or unsubstituted 9-carbazolyl group, and does not include forms in which the 9-carbazolyl group is fused to a moiety among polycyclic rings.

R ¹ to R ⁴ 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 C ₆ to C ₂₀ aryloxy groups, and adjacent groups may be bonded to each other to form a ring.

a and b are each integers from 0 to 4, c and d are each integers from 0 to 5, and when each of these is an integer of 2 or more, each of R ¹ , each of R ² , each of R ³ , and each of R ⁴ are equal to or Different.

A ring formed by combining adjacent groups, for example, adjacent R ¹ , adjacent R ² , adjacent R ³ , adjacent R ⁴ , adjacent R _a , and adjacent R _b . is an aromatic ring group of C ₆ to C ₆₀ ; fluorenylene group; C ₃ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a C ₆ to C ₆₀ aliphatic ring group.

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.

When at least one of R ¹ to R ⁴ , Ar ¹ , R', R _a , and R _b is an aryl group, the aryl group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to 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, phenyl, biphenyl, naphthyl. , terphenyl, 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 , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, tri. It may be phenylene, etc. Preferably, L ³ may be phenyl, biphenyl or terphenyl.

When at least one of R ¹ to R ⁴ , Ar ¹ , R', R _a , R _b , and 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 ~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 It may be a heterocyclic group such as 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, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyrido Quinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, Benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, Indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzopyridine Thiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, It may be 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc.

When at least one of R ¹ to R ⁴ , Ar ¹ , R', R _a , and R _b is a fluorenyl group, or at least one of L ¹ and L ² is a fluorenylene group, the fluorenyl group or fluorenylene The 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- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene, etc. .

When at least one of R ¹ to R ⁴ , Ar ¹ , L ¹ to L ³ , R', R _a , and R _b is an aliphatic ring group, the aliphatic ring group is, for example, C ₃ to C ₂₀ , C ₃ to 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 Aliphatic ring groups such as ~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 , C _18, etc. You can.

When at least one of R ¹ to R ⁴ , R', R _a and R _b is 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 It may be an alkyl group such as ₂ , C ₃ , or C ₄ , and may be, for example, a methyl group, an ethyl group, or a t-butyl group.

When at least one of R ¹ to R ⁴ , R', R _a and R _b is an alkoxy group, the alkoxy group is, for example, C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C It may be an alkoxy group such as ₂ , C ₃ , or C ₄ , and may be, for example, a methoxy group, an ethoxy group, or a t-butoxy group.

When at least one of R ¹ to R ⁴ , R', R _a and R _b is an alkenyl group, the alkenyl group is, for example, C ₂ to C ₂₀ , C ₂ to C ₁₀ , C ₂ to C ₄ , C ₂ It may be an alkene group such as , C ₃ , or C ₄ .

The aryl group, arylene group, phenyl group, biphenyl group, terphenyl group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, The rings formed by combining neighboring groups each contain 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; And it may be substituted with one or more substituents selected from the group consisting of C ₁ -C ₂₀ alkylthio groups.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings 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 , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ , C ₃₀ , etc. may be an aryl group.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings is substituted with 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 to C ₂₇ , C ₂ to C ₂₆ , C ₂ to 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 , C ₃₀ , etc.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings is substituted with a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobi Fluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9-(naphthalene -2-yl) 9-phenyl-9 H -fluorene, etc.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings is substituted with an aliphatic ring group, the aliphatic ring group is, for example, C ₃ to C ₂₀ , C ₃ to C ₁₉ , C ₃ to C ₁₈ , C ₃ to C ₁₇ , C ₃ to C ₁₆ , C ₃ to 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 , and C ₁₈ may be an aliphatic ring group.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings is substituted with an alkyl group, the alkyl group may be, 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 , or C ₄ .

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings is substituted with an alkoxy group, the alkoxy group may be, for example, an alkoxy group such as C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , or C ₄ .

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. When at least one of the rings is substituted with an alkenyl group, the alkenyl group may be, for example, an alkenyl group such as C ₂ to C ₂₀ , C ₂ to C ₁₀ , C ₂ to C ₄ , C ₂ , C ₃ , or C ₄ .

At least one of L ¹ to L ³ may be selected from the group consisting of the following formulas (a-1) to (a-15).

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

<Formula a-4> <Formula a-5> <Formula a-6>

<Formula a-7> <Formula a-8> <Formula a-9>

<Formula a-10> <Formula a-11> <Formula a-12>

<Formula a-13> <Formula a-14> <Formula a-15>

In Formulas (a-1) to (a-15), R ⁵ , R ⁶ , R ₇ and R ₈ are independently hydrogen; heavy hydrogen; 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; and C ₆ -C ₂₀ arylthio groups, and adjacent groups can combine with each other to form a ring, m and n are each integers from 0 to 4, and o' is from 0 to 5. It is an integer, and p' is an integer of 0 to 3, and when these are integers of 2 or more, each of R ⁵ , each of R ⁶ , each of R ₇ , and each of R ₈ are the same or different from each other.

Additionally, L ² and L ³ may be asymmetric with each other. Here, 'asymmetry' is a concept that includes not only different substituents but also substituents with different bonding positions even for the same substituent. For example, when one of L ² and L ³ is p-phenylene and the other is m-phenylene. , these substituents are all the same as 'phenylene', but the bonding positions are different, so they are considered asymmetric. Additionally, even when one of L ² and L ³ is unsubstituted phenylene and the other is substituted phenylene, it is considered asymmetric.

Additionally, L ³ may be a single bond.

At least one of R _a and R _b may be selected from the group consisting of an alkyl group of C ₁ to C ₂₀ and the following Formulas 2-1 to 2-7.

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

<Formula 2-5> <Formula 2-6> <Formula 2-7>

In Formulas 2-1 to 2-7, each symbol may be defined as follows.

R ⁷ to R ¹² are independently hydrogen; heavy hydrogen; 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; and arylthio groups of C ₆ -C ₂₀ , and adjacent groups may be bonded to each other to form a ring.

l is an integer from 0 to 5, o, q, r and s are each an integer from 0 to 4, p is an integer from 0 to 3, and when each of these is an integer of 2 or more, each of R ⁷ , R ⁸ , Each of R ⁹ and R ¹⁰ are the same as or different from each other.

Y is S or O.

R ^a is a single bond; C ₁ -C ₂₀ alkylene group; 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 ^b is hydrogen; heavy hydrogen; 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.

Additionally, Ar ¹ may be selected from the group consisting of Formulas 3-1 to 3-8 below.

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

<Formula 3-5> <Formula 3-6> <Formula 3-7> <Formula 3-8>

In Formulas 3-1 to 3-8, each symbol may be defined as follows.

R ¹³ to R ²¹ are independently hydrogen; heavy hydrogen; 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; and arylthio groups of C ₆ -C ₂₀ , and adjacent groups may be bonded to each other to form a ring.

t, za, zb and zc are each an integer from 0 to 5, u, w, x and y are each an integer from 0 to 4, and v is an integer from 0 to 3, and if they are each an integer of 2 or more, R ¹³ Each of R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are the same as or different from each other.

Y is S or O.

R ^a is a single bond; C ₁ -C ₂₀ alkylene group; 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 ^b is hydrogen; heavy hydrogen; 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.

Formula 3-8 corresponds to a silyl group substituted with an aryl group. In Formula 1, when Ar1 is Formula 3-8, Formula 1 may be expressed as Formula 1-1 below.

<Formula 1-1>

In ^{Formula 1-1 , Z 1 to} Z ^{3 , X 1} to Hydrogen independently; heavy hydrogen; 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; and an arylthio group of C ₆ -C ₂₀ , and adjacent groups can combine with each other to form a ring, and za, zb, and zc are each integers of 0 to 5.

In Formula 1, L ³ may be a single bond. In this case, Chemical Formula 1 may be expressed as Chemical Formula 1-2 below.

<Formula 1-2>

^{In Formula 1-2 , X 1 to _ _}

In Formula 1, Formula 1-1, and Formula 1-2, at least one of X ¹ to X ⁵ may be C(R _b ).

In one embodiment, at least one of R _a and R _b is an aryl group of C ₆ to C ₃₀ ; C ₁ ~ C ₄ alkyl group; C ₃ ~ C ₁₀ cycloalkyl group; carbazolyl group; Dibenzofuryl group; Dibenzothiophene diary; benzocarbazolyl group; Naphthobenzofuryl group; and naphthobenzothiophenyl group.

In another example, at least one of R _a and R _b may be an aryl group of C ₆ to C ₃₀ substituted with at least one deuterium, and Ar ¹ may be an aryl group of C ₂ to C ₆₀ substituted with at least one deuterium. It may be a heterocyclic group.

In Formulas a-1 to a-15, Formulas 2-1 to 2-7, and Formulas 3-1 to 3-8, R ⁵ to R ²¹ , R ^a , and R ^b 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; And it may be further substituted with one or more substituents selected from the group consisting of C ₆ -C ₂₀ arylthio groups.

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

.

In another aspect, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a compound represented by Formula 1 .

The organic material layer includes a light-emitting layer and a hole transport zone formed between the first electrode and the light-emitting layer, and the hole transport zone includes the compound represented by Formula 1. At this time, the hole transport zone includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer may include the compound of Formula 1.

The organic material layer may include two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode, and in this case, the organic material layer may further include a charge generation layer formed between the two or more stacks. there is.

The organic electric device further includes a light efficiency improvement layer, and the light efficiency improvement layer may be formed on both sides of the first electrode or both sides of the second electrode, which is not in contact with the organic material layer.

In another aspect, the present invention provides an electronic device including a display device and a control unit that drives the display device. At this time, the display device includes an organic electric element containing the compound represented by Chemical Formula 1.

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

[Synthesis example]

The compound (final products) represented by Chemical Formula 1 according to the present invention may be synthesized by the reaction route of Scheme 1-1 or Scheme 1-2 below, but is not limited thereto.

<Scheme 1-1> When L ³ is not a single bond

<Scheme 1-2> When L ³ is a single bond

I. Synthesis example of Sub 1

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

<Scheme 2-1> (Hal ¹ is Br, I or Cl)

<Scheme 2-2> (Hal ² is Br)

1. Sub 1-1 synthesis example

(1) Sub 1-1a synthesis example

Sub 1-1d (300 g, 606.92 mmol), Sub 1-1e (70 g, 551.74 mmol), Pd(PPh ₃ ) ₄ (25.5 g, 22.07 mmol) and K ₂ CO ₃ (228.8 g, 1655.23 mmol) was added, dissolved by adding tetrahydrofuran (1656 ml) and H ₂ O (184 mL), and stirred at 50°C for 12 hours. When the reaction was completed, the extract was extracted with TDCE (trans-1,2-Dichloroethylene) 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 produce the product. 220 g (yield: 73%) was obtained.

(2) Sub 1-1 synthesis example

Sub 1-1a (220 g, 404.71 mmol), bis(pinacolato)diboron (123.33 g, 485.65 mmol), Pd(dppf)Cl ₂ (14.81 g, 20.24 mmol) and KOAc (79.44 g, 809.42 mmol) in a round bottom flask. ) was added, dissolved by adding toluene (1349 mL), and stirred at 140°C for 5 hours. When the reaction was completed, extraction was performed with TDCE 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 produce the product 172 g (yield: 71%) was obtained.

2. Sub 1-8 synthesis example

(1) Sub 1-8a synthesis example

Sub 1-1a in a round bottom flask. (151 g, 277.78 mmol), Sub 1-2e (66.67 g, 333.34 mmol), Pd(PPh ₃ ) ₄ (16.05 g, 13.89 mmol) and K ₂ CO ₃ (115.18 g, 833.34 mmol) were added and THF (830 g) was added. ml) and H ₂ O (90 mL) were added to dissolve it, and then stirred at 60°C for 12 hours. When the reaction was completed, extraction was performed with TDCE 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 produce the product 117 g (yield: 79%) was obtained.

(2) Sub 1-8 synthesis example

Sub 1-8a ( 117 g, 204.32 mmol), (bis(pinacolato)diboron) (62.26 g, 245.18 mmol), Pd(dppf)Cl ₂ (7.48 g, 10.22 mmol) and KOAc (40.10 g, 408.64 mmol) was added, dissolved in 681 mL of toluene, and then synthesized in the same manner as in the synthesis example of Sub 1-1 above to produce the product. 92 g (yield: 73%) was obtained.

3. Sub 1-11 synthesis example

(1) Sub 1-11a synthesis example

Sub 1-1d (300 g, 606.92 mmol), Sub 1-3e (70 g, 551.74 mmol), Pd(PPh ₃ ) ₄ (25.5 g, 22.07 mmol) and K ₂ CO ₃ (228.8 g, 1655.23 mmol) was added, dissolved in HTHF (1656 ml)/H ₂ O (184 mL), and then synthesized in the same manner as in the synthesis example of Sub 1-1a to produce the product. 206 g (yield: 69%) was obtained.

(2) Sub 1-11 synthesis example

Sub 1-11a in a round bottom flask. (204 g, 415.06 mmol), (bis(pinacolato)diboron) (123.33 g, 498.07 mmol), Pd(dppf)Cl ₂ (15.18 g, 20.75 mmol) and KOAc (81.47 g, 830.12 mmol) were added, and toluene ( After dissolving in 1383 mL), synthesis was performed in the same manner as in the synthesis example of Sub 1-1 to produce the product. 163 g (yield: 72%) was obtained.

4. Sub 1-16 Synthesis Example

(1) Sub 1-16a synthesis example

Sub 1-2d (85 g, 149.02 mmol), Sub 1-4e in a round bottom flask. (57.43 g, 178.82 mmol), Pd(PPh ₃ ) ₄ (6.89 g, 5.96 mmol) and K ₂ CO ₃ (61.79 g, 447.06 mmol) were added, and dissolved in THF (450 ml)/H ₂ O (50 ml). After dissolving, synthesis was performed in the same manner as in the synthesis example of Sub 1-1a to obtain 75 g of product (yield: 73%).

(2) Sub 1-16 synthesis example

Sub 1-16a in a round bottom flask. (75 g, 109.54 mmol), (bis(pinacolato)diboron) (33.38 g, 131.44 mmol), Pd(dppf)Cl ₂ (4 g, 5.48 mmol) and KOAc (21.5 g, 219.07 mmol) were added, Toluene ( After dissolving in 365 mL), synthesis was performed in the same manner as in the synthesis example of Sub 1-1a to obtain 59 g of product (yield: 74%).

5. Sub 1-30 synthesis example

(1) Sub 1-30a synthesis example

Sub 1-1d (300 g, 606.92 mmol), Sub 1-5e (39.09 g, 551.74 mmol), Pd(PPh ₃ ) ₄ (25.5 g, 22.07 mmol) and K ₂ CO ₃ (228.8 g, 1655.23 mmol) was added, dissolved in THF (1656 ml)/H ₂ O (184 ml), and then synthesized in the same manner as in the synthesis example of Sub 1-1a to obtain the product. 181 g (yield: 74%) was obtained.

(2) Sub 1-30 synthesis example

Sub 1-30a in a round bottom flask. (181 g, 410.02 mmol), (bis(pinacolato)diboron) (124.95 g, 492.03 mmol), Pd(dppf)Cl ₂ (15 g, 20.50 mmol) and KOAc (80.48 g, 820.04 mmol) were added and Toluene (1374) was added. After dissolving in mL), synthesis was performed in the same manner as in the synthesis example of Sub 1-1 to produce the product. 141 g (yield: 70%) was obtained.

6. Sub 1-32 Synthesis Example

(1) Sub 1-32a synthesis example

Sub 1-1d (200 g, 404.61 mmol), Sub 1-6e (66.21 g, 367.83 mmol), Pd(PPh ₃ ) ₄ (21.25 g, 18.39 mmol) and K ₂ CO ₃ (152.51 g, 1103.48 mmol) was added, dissolved in THF (1100 ml)/H ₂ O (126 ml), and then synthesized in the same manner as in the synthesis example of Sub 1-1a to obtain the product. 152 g (yield: 75%) was obtained.

(2) Sub 1-32 synthesis example

Sub 1-32a in a round bottom flask. (152 g, 276.55 mmol), (bis(pinacolato)diboron) (84.27 g, 331.86 mmol), Pd(dppf)Cl ₂ (10.12 g, 13.83 mmol) and KOAc (54.28 g, 553.1 mmol) were added and Toluene (922) was added. After dissolving in mL), synthesis was performed in the same manner as in the synthesis example of Sub 1-1 to produce the product. 119 g (yield: 72%) was obtained.

7. Sub 1-64 synthesis example

After adding Sub 1-1c (20 g, 85.79 mmol) and Ethyl ether (245 ml) to the round bottom flask, the temperature was brought to -78°C, and 2.5M n-butyllithium in Hexane (34 ml, 85.79 mmol) was added dropwise. After dropwise, stir for 1 hour. Afterwards, while maintaining -78°C, Sub 1-1b (19.74 g, 77.99 mmol) was dissolved in 100 ml of ethyl ether and applied dropwise. After stirring for 30 minutes, the mixture was slowly stirred at RT for 12 hours. When the reaction is complete, the solvent is concentrated, the concentrate is separated using a silica gel column, and then recrystallized to produce the product. 18 g (yield: 61%) was obtained.

8. Sub 1-86 synthesis example

After adding Sub 1-2c (20 g, 60.56 mmol) and Ethyl ether (170 ml) to the round bottom flask, the temperature was brought to -78°C, and 2.5M n-butyllithium in Hexane (24.22 ml, 60.56 mmol) was added dropwise. After dropwise, stir for 1 hour. Afterwards, while maintaining -78°C, dissolve Sub 1-1b (13.93 g, 55.05 mmol) in 73 ml of ethyl ether and apply dropwise. After stirring for 30 minutes, the mixture was slowly stirred at RT for 12 hours. When the reaction is complete, the solvent is concentrated, the concentrate is separated using a silica gel column, and then recrystallized to produce the product. 13.7 g (yield: 69%) was obtained.

Compounds belonging to Sub 1 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 1.

compound	FD-MS	compound	FD-MS
Sub 1-1	m/z= 443.28 (C 36 H 30 D 5 BO 2 Si= 443.60)	Sub 1-2	m/z=518.28 (C 34 H 39 BO 2 Si= 518.58)
Sub 1-3	m/z= 467.25 (C 30 H 26 D 5 BO 2 Si= 467.50)	Sub 1-4	m/z=672.36 (C 46 H 49 BO 2 Si= 672.79)
Sub 1-5	m/z= 578.28 (C 39 H 39 BO 2 Si= 578.63)	Sub 1-6	m/z=753.32 (C 52 H 44 BNO 2 Si= 753.82)
Sub 1-7	m/z=614.28 (C 42 H 39 BO 2 Si= 614.67)	Sub 1-8	m/z=619.31(C 42 H 34 D 5 BO 2 Si= 619.70)
Sub 1-9	m/z=579.24 (C 37 H 34 BNO 3 Si= 579.58)	Sub 1-10	m/z=556.29(C 37 H 33 D 4 BO 2 Si= 556.62)
Sub 1-11	m/z= 538.25 (C 36 H 35 BO 2 Si= 538.57)	Sub 1-12	m/z=543.28(C 36 H 30 D 5 BO 2 Si= 543.60)
Sub 1-13	m/z= 703.31 (C 48 H 42 BNO 2 Si= 703.76)	Sub 1-14	m/z=711.36(C 48 H 34 D 8 BNO 2 Si= 711.81)
Sub 1-15	m/z=695.34 (C 48 H 38 D 5 BO 2 Si= 695.80)	Sub 1-16	m/z=731.30(C 49 H 42 BNO 3 Si= 731.77)
Sub 1-17	m/z=628.26 (C 42 H 37 BO 3 Si= 628.65)	Sub 1-18	m/z=658.25(C 43 H 39 BO 2 SSi= 658.74)
Sub 1-19	m/z= 538.25 (C 36 H 35 BO 2 Si= 538.57)	Sub 1-20	m/z=619.31(C 42 H 34 D 5 BO 2 Si= 619.70)
Sub 1-21	m/z= 476.23 (C 31 H 33 BO 2 Si= 476.50)	Sub 1-22	m/z=810.32(C 55 H 47 BO 2 SSi= 810.93)
Sub 1-23	m/z=619.31 (C 42 H 34 D 5 BO 2 Si= 619.70)	Sub 1-24	m/z= 538.25 (C 36 H 35 BO 2 Si= 538.57)
Sub 1-25	m/z= 552.27 (C 37 H 37 BO 2 Si= 552.60)	Sub 1-26	m/z= 690.31 (C 48 H 43 BO 2 Si= 690.77)
Sub 1-27	m/z= 566.28 (C 38 H 39 BO 2 Si= 566.62)	Sub 1-28	m/z=614.28 (C 42 H 39 BO 2 Si= 614.67)
Sub 1-29	m/z=619.31 (C 42 H 34 D 5 BO 2 Si= 619.70)	Sub 1-30	m/z= 488.23 (C 32 H 33 BO 2 Si= 488.51)
Sub 1-31	m/z=701.35(C 47 H 36 D 7 BNO 3 Si= 701.80)	Sub 1-32	m/z= 596.33 (C 40 H 45 BO 2 Si= 596.69)
Sub 1-33	m/z=588.27(C 40 H 37 BO 2 Si= 588.63)	Sub 1-34	m/z= 588.27 (C 40 H 37 BO 2 Si= 588.63)
Sub 1-35	m/z= 690.31 (C 48 H 43 BO 2 Si= 690.77)	Sub 1-36	m/z=543.28(C 36 H 30 D 5 BO 2 Si= 543.60)
Sub 1-37	m/z=614.28 (C 42 H 39 BO 2 Si= 614.67)	Sub 1-38	m/z=619.31(C 42 H 34 D 5 BO 2 Si= 619.70)
Sub 1-39	m/z=707.33(C 48 H 38 D 4 BNO 2 Si= 707.79)	Sub 1-40	m/z=711.36(C 48 H 34 D 8 BNO 2 Si= 711.81)
Sub 1-41	m/z=671.25(C 43 H 38 BNO 2 SSi= 671.74)	Sub 1-42	m/z=703.31(C 48 H 42 BNO 2 Si= 703.76)
Sub 1-43	m/z= 703.31 (C 48 H 42 BNO 2 Si= 703.76)	Sub 1-44	m/z=711.36(C 48 H 34 D 8 BNO 2 Si= 711.81)
Sub 1-45	m/z= 490.25 (C 32 H 35 BO 2 Si= 490.53)	Sub 1-46	m/z=480.21(C 30 H 30 BFO 2 Si= 480.46)
Sub 1-47	m/z=614.28 (C 42 H 39 BO 2 Si= 614.67)	Sub 1-48	m/z=776.33 (C 55 H 45 BO 2 Si= 776.86)
Sub 1-49	m/z= 659.34 (C 45 H 38 BO 2 Si= 659.76)	Sub 1-50	m/z=561.33(C 37 H 36 D 5 BO 2 Si= 561.66)
Sub 1-51	m/z=658.34 (C 45 H 39 D 4 BO 2 Si= 658.76)	Sub 1-52	m/z=614.28 (C 42 H 39 BO 2 Si= 614.67)
Sub 1-53	m/z= 690.31 (C 48 H 43 BO 2 Si= 690.77)	Sub 1-54	m/z=624.34(C 42 H 29 D 10 BO 2 Si= 624.73)
Sub 1-55	m/z= 578.24 (C 38 H 35 BO 3 Si= 578.59)	Sub 1-56	m/z=497.26(C 31 H 28 D 5 BO 3 Si= 497.53)
Sub 1-57	m/z=614.28 (C 42 H 39 BO 2 Si= 614.67)	Sub 1-58	m/z=543.28(C 36 H 30 D 5 BO 2 Si= 543.60)
Sub 1-59	m/z=379.15 (C 24 H 10 D 9 ClSi=380.01)	Sub 1-60	m/z=375.13 (C 24 H 14 D 5 ClSi=375.98)
Sub 1-61	m/z=446.13 (C 30 H 23 ClSi=447.05)	Sub 1-62	m/z=459.21 (C 30 H 10 D 13 ClSi=460.13)
Sub 1-63	m/z=446.13 (C 30 H 23 ClSi=447.05)	Sub 1-64	m/z=370.09 (C 24 H 19 ClSi=370.95)
Sub 1-65	m/z=420.11 (C 28 H 21 ClSi=421.01)	Sub 1-66	m/z=420.11 (C 28 H 21 ClSi=421.01)
Sub 1-67	m/z=446.13 (C 30 H 23 ClSi=447.05)	Sub 1-68	m/z=496.14 (C 34 H 25 ClSi=497.11)
Sub 1-69	m/z=446.13 (C 30 H 23 ClSi=447.05)	Sub 1-70	m/z=375.13 (C 24 H 14 D 5 ClSi=375.98)
Sub 1-71	m/z=470.13 (C 32 H 23 ClSi=471.07)	Sub 1-72	m/z=460.11 (C 30 H 21 ClOSi=461.03)
Sub 1-73	m/z=476.08 (C 30 H 21 ClSSi=477.09)	Sub 1-74	m/z=486.16 (C 33 H 27 ClSi=487.11)
Sub 1-75	m/z=610.19 (C 43 H 31 ClSi=611.26)	Sub 1-76	m/z=610.19 (C 43 H 31 ClSi=611.26)
Sub 1-77	m/z=411.08 (C 25 H 18 ClNOSi=411.96)	Sub 1-78	m/z=388.14 (C 25 H 25 ClSi=389.01)
Sub 1-79	m/z=500.17 (C 34 H 29 ClSi=501.14)	Sub 1-80	m/z=428.17 (C 28 H 29 ClSi=429.07)
Sub 1-81	m/z=427.15 (C 28 H 14 D 7 ClSi=428.05)	Sub 1-82	m/z=370.09 (C 24 H 19 ClSi=370.95)
Sub 1-83	m/z=459.12 (C 30 H 22 ClNSi=460.05)	Sub 1-84	m/z=459.12 (C 30 H 22 ClNSi=460.05)
Sub 1-85	m/z=375.13 (C 24 H 14 D 5 ClSi=375.98)	Sub 1-86	m/z=467.17 (C 30 H 14 D 8 ClNSi=468.10)
Sub 1-87	m/z= 462.22 (C 30 H 31 BO 2 Si= 462.47)	Sub 1-88	m/z=543.28(C 36 H 30 D 5 BO 2 Si= 543.60)
Sub 1-89	m/z=627.28(C 42 H 38 BNO 2 Si= 627.67)	Sub 1-90	m/z=635.33 (C 42 H 30 D 8 BNO 2 Si=635.71)
Sub 1-91	m/z=635.33(C 42 H 30 D 8 BNO 2 Si= 635.71)	Sub 1-92	m/z=641.36(C 42 H 24 D 14 BNO 2 Si=641.75)
Sub 1-93	m/z=641.36(C 42 H 24 D 14 BNO 2 Si= 641.75)	Sub 1-94	m/z=711.36 (C 48 H 34 D 8 BNO 2 Si=711.81)
Sub 1-95	m/z=462.22 (C 30 H 31 BO 2 Si=462.47)	Sub 1-98	m/z=588.27 (C 40 H 37 BO 2 Si=588.63)
Sub 1-97	m/z=538.25 (C 36 H 35 BO 2 Si=538.57)	Sub 1-100	m/z=543.28 (C 36 H 30 D 5 BO 2 Si=543.6)
Sub 1-99	m/z=481.34 (C 30 H 12 D 19 BO 2 Si=481.59)	Sub 1-102	m/z=518.28 (C 34 H 39 BO 2 Si=518.58)
Sub 1-101	m/z=462.22 (C 30 H 31 BO 2 Si=462.47)	Sub 1-104	m/z=538.25 (C 36 H 35 BO 2 Si=538.57)
Sub 1-103	m/z=627.28 (C 42 H 38 BNO 2 Si=627.67)	Sub 1-106	m/z=627.28 (C 42 H 38 BNO 2 Si=627.67)
Sub 1-105	m/z=627.28 (C 42 H 38 BNO 2 Si=627.67)	Sub 1-108	m/z=538.25 (C 36 H 35 BO 2 Si=538.57)
Sub 1-107	m/z=627.28 (C 42 H 38 BNO 2 Si=627.67)	Sub 1-110	m/z=552.23 (C 36 H 33 BO 3 Si=552.55)
Sub 1-109	m/z=481.34 (C 30 H 12 D 19 BO 2 Si=481.59)	Sub 1-112	m/z=568.21 (C 36 H 33 BO 2 SSi=568.61)
Sub 1-111	m/z=552.23 (C 36 H 33 BO 3 Si=552.55)	Sub 1-114	m/z=579.24 (C 37 H 34 BNO 3 Si=579.58)

II. Synthesis example of Sub 2

Sub 2 of Schemes 1-1 and 1-2 can be synthesized by the reaction route of Scheme 3 below, and when Ar ¹ is a silyl group (-Si(R) ₃ ), by the reaction route of Scheme 4 below. However, it is not limited to this.

<Scheme 3> (Q is H, Br or Cl, Hal ³ is Br or Cl)

<Scheme 4>

1. Sub 2-2 Synthesis Example

After dissolving Sub 2-2b (6.7 g, 38.03 mmol) in Tetrahydrofuran (152 ml), 2.5M n-butyllithium in Hexane (16 ml, 38.03 mmol) was added dropwise while maintaining 0°C, and stirred for 1 hour. . Afterwards, while maintaining 0 ℃, a solution of Sub 2-2a (12 g, 38.03 mmol) dissolved in tetrahydrofuran (127 ml) was added dropwise, the temperature of the mixture was raised to room temperature, stirred for 1 hour, and then cooled to 80 ℃. After raising it to , it was stirred for 6 hours. When the reaction was completed, the reaction product was concentrated to remove the solvent, and then the concentrate was filtered and recrystallized to obtain 11 g of product (yield: 64%).

2. Sub 2-3 synthesis example

After dissolving Sub 2-2b (9.5 g, 54.22 mmol) in Tetrahydrofuran (216 ml), 2.5M n-butyllithium in Hexane (22 ml, 54.22 mmol) was added dropwise while maintaining 0°C, and stirred for 1 hour. . Afterwards, while maintaining 0 ℃, a solution of Sub 2-3a (5 g, 27.12 mmol) dissolved in tetrahydrofuran (90 ml) was added dropwise, the temperature of the mixture was raised to room temperature, stirred for 1 hour, and then cooled to 80 ℃. After raising it to , it was stirred for 6 hours. When the reaction was completed, the reaction product was concentrated to remove the solvent, and then the concentrate was filtered and recrystallized to obtain 8.5 g of product (yield: 68%).

3. Sub 2-5 synthesis example

(1) Sub 2-2a synthesis example

After dissolving Sub 2-1b (9.5 g, 54.22 mmol) in Tetrahydrofuran (216 ml), 2.5M n-butyllithium in Hexane (22 ml, 54.22 mmol) was added dropwise while maintaining 0°C, and stirred for 1 hour. . Afterwards, while maintaining 0 ℃, a solution of Sub 2-3a (10 g, 54.22 mmol) dissolved in tetrahydrofuran (180 ml) was added dropwise, the temperature of the mixture was raised to room temperature, stirred for 1 hour, and then cooled to 80 ℃. After raising it to , it was stirred for 6 hours. When the reaction was completed, the reaction product was concentrated to remove the solvent, and then the concentrate was filtered and recrystallized to obtain 12.8 g of product (yield: 75%).

(2) Sub 2-5 synthesis example

Sub 2-2a in a round bottom flask (12.8 g, 40.1 mmol), Sub 2-5c (18 g, 48.74 mmol), Pd(PPh ₃ ) ₄ (1.87 g, 1.62 mmol) and K ₂ CO ₃ (16.84 g, 121.83 mmol) were added and toluene (120 g) was added. ml)/H ₂ O (15 mL) and stirred at 110°C for 12 hours. When the reaction was completed, extraction was performed with TDCE 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 produce the product. 16.7 g (yield: 79%) was obtained.

4. Sub 2-6 synthesis example

After dissolving Sub 2-1b (7.11 g, 42.50 mmol) in Tetrahydrofuran (170 ml), 2.5M n-butyllithium in Hexane (17 ml, 42.50 mmol) was added dropwise while maintaining 0°C, and stirred for 1 hour. . Afterwards, while maintaining 0 ℃, a solution of Sub 2-6a (12.8 g, 42.50 mmol) dissolved in tetrahydrofuran (140 ml) was added dropwise, the temperature of the mixture was raised to room temperature, stirred for 1 hour, and then cooled to 80 ℃. After raising it to , it was stirred for 6 hours. When the reaction was completed, the reaction product was concentrated to remove the solvent, and then the concentrate was filtered and recrystallized to obtain 14.2 g of product (yield: 77%).

5. Sub 2-8 synthesis example

After dissolving Sub 2-3b (10 g, 25.11 mmol) in Tetrahydrofuran (100 ml), 2.5M n-butyllithium in Hexane (10 ml, 25.11 mmol) was added dropwise while maintaining 0°C, and stirred for 1 hour. . Afterwards, while maintaining 0 ℃, a solution of Sub 2-8a (5.68 g, 25.11 mmol) dissolved in tetrahydrofuran (84 ml) was added dropwise, the temperature of the mixture was raised to room temperature, stirred for 1 hour, and then cooled to 80 ℃. After raising it to , it was stirred for 6 hours. When the reaction was completed, the reaction product was concentrated to remove the solvent, and then the concentrate was filtered and recrystallized to obtain 9.1 g of product (yield: 71%).

6. Sub 2-42 Synthesis Example

After dissolving Sub 2-1b (4.59 g, 27.49 mmol) in Tetrahydrofuran (110 ml), 2.5M n-butyllithium in Hexane (11 ml, 27.49 mmol) was added dropwise while maintaining 0°C, and stirred for 1 hour. . Afterwards, while maintaining 0 ℃, a solution of Sub 2-42a (10.7 g, 27.49 mmol) dissolved in tetrahydrofuran (92 ml) was added dropwise, the temperature of the mixture was raised to room temperature, stirred for 1 hour, and then cooled to 80 ℃. After raising it to , it was stirred for 6 hours. When the reaction was completed, the reaction product was concentrated to remove the solvent, and then the concentrate was filtered and recrystallized to obtain 10.1 g of product (yield: 76%).

7. Sub 2-81 Synthesis example

Sub 2-2a (9.46 g, 30 mmol), Sub 2-81b' (13.87 g, 30 mmol), Pd(PPh ₃ ) ₄ (1.04 g, 0.9 mmol) and K ₂ CO ₃ (8.28 g, 60 mmol) was placed in a round bottom flask, dissolved in 75 mL of toluene and 25 mL of H ₂ O, and stirred at 130°C for 8 hours. After completion of the reaction, extraction was performed with toluene 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 13.10 g of product (yield: 71%).

Compounds belonging to Sub 2 may be, but are not limited to, the following compounds, and the FD-MS values of the following compounds are shown in Table 2.

compound	FD-MS	compound	FD-MS
Sub 2-1	m/z= 445.11 (C 27 H 16 ClN 5 = 445.91)	Sub 2-2	m/z= 453.16 (C 27 H 8 D 8 ClN 5 = 453.96)
Sub 2-3	m/z= 462.21 (C 27 D 16 ClN 5 = 461.01)	Sub 2-4	m/z= 356.08 (C 21 H 13 ClN 4 = 356.81)
Sub 2-5	m/z=522.14 (C 33 H 20 ClN 5 =521.01)	Sub 2-6	m/z=431.12 (C 28 H 18 ClN 3 =431.92)
Sub 2-7	m/z=456.11 (C 29 H 17 ClN 4 =456.93)	Sub 2-8	m/z=508.15 (C 33 H 21 ClN 4 =509.01)
Sub 2-9	m/z=530.17(C 33 H 11 D 8 ClN 4 O= 531.04)	Sub 2-10	m/z= 377.15 (C 23 H 8 D 8 ClN 3 = 377.90)
Sub 2-11	m/z=432.11 (C 27 H 17 ClN 4 = 432.91)	Sub 2-12	m/z= 508.15C 33 H 21 ClN 4 = 509.01)
Sub 2-13	m/z= 513.18 (C 33 H 16 D 5 ClN 4 = 514.04)	Sub 2-14	m/z=522.19 (C 36 H 27 ClN 2 =523.08)
Sub 2-15	m/z=535.18 (C 36 H 26 ClN 3 = 536.08)	Sub 2-16	m/z=757.28 (C 51 H 24 D 8 ClN 5 =758.35)
Sub 2-17	m/z= 361.11 (C 21 H 8 D 5 ClN 4 = 361.84)	Sub 2-18	m/z=374.07 (C 21 H 12 ClFN 4 = 374.80)
Sub 2-19	m/z= 386.09 (C 22 H 15 ClN 4 O= 386.84)	Sub 2-20	m/z=521.14 (C 33 H 20 ClN 5 = 522.01)
Sub 2-21	m/z=463.10 (C 27 H 15 ClFN 5 = 463.90)	Sub 2-22	m/z=670.19 (C 46 H 27 ClN 4 = 671.20)
Sub 2-23	m/z=610.19 (C 41 H 27 ClN 4 = 611.15)	Sub 2-24	m/z=610.19 (C 41 H 27 ClN 4 = 611.15)
Sub 2-25	m/z=597.17 (C 39 H 24 ClN 5 = 598.11)	Sub 2-26	m/z= 363.14 (C 22 H 6 D 8 ClN 3 = 363.87)
Sub 2-27	m/z= 363.14 (C 22 H 6 D 8 ClN 3 = 363.87)	Sub 2-28	m/z= 364.13 (C 21 H 5 D 8 ClN 4 = 364.86)
Sub 2-29	m/z= 439.17 (C 28 H 10 D 8 ClN 3 = 439.97)	Sub 2-30	m/z= 515.20 (C 34 H 14 D 8 ClN 3 = 516.07)
Sub 2-31	m/z=432.11 (C 27 H 17 ClN 4 = 432.91)	Sub 2-32	m/z= 493.20 (C 31 H 8 D 11 ClN 4 = 494.04)
Sub 2-33	m/z=537.17 (C 34 H 24 ClN 5 = 538.05)	Sub 2-34	m/z= 439.17 (C 28 H 10 D 8 ClN 3 = 439.97)
Sub 2-35	m/z= 598.16 (C 39 H 23 ClN 4 O= 599.09)	Sub 2-36	m/z=432.11 (C 27 H 17 ClN 4 = 432.91)
Sub 2-37	m/z=674.21 (C 47 H 31 ClN 2 O= 675.23)	Sub 2-38	m/z=615.22 (C 41 H 22 D 5 ClN 4 = 616.18)
Sub 2-39	m/z= 493.21 (C 31 H 20 D 5 ClN 4 =494.05)	Sub 2-40	m/z=520.15 (C 34 H 21 ClN 4 =521.02)
Sub 2-41	m/z= 527.20 (C 35 H 14 D 8 ClN 3 = 528.08)	Sub 2-42	m/z=551.21 (C 37 H 30 ClN 3 = 552.12)
Sub 2-43	m/z=685.23 (C 48 H 32 ClN 3 = 686.26)	Sub 2-44	m/z= 711.21 (C 45 H 18 D 8 ClN 5 S= 712.30)
Sub 2-45	m/z= 529.19 (C 33 H 12 D 8 ClN 5 = 530.06)	Sub 2-46	m/z= 528.20 (C 34 H 13 D 8 ClN 4 = 529.07)
Sub 2-47	m/z=681.25 (C 45 H 20 D 8 ClN 5 = 682.25)	Sub 2-48	m/z=605.22 (C 39 H 16 D 8 ClN 5 = 606.15)
Sub 2-49	m/z=545.22 (C 34 H 16 D 8 ClN 5 = 546.10)	Sub 2-50	m/z=612.21 (C 41 H 29 ClN 4 = 613.16)
Sub 2-51	m/z=462.07 (C 27 H 15 ClN 4 S= 462.96)	Sub 2-52	m/z= 522.12 (C 33 H 19 ClN 4 O= 522.99)
Sub 2-53	m/z=512.09 (C 31 H 17 ClN 4 S= 513.02)	Sub 2-54	m/z=610.16 (C 40 H 23 ClN 4 O= 611.10)
Sub 2-55	m/z=673.20 (C 45 H 28 ClN 5 = 674.20)	Sub 2-56	m/z= 562.13 (C 34 H 19 ClN 6 O= 563.02)
Sub 2-57	m/z=614.13 (C 39 H 23 ClN 4 S= 615.15)	Sub 2-58	m/z=558.16 (C 37 H 23 ClN 4 = 559.07)
Sub 2-59	m/z=558.16 (C 37 H 23 ClN 4 = 559.07)	Sub 2-60	m/z=674.20 (C 45 H 28 ClN 5 = 674.20)
Sub 2-61	m/z=748.24 (C 52 H 33 ClN 4 = 749.31)	Sub 2-62	m/z=735.22 (C 50 H 30 ClN 5 = 736.28)
Sub 2-63	m/z=634.19 (C 43 H 27 ClN 4 = 635.17)	Sub 2-64	m/z=508.15 (C 33 H 21 ClN 4 =509.01)
Sub 2-65	m/z=432.11 (C 27 H 17 ClN 4 =432.91)	Sub 2-66	m/z=532.15 (C 35 H 21 ClN 4 =533.03)
Sub 2-67	m/z=597.17 (C 39 H 24 ClN 5 =598.11)	Sub 2-68	m/z=570.16 (C 38 H 23 ClN 4 =571.08)
Sub 2-69	m/z=521.14 (C 33 H 20 ClN 5 =522.01)	Sub 2-70	m/z=597.17 (C 39 H 24 ClN 5 =598.11)
Sub 2-71	m/z=597.17 (C 39 H 24 ClN 5 =598.11)	Sub 2-72	m/z=449.22 (C 27 D 17 ClN 4 =450.01)
Sub 2-73	m/z=495.13 (C 31 H 18 ClN 5 =495.97)	Sub 2-74	m/z=495.13 (C 31 H 18 ClN 5 =495.97)
Sub 2-75	m/z=556.23 (C 36 H 17 D 8 ClN 4 =557.12)	Sub 2-76	m/z=439.17 (C 28 H 10 D 8 ClN 3 =439.97)
Sub 2-77	m/z=446.09 (C 27 H 15 ClN 4 O=446.89)	Sub 2-78	m/z=614.13 (C 39 H 23 ClN 4 S=615.15)
Sub 2-79	m/z=572.14 (C 37 H 21 ClN 4 O=573.05)	Sub 2-80	m/z=438.16 (C 27 H 23 ClN 4 =438.96)
Sub 2-81	m/z=614.17 (C 39 H 27 ClN 4 Si=615.21)	Sub 2-82	m/z=614.17 (C 39 H 27 ClN 4 Si=615.21)
Sub 2-83	m/z=690.20 (C 45 H 31 ClN 4 Si=691.31)	Sub 2-84	m/z=690.20 (C 45 H 31 ClN 4 Si=691.31)
Sub 2-85	m/z=690.20 (C 45 H 31 ClN 4 Si=691.31)	Sub 2-86	m/z=690.20 (C 45 H 31 ClN 4 Si=691.31)
Sub 2-87	m/z=766.23 (C 51 H 35 ClN 4 Si=767.40)	Sub 2-88	m/z=695.23 (C 45 H 26 D 5 ClN 4 Si=696.34)
Sub 2-89	m/z=709.32(C 45 H 12 D 19 ClN 4 Si=710.42)	Sub 2-90	m/z=726.29 (C 47 H 43 ClN 4 Si=727.42)
Sub 2-91	m/z=664.16 (C 41 H 25 ClN 6 Si=665.23)	Sub 2-92	m/z=766.23 (C 51 H 35 ClN 4 Si=767.40)
Sub 2-93	m/z=626.24(C 39 H 15 D 12 ClN 4 Si=627.28)	Sub 2-94	m/z=702.28 (C 45 H 19 D 12 ClN 4 Si=703.38)
Sub 2-95	m/z=622.22 (C 39 H 19 D 8 ClN 4 Si=623.26)

Ⅲ. Synthesis example of final compound

1. P-1 synthesis example

Sub 1-1 (12.94 g, 23.81 mmol), Sub 2-1 (10 g, 21.65 mmol), Pd(PPh ₃₎₄ (0.5 g, 0.43 mmol) and NaOH (2.6 g, 64.94 mmol) in a round bottom flask. was added and dissolved by adding toluene (196 ml) and H ₂ O (20 mL), and then stirred at 140°C for 12 hours. When the reaction was completed, extraction was performed with TDCE 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 13.78 g of product (yield: 77%).

2. P-2 synthesis example

Sub 1-11 (12.94 g, 23.81 mmol), Sub 2-1 (10 g, 21.65 mmol), Pd(PPh ₃₎₄ (0.5 g, 0.43 mmol) and NaOH (2.6 g, 64.94 mmol) in a round bottom flask. was added and dissolved by adding toluene (196 ml) and H ₂ O (20 mL), and then synthesized in the same manner as in the synthesis example of P-1 to obtain 13.78 g of product (yield: 77%).

3. P-23 synthesis example

The reaction was carried out in the same manner as in the synthesis example of P-1 using Sub 1-7 (10.25 g, 16.67 mmol) and Sub 2-1 (7 g, 15.15 mmol) as reactants to obtain 9.72 g of product (yield: 71 %) was obtained.

4. P-30 synthesis example

The reaction was carried out in the same manner as in the synthesis example of P-1 using Sub 1-16 (15.47 g, 23.6 mmol) and Sub 2-4 (8 g, 21.46 mmol) as reactants to obtain 15.63 g of product (yield: 86 %) was obtained.

5. P-70 synthesis example

The reaction was carried out in the same manner as in the synthesis example of P-1 using Sub 1-11 (13.72 g, 25.47 mmol) and Sub 2-6 (10 g, 23.15 mmol) as reactants to obtain 15.14 g of product (yield: 80 %) was obtained.

6. P-87 synthesis example

The reaction was carried out in the same manner as in the synthesis example of P-1 using Sub 1-8 (13.11 g, 21.15 mmol) and Sub 2-15 (10 g, 19.23 mmol) as reactants to obtain 15.97 g of product (yield: 83 %) was obtained.

7. P-113 synthesis example

Dissolve Sub 1-59 (10.0 g, 26.32 mmol) in Tetrahydrofuran (100 ml), bring to -78°C, and add 2.5M n-butyllithium in Hexane (10.53 ml, 26.32 mmol) dropwise. After dropwise, gradually increase to RT and stir for 2 hours. Dissolve Sub 2-3 (12.16 g, 26.32 mmol) in Tetrahydrofuran (200 ml) and make the mixture at -78°C. After Lithiating Sub 1-59, bring it back to -78 ℃ and dropwise into Sub 2-3. After stirring for 30 minutes, the mixture was stirred at 80°C for 12 hours. When the reaction is complete, it is concentrated to remove the solvent. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 11.0 g of product (yield: 66%).

8. P-155 synthesis example

The reaction was carried out in the same manner as in the synthesis example of P-113 using Sub 1-83 (10.0 g, 26.32 mmol) and Sub 2-80 (12.16 g, 26.32 mmol) as reactants to obtain 11.3 g of product (yield: 63 %) was obtained.

9. P-190 synthesis example

Sub 2-81 (12.30 g, 20 mmol), Sub 1-95 (9.25 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (5.52 g, 40 mmol) It was placed in a round bottom flask, dissolved in 75 mL of toluene and 25 mL of H ₂ O, and stirred at 130°C for 8 hours. After completion of the reaction, extraction was performed with toluene 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 14.46 g of product (yield: 79%).

The FD-MS values of the compounds 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=826.33 (C 57 H 34 D 5 N 5 Si=827.09)	P-2	m/z=821.30 (C 57 H 39 N 5 Si=822.06)
P-3	m/z=986.38 (C 71 H 50 N 4 Si=987.29)	P-4	m/z= 1018.42 (C 72 H 46 D 5 N 5 Si=1019.35)
P-5	m/z= 1031.44 (C 73 H 57 N 5 Si=1032.38)	P-6	m/z=941.30 (C 64 H 43 N 5 SSi=942.23)
P-7	m/z=829.35 (C 57 H 31 D 8 N 5 Si=830.11)	P-8	m/z=986.38 (C 71 H 50 N 4 Si=987.29)
P-9	m/z=821.30 (C 57 H 39 N 5 Si=822.06)	P-10	m/z=991.41 (C 71 H 45 D 5 N 4 Si=992.32)
P-11	m/z=902.36 (C 63 H 38 D 5 N 5 Si=903.19)	P-12	m/z=813.33 (C 57 H 35 D 5 N 4 Si=814.09)
P-13	m/z=877.36 (C 61 H 47 N 5 Si=878.17)	P-14	m/z=819.32 (C 55 H 42 FN 5 Si=820.06)
P-15	m/z=861.33 (C 60 H 43 N 5 Si=862.12)	P-16	m/z=849.33 (C 59 H 43 N 5 Si=850.11)
P-17	m/z= 1016.37 (C 70 H 48 N 6 OSi=1017.28)	P-18	m/z=1036.37 (C 73 H 48 N 6 Si=1037.31)
P-19	m/z=835.31 (C 58 H 41 N 5 Si=836.09)	P-20	m/z=973.36 (C 69 H 47 N 5 Si=974.26)
P-21	m/z=839.34 (C 58 H 37 D 4 N 5 Si=840.11)	P-22	m/z=897.33 (C 63 H 43 N 5 Si=898.16)
P-23	m/z=897.16 (C 63 H 43 N 5 Si=898.16)	P-24	m/z=905.38 (C 63 H 35 D 8 N 5 Si=906.21)
P-25	m/z=902.36 (C 63 H 38 D 5 N 5 Si=903.19)	P-26	m/z=902.36 (C 63 H 38 D 5 N 5 Si=903.19)
P-27	m/z=902.36 (C 63 H 38 D 5 N 5 Si=903.19)	P-28	m/z=842.43 (C 57 H 18 D 21 N 5 Si=843.19)
P-29	m/z=861.34 (C 58 H 39 D 5 N 4 SSi=862.19)	P-30	m/z=849.29 (C 58 H 39 N 5 OSi=850.07)
P-31	m/z=666.30 (C 45 H 22 D 10 N 4 Si=666.93)	P-32	m/z=970.35 (C 70 H 46 N 4 Si=971.25)
P-33	m/z=897.33 (C 63 H 43 N 5 Si 2 =898.16)	P-34	m/z=732.27 (C 51 H 36 N 4 Si=732.96)
P-35	m/z=788.33 (C 55 H 44 N 4 Si=789.07)	P-36	m/z=1046.38 (C 76 H 50 N 4 Si=1047.35)
P-37	m/z=737.30 (C 51 H 31 D 5 N 4 Si=737.99)	P-38	m/z=755.29 (C 51 H 30 D 5 FN 4 Si=755.98)
P-39	m/z= 767.31 (C 52 H 33 D 5 N 4 OSi=768.08)	P-40	m/z=782.29 (C 55 H 38 N 4 Si=783.02)
P-41	m/z=782.29 (C 55 H 38 N 4 Si=783.02)	P-42	m/z=921.33 (C 65 H 43 N 5 Si=922.18)
P-43	m/z=808.30 (C 57 H 40 N 4 Si=809.06)	P-44	m/z=865.27 (C 58 H 39 N 5 SSi=866.13)
P-45	m/z=808.30 (C 57 H 40 N 4 Si=809.06)	P-46	m/z=808.30 (C 57 H 40 N 4 Si=809.06)
P-47	m/z=813.33 (C 57 H 35 D 5 N 4 Si=814.09)	P-48	m/z=821.38 (C 57 H 27 D 13 N 4 Si=822.14)
P-49	m/z=818.36 (C 57 H 30 D 10 N 4 Si=819.12)	P-50	m/z=960.36 (C 69 H 48 N 4 Si=961.26)
P-51	m/z= 1054.42 (C 75 H 46 D 5 N 5 Si=1055.38)	P-52	m/z=820.39 (C 58 H 28 D 13 N 3 Si=821.15)
P-53	m/z=820.39 (C 58 H 28 D 13 N 3 Si=821.15)	P-54	m/z=834.40 (C 59 H 30 D 13 N 3 Si=835.18)
P-55	m/z=982.29 (C 69 H 38 D 8 N 4 OSi=983.29)	P-56	m/z=816.35 (C 57 H 32 D 8 N 4 Si=817.11)
P-57	m/z=891.39 (C 64 H 37 D 8 N 3 Si=892.22)	P-58	m/z=1084.44 (C 77 H 44 D 8 N 4 OSi=1085.42)
P-59	m/z=905.38 (C 63 H 35 D 8 N 5 Si=906.21)	P-60	m/z=905.38 (C 63 H 35 D 8 N 5 Si=906.21)
P-61	m/z=837.40 (C 57 H 23 D 16 N 5 Si=838.16)	P-62	m/z=1112.40 (C 79 H 52 N 6 Si=1113.41)
P-63	m/z=901.35 (C 63 H 39 D 4 N 5 Si=902.18)	P-64	m/z=981.41 (C 69 H 39 D 8 N 5 Si=982.30)
P-65	m/z=905.38 (C 63 H 35 D 8 N 5 Si=906.21)	P-66	m/z=834.38 (C 57 H 26 D 13 N 5 Si=835.14)
P-67	m/z=758.29 (C 53 H 38 N 4 Si=759.00)	P-68	m/z=866.38 (C 61 H 50 N 4 Si=867.18)
P-69	m/z=760.30 (C 53 H 40 N 4 Si=761.02)	P-70	m/z=807.31 (C 58 H 41 N 3 Si=808.07)
P-71	m/z=757.32 (C 52 H 28 D 8 FN 3 Si=758.01)	P-72	m/z=912.33 (C 64 H 44 N 4 OSi=913.17)
P-73	m/z=822.32 (C 58 H 42 N 4 Si=823.09)	P-74	m/z=889.36 (C 63 H 39 D 5 N 4 Si=890.19)
P-75	m/z=882.34 (C 65 H 46 N 2 Si=883.18)	P-76	m/z=979.40 (C 71 H 45 D 5 N 2 OSi=980.31)
P-77	m/z=831.36 (C 57 H 29 D 10 N 5 Si=832.12)	P-78	m/z=844.38 (C 59 H 32 D 10 N 4 Si=845.16)
P-79	m/z=1148.51 (C 83 H 48 D 10 N 4 Si=1149.55)	P-80	m/z=1053.43 (C 76 H 47 D 5 N 4 Si=1054.40)
P-81	m/z=798.40 (C 55 H 34 D 10 N 4 Si=799.13)	P-82	m/z=989.39 (C 70 H 51 N 5 Si=990.30)
P-83	m/z=994.42 (C 70 H 46 D 5 N 5 Si=995.33)	P-84	m/z=1185.43 (C 83 H 59 N 5 SSi=1186.57)
P-85	m/z=989.39 (C 70 H 5 1N 5 Si=990.30)	P-86	m/z=995.45 (C 72 H 45 D 8 N 3 Si=996.37)
P-87	m/z=992.43 (C 72 H 48 D 5 N 3 Si=993.35)	P-88	m/z=1053.43 (C 76 H 47 D 5 N 4 Si=1054.40)
P-89	m/z=1142.48 (C 84 H 54 D 5 N 3 Si=1143.53)	P-90	m/z=986.44 (C 69 H 34 D 13 N 5 Si=987.33)
P-91	m/z=1239.46 (C 87 H 49 D 8 N 5 SSi=1240.64)	P-92	m/z=986.44 (C 69 H 34 D 13 N 5 Si=987.33)
P-93	m/z=985.45 (C 70 H 35 D 13 N 4 Si=986.35)	P-94	m/z=986.44 (C 69 H 34 D 13 N 5 Si=987.33)
P-95	m/z=1062.47 (C 75 H 38 D 13 N 5 Si=1063.43)	P-96	m/z=986.44 (C 69 H 34 D 13 N 5 Si=987.33)
P-97	m/z=986.44 (C 69 H 34 D 13 N 5 Si=987.33)	P-98	m/z=1062.47 (C 75 H 38 D 13 N 5 Si=1063.43)
P-99	m/z=1214.54 (C 87 H 46 D 13 N 5 Si=1215.63)	P-100	m/z=986.44 (C 69 H 34 D 13 N 5 Si=987.33)
P-101	m/z=903.34 (C 63 H 37 D 5 N 4 OSi=904.17)	P-102	m/z=964.31 (C 67 H 44 N 4 SSi=965.26)
P-103	m/z=1138.41 (C 82 H 54 N 4 OSi=1139.45)	P-104	m/z=1169.48 (C 84 H 55 D 4 N 5 Si=1170.54)
P-105	m/z=1024.41 (C 70 H 36 D 10 N 6 OSi=1025.33)	P-106	m/z=990.32 (C 69 H 46 N 4 SSi=991.30)
P-107	m/z=974.34 (C 69 H 46 N 4 OSi=975.24)	P-108	m/z=893.36 (C 62 H 39 D 5 N 4 OSi=894.18)
P-109	m/z=1054.42 (C 75 H 46 D 5 N 5 Si=1055.38)	P-110	m/z=1124.43 (C 82 H 56 N 4 Si=1125.46)
P-111	m/z=1187.44 (C 86 H 57 N 5 Si=1188.52)	P-112	m/z=1015.41 (C 73 H 45 D 5 N 4 Si=1016.35)
P-113	m/z=770.42 (C 51 H 10 D 25 N 5 Si=771.11)	P-114	m/z=762.37 (C 51 H 18 D 17 N 5 Si=763.06)
P-115	m/z=754.32 (C 51 H 26 D 9 N 5 Si=755.02)	P-116	m/z=750.30 (C 51 H 30 D 5 N 5 Si=750.99)
P-117	m/z=821.30 (C 57 H 39 N 5 Si=822.06)	P-118	m/z=834.38 (C 57 H 26 D 13 N 5 Si=835.14)
P-119	m/z=842.43 (C 57 H 18 D 21 N 5 Si=843.19)	P-120	m/z=821.30 (C 57 H 39 N 5 Si=822.06)
P-121	m/z=744.27 (C 52 H 36 N 4 Si=744.97)	P-122	m/z=745.27 (C 51 H 35 N 5 Si=745.96)
P-123	m/z=795.28 (C 55 H 37 N 5 Si=796.02)	P-124	m/z=795.28 (C 55 H 37 N 5 Si=796.02)
P-125	m/z=744.27 (C 52 H 36 N 4 Si=744.97)	P-126	m/z=820.30 (C 58 H 40 N 4 Si=821.07)
P-127	m/z=820.30 (C 58 H 40 N 4 Si=821.07)	P-128	m/z=879.36 (C 61 H 33 D 8 N 5 Si=880.17)
P-129	m/z=732.27 (C 51 H 36 N 4 Si=732.96)	P-130	m/z=750.30 (C 51 H 30 D 5 N 5 Si=750.99)
P-131	m/z=845.30 (C 59 H 39 N 5 Si=846.08)	P-132	m/z=808.30 (C 57 H 40 N 4 Si=809.06)
P-133	m/z=835.28 (C 57 H 37 N 5 OSi=836.04)	P-134	m/z=838.26 (C 57 H 38 N 4 SSi=839.10)
P-135	m/z=777.33 (C 54 H 35 D 5 N 4 Si=778.06)	P-136	m/z=985.36 (C 70 H 47 N 5 Si=986.27)
P-137	m/z=972.36 (C 70 H 48 N 4 Si=973.27)	P-138	m/z=882.32 (C 63 H 42 N 4 Si=883.14)
P-139	m/z=897.33 (C 63 H 43 N 5 Si=898.16)	P-140	m/z=697.23 (C 46 H 31 N 5 OSi=697.87)
P-141	m/z=870.32 (C 62 H 42 N 4 Si=871.13)	P-142	m/z=839.34 (C 58 H 45 N 5 Si=840.12)
P-143	m/z=1027.41 (C 73 H 53 N 5 Si=1028.35)	P-144	m/z=955.41 (C 67 H 53 N 5 Si=956.28)
P-145	m/z=818.43 (C 55 H 14 D 23 N 5 Si=819.16)	P-146	m/z=758.43 (C 51 H 10 D 26 N 4 Si=759.12)
P-147	m/z=804.34 (C 55 H 28 D 9 N 5 Si=805.08)	P-148	m/z=800.31 (C 55 H 32 D 5 N 5 Si=801.05)
P-149	m/z=856.38 (C 60 H 36 D 8 N 4 Si=857.17)	P-150	m/z=828.35 (C 58 H 32 D 8 N 4 Si=829.12)
P-151	m/z=753.32 (C 51 H 27 D 8 N 5 Si=754.01)	P-152	m/z=835.28 (C 57 H 37 N 5 OSi=836.04)
P-153	m/z=919.32 (C 63 H 37 D 5 N 4 SSi=920.23)	P-154	m/z=961.32 (C 67 H 43 N 5 OSi=962.20)
P-155	m/z=827.34 (C 57 H 45 N 5 Si=828.11)	P-156	m/z=758.35 (C 51 H 22 D 13 N 5 Si=759.04)
P-157	m/z=821.30 (C 57 H 39 N 5 Si=822.06)	P-158	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)
P-159	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)	P-160	m/z=829.35 (C 57 H 31 D 8 N 5 Si=830.11)
P-161	m/z=829.35 (C 57 H 31 D 8 N 5 Si=830.11)	P-162	m/z=829.35 (C 57 H 31 D 8 N 5 Si=830.11)
P-163	m/z=837.40 (C 57 H 23 D 16 N 5 Si=838.16)	P-164	m/z=834.38 (C 57 H 26 D 13 N 5 Si=835.14)
P-165	m/z=840.42 (C 57 H 20 D 19 N 5 Si=841.17)	P-166	m/z=835.39 (C 57 H 25 D 14 N 5 Si=836.14)
P-167	m/z=843.44 (C 57 H 17 D 22 N 5 Si=844.19)	P-168	m/z=848.47 (C 57 H 12 D 27 N 5 Si=849.22)
P-169	m/z=829.35 (C 57 H 31 D 8 N 5 Si=830.11)	P-170	m/z=905.38 (C 63 H 35 D 8 N 5 Si=906.21)
P-171	m/z=1004.37 (C 70 H 52 N 4 Si 2 =1005.38)	P-172	m/z=970.39 (C 67 H 54 N 4 Si 2 =971.37)
P-173	m/z=1040.37 (C 73 H 52 N 4 Si 2 =1041.42)	P-174	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-175	m/z=995.39 (C 69 H 45 D 5 N 4 Si 2 =996.39)	P-176	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-177	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)	P-178	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-179	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)	P-180	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-181	m/z=995.39 (C 69 H 45 D 5 N 4 Si 2 =996.39)	P-182	m/z=1066.39 (C 75 H 54 N 4 Si 2 =1067.45)
P-183	m/z=1028.6 (C 69 H 12 D 38 N 4 Si 2 =1029.59)	P-184	m/z=1066.39 (C 75 H 54 N 4 Si 2 =1067.45)
P-185	m/z=1032.62 (C 69 H 8 D 42 N 4 Si 2 =1033.61)	P-186	m/z=970.39 (C 67 H 54 N 4 Si 2 =971.37)
P-187	m/z=998.41 (C 69 H 42 D 8 N 4 Si 2 =999.41)	P-188	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-189	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)	P-190	m/z=914.33 (C 63 H 46 N 4 Si 2 =915.26)
P-191	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)	P-192	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)
P-193	m/z=995.39 (C 69 H 45 D 5 N 4 Si 2 =996.39)	P-194	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-195	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)	P-196	m/z=922.38 (C 63 H 38 D 8 N 4 Si 2 =923.31)
P-197	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)	P-198	m/z=914.33 (C 63 H 46 N 4 Si 2 =915.26)
P-199	m/z=914.33 (C 63 H 46 N 4 Si 2 =915.26)	P-200	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)
P-201	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)	P-202	m/z=990.36 (C 69 H 50 N 4 Si 2 =991.36)
P-203	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)	P-204	m/z=1003.44 (C 69 H 37 D 13 N 4 Si 2 =1004.44)
P-205	m/z=941.50 (C 63 H 19 D 27 N 4 Si 2 =942.42)	P-206	m/z=941.50 (C 63 H 19 D 27 N 4 Si 2 =942.42)
P-207	m/z=960.61 (C 63 D 46 N 4 Si 2 =961.54)	P-208	m/z=1026.45 (C 71 H 62 N 4 Si 2 =1027.47)
P-209	m/z=964.32 (C 65 H 44 N 6 Si 2 =965.28)	P-210	m/z=1066.39 (C 75 H 54 N 4 Si 2 =1067.45)
P-211	m/z=1079.38 (C 75 H 53 N 5 Si 2 =1080.45)	P-212	m/z=1004.34 (C 69 H 48 N 4 OSi 2 =1005.34)
P-213	m/z=1020.31 (C 69 H 48 N 4 SSi 2 =1021.4)	P-214	m/z=1004.34 (C 69 H 48 N 4 OSi 2 =1005.34)
P-215	m/z=1031.35 (C 70 H 49 N 5 OSi 2 =1032.37)	P-216	m/z=1004.34 (C 69 H 48 N 4 OSi 2 =1005.34)
P-217	m/z=1020.31 (C 69 H 48 N 4 SSi 2 =1021.40)	P-218	m/z=1003.44 (C 69 H 37 D 13 N 4 Si 2 =1004.44)
P-219	m/z=1022.56 (C 69 H 18 D 32 N 4 Si 2 =1023.55)	P-220	m/z=1040.67 (C 69 D 50 N 4 Si 2 =1041.66)
P-221	m/z=1091.55 (C 75 H 29 D 25 N 4 Si 2 =1092.61)	P-222	m/z=1002.43 (C 69 H 38 D 12 N 4 Si 2 =1003.43)

[Example 1] Blue organic electroluminescent device (phosphorescent host)

A 60nm thick hole injection layer was created by vacuum depositing 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) on the ITO layer (anode) formed on the glass substrate. After forming, N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as NPB) on the hole injection layer. (abbreviated as ) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.

Next, on the hole transport layer, compound P-1 of the present invention was applied as a host material, and meridional-tris-(N-phenyl, N-methyl-pyridoimidazol-2-yl)iridium (III) (hereinafter referred to as 'mer') was applied as a dopant material. -Ir(pmp) ₃ ') was used and the dopant was doped at a weight of 95:5 to form a 30 nm thick light emitting layer.

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, tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was vacuum deposited to a thickness of 40 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.

[Example 2] to [Example 25]

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention shown in Table 4 below were used as host materials instead of Compound P-1 of the present invention.

[Comparative Example 1] to [Comparative Example 5]

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

<Comparative compound A> <Comparative compound B> <Comparative compound C>

<Comparative compound D> <Comparative compound E>

Electroluminescence (EL) characteristics were obtained using PR-650 from PhotoResearch by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured in Examples 1 to 25 and Comparative Examples 1 to 5 of the present invention. The T95 lifespan was measured using a lifespan measuring device manufactured by McScience at a standard luminance of 1,000 cd/m ² . The measurement results are shown in Table 4 below.

	compound	driving voltage (V)	electric current (mA/ cm2 )	Luminance (cd/ m2 )	efficiency (cd/A)	T(95)
Comparative example (1)	Comparative compound A	6.2	8.8	1000.0	11.3	75.6
Comparative example (2)	Comparative compound B	5.6	7.3	1000.0	13.7	86.3
Comparative example (3)	Comparative compound C	5.8	7.0	1000.0	14.2	92.6
Comparative example (4)	Comparative compound D	5.9	7.2	1000.0	13.8	87.4
Comparative example (5)	Comparative compound E	5.9	7.2	1000.0	13.9	89.1
Example (1)	P-1	5.3	4.6	1000.0	21.8	114.4
Example (2)	P-2	5.3	4.9	1000.0	20.6	111.3
Example (3)	P-7	5.3	4.7	1000.0	21.3	112.6
Example (4)	P-9	5.5	5.2	1000.0	19.1	107.5
Example (5)	P-24	5.5	5.1	1000.0	19.8	112.2
Example (6)	P-28	5.3	4.9	1000.0	20.3	114.1
Example (7)	P-34	5.4	5.1	1000.0	19.5	107.9
Example (8)	p-55	5.5	5.5	1000.0	18.2	107.1
Example (9)	P-60	5.6	5.1	1000.0	19.5	111.8
Example (10)	P-61	5.3	5.0	1000.0	19.9	113.0
Example (11)	P-66	5.3	5.2	1000.0	19.3	113.5
Example (12)	P-70	5.5	5.7	1000.0	17.6	109.3
Example (13)	P-74	5.5	5.3	1000.0	18.8	110.2
Example (14)	P-85	5.4	5.4	1000.0	18.5	108.3
Example (15)	P-102	5.6	5.6	1000.0	17.9	110.7
Example (16)	P-114	5.3	4.7	1000.0	21.1	113.2
Example (17)	P-116	5.3	4.9	1000.0	20.3	112.5
Example (18)	P-152	5.4	4.8	1000.0	20.6	112.9
Example (19)	P-157	5.4	4.9	1000.0	20.3	110.0
Example (20)	P-158	5.5	5.6	1000.0	18.0	108.8
Example (21)	P-161	5.4	4.8	1000.0	20.7	113.7
Example (22)	P-174	5.4	5.3	1000.0	19.0	111.9
Example (23)	P-179	5.3	5.1	1000.0	19.7	112.4
Example (24)	P-190	5.4	5.2	1000.0	19.4	110.9
Example (25)	P-195	5.3	5.0	1000.0	20.0	111.4

[Example 26] Blue organic electroluminescent device (fluorescent host)

An organic electroluminescent device was manufactured in the same manner as Example 1, except that BD-052X (manufactured by Idemitsu Kosan) was used as a dopant material, and the dopant was doped so that the weight ratio of host and dopant was 96:4. did.

[Example 27] to [Example 46]

An organic electroluminescent device was manufactured in the same manner as Example 24, except that the compound of the present invention shown in Table 5 below was used as the host material instead of the compound P-1 of the present invention.

[Comparative Example 6] to [Comparative Example 9]

Organic compound was prepared in the same manner as in Example 24, except that the following comparative compound F and comparative compounds B, C, and E used in Comparative Examples 2, 3, and 5 were used as the host material instead of the compound P-1 of the present invention. An electroluminescent device was manufactured.

<Comparative compound F>

Electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured in Examples 26 to 46 and Comparative Examples 6 to 9 of the present invention. The T95 lifespan was measured using a lifespan measuring device manufactured by McScience at a standard luminance of 500 cd/m ² . The measurement results are shown in Table 5 below.

	compound	driving voltage (V)	electric current (mA/ cm2 )	Luminance (cd/ m2 )	efficiency (cd/A)	T(95)
Comparative example (6)	Comparative compound F	5.9	16.1	500.0	3.1	75.6
Comparative example (7)	Comparative compound B	5.4	9.4	500.0	5.3	86.3
Comparative example (8)	Comparative compound C	5.7	9.4	500.0	5.3	92.6
Comparative example (9)	Comparative compound E	5.7	9.8	500.0	5.1	87.4
Example (26)	P-1	4.9	7.8	500.0	6.4	118.7
Example (27)	P-2	5.0	8.1	500.0	6.2	115.6
Example (28)	P-7	5.0	7.9	500.0	6.3	116.2
Example (29)	P-9	5.2	8.2	500.0	6.1	111.6
Example (30)	P-24	5.3	8.9	500.0	5.6	116.0
Example (31)	P-28	5.0	8.5	500.0	5.9	118.1
Example (32)	P-35	5.1	8.8	500.0	5.7	111.1
Example (33)	p-46	5.2	8.9	500.0	5.6	113.8
Example (34)	P-60	5.3	9.4	500.0	5.3	116.1
Example (35)	P-61	5.0	8.3	500.0	6.0	117.7
Example (36)	P-70	5.3	9.1	500.0	5.5	107.3
Example (37)	P-72	5.3	9.6	500.0	5.2	108.4
Example (38)	P-84	5.2	9.4	500.0	5.3	102.9
Example (39)	P-87	5.4	9.4	500.0	5.3	109.5
Example (40)	P-103	5.2	9.3	500.0	5.4	106.8
Example (41)	P-122	5.0	8.1	500.0	6.2	113.7
Example (42)	P-157	5.1	8.2	500.0	6.1	114.9
Example (43)	P-177	5.1	8.5	500.0	5.9	113.5
Example (44)	P-187	5.2	8.3	500.0	6.0	115.2
Example (45)	P-196	5.2	8.5	500.0	5.9	115.8
Example (46)	P-204	5.1	8.6	500.0	5.8	116.3

From Tables 4 and 5, it can be seen that according to the Examples of the present invention, the efficiency and lifespan are significantly improved while the driving voltage of the organic electric device is lowered compared to the Comparative Example. In the case of Comparative Compound B, the azine moiety contains 9- It is similar to the compound of the present invention in that the carbazole group and the tetraphenylsilyl group are substituted, but the compound of the present invention differs in that at least one of the phenyl groups of the tetraphenylsilyl group is substituted with a substituent other than hydrogen or deuterium. Due to this difference, the compound of the present invention has greater steric hindrance than comparative compound B.

Due to this steric hindrance effect, when depositing the compound of the present invention, the Dexter energy transfer effect between the host and the dopant decreases and the Forster energy transfer effect increases, especially TTA (triplet -triplet annihilation) is reduced. As a result, the performance, especially the lifespan, of organic electric devices using the compound of the present invention as a host is significantly improved.

It can be seen that the lifespan improvement effect due to this steric hindrance is further increased when a substituent is substituted at the meta position among the compounds of the present invention.

Comparative Compound C and Comparative Compound D are similar to the compounds of the present invention in that an additional substituent is introduced to the phenyl of the tetraphenylsilyl group, but the packing density is reduced due to excessive hindrance effect during material deposition, resulting in a decrease in packing density. Electron mobility decreases and the characteristics of the device deteriorate compared to the present invention.

Comparative compound E is similar to the compound of the present invention, but differs in that both the silyl group and the azine group are substituted with 9-carbazolyl group. To confirm this difference in substituents, the LUMO values of comparative compounds E and P-157 were measured using the DFT method (B3LYP/6-31g(D)) of the Gaussian program. The measurement results are shown in Table 6 below.

	LUMO (eV)
Comparative compound E	-1.812
P-157	-1.944

As can be seen in Table 6, the compound P-157 of the present invention shows a lower LUMO value than the comparative compound E. Therefore, when the compound of the present invention is used as a host, electron injection from the electron transport layer to the light-emitting layer is smoother than that of comparative compound E, and thus excitons are better generated in the light-emitting layer, thereby improving device characteristics.

These results show that even if the basic structure is similar to Comparative Compound E and the compound of the present invention, the charge characteristics, light efficiency characteristics, energy level (HOMO, LUMO), hole injection and mobility characteristics, hole injection and mobility characteristics, depending on the type of substituent and the position of substitution. This suggests that the physical properties of the compound, such as the charge balance of electrons, etc., may vary, which may lead to changes in the properties of the device.

In addition, Comparative Compound F is a commonly used host, and it can be seen that the device characteristics are significantly improved when the compound of the present invention is used as a host compared to this general host.

Among the compounds of the present invention, it can be seen that the lifespan of compounds in which at least one of R _a , R _b or Ar ¹ is substituted with deuterium is slightly improved.

This appears to be because when a deuterium-substituted substituent is introduced, the deuterium-carbon bond length becomes shorter than the hydrogen-carbon bond length, which reduces the molecular core volume and reduces electrical polarizability. . As the electrical polarization degree decreases, the effect of lowering the crystallinity of the thin film occurs, that is, it becomes more easily amorphous, thus improving hole mobility, and as a result, it appears to affect the lifespan.

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 the present invention.

Claims (19)

1. Compound represented by Formula 1:

   <Formula 1>

   

   In Formula 1,

   Z ¹ to Z ³ are C(R') or N, and at least one of Z ¹ to Z ³ is N,

   X ¹ to X ⁵ are independently C(R _a ) or C(R _b ),

   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 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 is selected from the group consisting of a silyl group,

   R ¹ to R ⁴ , R' and R _a 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 ₂₀ , and adjacent groups may bond to each other to form a ring;

   a and b are each integers from 0 to 4, c and d are each integers from 0 to 5, and when each of these is an integer of 2 or more, each of R ¹ , each of R ² , each of R ³ , and each of R ⁴ are equal to or are different, each of R' is the same as or different from each other, and each of R _a is the same as or different from each other,

   R _b are the same or different from each other and are independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A C ₂ to C ₁₆ 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 ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne group; C ₁ ~ C ₃₀ alkoxy group; and aryloxy groups of C ₆ to C ₃₀ , and adjacent groups may bond to each other to form a ring.

   The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other. Each ring is 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; and may be substituted with one or more substituents selected from the group consisting of C ₆ -C ₂₀ arylthio groups,

   However, in Formula 1, the case where Ar ¹ and R _b both include a 9-carbazolyl group is excluded.
2. According to clause 1,

   A compound wherein at least one of X ¹ to X ⁵ is C(R _b ).
3. According to clause 2,

   A compound characterized in that L ³ is a single bond.
4. According to clause 1,

   Compounds wherein at least one of L ¹ to L ³ is selected from the group consisting of the following formulas (a-1) to (a-15):

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

   

   <Formula a-4> <Formula a-5> <Formula a-6>

   

   <Formula a-7> <Formula a-8> <Formula a-9>

   

   <Formula a-10> <Formula a-11> <Formula a-12>

   

   <Formula a-13> <Formula a-14> <Formula a-15>

   

   In Formulas a-1 to Formulas a-15,

   R ⁵ , R ⁶ , R ₇ and R ₈ are independently hydrogen; heavy hydrogen; 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; and C ₆ -C ₂₀ arylthio groups, and adjacent groups can be combined to form a ring,

   m and n are each an integer from 0 to 4, o' is an integer from 0 to 5, and p' is an integer from 0 to 3.
5. According to clause 1,

   A compound characterized in that L ² and L ³ are asymmetric to each other.
6. According to clause 1,

   A compound characterized in that Ar ¹ is selected from the group consisting of the following formulas 3-1 to 3-8:

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

   

   <Formula 3-5> <Formula 3-6> <Formula 3-7> <Formula 3-8>

   

   In Formulas 3-1 to 3-8,

   R ¹³ to R ²¹ are independently hydrogen; heavy hydrogen; 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; and C ₆ -C ₂₀ arylthio groups, and adjacent groups can be combined to form a ring,

   t, za, zb and zc are each integers from 0 to 5, u, w, x and y are each integers from 0 to 4, v is an integer from 0 to 3,

   Y is S or O,

   R ^a is a single bond; C ₁ -C ₂₀ alkylene group; 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 ^b is hydrogen; heavy hydrogen; 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.
7. According to clause 1,

   The above Chemical Formula 1 is a compound characterized in that it is represented by the following Chemical Formula 1-1:

   <Formula 1-1>

   

   In Formula 1-1, Z ¹ to Z ³ , X ¹ to X ⁵ , L ¹ to L ³ , R ¹ to R ⁴ , and a to d are as defined in claim 1,

   R ¹⁹ to R ²¹ are independently hydrogen; heavy hydrogen; 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; and C ₆ -C ₂₀ arylthio groups, and adjacent groups can be combined to form a ring,

   za, zb, and zc are each integers from 0 to 5.
8. According to clause 1,

   At least one of R _a and R _b is an alkyl group of C ₁ to C ₂₀ and a compound selected from the group consisting of the following Formulas 2-1 to 2-7:

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

   

   <Formula 2-5> <Formula 2-6> <Formula 2-7>

   

   In Formulas 2-1 to 2-7,

   R ⁷ to R ¹² are independently hydrogen; heavy hydrogen; 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; and C ₆ -C ₂₀ arylthio groups, and adjacent groups can be combined to form a ring,

   l is an integer from 0 to 5, o, q, r and s are each an integer from 0 to 4, p is an integer from 0 to 3, and when each of these is an integer of 2 or more, each of R ⁷ , R ⁸ , Each of R ⁹ and R ¹⁰ are the same or different from each other,

   Y is S or O,

   R ^a is a single bond; C ₁ -C ₂₀ alkylene group; 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 ^b is hydrogen; heavy hydrogen; 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.
9. According to clause 1,

   At least one of R _a and R _b is an aryl group of C ₆ to C ₃₀ ; C ₁ ~ C ₄ alkyl group; C ₃ ~ C ₁₀ cycloalkyl group; carbazolyl group; Dibenzofuryl group; Dibenzothiophene diary; benzocarbazolyl group; Naphthobenzofuryl group; and a compound selected from the group consisting of a naphthobenzothiophenyl group.
10. According to clause 1,

    A compound wherein at least one of R _a and R _b is a C ₆ to C ₃₀ aryl group substituted with at least one deuterium.
11. According to clause 1,

    A compound characterized in that Ar ¹ is a C ₂ to C ₆₀ heterocyclic group substituted with at least one deuterium.
12. According to clause 1,

    The compound represented by Formula 1 is characterized in that it is one of the following compounds:

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

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13. In an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,

    The organic material layer is an organic electric device characterized in that it contains the compound of formula 1 of claim 1.
14. According to clause 13,

    The organic material layer is an organic electric device, characterized in that it includes a light-emitting layer containing the compound.
15. According to clause 13,

    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.
16. According to clause 15,

    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.
17. According to clause 13,

    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 sides of the first electrode or both sides of the second electrode.
18. A display device including the organic electric element of claim 13; and

    An electronic device comprising a control unit that drives the display device.
19. According to clause 18,

    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.

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