KR20240081346A - An organic electronic element comprising compound for organic electronic element and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric device comprising an anode, a cathode, and an organic layer between the anode and the cathode, and an electronic device including the organic electric device, wherein the organic material layer contains each compound represented by Formula 1 and Formula 2 of the present invention. By including, the driving voltage of the organic electric device can be lowered and the luminous efficiency and lifespan can be improved.

Description

Organic electric device containing a compound for organic electric device and its electronic device {AN ORGANIC ELECTRONIC ELEMENT COMPRISING COMPOUND FOR ORGANIC ELECTRONIC ELEMENT AND AN ELECTRONIC DEVICE THEREOF}

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

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

Materials used as organic layers in organic electric devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.

The biggest issues with organic electroluminescent devices are lifespan and efficiency, and as displays become larger in area, these efficiency and lifespan issues must be resolved. Efficiency, lifespan, driving voltage, etc. are related to each other. As efficiency increases, driving voltage relatively decreases, and as driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase.

However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

In addition, in order to solve the problem of light emission from the hole transport layer in recent organic electroluminescent devices, a light emission auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary layers are required for each light emitting layer (R, G, B). It is time for layered development.

In general, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated by recombination.

However, the material used in the hole transport layer must have a low HOMO value, so most of them have a low T1 value. This causes the exciton generated in the light-emitting layer to pass to the hole transport layer, resulting in a charge unbalance in the light-emitting layer. This causes light to be emitted at the hole transport layer interface.

When light is emitted from the hole transport layer interface, the color purity and efficiency of the organic electric device are reduced and the lifespan is shortened. Therefore, there is an urgent need for the development of a light-emitting auxiliary layer that has a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

Meanwhile, it delays the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortened lifespan of organic electric devices, and provides stable characteristics against Joule heating generated during device operation, that is, high glass transition. There is a need for development of hole injection layer materials with temperature. The low glass transition temperature of the hole transport layer material has the property of reducing the uniformity of the thin film surface when driving the device, and this is reported to have a significant impact on device lifespan. In addition, OLED devices are mainly formed by deposition methods, and there is a need to develop materials that can withstand deposition for a long time, that is, materials with strong heat resistance properties.

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

The purpose of the present invention is to provide an organic electric device and its electronic device containing a compound that can lower the driving voltage of the device and improve the luminous efficiency, color purity, stability, and lifespan of the device.

The present invention provides a compound represented by the following formula (1).

<Formula 1>

In another aspect, the present invention provides an organic electric device and an electronic device containing the compound represented by Formula 1 above.

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

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

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

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the essence, order, or order of the component is not limited by the term. When a component is described as being “connected,” “coupled,” or “connected” to another component, that component may be directly connected or connected to that other component, but there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

As used in this specification and the appended claims, unless otherwise noted, the following terms have the following meanings:

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl), or iodine (I), unless otherwise specified.

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

As used in the present invention, the term "alkenyl group", "alkenyl group" or "alkynyl group", unless otherwise specified, each has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group. , but is not limited to this.

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

As used in the present invention, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited thereto. That is not the case.

The term “aryloxyl group” or “aryloxy group” used in the present invention refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

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 refers to an aromatic group of a single ring or multiple rings, and includes an aromatic ring formed when neighboring substituents participate in a bond or reaction. For example, the aryl group may be a phenyl group, biphenyl group, fluorene group, or spirofluorene group.

The prefix “aryl” or “ar” refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has the carbon number described in this specification.

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

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has a carbon number of 2 to 60, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heterocyclic group. Contains an aromatic ring. It may also be formed by combining neighboring functional groups.

As used herein, the term “heteroatom” refers to N, O, S, P or Si, unless otherwise specified.

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

As used in the present invention, the term "fluorenyl group" or "fluorenylene group" refers to a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structure, respectively, unless otherwise specified. Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other and the carbon to which they are bonded This includes cases where they form a spiro compound together.

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

Unless otherwise specified, the term “aliphatic” used in the present invention refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term “aliphatic ring” refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a fused ring consisting of a combination thereof, Contains saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the above-described heterocompounds include one or more heteroatoms, but are not limited thereto.

Also, unless explicitly stated otherwise, in the term “substituted or unsubstituted” used in the present invention, “substituted” refers to deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ arylthiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and C ₂ to C ₂₀ heterocyclic group, but is not limited to these substituents.

Additionally, unless explicitly stated otherwise, the chemical formula used in the present invention is applied identically to the substituent definition by the index definition in the following chemical formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and 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, Each is bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while indicating the hydrogen bonded to the carbon forming the benzene ring is omitted.

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.

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

Referring to Figure 1, the organic electric device 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) and an organic layer formed between the second electrode 170.

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

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

Preferably, the luminous efficiency improvement layer 180 may be formed on one side of both sides of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the luminous efficiency improvement layer 180 is formed, The light efficiency of organic electric devices 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 improve 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 layer may be formed in a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer. This will be explained with reference to FIG. 3 .

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

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

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

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 compounds represented by Formula 1 and Formula 2 of the present invention include a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), an auxiliary light emitting layer (220), and an electron transport layer ( 150, 350, 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or the light efficiency improvement layer 180, but preferably represented by Formula 1 and Formula 2 of the present invention. The compound may 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 T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved simultaneously.

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

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

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

Hereinafter, an organic electric device according to one aspect of the present invention will be described.

The present invention provides a compound represented by the following formula (1).

<Formula 1>

{In Formula 1 above,

R ¹ , R ² and R ³ are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; C ₁ ~ C ₆₀ alkyl group;

R ⁴ is hydrogen; heavy hydrogen; Aryl group of C ₆ to C ₆₀ ; Or an aryl group of C ₆ to C ₆₀ substituted with deuterium;

L ¹ is a single bond; or an arylene group of C ₆ to C ₆₀ ;

When R ⁴ is a substituted or unsubstituted aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₄ aryl group, such as phenyl, biphenyl, terphenyl, naphthalene, etc. there is.

Ar ¹ is a C ₆ to C ₆₀ aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₄ aryl group, such as phenyl, biphenyl, terphenyl, naphthalene, etc. there is.

a is an integer from 0 to 5, b is an integer from 0 to 6, c is an integer from 0 to 4, d is an integer from 0 to 7,

Here, the alkyl group, aryl group, or arylene group each has deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ Refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}

Additionally, the present invention provides a compound where Formula 1 is represented by the following Formula 1-1 or Formula 1-2.

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

{In Formula 1-1 and Formula 1-2, R ¹ , R ² , R ³ , a, b, c, L ¹ and Ar ¹ are as defined in Formula 1.}

Additionally, the present invention provides a compound where Formula 1 is represented by the following Formula 1-3 or Formula 1-4.

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

{In Formulas 1-3 and 1-4 above,

R ¹ , R ² , R ³ , R ⁴ , a, b, c, L ¹ and Ar ¹ are the same as defined in Formula 1 above,

d' is an integer from 0 to 6, e is an integer from 0 to 5,

R ⁵ is hydrogen; or deuterium; is.}

Additionally, the present invention provides a compound where Formula 1 is represented by any one of the following Formulas 1-3-1 to 1-3-3.

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

<Formula 1-3-3>

{In Formula 1-3-1 to Formula 1-3-3,

R ¹ , R ² , R ³ , R ⁴ , a, b, c, L ¹ and Ar ¹ are the same as defined in Formula 1 above,

d' is an integer from 0 to 6, e is an integer from 0 to 5,

R ⁵ is hydrogen; or deuterium; is.}

Additionally, the present invention provides a compound where Formula 1 is represented by any one of the following Formulas 1-4-1 to 1-4-4.

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

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

{In Formula 1-4-1 to Formula 1-4-4,

R ¹ , R ² , R ³ , R ⁴ , a, b, c, L ¹ and Ar ¹ are the same as defined in Formula 1 above,

d' is an integer from 0 to 6, e is an integer from 0 to 5,

R ⁵ is hydrogen; or deuterium; is.}

Additionally, the present invention provides a compound in which L ¹ of Formula 1 is represented by the following Formula L1 or Formula L2.

<Formula L1> <Formula L2>

{In Formula L1 and Formula L2 above,

R ⁶ is hydrogen; or deuterium;

f is an integer from 0 to 4, g is an integer from 0 to 6,

* means the position where it is combined.}

Additionally, the present invention provides a compound in which Ar ¹ of Formula 1 is represented by any of the following formulas Ar1 to Ar3.

<Formula Ar1> <Formula Ar2> <Formula Ar3>

{In the above formula Ar1 to formula Ar3,

R ⁷ is hydrogen; or deuterium;

h is an integer from 0 to 5, i is an integer from 0 to 7, j is an integer from 0 to 9,

* means the position where it is combined.}

In addition, the present invention provides a compound represented by Formula 1 above, represented by any one of the following compounds P-1 to P-104.

In addition, from another aspect, the present invention In the 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 includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer according to claim 1. An organic electric device is provided including a first host compound represented by Formula 1 and a second host compound represented by Formula 2 or Formula 3 below.

<Formula 2> <Formula 3>

{In Formula 2 or Formula 3,

L ⁴ , L ⁵ , L ⁶ and L ⁷ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of,

When L ⁴ , L ⁵ , L ⁶ and L ⁷ are arylene groups, they are preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₂₅ arylene groups, such as phenylene and biphenylene. , naphthylene, terphenylene, etc.

When L ⁴ , L ⁵ , L ⁶ and L ⁷ are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, exemplified by Pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, benzothienopyrimidine, It may be benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

When L ⁴ , L ⁵ , L ⁶ and L ⁷ are fused ring groups, preferably a fused ring group of an aliphatic ring from C ₃ to C ₃₀ and an aromatic ring from C ₆ to C ₃₀ , more preferably from C ₃ to It may be a fused ring group of an aliphatic ring at C ₂₄ and an aromatic ring at C ₆ to C ₂₄ .

Ar ³ , Ar ⁴ and Ar ⁵ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,

Ar ⁶ is an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and -L'-N(R ^b )(R ^c );

When Ar ³ , Ar ⁴ , Ar ⁵ and Ar ⁶ are an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₅ aryl group, such as phenyl, biphenyl, terphenyl. , naphthalene, etc.

When Ar ³ , Ar ⁴ , Ar ⁵ and Ar ⁶ are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, exemplified by Pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiene It may be nopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

When Ar ³ , Ar ⁴ , Ar ⁵ and Ar ⁶ are fused ring groups, they are preferably a fused ring group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C ₃₀ aromatic ring, more preferably C ₃ to It may be a fused ring group of an aliphatic ring at C ₂₄ and an aromatic ring at C ₆ to C ₂₄ .

L' is a single bond; C ₆ ~ C ₆₀ arylene group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;

R ^b and R ^c are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxy group; and an aryloxy group of C ₆ to C ₃₀ ; selected from the group consisting of,

Z is O, S, CR'R'' or NRa,

B is an aryl group from C ₆ to C ₂₀ ,

R' and R" are independently of each other a C ₆ -C ₆₀ aryl group; a fluorenyl group; a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C _{60 aliphatic} ring and C ₆ ~ C ₆₀ alkyl group of C ₂ ~ C ₂₀ ; alkynyl group of C ₂ ~ _{C 20 ;} ~C ₃₀ alkoxy group; and C ₆ ~C ₃₀ aryloxy group; or R' and R" may be combined with each other to form a ring,

R ¹¹ and R ¹² are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkyne group; C ₁ ~ C ₆₀ alkoxy group; and an aryloxy group of C ₆ to C ₆₀ ; or a plurality of adjacent R ¹¹ groups or a plurality of R ¹² groups may be bonded to each other to form a ring;

When R', R", R ¹¹ and R ¹² are an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₅ aryl group, such as phenyl, biphenyl, terphenyl. , naphthalene, etc.

When R', R", R ¹¹ and R ¹² are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, exemplified by Pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiene It may be nopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

When R', R", R ¹¹ and R ¹² are a fused ring group, preferably a fused ring group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C ₃₀ aromatic ring, more preferably a C ₃ to It may be a fused ring group of an aliphatic ring at C ₂₄ and an aromatic ring at C ₆ to C ₂₄ .

When R', R", R ¹¹ and R ¹² are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When R', R", R ¹¹ and R ¹² are alkoxyl groups, they may preferably be a C ₁ to C ₂₄ alkoxyl group.

When R', R", R ¹¹ and R ¹² are aryloxy groups, they may preferably be a C ₆ to C ₂₄ aryloxy group.

n and o are independently integers from 0 to 4,

Ra is an aryl group from C ₆ to C ₆₀ ; or a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;

When Ra is an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₅ aryl group, such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When Ra is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group, examples include pyrazine, thiophene, pyridine, and pyrimidoindole. , 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, It may be phenothiazine, phenylphenothiazine, etc.

Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group each contain deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ Refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}

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

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

<Formula 2-3>

{In Formula 2-1 to Formula 2-3,

Ar ⁴ , Ar ⁵ , L ⁴ , L ⁵ and L ⁶ are the same as defined in Formula 2 above,

X ¹ , X ² and X ³ are the same as the definition of Z above,

R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are the same as the definition of R ¹¹ above, or are used among a plurality of adjacent R ¹³ or between a plurality of R ¹⁴ or between a plurality of R ¹⁵ or between a plurality of adjacent R 13 R ¹⁶ or a plurality of R ¹⁷ or a plurality of R ¹⁸ can combine with each other to form a ring,

p, r and t are integers from 0 to 4, and q, s and u are independently integers from 0 to 3.}

Formula 3 may be represented by any one of the following Formulas 3-1 to 3-6.

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

<Formula 3-3> <Formula 3-4>

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

{In Formula 3-1 to Formula 3-6,

Z, R ¹¹ , R ¹² , Ar ⁶ , L ⁷ , n, o are the same as defined in Formula 3 above,

R ¹⁹ is the same as the definition of R ¹¹ above,

v is an integer from 0 to 2.}

Formula 3 may be represented by any one of the following Formulas 3-7 to 3-9.

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

<Formula 3-9>

{In Formulas 3-7 to 3-9,

Z, B, R ¹² , o, Ar ⁶ and L ⁷ are the same as defined in Formula 3 above,

R ²⁰ is the same as the definition of R ¹¹ above,

w is an integer from 0 to 6.}

Formula 3 may be represented by any one of the following Formulas 3-10 to 3-12.

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

<Formula 3-12>

{In Formulas 3-10 to 3-12,

Z, B, Ar ⁶ , L ⁷ , R ¹¹ and n are the same as defined in Formula 3 above,

R ²¹ is the same as the definition of R ¹¹ above,

x is an integer from 0 to 6.}

Formula 3 may be represented by the following Formulas 3-13 to 3-18.

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

<Formula 3-15> <Formula 3-16>

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

{In Formulas 3-13 to 3-18,

Z, L ⁷ , Ar ⁶ , R ¹¹ , R ¹² , n and o are the same as defined in Formula 3 above,

R ¹⁹ , R ²⁰ and R ²¹ are the same as the definition of R ¹¹ above,

v is an integer from 0 to 2, and w and x are independently integers from 0 to 6.}

Chemical Formula 3 may be expressed as Chemical Formula 3-19 below.

<Formula 3-19>

{In Formula 3-19 above,

L ⁷ , Ar ⁶ , Ra, R ¹² and o are the same as defined in Formula 3 above,

R ¹⁹ and R ²⁰ are the same as the definition of R ¹¹ above,

v is an integer from 0 to 2, and w is an integer from 0 to 6.}

Additionally, the present invention provides a compound where the compound represented by Formula 2 is any one of the following compounds N-1 to N-96.

Additionally, the present invention provides a compound represented by Formula 3, which is any one of the following compounds S-1 to S-108.

The present invention may further include a light efficiency improvement layer formed on at least one side of the first electrode and the second electrode opposite to the organic layer.

In addition, 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 anode, and the organic material layer may further include a charge generation layer formed between the two or more stacks.

In another aspect, the present invention provides a display device including the organic electric element; and a control unit that drives the display device. At this time, the organic electric device may be at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.

Hereinafter, examples of synthesis of compounds represented by chemical formulas and examples of manufacturing organic electric devices 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 was synthesized in the following manner.

The compound (final products) represented by Chemical Formula 1 according to the present invention is represented by the following <Scheme 1>, but is not limited thereto.

<Scheme 1>

I. Synthesis of Core

The core of <Scheme 1> can be synthesized through the reaction route of <Scheme 2> below, but is not limited thereto.

<Scheme 2>

1. Core 5 synthesis example

(1) Synthesis of Core a-5-1

In a round bottom flask, 1-bromobenzene-2,3,4,5,6-d5 (50 g, 1 eqiv.), (4-chloronaphthalen-1-yl)boronic acid (63.7 g, 1 eqiv.), Pd( PPh ₃ ) ₄ (10.7 g, 0.03 eqiv.), K ₂ CO ₃ (128 g, 2 eqiv.), THF (1030 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 45.1 g of Core a-5-1 (yield: 60%).

(2) Synthesis of Core a-5

In a round bottom flask, core a-5-1 (45 g, 1 eqiv.), (3-chlorophenyl)boronic acid (43.4 g, 1 eqiv.), Pd(PPh ₃ ) ₄ (9.6 g, 0.03 eqiv.), K ₂ CO ₃ (115 g, 2 eqiv.), THF (925 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 48 g of Core a-5 (yield: 55%).

(3) Synthesis of Core 5

In a round bottom flask, Core a-5 (45 g, 1 eqiv.), bis(pinacolato)diboron (43 g, 1.2 eqiv.), Pd ₂ (dba) ₃ (3.9 g, 0.03 eqiv.), X-phos ( 2.3 g, 0.06 equiv.) and KOAc (41 g, 2 eqiv.) were dissolved in Toluene (470 mL, 0.3 M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 41 g of Core 5 (yield: 71%).

2. Core 6 synthesis example

(1) Synthesis of Core a-6-1

1-bromobenzene (38 g, 1 eqiv.), (4-chloronaphthalen-1-yl)boronic acid (50 g, 1 eqiv.), and Pd(PPh ₃ ) ₄ (8.4 g, 0.03 eqiv.) in a round bottom flask. , K ₂ CO ₃ (100 g, 2 eqiv.), THF (807 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 31 g of Core a-6-1 (yield: 53%).

(2) Synthesis of Core a-6

In a round bottom flask, core a-6-1 (30 g, 1 eqiv.), (3-chlorophenyl)boronic acid (20 g, 1 eqiv.), Pd(PPh ₃ ) ₄ (4.4 g, 0.03 eqiv.), K ₂ CO ₃ (52 g, 2 eqiv.), THF (419 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 26 g of Core a-6 (yield: 66%).

(3) Synthesis of Core 6

In a round bottom flask, Core a-6 (25 g, 1 eqiv.), bis(pinacolato)diboron (24 g, 1.2 eqiv.), Pd ₂ (dba) ₃ (2.2 g, 0.03 eqiv.), X-phos ( 2.3 g, 0.06 equiv.) and KOAc (24 g, 2 eqiv.) were dissolved in Toluene (265 mL, 0.3 M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 25 g of Core 6 (yield: 80%).

3. Core 17 synthesis example

(1) Synthesis of Core a-17-1

In a round bottom flask, 1-bromobenzene-2,3,4,5,6-d5 (50 g, 1 eqiv.), (4-chloronaphthalen-1-yl)boronic acid (63.7 g, 1 eqiv.), Pd( PPh ₃ ) ₄ (10.7 g, 0.03 eqiv.), K ₂ CO ₃ (128 g, 2 eqiv.), THF (1030 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 56 g of Core a-17-1 (yield: 78%).

(2) Synthesis of Core a-17

In a round bottom flask, core a-17-1 (55 g, 1 eqiv.), (3-chlorophenyl)boronic acid (35 g, 1 eqiv.), Pd(PPh ₃ ) ₄ (7.8 g, 0.03 eqiv.), K ₂ CO ₃ (94 g, 2 eqiv.), THF (750 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 46 g of Core a-17 (yield: 64%).

(3) Synthesis of Core 17

In a round bottom flask, Core a-17 (45 g, 1 eqiv.), bis(pinacolato)diboron (43 g, 1.2 eqiv.), Pd ₂ (dba) ₃ (3.9 g, 0.03 eqiv.), X-phos ( 4.0 g, 0.06 equiv.) and KOAc (41 g, 2 eqiv.) were dissolved in Toluene (470 mL, 0.3 M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 42 g of Core 17 (yield: 73%).

4. Core 20 synthesis example

(1) Synthesis of Core a-20-1

2-bromonaphthalene (50 g, 1 eqiv.), (5-chloronaphthalen-1-yl)boronic acid (50 g, 1 eqiv.), Pd(PPh ₃ ) ₄ (8.4 g, 0.03 eqiv.) in a round bottom flask. , K ₂ CO ₃ (100 g, 2 eqiv.), THF (800 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 58 g of Core a-20-1 (yield: 83%).

(2) Synthesis of Core a-20

In a round bottom flask, core a-20-1 (39 g, 1 eqiv.), (3-chlorophenyl)boronic acid (21 g, 1 eqiv.), Pd(PPh ₃ ) ₄ (4.7 g, 0.03 eqiv.), K ₂ CO ₃ (56 g, 2 eqiv.), THF (450 mL, 0.3 M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 32 g of Core a-20 (yield: 66%).

(3) Synthesis of Core 20

In a round bottom flask, Core a-20 (32 g, 1 eqiv.), bis(pinacolato) diboron (27 g, 1.2 eqiv.), Pd ₂ (dba) ₃ (2.4 g, 0.03 eqiv.), X-phos ( 2.5 g, 0.06 equiv.) and KOAc (26 g, 2 eqiv.) were dissolved in Toluene (290 mL, 0.3 M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 25 g of Core 20 (yield: 63%).

5. Core 33 synthesis example

(1) Synthesis of Core a-33

1-bromonaphthalene-2,3,4,5,6,7,8-d7 (50g, 1eqiv.), (3-chlorophenyl) boronic acid (36.5g, 1eqiv.), Pd(PPh ₃ ) in a round bottom flask. ₄ (8.1g, 0.03eqiv.), K ₂ CO ₃ (97g, 2eqiv.), THF (778mL, 0.3M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 38.5 g of Core a-33 (yield: 67%).

(2) Synthesis of Core 33

Core a-33 (30g, 1eqiv.), bis(pinacolato) diboron (37.2g, 1.2eqiv.), Pd ₂ (dba) ₃ (3.4g, 0.03eqiv.), X-phos (4.0g) in a round bottom flask. , 0.06equiv.), KOAc (36g, 2eqiv.) were dissolved in Toluene (407mL, 0.3M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 32.9 g of Core 33 (yield: 80%).

6. Core 34 synthesis example

(1) Synthesis of Core a-34-1

1-bromonaphthalene-2,3,4,5,6,7,8-d7 (50g, 1eqiv.), (4-chloronaphthalen-1-yl)boronic acid (48g, 1eqiv.), Pd( PPh ₃ ) ₄ (8.1g, 0.03eqiv.), K ₂ CO ₃ (97g, 2eqiv.), THF (780mL, 0.3M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 49g of Core a-34-1 (yield: 71%).

(2) Synthesis of Core a-34

Core a-34-1 (49g, 1eqiv.), (3-chlorophenyl)boronic acid (26g, 1eqiv.), Pd(PPh ₃ ) ₄ (5.7g, 0.03eqiv.), K ₂ CO ₃ in a round bottom flask. (69g, 2eqiv.), THF (550mL, 0.3M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 47 g of Core a-34 (yield: 77%).

(3) Synthesis of Core 34

In a round bottom flask, Core a-34 (45g, 1eqiv.), bis(pinacolato)diboron (37g, 1.2eqiv), Pd ₂ (dba) ₃ (3.3g, 0.03eqiv.), X-Phos (3.5g, 0.06) equiv.), KOAc (35g, 2eqiv.) were dissolved in Toluene (400mL, 0.3M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 38g of Core 34 (yield: 68%).s

7. Core 35 synthesis example

(1) Synthesis of Core a-35-1

1-bromonaphthalene-2,3,4,5,6,7,8-d7 (50g, 1eqiv.), (4-chloronaphthalen-1-yl)boronic acid (48.2g, 1eqiv.), Pd in a round bottom flask. (PPh ₃ ) ₄ (8.1g, 0.03eqiv.), K ₂ CO ₃ (97g, 2eqiv.), THF (780mL, 0.3M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 54g of Core a-35-1 (yield: 79%).

(2) Synthesis of Core a-35

Core a-35-1 (54g, 1eqiv.), (3-chlorophenyl)boronic acid (28.5g, 1eqiv.), Pd(PPh ₃ ) ₄ (6.3g, 0.03eqiv.), K ₂ CO in a round bottom flask. ₃ (76g, 2eqiv.), THF (600mL, 0.3M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 46 g of Core a-35 (yield: 68%).

(3) Synthesis of Core 35

In a round bottom flask, Core a-35 (45g, 1eqiv.), bis(pinacolato) diboron (37g, 1.2eqiv.), Pd ₂ (dba) ₃ (3.3g, 0.03eqiv.), X-Phos (3.5g, 0.06equiv.), KOAc (36g, 2eqiv.) were dissolved in Toluene (400mL, 0.3M) and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 43g of Core 35 (yield: 77%).

Meanwhile, the compounds belonging to the Core may be, but are not limited to, the following compounds, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to the Core.

compound FD-MS compound FD-MS Core1 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Core2 m/z=338.23(C ₂₂ H ₁₅ D ₈ BO ₂ =338.28) Core3 m/z=339.24(C ₂₂ H ₁₄ D ₉ BO ₂ =339.29) Core4 m/z=340.24(C ₂₂ H ₁₃ D ₁₀ BO ₂ =340.30) Core5 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core6 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core7 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core8 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core9 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core10 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core11 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core12 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core13 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core14 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core15 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core16 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core17 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core18 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core19 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core20 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core21 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core22 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core23 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core24 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core25 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core26 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core27 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core28 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core29 m/z=411.24(C ₂₈ H ₂₂ D ₅ BO ₂ =411.36) Core30 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Core31 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core32 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Core33 m/z=337.22(C ₂₂ H ₁₆ D ₇ BO ₂ =337.28) Core34 m/z=463.27(C ₃₂ H ₂₂ D ₇ BO ₂ =463.43) Core35 m/z=463.27(C ₃₂ H ₂₂ D ₇ BO ₂ =463.43)

II. Synthesis of Sub

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

<Scheme 3>

1. Sub 1 synthesis example

2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 2 equiv.), Sub 1-1 (22 g, 1 equiv.), Pd(PPh ₃ ) ₄ ( 2.3 g, 0.03 equiv.), K ₂ CO ₃ (28 g, 2 equiv.), Toluene (220 mL, 0.3M), and water were added and stirred at 50°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 12 g of Sub 1 (yield: 48%).

2. Sub 2 synthesis example

2,4-dichloro-6-phenyl-1,3,5-triazine (30g, 2equiv.), Sub1-1 (18g, 1equiv.), Pd(PPh ₃ ) ₄ (1.9g, 0.03equiv.) in a round bottom flask. .), K ₂ CO ₃ (23g, 2equiv.), Toluene (180mL, 0.3M), and water were added and stirred at 50°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 11g of Sub 2 (yield: 45%).

3. Sub 26 synthesis example

2,4-dichloro-6-phenyl-1,3,5-triazine (30g, 2equiv.), Sub 26-1 (22g, 1equiv.), Pd(PPh ₃ ) ₄ (2.3g, 0.03) in a round bottom flask. equiv.), K ₂ CO ₃ (28g, 2equiv.), Toluene (220mL, 0.3M), and water were added and stirred at 50°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 11 g of Sub 26 (yield: 43%).

4. Sub 41 synthesis example

(1) Synthesis of Sub b-41-1

In a round bottom flask, 1-bromo-3-iodobenzene (25g, 2eqiv.), naphthalen-1-ylboronic acid (30g, 1eqiv.), Pd(PPh ₃ ) ₄ (3g, 0.03eqiv.), K ₂ CO ₃ ( 36g, 2eqiv.), THF (300mL, 0.3M), and water were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 18 g (yield: 75%) of sub b-41-1.

(2) Synthesis of Sub b-41

Add Mg (5.3g, 2eqiv.) and THF (360mL, 0.3M) to round bottom flask 1 filled with nitrogen, stir at 50°C, and then slowly add sub b-41-1 (20g, 1eqiv.) dropwise. . After 6 hours, stop stirring and withdraw the solution using a syringe. 2,4,6-trichloro-1,3,5-triazine (40g, 2eqiv.) was dissolved in THF in round bottom flask 2, and Grignard reagent was slowly added dropwise and stirred for 12 hours. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 15 g of sub b-41 (yield: 40%).

(3) Synthesis of Sub 41

2,4-dichloro-6-phenyl-1,3,5-triazine (30g, 2equiv.), Sub 26-1 (14g, 1equiv.), Pd(PPh ₃ ) ₄ (1.5g, 0.03) in a round bottom flask. equiv.), K ₂ CO ₃ (18g, 2equiv.), Toluene (140mL, 0.3M), and water were added and stirred at 50°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 9g of Sub 41 (yield: 40%).

Meanwhile, the compounds belonging to Sub may be the following compounds, but are not limited thereto, and Table 2 below shows the FD-MS values of the compounds belonging to Sub.

compound FD-MS compound FD-MS sub1 m/z=393.10(C ₂₅ H ₁₆ ClN ₃ =393.87) sub2 m/z=443.12(C ₂₉ H ₁₈ ClN ₃ =443.93) sub3 m/z=443.12(C ₂₉ H ₁₈ ClN ₃ =443.93) sub4 m/z=469.13(C ₃₁ H ₂₀ ClN ₃ =469.97) sub5 m/z=469.13(C ₃₁ H ₂₀ ClN ₃ =469.97) sub6 m/z=469.13(C ₃₁ H ₂₀ ClN ₃ =469.97) sub7 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub8 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub9 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub10 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub11 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub12 m/z=543.15(C ₃₇ H ₂₂ ClN ₃ =544.05) sub13 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub14 m/z=493.13(C ₃₃ H ₂₀ ClN ₃ =493.99) sub15 m/z=543.15(C ₃₇ H ₂₂ ClN ₃ =544.05) sub16 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub17 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub18 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub19 m/z=543.15(C ₃₇ H ₂₂ ClN ₃ =544.05) sub20 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub21 m/z=519.15 C ₃₅ H ₂₂ ClN ₃ =520.03) sub22 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub23 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub24 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub25 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) sub26 m/z=398.13(C ₂₅ H ₁₁ D ₅ ClN ₃ =398.90) sub27 m/z=448.15(C ₂₉ H ₁₃ D ₅ ClN ₃ =448.96) sub28 m/z=448.15(C ₂₉ H ₁₃ D ₅ ClN ₃ =448.96) sub29 m/z=474.17(C ₃₁ H ₁₅ D ₅ ClN ₃ =475.00) sub30 m/z=474.17(C ₃₁ H ₁₅ D ₅ ClN ₃ =475.00) sub31 m/z=474.17(C ₃₁ H ₁₅ D ₅ ClN ₃ =475.00) sub32 m/z=498.17(C ₃₃ H ₁₅ D ₅ ClN ₃ =499.02) sub33 m/z=498.17(C ₃₃ H ₁₅ D ₅ ClN ₃ =499.02) sub34 m/z=498.17(C ₃₃ H ₁₅ D ₅ ClN ₃ =499.02) sub35 m/z=498.17(C ₃₃ H ₁₅ D ₅ ClN ₃ =499.02) sub36 m/z=498.17(C ₃₃ H ₁₅ D ₅ ClN ₃ =499.02) sub37 m/z=548.18(C ₃₇ H ₁₇ D ₅ ClN ₃ =549.08) sub38 m/z=548.18(C ₃₇ H ₁₇ D ₅ ClN ₃ =549.08) sub39 m/z=498.17(C ₃₃ H ₁₅ D ₅ ClN ₃ =499.02) sub40 m/z=548.18(C ₃₇ H ₁₇ D ₅ ClN ₃ =549.08) sub41 m/z=524.18(C ₃₅ H ₁₇ D ₅ ClN ₃ =525.06) sub42 m/z=524.18(C ₃₅ H ₁₇ D ₅ ClN ₃ =525.06) sub43 m/z=524.18(C ₃₅ H ₁₇ D ₅ ClN ₃ =525.06) sub44 m/z=524.18(C ₃₅ H ₁₇ D ₅ ClN ₃ =525.06) sub45 m/z=524.18(C ₃₅ H ₁₇ D ₅ ClN ₃ =525.06)

III. Synthesis of Final Product

1. P-1 synthesis example

In a round bottom flask, Core 1 (8.4g, 1equiv.), sub 1 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.9g, 0.03equiv.), K ₂ CO ₃ (10.5g, 2equiv.), Toluene (44mL), Ethanol (5mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 11 g of P-1 (yield: 77%).

2. P-22 synthesis example

In a round bottom flask, Core 6 (10.3g, 1equiv.), sub 1 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.9g, 0.03equiv.), K ₂ CO ₃ (10.5g, 2equiv.), Toluene (85mL), Ethanol (9mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 134 g of P-22 (yield: 83%).

3. P-43 synthesis example

In a round bottom flask, Core 33 (6.9g, 1equiv.), sub 2 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.7g, 0.03equiv.), K ₂ CO ₃ (8.5g, 2equiv.), Toluene (68mL), Ethanol (7mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 8.5 g of P-43 (yield: 67%).

4. P-63 synthesis example

In a round bottom flask, Core 5 (9.5g, 1equiv.), sub 1 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.8g, 0.03equiv.), K ₂ CO ₃ (9.6g, 2equiv.), Toluene (77mL), Ethanol (8mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 10.4 g of P-63 (yield: 70%).

5. P-66 synthesis example

In a round bottom flask, Core 17 (9.5g, 1equiv.), sub 1 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.8g, 0.03equiv.), K ₂ CO ₃ (9.6g, 2equiv.), Toluene (77mL), Ethanol (8mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.8 g of P-66 (yield: 66%).

6. P-72 synthesis example

In a round bottom flask, Core 34 (11.8g, 1equiv.), sub 1 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.9g, 0.03equiv.), K ₂ CO ₃ (10.5g, 2equiv.), Toluene (85mL), Ethanol (8mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 12.9 g of P-72 (yield: 73%).

7. P-83 synthesis example

In a round bottom flask, Core 5 (10.3g, 1equiv.), sub 26 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.9g, 0.03equiv.), K ₂ CO ₃ (10.4g, 2equiv.), Toluene (84mL), Ethanol (8mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized on a silicagel column to obtain 8.9 g of P-83 (yield: 55%).

8. P-92 synthesis example

In a round bottom flask, Core 33 (6.4g, 1equiv.), sub 41 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.7g, 0.03equiv.), K ₂ CO ₃ (7.9g, 2equiv.), Toluene (64mL), Ethanol (6mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.8 g of P-92 (yield: 74%).

9. P-98 synthesis example

In a round bottom flask, Core 6 (8.5g, 1equiv.), sub 26 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.9g, 0.03equiv.), K ₂ CO ₃ (10.4g, 2equiv.), Toluene (84mL), Ethanol (8mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.8 g of P-98 (yield: 61%).

10. P-102 synthesis example

In a round bottom flask, Core 20 (11.4g, 1equiv.), sub 26 (10g, 1equiv.), Pd(PPh ₃ ) ₄ (0.9g, 0.03equiv.), K ₂ CO ₃ (10.4g, 2equiv.), Toluene (84mL), Ethanol (8mL) and water were added and stirred at 120°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.2 g (yield: 53%) of P-102.

Meanwhile, the FD-MS values of compounds P-1 to P-104 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=561.22(C ₄₁ H ₂₇ N ₃ =561.69) P-2 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-3 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-4 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-5 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-6 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-7 m/z=661.25(C ₄₉ H ₃₁ N ₃ =661.81) P-8 m/z=661.25 (C ₄₉ H ₃₁ N ₃ =661.81) P-9 m/z=711.27(C ₅₃ H ₃₃ N ₃ =711.87) P-10 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-11 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-12 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-13 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-14 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-15 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-16 m/z=737.28 (C ₅₅ H ₃₅ N ₃ =737.91) P-17 m/z=737.28 (C ₅₅ H ₃₅ N ₃ =737.91) P-18 m/z=737.28 (C ₅₅ H ₃₅ N ₃ =737.91) P-19 m/z=763.30 (C ₅₇ H ₃₇ N ₃ =763.94) P-20 m/z=763.30 (C ₅₇ H ₃₇ N ₃ =763.94) P-21 m/z=763.30 (C ₅₇ H ₃₇ N ₃ =763.94) P-22 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) P-23 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) P-24 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) P-25 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) P-26 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) P-27 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) P-28 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-29 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-30 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-31 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-32 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-33 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-34 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-35 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-36 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-37 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-38 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-39 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-40 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-41 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-42 m/z=568.26 (C ₄₁ H ₂₀ D ₇ N ₃ =568.73) P-43 m/z=618.28 (C ₄₅ H ₂₂ D ₇ N ₃ =618.79) P-44 m/z=618.28 (C ₄₅ H ₂₂ D ₇ N ₃ =618.79) P-45 m/z=644.30 (C ₄₇ H ₂₄ D ₇ N ₃ =644.83) P-46 m/z=644.30 (C ₄₇ H ₂₄ D ₇ N ₃ =644.83) P-47 m/z=644.30 (C ₄₇ H ₂₄ D ₇ N ₃ =644.83) P-48 m/z=668.30 (C ₄₉ H ₂₄ D ₇ N ₃ =668.85) P-49 m/z=668.30 (C ₄₉ H ₂₄ D ₇ N ₃ =668.85) P-50 m/z=718.31 (C ₅₃ H ₂₆ D ₇ N ₃ =718.91) P-51 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-52 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-53 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-54 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-55 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-56 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-57 m/z=770.34 (C ₅₇ H ₃₀ D ₇ N ₃ =770.99) P-58 m/z=744.33 (C ₅₅ H ₂₈ D ₇ N ₃ =744.95) P-59 m/z=744.33 (C ₅₅ H ₂₈ D ₇ N ₃ =744.95) P-60 m/z=770.34 (C ₅₇ H ₃₀ D ₇ N ₃ =770.99) P-61 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-62 m/z=770.34 (C ₅₇ H ₃₀ D ₇ N ₃ =770.99) P-63 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-64 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-65 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-66 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-67 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-68 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-69 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-70 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-71 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-72 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-73 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-74 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-75 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-76 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-77 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-78 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-79 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-80 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-81 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-82 m/z=694.31 (C ₅₁ H ₂₆ D ₇ N ₃ =694.89) P-83 m/z=647.31 (C ₄₇ H ₂₁ D ₁₀ N ₃ =647.85) P-84 m/z=647.31 (C ₄₇ H ₂₁ D ₁₀ N ₃ =647.85) P-85 m/z=647.31 (C ₄₇ H ₂₁ D ₁₀ N ₃ =647.85) P-86 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-87 m/z=573.30 (C ₄₁ H ₁₅ D ₁₂ N ₃ =573.76) P-88 m/z=623.31 (C ₄₅ H ₁₇ D ₁₂ N ₃ =623.82) P-89 m/z=623.31 (C ₄₅ H ₁₇ D ₁₂ N ₃ =623.82) P-90 m/z=649.33 (C ₄₇ H ₁₉ D ₁₂ N ₃ =649.86) P-91 m/z=649.33 (C ₄₇ H ₁₉ D ₁₂ N ₃ =649.86) P-92 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-93 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-94 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-95 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-96 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-97 m/z=699.34 (C ₅₁ H ₂₁ D ₁₂ N ₃ =699.92) P-98 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-99 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-100 m/z=642.28 (C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-101 m/z=692.30 (C ₅₁ H ₂₈ D ₅ N ₃ =692.88) P-102 m/z=692.30 (C ₅₁ H ₂₈ D ₅ N ₃ =692.88) P-103 m/z=692.30 (C ₅₁ H ₂₈ D ₅ N ₃ =692.88) P-104 m/z=692.30 (C ₅₁ H ₂₈ D ₅ N ₃ =692.88)

[Synthesis Example 2]

1. N-12 synthesis example

N-12a (30 g, 0.08 mol), N-12b (34.8 g, 0.08 mol), Pd ₂ (dba) ₃ (2.3 g, 0.003 mol), NaOt-Bu (24.5 g, 0.25 mol), P(t -Bu) ₃ (2.1 g, 0.005 mol) and Toluene (170mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 53 g (85.8%) of product N-12 was obtained using the separation method of P-1 described above.

2. N-19 synthesis example

N-19a (50 g, 0.13 mol), N-19b (35 g, 0.13 mol), Pd ₂ (dba) ₃ (3.6 g, 0.004 mol), NaOt-Bu (37.6 g, 0.40 mol), P(t -Bu) ₃ (3.2 g, 0.008 mol) and Toluene (260mL) were added and reacted at 135°C for 6 hours. Upon completion of the reaction, 67 g (83.4%) of product N-19 was obtained using the separation method of P-1 indicated above.

3. S-32 synthesis example

S-32a (10 g, 0.04 mol), S-32b (15.6 g, 0.04 mol), Pd ₂ (dba) ₃ (1.1 g, 0.001 mol), NaOt-Bu (11.7 g, 0.12 mol), P(t -Bu) ₃ (1.0 g, 0.002 mol) and Toluene (80mL) were added and reacted at 135°C for 6 hours. Upon completion of the reaction, 18 g (80.8%) of product S-32 was obtained using the separation method of P-1 indicated above.

4. S-74 synthesis example

S-74a (15 g, 0.06 mol), S-74b (20.9 g, 0.06 mol), Pd ₂ (dba) ₃ (1.6 g, 0.002 mol), NaOt-Bu (16.9 g, 0.18 mol), P(t -Bu) ₃ (1.4 g, 0.004 mol) and Toluene (120mL) were added and reacted at 135°C for 6 hours. Upon completion of the reaction, 27 g (86.4%) of product S-74 was obtained using the separation method of P-1 indicated above.

5. S-104 synthesis example

S-104a (30 g, 0.13 mol), S-104b (48.2.9 g, 0.13 mol), Pd ₂ (dba) ₃ (3.5 g, 0.004 mol), NaOt-Bu (36.4 g, 0.38 mol), P (t-Bu) ₃ (3.1 g, 0.008 mol) and Toluene (250 mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 60 g (81.5%) of product S-104 was obtained using the separation method of P-1 described above.

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

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

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

[Device data]

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

An organic electroluminescent device was manufactured according to a conventional method using the compound obtained through synthesis as a light-emitting host material for the light-emitting layer. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1 ,4-diamine (hereinafter, 2-TNATA) film was vacuum deposited to form a 60 nm thick hole injection layer, and then 4,4-bis[N-(1-naphthyl)-N was applied as a hole transport compound on the hole injection layer. -phenylamino]biphenyl (hereinafter, -NPD) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. As a light emitting auxiliary layer material, tris(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter, TCTA) was vacuum deposited to a thickness of 10 nm on the top of the hole transport layer to form a light emitting auxiliary layer. After forming the light-emitting auxiliary layer, the present invention compound P-1 represented by the formula (1) and the present invention compound N-12 represented by the formula (2) are used as a host on the top of the light-emitting auxiliary layer in a weight ratio (5:5). A light emitting layer was deposited to a thickness of 30 nm by doping (piq) ₂ Ir(acac) at a weight ratio of 95:5 as a dopant material. Next, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter referred to as BAlq) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and bis(10-) was deposited as an electron transport layer. Hydroxybenzo[h]quinolinato)beryllium (hereinafter referred to as BeBq ₂ ) was formed into a film with a thickness of 45 nm. Afterwards, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

[Example 2] to [Example 32]

Except for using the compound of the present invention shown in Table 6 below instead of the compound P-1 of the present invention as the host material of the light emitting layer, the compound of the present invention shown in Table 6 below was used instead of the compound N-12 of the present invention. An organic electroluminescent device was manufactured in the same manner as in Example 1, except that.

[Comparative Example 1] and [Comparative Example 2]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that Comparative Compound A or Comparative Compound B was used instead of Compound P-1 of the present invention as the host material of the light-emitting layer.

<Comparative compound A> <Comparative compound B>

A forward bias direct current voltage was applied to the organic electric devices manufactured according to the Examples and Comparative Examples manufactured in this way, and the electroluminescence (EL) characteristics were measured using Photo Research's PR-650, and the measurement results were 2500 cd/ The T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience at a standard luminance of m ² . Table 6 below shows the results of device fabrication and evaluation.

first compound second compound driving voltage Current (mA/cm ² ) Efficiency (cd/A) T(95) Comparative Example 1 Comparative compound A Compound (N-12) 4.9 8.8 28.5 114.5 Comparative example 2 Comparative compound B Compound (N-12) 5.2 11.0 22.6 102.1 Example 1 Compound (P-1) Compound (N-12) 4.8 8.1 30.8 123.8 Example 2 Compound (P-5) Compound (N-12) 4.8 8.1 31.0 125.0 Example 3 Compound (P-22) Compound (N-12) 4.7 7.9 31.6 123.3 Example 4 Compound (P-25) Compound (N-12) 4.7 8.3 30.1 129.1 Example 5 Compound (P-42) Compound (N-12) 4.7 7.9 31.7 129.4 Example 6 Compound (P-63) Compound (N-12) 4.7 7.7 32.5 127.4 Example 7 Compound (P-72) Compound (N-12) 4.7 7.6 32.8 125.5 Example 8 Compound (P-98) Compound (N-12) 4.7 7.8 32.1 125.1 Example 9 Compound (P-1) Compound (N-17) 4.6 7.7 32.4 131.0 Example 10 Compound (P-1) Compound (N-82) 4.7 8.0 31.1 129.4 Example 11 Compound (P-1) Compound (S-32) 4.7 7.8 32.1 136.9 Example 12 Compound (P-1) Compound (S-108) 4.6 7.5 33.4 139.9 Example 13 Compound (P-22) Compound (N-17) 4.5 7.5 33.2 129.8 Example 14 Compound (P-22) Compound (N-82) 4.6 7.8 31.9 127.4 Example 15 Compound (P-22) Compound (S-32) 4.6 7.6 32.8 134.7 Example 16 Compound (P-22) Compound (S-108) 4.5 7.3 34.1 138.7 Example 17 Compound (P-25) Compound (N-17) 4.5 7.9 31.6 136.7 Example 18 Compound (P-25) Compound (N-82) 4.6 8.3 30.3 134.3 Example 19 Compound (P-25) Compound (S-32) 4.6 8.0 31.2 141.7 Example 20 Compound (P-25) Compound (S-108) 4.5 7.7 32.5 146.2 Example 21 Compound (P-42) Compound (N-17) 4.5 7.5 33.4 136.7 Example 22 Compound (P-42) Compound (N-82) 4.6 7.8 32.0 134.3 Example 23 Compound (P-42) Compound (S-32) 4.7 7.6 32.9 141.6 Example 24 Compound (P-42) Compound (S-108) 4.6 7.3 34.2 145.7 Example 25 Compound (P-63) Compound (N-17) 4.4 7.3 34.2 135.3 Example 26 Compound (P-63) Compound (N-82) 4.5 7.6 32.8 133.2 Example 27 Compound (P-63) Compound (S-32) 4.6 7.4 33.8 140.5 Example 28 Compound (P-63) Compound (S-108) 4.5 7.1 35.1 144.4 Example 29 Compound (P-98) Compound (N-17) 4.5 7.4 33.9 133.2 Example 30 Compound (P-98) Compound (N-82) 4.5 7.7 32.5 130.6 Example 31 Compound (P-98) Compound (S-32) 4.6 7.5 33.5 138.0 Example 32 Compound (P-98) Compound (S-108) 4.5 7.2 34.7 141.9

Referring to Table 6 above, it can be seen that when the compound of the present invention is used as a light emitting layer material, the driving voltage is lowered and efficiency and lifespan are improved compared to when comparative compound A or comparative compound B is used.

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

Comparing Comparative Compound A and the compound of the present invention, Comparative Compound A and the compound of the present invention have similar structures, but the substituent of Comparative Compound A is -p-phenyl-naphthyl structure, and the substituent of the compound of the present invention is -m-phenyl. -It has a naphthyl structure. In addition, as can be seen in Table 6 above, it can be seen that the overall performance of the device is improved when the compound of the present invention is applied to the device.

Table 7 below shows data measured for Comparative Compound A and Compound P-1 of the present invention using the DFT Method (B3LYP/6-31g(D)) of the Gaussian program.

G.HOMO G.LUMO G.B.G. G.S1 G.T1 Comparative compound A -5.7084 -1.9862 3.7222 3.3427 2.403 P-1 -5.673 -1.9682 3.7048 3.3016 2.3999

As can be seen in Table 7, compared to Comparative Compound A, Compound P-1 of the present invention has a similar T1, but the energy band gap is slightly decreased, and in particular, S1 is lowered. As a result, the wavelength of energy emitted from the host increases, and energy is better transmitted to the red dopant. In other words, the low S1 of compound P-1 of the present invention facilitates the transfer of Förster energy to the dopant, which appears to affect the overall performance of the device.

The above description is merely an illustrative description of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

100, 200, 300: Organic electric 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: 1st stack ST2: 2nd stack

Claims (15)

Compound represented by the following formula 1:
<Formula 1>

R ¹ , R ² and R ³ are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; C ₁ ~ C ₆₀ alkyl group;
R ⁴ is hydrogen; heavy hydrogen; Aryl group of C ₆ to C ₆₀ ; Or an aryl group of C ₆ to C ₆₀ substituted with deuterium;
L ¹ is a single bond; or an arylene group of C ₆ to C ₆₀ ;
Ar ¹ is an aryl group from C ₆ to C ₆₀ ,
a is an integer from 0 to 5, b is an integer from 0 to 6, c is an integer from 0 to 4, d is an integer from 0 to 7,
Here, the alkyl group, aryl group, or arylene group each has deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ It refers to a fused ring consisting of an aliphatic ring, an aromatic ring from C ₆ to C ₆₀ , a heterocycle from C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.
The compound according to claim 1, wherein Formula 1 is represented by the following Formula 1-3 or Formula 1-4:
<Formula 1-3><Formula1-4>

{In Formulas 1-3 and 1-4 above,
R ¹ , R ² , R ³ , R ⁴ , a, b, c, L ¹ and Ar ¹ are the same as defined in claim 1 above,
d' is an integer from 0 to 6, e is an integer from 0 to 5,
R ⁵ is hydrogen; or deuterium; is.}
The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-3-1 to 1-3-3:
<Formula 1-3-1><Formula1-3-2>

<Formula 1-3-3>

{In Formula 1-3-1 to Formula 1-3-3,
R ¹ , R ² , R ³ , R ⁴ , a, b, c, L ¹ and Ar ¹ are the same as defined in claim 1 above,
d' is an integer from 0 to 6, e is an integer from 0 to 5,
R ⁵ is hydrogen; or deuterium; is.}
The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-4-1 to Formula 1-4-4:
<Formula 1-4-1><Formula1-4-2>

<Formula 1-4-3><Formula1-4-4>

{In Formula 1-4-1 to Formula 1-4-4,
R ¹ , R ² , R ³ , R ⁴ , a, b, c, L ¹ and Ar ¹ are the same as defined in claim 1 above,
d' is an integer from 0 to 6, e is an integer from 0 to 5,
R ⁵ is hydrogen; or deuterium; is.}
The compound according to claim 1, wherein L ¹ of Formula 1 is represented by the following Formula L1 or Formula L2:
<Formula L1><FormulaL2>

{In Formula L1 and Formula L2 above,
R ⁶ is hydrogen; or deuterium;
f is an integer from 0 to 4, g is an integer from 0 to 6,
* means the position where it is combined.}
The compound according to claim 1, wherein Ar ¹ of Formula 1 is represented by any one of the following Formulas Ar1 to Formula Ar3:
<Formula Ar1><FormulaAr2><FormulaAr3>

{In the above formula Ar1 to formula Ar3,
R ⁷ is hydrogen; or deuterium;
h is an integer from 0 to 5, i is an integer from 0 to 7, j is an integer from 0 to 9,
* means the position where it is combined.}
The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds P-1 to P-104:

In the 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 includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer according to claim 1. An organic electric device comprising a first host compound represented by Formula 1 and a second host compound represented by Formula 2 or Formula 3 below.
<Formula 2><Formula3>

{In Formula 2 or Formula 3 above,
L ⁴ , L ⁵ , L ⁶ and L ⁷ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of,
Ar ³ , Ar ⁴ and Ar ⁵ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,
Ar ⁶ is an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and -L'-N(R ^b )(R ^c );
L' is a single bond; C ₆ ~ C ₆₀ arylene group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
R ^b and R ^c are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxy group; and an aryloxy group of C ₆ to C ₃₀ ; selected from the group consisting of,
Z is O, S, CR'R'' or NRa,
B is an aryl group from C ₆ to C ₂₀ ,
R' and R" are independently of each other a C ₆ -C ₆₀ aryl group; a fluorenyl group; a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C _{60 aliphatic} ring and C ₆ ~ C ₆₀ alkyl group of C ₂ ~ C ₂₀ ; alkynyl group of C ₂ ~ _{C 20 ;} ~C ₃₀ alkoxy group; and C ₆ ~C ₃₀ aryloxy group; or R' and R" may be combined with each other to form a ring,
R ¹¹ and R ¹² are each the same or different and are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkyne group; C ₁ ~ C ₆₀ alkoxy group; and an aryloxy group of C ₆ to C ₆₀ ; or a plurality of adjacent R ¹¹ groups or a plurality of R ¹² groups may be bonded to each other to form a ring,
n and o are independently integers from 0 to 4,
Ra is an aryl group of C ₆ to C ₆₀ ; or a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group each contain deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ Refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}
The compound according to claim 8, wherein the compound represented by Formula 2 is any one of the following compounds N-1 to N-96:
























The compound according to claim 8, wherein the compound represented by Formula 3 is any one of the following compounds S-1 to S-108:



























The organic electric device of claim 8, further comprising a light efficiency improvement layer formed on at least one side of the first electrode and the second electrode opposite to the organic material layer.
The organic electric device of claim 8, wherein the organic material layer includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode.
The organic electric device of claim 12, wherein the organic material layer further includes a charge generation layer formed between the two or more stacks.
A display device comprising the organic electric element of claim 8; and a control unit that drives the display device.
The electronic device of claim 14, wherein the organic electric device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.