KR20230173757A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound that can improve the luminous efficiency, stability, and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

Description

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

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

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

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

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

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

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

Therefore, it must have stable characteristics against Joule heating generated during device operation while delaying 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. , 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, and electron injection materials, must be supported by stable and efficient materials. This should take precedence, but the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently developed. Therefore, the development of new materials continues to be required, and in particular, the development of host materials for the light-emitting layer is urgently required.

In order to solve the problems of the above-mentioned background technology, the present invention has discovered a compound with a novel structure, and the fact that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be greatly improved. revealed.

Accordingly, the purpose of the present invention is to provide a novel compound, an organic electric device using the same, and an electronic device thereof.

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

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 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 terms "alkenyl group", "alkenyl group" or "alkynyl group", unless otherwise specified, each have a double or triple bond of 2 to 60 carbon atoms, and include 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 has a carbon number of 1 to 60, and is limited thereto, unless otherwise specified. 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 by combining adjacent substituents or participating in a 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, a compound according to one aspect of the present invention and an organic electric device containing the same will be described.

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

Compound represented by the following formula 1:

<Formula 1>

<Formula 2>

In Formula 1 and Formula 2, each symbol may be defined as follows.

1) R ¹ , R ² and R ³ are each the same or different and are independently hydrogen; heavy hydrogen; halogen; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkyne group; C ₁ ~ C ₆₀ alkoxyl group; And C ₃ ~ C ₆₀ cycloalkyl group; selected from the group consisting of,

Alternatively, a plurality of adjacent R ^3s may be bonded to each other to form a ring. In this case, the ring may be an aromatic ring or a hetero ring, preferably an aromatic ring, and more preferably a benzene ring. can be formed.

When R ¹ , R ² and R ³ are an alkyl group, they are preferably an alkyl group of C ₁ to C ₃₀ , and more preferably an alkyl group of C ₁ to C ₂₄ .

When R ¹ , R ² and R ³ are alkenyl groups, they may be preferably alkenyl groups of C ₂ to C ₃₀ , and more preferably alkenyl groups of C ₂ to C ₂₄ .

When R ¹ , R ² and R ³ are an alkynyl group, they may be preferably an alkynyl group of C ₂ to C ₃₀ , and more preferably an alkynyl group of C ₂ to C ₂₄ .

When R ¹ , R ² and R ³ are an alkoxyl group, they are preferably an alkoxyl group of C ₁ to C ₃₀ , and more preferably an alkoxyl group of C ₁ to C ₂₄ .

When R ¹ , R ² and R ³ are cycloalkyl groups, they are preferably C ₃ to C ₃₀ cycloalkyl groups, and more preferably C ₃ to C ₂₄ cycloalkyl groups.

2) a is an integer from 0 to 3, b is an integer from 0 to 6, c is an integer from 0 to 7,

3) L ¹ , L ² and L ³ are independently single bonds; or an arylene group of C ₆ to C ₆₀ ;

When L ¹ , L ² and L ³ are arylene groups, they may be preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₂₅ arylene groups, such as phenylene or biphenyl. , naphthalene, etc.

4) Ar ¹ and Ar ² are independently C ₆ to C ₆₀ aryl groups; or a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;

When Ar ¹ and Ar ² are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenylene, biphenyl, naphthalene, terphenyl, etc. .

When Ar ¹ and Ar ² are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, examples include pyrazine, thiophene, and pyridine. , pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofyu. It may be lopyrimidine, phenothiazine, phenylphenothiazine, etc.

5) A is a substituent represented by Formula 2 above,

6) means the binding position,

7) Here, the aryl group, arylene group, heterocyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and cycloalkyl group are each hydrogen; 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 It 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 2 is represented by the following Formula 2-1 or Formula 2-2.

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

{In Formula 2-1 and Formula 2-2, R ³ , c and is as defined above.}

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 Formulas 1-1 and 1-2, A, R ¹ , R ² , L ¹ , L ² , L ³ , Ar ¹ , Ar ² , a and b are as defined above.}

Additionally, the present invention provides a compound where Formula 1 is represented by any one of the following Formulas 1-3 to 1-6.

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

<Formula 1-5> <Formula 1-6>

{In Formulas 1-3 to 1-6, R ¹ , R ² , R ³ , L ¹ , L ² , L ³ , Ar ¹ , Ar ² , a, b and c are as defined above. }

Additionally, the present invention provides a compound wherein L ¹ is a single bond.

Additionally, Chemical Formula 1 may be expressed as Chemical Formula 1-7 below.

<Formula 1-7>

{In Formula 1-7, R ¹ , R ² , L ² , L ³ , Ar ¹ , Ar ² , A, a and b are as defined above.}

Additionally, Formula 1 may be represented by Formula 1-8 or Formula 1-9 below.

<Formula 1-8> <Formula 1-9>

{In Formulas 1-8 and 1-9, R ¹ , R ² , L ² , L ³ , Ar ¹ , Ar ² , A, a and b are as defined above.}

Additionally, Formula 1 may be represented by any one of the following Formulas 1-10 to 1-13.

<Formula 1-10> <Formula 1-11>

<Formula 1-12> <Formula 1-13>

{In Formulas 1-10 to 1-13, R ¹ , R ² , R ³ , L ² , L ³ , Ar ¹ , Ar ² , a, b and c are as defined above.}

Additionally, the present invention provides a compound wherein L ¹ to L ³ are represented by any one of the following formulas L1 to L3.

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

In the above formulas L1 to formula L3, each symbol may be defined as follows.

1) R ⁴ , R ⁵ , R ⁶ and R ⁷ are each the same or different and, independently of each other, hydrogen; heavy hydrogen; 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; C ₈ ~ C ₂₀ arylalkenyl group; and a fused ring group of an aliphatic ring from C ₃ to C ₂₀ and an aromatic ring from C ₆ to C ₂₀ ; selected from the group consisting of,

2) d, e and f are integers from 0 to 4, g is an integer from 0 to 6,

3) * means the part that is combined.

Additionally, L ¹ to L ³ may be represented by any one of the following formulas L1-1 to L1-3.

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

{In Formula L1-1 to Formula L1-3, R ⁴ , d and * are as defined above.}

Additionally, L ¹ to L ³ may be represented by any one of the following formulas L2-1 to L2-6.

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

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

{In Formula L2-1 to Formula L2-6, R ⁵ , R ⁶ , e, f and * are as defined above.}

Additionally, L ¹ to L ³ may be represented by the following formulas L3-1 to L3-10.

<Formula L3-1> <Formula L3-2> <Formula L3-3> <Formula L3-4> <Formula L3-5>

<Formula L3-6> <Formula L3-7> <Formula L3-8> <Formula L3-9> <Formula L3-10>

{In Formula L3-1 to Formula L3-10, R ⁷ , g and * are as defined above.}

Additionally, Ar ¹ or Ar ² may be represented by any one of the following compounds Ar-1 to Ar-63.

{In the compounds Ar-1 to Ar-63, hydrogen is 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 an arylalkenyl group of C ₈ to C ₂₀ ; may be replaced with one or more substituents selected from the group consisting of.}

Additionally, the present invention provides a compound of Formula 1 containing at least one deuterium.

Additionally, the present invention provides a compound in which at least one of R ¹ and R ² contains deuterium.

Additionally, the present invention provides a compound in which R ³ includes at least one deuterium.

Additionally, in Formula 1, R ¹ and R ² preferably contain at least one deuterium, and R ³ in Formula 2 preferably contains at least one deuterium.

Specifically, the compound represented by Formula 1 may be any one of Compound P-1 to Compound P-130 below.

In addition, the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer. It provides an organic electric device comprising a first host compound represented by Formula 1 of claim 1 and a second host compound represented by Formula 3 or Formula 4 below.

<Formula 3> <Formula 4>

In Formula 3 and Formula 4, each symbol may be defined as follows.

1) 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 ;

When Ar ³ , Ar ⁴ and Ar ⁵ are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenylene, biphenyl, naphthalene, terphenyl. It may be, etc.

When Ar ³ , Ar ⁴ and Ar ⁵ are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, examples of which include pyrazine and cylindrical groups. Ophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine , benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

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

2) 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 selected from O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and -L'-NR ^b R ^c ;,

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

When Ar ⁶ is a heterocyclic group, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group, examples of which include pyrazine, thiophene, pyridine, and pyrimido. Indole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine , phenothiazine, phenylphenothiazine, etc.

When Ar ⁶ is a fused ring group, it is 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 C ₂₄ aliphatic ring and a C _{6 to C 6} It may be a fused ring group of the aromatic ring of C ₂₄ .

3) L ⁴ , L ⁵ , L ⁶ , L ⁷ and L' are independently single bonds; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; And C ₃ ~ C ₆₀ aliphatic ring; selected from the group consisting of,

When L ⁴ , L ⁵ , L ⁶ , L ⁷ and L' are arylene groups, they may be preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₂₄ arylene groups, such as , phenylene, biphenyl, naphthalene, terphenyl, etc.

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

When L ⁴ , L ⁵ , L ⁶ , L ⁷ and L' are aliphatic ring groups, they may be preferably a C ₃ to C ₃₀ aliphatic ring group, and more preferably a C ₃ to C ₂₄ aliphatic ring group.

4) Y is O, S, CR'R" or NR ^a ,

5) Ring B is an aryl group from C ₆ to C ₂₀ ,

6) R ⁸ , R ⁹ , R' and R" are each the same or different, and independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom among N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkynyl group; C ₁ ~ C ₆₀ alkoxy group; and C ₆ ~ C ₆₀ aryloxy group; selected from the group consisting of , or a plurality of adjacent R ^8s or a plurality of R ^9s may combine with each other to form a ring, or R' and R" may combine with each other to form a spiro ring,

When R ⁸ , R ⁹ , R' and R" are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenylene, biphenyl, naphthalene. , terphenyl, etc.

When R ⁸ , R ⁹ , R' and R" are heterocyclic groups, they may preferably be heterocyclic groups of C ₂ to C ₃₀ , more preferably heterocyclic groups of C ₂ to C ₂₄ , 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 ⁸ , R ⁹ , R' and R" 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 .

When R ⁸ , R ⁹ , R' and R" are an alkyl group, they may preferably be an alkyl group of C ₁ to C ₃₀ , and more preferably an alkyl group of C ₁ to C ₂₄ .

When R ⁸ , R ⁹ , R' and R" are alkenyl groups, they may preferably be alkenyl groups of C ₂ to C ₃₀ , and more preferably alkenyl groups of C ₂ to C ₂₄ .

When R ⁸ , R ⁹ , R' and R" are an alkynyl group, they may preferably be an alkynyl group of C ₂ to C ₃₀ , and more preferably an alkynyl group of C ₂ to C ₂₄ .

When R ⁸ , R ⁹ , R' and R" are an alkoxyl group, they may preferably be an alkoxyl group of C ₁ to C ₃₀ , and more preferably an alkoxy group of C ₁ to C ₂₄ .

When R ⁸ , R ⁹ , R' and R" are aryloxy groups, they may be preferably C ₆ to C ₃₀ aryloxy groups, and more preferably C ₆ to C ₂₄ aryloxy groups.

7) R ^a 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;

When R ^a is an aryl group, it is preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₅ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc.

When R ^a 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 pyrimido. Indole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine , phenothiazine, phenylphenothiazine, etc.

8) R ^b and R ^c are each independently 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; And C ₃ ~ C ₆₀ aliphatic ring; selected from the group consisting of,

When R ^b and R ^c are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenylene, biphenyl, naphthalene, terphenyl, etc. .

When R ^b and R ^c are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, examples of which include pyrazine, thiophene, and pyridine. , pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofyu. It may be lopyrimidine, phenothiazine, phenylphenothiazine, etc.

When R ^b and R ^c are aliphatic ring groups, they may be preferably a C ₃ to C ₃₀ aliphatic ring group, and more preferably a C ₃ to C ₂₄ aliphatic ring group.

9) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl 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 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 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, Formula 3 may be represented by any one of Formulas 3-1 to 3-3 below.

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

<Formula 3-3>

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

1) Ar ⁴ , Ar ⁵ , L ⁴ , L ⁵ and L ⁶ are as defined above,

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

3) R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are the same as the definition of R ⁸ above, or between a plurality of adjacent R ¹⁰ or between a plurality of R ¹¹ or between a plurality of R 12 or between a plurality of adjacent R ¹⁰ R ¹³ or a plurality of R ¹⁴ or a plurality of R ¹⁵ may combine with each other to form a ring,

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

Additionally, Formula 4 may be represented by any one of the following Formulas 4-1 to 4-6.

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

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

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

{In Formula 4-1 to Formula 4-6,

1) Y, R ⁸ , R ⁹ , Ar ⁶ , L ⁷ , n and o are the same as defined above,

2) R ¹⁶ is the same as the definition of R ⁸ above,

3) v is an integer from 0 to 2.}

Additionally, Formula 4 may be represented by any one of the following Formulas 4-7 to 4-9.

<Formula 4-7> <Formula 4-8>

<Formula 4-9>

In Formulas 4-7 to 4-9,

1) Y, B ring, R ⁹ , o, L ⁷ and Ar ⁶ are the same as defined above,

2) R ¹⁷ is the same as the definition of R ⁸ above,

3) w is an integer from 0 to 6.}

Additionally, Formula 4 may be represented by any one of Formulas 4-10 to 4-12 below.

<Formula 4-10> <Formula 4-11>

<Formula 4-12>

{In Formulas 4-10 to 4-12,

1) Y, B, Ar ⁶ , L ⁷ , R ⁸ and n are the same as defined above,

2) R ¹⁸ is the same as the definition of R ⁸ above,

3) x is an integer from 0 to 6.}

Additionally, Formula 4 may be represented by the following Formulas 4-13 to 4-18.

<Formula 4-13> <Formula 4-14>

<Formula 4-15> <Formula 4-16>

<Formula 4-17> <Formula 4-18>

{In Formulas 4-13 to 4-18, Y, L ⁷ , Ar ⁶ , R ⁸ , R ⁹ , R ¹⁶ , R ¹⁷ , R ¹⁸ , n, o, v, w and x are defined above. Same as bar.}

Additionally, Chemical Formula 4 may be expressed as Chemical Formula 4-19 below.

<Formula 4-19>

{In Formula 4-19, L ⁷ , Ar ⁶ , R ^a , R ⁹ , R ¹⁶ , R ¹⁷ , o, v and w are the same as defined above.}

Specifically, the compound represented by Formula 3 may be any one of the following compounds N-1 to N-96.

Specifically, the compound represented by Formula 4 may be any one of the following compounds S-1 to S-108.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 110, a second electrode 170, and a structure of formula 1 between the first electrode 110 and the second electrode 170. It is provided with an organic material layer containing a single compound or two or more types of compounds represented by . At this time, the first electrode 110 may be an anode or an anode, and the second electrode 170 may be a cathode or a cathode. In the case of the inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially 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 on the first electrode 110. At this time, the remaining layers except for the light emitting layer 140 may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 220, a buffer layer 210, etc., and an electron transport layer 150, etc. may serve as a hole blocking layer. (see Figure 2)

In addition, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improvement layer 180. This light efficiency improvement layer may be formed on a side of both sides of the first electrode that is not in contact with the organic material layer, or on a side of both sides of the second electrode that is not in contact with the organic material layer. The compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 120, a hole transport layer 130, a light emitting auxiliary layer 220, an electron transport auxiliary layer, an electron transport layer 150, an electron injection layer ( 160), it may be used as a host or dopant of the light emitting layer 140, or as a material for a light efficiency improvement layer. Preferably, for example, the compound according to Formula 1 of the present invention can be used as a host material for the light-emitting layer.

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 may further include a charge generation layer formed between the two or more stacks. (see Figure 3)

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

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and It can be manufactured by forming an organic material layer including the electron injection layer 160 and then depositing a material that can be used as a cathode thereon.

In addition, in the present invention, the organic layer is formed by any one of a spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, and roll-to-roll process, and the organic layer contains the compound as an electron transport material. Provided is an organic electric device characterized in that:

As another specific example, the present invention provides an organic electric device characterized in that the same or different compounds of the compound represented by Formula 1 are mixed in the organic material layer.

Additionally, the present invention provides a light-emitting layer composition containing the compound represented by Formula 1, and provides an organic electric device containing the light-emitting layer.

In addition, the present invention provides a display device including the above-described organic electric device; and a control unit that drives the display device.

In another aspect, the present invention provides an electronic device 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. 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 devices, game consoles, various TVs, and various computers.

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

[Synthesis example]

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

<Scheme 1>

{In Scheme 1, A is a naphthalene group or a phenanthrene group.}

I. Synthesis of Sub1

Sub1 of Scheme 1 is synthesized through the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2>

{In Scheme 2, A is a naphthalene group or a phenanthrene group.}

1. Sub1-1 synthesis example

(1) Sub1-c-1 synthesis example

After dissolving Sub1-a-1 (30.0 g, 90.8 mmol) in THF (454 mL) in a round bottom flask, Sub1-b-1 (21.9 g, 90.8 mmol), NaOH (10.9 g, 273 mmol), Pd ( PPh ₃ ) ₄ (6.30 g, 5.45 mmol) and water (227 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the produced compound was recrystallized by applying a silica gel column to obtain 27.5 g of product. (yield 83%)

(2) Sub1-1 synthesis example

Sub1-c-1 (27.5 g, 75.4 mmol) obtained in the above synthesis was dissolved in DMF (Dimethylformamide) (377 mL) in a round bottom flask, then bis(pinacolato)diboron (21.1 g, 82.9 mmol) and KOAc (22.2 g) , 226 mmol), PdCl ₂ (dppf) (1.66 g, 2.26 mmol) were added and stirred at 120°C. When the reaction was completed, DMF was removed through distillation, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the produced compound was recrystallized by applying a silica gel column to obtain 25.5 g of product. (yield 74%)

2. Sub1-2 synthesis example

(1) Sub1-c-2 synthesis example

After dissolving Sub1-a-2 (10.0 g, 29.6 mmol) in THF (148 mL) in a round bottom flask, Sub1-b-1 (7.2 g, 29.6 mmol), NaOH (3.6 g, 88.9 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.06 g, 1.78 mmol) and water (74 mL), 8.9 g of product was obtained using the same method as Sub1-c-1. (yield 81%)

(2) Sub1-2 synthesis example

Sub1-c-2 (8.9 g, 24.0 mmol), bis(pinacolato)diboron (6.7 g, 26.4 mmol), KOAc (7.1 g, 72.0 mmol), PdCl ₂ (dppf) (0.53 g, 0.72 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 8.0 g of product. (yield 72%)

3. Sub1-6 synthesis example

(1) Sub1-c-6 synthesis example

After dissolving Sub1-a-6 (10.0 g, 25.9 mmol) in THF (129 mL) in a round bottom flask, Sub1-b-1 (6.3 g, 25.9 mmol), NaOH (3.1 g, 77.7 mmol), and Pd ( After adding PPh ₃ ) ₄ (1.79 g, 1.55 mmol) and water (65 mL), 8.6 g of product was obtained using the same method as Sub1-c-1. (yield 79%)

(2) Sub1-6 synthesis example

Sub1-c-6 (8.6 g, 20.4 mmol), bis(pinacolato)diboron (5.7 g, 22.5 mmol), KOAc (6.0 g, 61.3 mmol), PdCl ₂ (dppf) (0.45 g, 0.61 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 7.8 g of product. (yield 74%)

4. Sub1-9 synthesis example

(1) Sub1-c-9 synthesis example

After dissolving Sub1-a-1 (10.0 g, 30.3 mmol) in THF (151 mL) in a round bottom flask, Sub1-b-9 (9.6 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.10 g, 1.82 mmol) and water (76 mL), 10.9 g of product was obtained using the same method as Sub1-c-1. (yield 82%)

(2) Sub1-9 synthesis example

Sub1-c-9 (10.9 g, 24.8 mmol), bis(pinacolato)diboron (6.9 g, 27.3 mmol), KOAc (7.3 g, 74.5 mmol), PdCl ₂ (dppf) (0.55 g, 0.74 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 9.3 g of product. (yield 70%)

5. Sub1-17 synthesis example

(1) Sub1-c-17 synthesis example

After dissolving Sub1-a-17 (10.0 g, 30.3 mmol) in THF (151 mL) in a round bottom flask, Sub1-b-1 (7.3 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.10 g, 1.82 mmol) and water (76 mL), 8.8 g of product was obtained using the same method as Sub1-c-1. (yield 80%)

(2) Sub1-17 synthesis example

Sub1-c-17 (8.8 g, 24.2 mmol), bis(pinacolato)diboron (6.8 g, 26.6 mmol), KOAc (7.1 g, 72.7 mmol), PdCl ₂ (dppf) (0.53 g, 0.73 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 8.1 g of product. (yield 73%)

6. Sub1-25 synthesis example

(1) Sub1-c-25 synthesis example

After dissolving Sub1-a-17 (10.0 g, 30.3 mmol) in THF (151 mL) in a round bottom flask, Sub1-b-25 (9.6 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.10 g, 1.82 mmol) and water (76 mL), 10.4 g of product was obtained using the same method as Sub1-c-1. (yield 78%)

(2) Sub1-25 synthesis example

Sub1-c-25 (10.4 g, 23.6 mmol), bis(pinacolato)diboron (6.6 g, 26.0 mmol), KOAc (7.0 g, 70.9 mmol), PdCl ₂ (dppf) (0.52 g, 0.71 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 9.1 g of product. (yield 72%)

7. Sub1-32 synthesis example

(1) Sub1-c-32 synthesis example

After dissolving Sub1-a-32 (10.0 g, 30.3 mmol) in THF (151 mL) in a round bottom flask, Sub1-b-1 (7.3 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.10 g, 1.82 mmol) and water (76 mL), 8.2 g of product was obtained using the same method as Sub1-c-1. (yield 74%)

(2) Sub1-32 synthesis example

Sub1-c-32 (8.2 g, 22.4 mmol), bis(pinacolato)diboron (6.3 g, 24.6 mmol), KOAc (6.6 g, 67.2 mmol), PdCl ₂ (dppf) (0.49 g, 0.67 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 7.3 g of product. (yield 71%)

8. Sub1-45 synthesis example

(1) Sub1-c-45 synthesis example

After dissolving Sub1-a-45 (10.0 g, 30.3 mmol) in THF (151 mL) in a round bottom flask, Sub1-b-1 (7.3 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.10 g, 1.82 mmol) and water (76 mL), 8.0 g of product was obtained using the same method as Sub1-c-1. (yield 72%)

(2) Sub1-45 synthesis example

Sub1-c-45 (8.0 g, 21.8 mmol), bis(pinacolato)diboron (6.1 g, 24.0 mmol), KOAc (6.4 g, 65.4 mmol), PdCl ₂ (dppf) (0.48 g, 0.65 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 7.3 g of product. (yield 73%)

9. Sub1-58 synthesis example

(1) Sub1-c-58 synthesis example

After dissolving Sub1-a-58 (10.0 g, 26.3 mmol) in THF (131 mL) in a round bottom flask, Sub1-b-1 (6.4 g, 26.3 mmol), NaOH (3.2 g, 78.9 mmol), Pd ( After adding PPh ₃ ) ₄ (1.82 g, 1.58 mmol) and water (66 mL), 9.1 g of product was obtained using the same method as Sub1-c-1. (yield 83%)

(2) Sub1-58 synthesis example

Sub1-c-58 (9.1 g, 21.8 mmol), bis(pinacolato)diboron (6.1 g, 24.0 mmol), KOAc (6.4 g, 65.5 mmol), PdCl ₂ (dppf) (0.48 g, 0.65 mmol) obtained from the above synthesis. ) was obtained using the same method as Sub1-1 above to obtain 7.8 g of product. (yield 71%)

Compounds belonging to Sub1 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 Sub1.

compound FD-MS compound FD-MS Sub1-1 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Sub1-2 m/z=463.27(C ₃₂ H ₂₂ D ₇ BO ₂ =463.43) Sub1-3 m/z=459.24(C ₃₂ H ₂₆ D ₃ BO ₂ =459.41) Sub1-4 m/z=462.26(C ₃₂ H ₂₃ D ₆ BO ₂ =462.43) Sub1-5 m/z=472.33(C ₃₂ H ₁₃ D ₁₆ BO ₂ =472.49) Sub1-6 m/z=512.29(C ₃₆ H ₃₇ BO ₂ =512.5) Sub1-7 m/z=582.16(C ₃₂ H ₂₂ BF ₇ O ₂ =582.32) Sub1-8 m/z=512.29(C ₃₆ H ₃₇ BO ₂ =512.5) Sub1-9 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-10 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-11 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-12 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-13 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-14 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-15 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-16 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-17 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Sub1-18 m/z=463.27(C ₃₂ H ₂₂ D ₇ BO ₂ =463.43) Sub1-19 m/z=462.26(C ₃₂ H ₂₃ D ₆ BO ₂ =462.43) Sub1-20 m/z=472.33(C ₃₂ H ₁₃ D ₁₆ BO ₂ =472.49) Sub1-21 m/z=512.29(C ₃₆ H ₃₇ BO ₂ =512.5) Sub1-22 m/z=582.16(C ₃₂ H ₂₂ BF ₇ O ₂ =582.32) Sub1-23 m/z=538.3(C ₃₈ H ₃₉ BO ₂ =538.54) Sub1-24 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-25 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-26 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-27 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-28 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-29 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-30 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-31 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-32 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Sub1-33 m/z=463.27(C ₃₂ H ₂₂ D ₇ BO ₂ =463.43) Sub1-34 m/z=462.26(C ₃₂ H ₂₃ D ₆ BO ₂ =462.43) Sub1-35 m/z=512.29(C ₃₆ H ₃₇ BO ₂ =512.5) Sub1-36 m/z=512.29(C ₃₆ H ₃₇ BO ₂ =512.5) Sub1-37 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-38 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-39 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-40 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-41 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-42 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-43 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-44 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-45 m/z=456.23(C ₃₂ H ₂₉ BO ₂ =456.39) Sub1-46 m/z=463.27(C ₃₂ H ₂₂ D ₇ BO ₂ =463.43) Sub1-47 m/z=462.26(C ₃₂ H ₂₃ D ₆ BO ₂ =462.43) Sub1-48 m/z=512.29(C ₃₆ H ₃₇ BO ₂ =512.5) Sub1-49 m/z=582.16(C ₃₂ H ₂₂ BF ₇ O ₂ =582.32) Sub1-50 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-51 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-52 m/z=532.26(C ₃₈ H ₃₃ BO ₂ =532.49) Sub1-53 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-54 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-55 m/z=582.27(C ₄₂ H ₃₅ BO ₂ =582.55) Sub1-56 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-57 m/z=608.29(C ₄₄ H ₃₇ BO ₂ =608.59) Sub1-58 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-59 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-60 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-61 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-62 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-63 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-64 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-65 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-66 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45) Sub1-67 m/z=506.24(C ₃₆ H ₃₁ BO ₂ =506.45)

II. Synthesis of Sub2

Sub2 of Scheme 1 is synthesized through the reaction route of Scheme 3 below, but is not limited thereto.

<Scheme 3>

1. Sub2-7 synthesis example

After dissolving Sub2-a-7 (7.0 g, 31.0 mmol) in THF (155 mL) in a round bottom flask, Sub2-b-7 (9.2 g, 31.0 mmol), NaOH (3.7 g, 92.9 mmol), and Pd ( PPh ₃ ) ₄ (2.15 g, 1.86 mmol) and water (77 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the produced compound was recrystallized by applying a silica gel column to obtain 9.4 g of product. (yield 84%)

2. Sub2-34 synthesis example

After dissolving Sub2-a-7 (7.0 g, 31.0 mmol) in THF (155 mL) in a round bottom flask, Sub2-b-34 (9.1 g, 31.0 mmol), NaOH (3.7 g, 92.9 mmol), and Pd ( After adding PPh ₃ ) ₄ (2.15 g, 1.86 mmol) and water (77 mL), 9.0 g of product was obtained using the same method as Sub2-7 above. (yield 81%)

3. Sub2-43 synthesis example

After dissolving Sub2-a-7 (7.0 g, 31.0 mmol) in THF (155 mL) in a round bottom flask, Sub2-b-43 (10.7 g, 31.0 mmol), NaOH (3.7 g, 92.9 mmol), Pd ( After adding PPh ₃ ) ₄ (2.15 g, 1.86 mmol) and water (77 mL), 9.7 g of product was obtained using the same method as Sub2-7 above. (yield 77%)

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

compound FD-MS compound FD-MS Sub2-1 m/z=267.06(C ₁₅ H ₁₀ ClN ₃ =267.72) Sub2-2 m/z=272.09(C ₁₅ H ₅ D ₅ ClN ₃ =272.75) Sub2-3 m/z=277.12(C ₁₅ D ₁₀ ClN ₃ =277.78) Sub2-4 m/z=357.01(C ₁₅ H ₅ ClF ₅ N ₃ =357.67) Sub2-5 m/z=446.96(C ₁₅ ClF ₁₀ N ₃ =447.62) Sub2-6 m/z=349.13(C ₂₁ H ₂₀ ClN ₃ =349.86) Sub2-7 m/z=361.13(C ₂₂ H ₂₀ ClN ₃ =361.87) Sub2-8 m/z=401.17(C ₂₅ H ₂₄ ClN ₃ =401.94) Sub2-9 m/z=317.07(C ₁₉ H ₁₂ ClN ₃ =317.78) Sub2-10 m/z=317.07(C ₁₉ H ₁₂ ClN ₃ =317.78) Sub2-11 m/z=367.09(C ₂₃ H ₁₄ ClN ₃ =367.84) Sub2-12 m/z=367.09(C ₂₃ H ₁₄ ClN ₃ =367.84) Sub2-13 m/z=367.09(C ₂₃ H ₁₄ ClN ₃ =367.84) Sub2-14 m/z=343.09(C ₂₁ H ₁₄ ClN ₃ =343.81) Sub2-15 m/z=348.12(C ₂₁ H ₉ D ₅ ClN ₃ =348.84) Sub2-16 m/z=347.11(C ₂₁ H ₁₀ D ₄ ClN ₃ =347.84) Sub2-17 m/z=343.09(C ₂₁ H ₁₄ ClN ₃ =343.81) Sub2-18 m/z=343.09(C ₂₁ H ₁₄ ClN ₃ =343.81) Sub2-19 m/z=347.11(C ₂₁ H ₁₀ D ₄ ClN ₃ =347.84) Sub2-20 m/z=422.14(C ₂₇ H ₁₅ D ₃ ClN ₃ =422.93) Sub2-21 m/z=393.1(C ₂₅ H ₁₆ ClN ₃ =393.87) Sub2-22 m/z=393.1(C ₂₅ H ₁₆ ClN ₃ =393.87) Sub2-23 m/z=393.1(C ₂₅ H ₁₆ ClN ₃ =393.87) Sub2-24 m/z=393.1(C ₂₅ H ₁₆ ClN ₃ =393.87) Sub2-25 m/z=393.1(C ₂₅ H ₁₆ ClN ₃ =393.87) Sub2-26 m/z=393.1(C ₂₅ H ₁₆ ClN ₃ =393.87) Sub2-27 m/z=373.04(C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub2-28 m/z=373.04(C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub2-29 m/z=373.04(C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub2-30 m/z=373.04(C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub2-31 m/z=449.08(C ₂₇ H ₁₆ ClN ₃ S=449.96) Sub2-32 m/z=357.07(C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub2-33 m/z=357.07(C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub2-34 m/z=357.07(C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub2-35 m/z=433.1(C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub2-36 m/z=433.1(C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub2-37 m/z=483.11(C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub2-38 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-39 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-40 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-41 m/z=423.06(C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub2-42 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-43 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub2-44 m/z=407.08(C ₂₅ H ₁₄ ClN ₃ O=407.86)

III. Final product synthesis

1. P-1 synthesis example

After dissolving Sub1-1 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-1 (2.9 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the produced compound was recrystallized by applying a silica gel column to obtain 5.1 g of product. (yield 83%)

2. P-9 synthesis example

After dissolving Sub1-2 (5.0 g, 10.8 mmol) in THF (54 mL) in a round bottom flask, Sub2-1 (2.9 g, 10.8 mmol), NaOH (1.3 g, 32.4 mmol), Pd(PPh ₃ ) ₄ (0.75 g, 0.65 mmol) and water (27 mL) were added, and then 5.2 g of product was obtained using the same method as P-1. (yield 84%)

3. P-17 synthesis example

After dissolving Sub1-6 (5.0 g, 9.8 mmol) in THF (49 mL) in a round bottom flask, Sub2-1 (2.6 g, 9.8 mmol), NaOH (1.2 g, 29.3 mmol), Pd(PPh ₃ ) ₄ (0.68 g, 0.59 mmol) and water (24 mL) were added, and then 5.2 g of product was obtained using the same method as P-1. (yield 86%)

4. P-20 synthesis example

After dissolving Sub1-1 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-7 (4.0 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added, and then 5.8 g of product was obtained using the same method as P-1. (yield 81%)

5. P-24 synthesis example

After dissolving Sub1-1 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-34 (3.9 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added, and then 5.9 g of product was obtained using the same method as P-1. (yield 83%)

6. P-28 synthesis example

After dissolving Sub1-1 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-43 (4.5 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added, and then 6.2 g of product was obtained using the same method as P-1. (yield 80%)

7. P-29 synthesis example

After dissolving Sub1-9 (5.0 g, 9.4 mmol) in THF (47 mL) in a round bottom flask, Sub2-1 (2.5 g, 9.4 mmol), NaOH (1.1 g, 28.2 mmol), Pd(PPh ₃ ) ₄ (0.65 g, 0.56 mmol) and water (23 mL) were added, and then 4.7 g of product was obtained using the same method as P-1 above. (yield 79%)

8. P-37 synthesis example

After dissolving Sub1-17 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-1 (2.9 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added, and then 5.0 g of product was obtained using the same method as P-1. (yield 82%)

9. P-58 synthesis example

After dissolving Sub1-25 (5.0 g, 9.4 mmol) in THF (47 mL) in a round bottom flask, Sub2-1 (2.5 g, 9.4 mmol), NaOH (1.1 g, 28.2 mmol), Pd(PPh ₃ ) ₄ (0.65 g, 0.56 mmol) and water (23 mL) were added, and then 4.8 g of product was obtained using the same method as P-1. (yield 80%)

10. P-65 synthesis example

After dissolving Sub1-32 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-1 (2.9 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added, and then 5.2 g of product was obtained using the same method as P-1. (yield 84%)

11. P-93 synthesis example

After dissolving Sub1-45 (5.0 g, 11.0 mmol) in THF (55 mL) in a round bottom flask, Sub2-1 (2.9 g, 11.0 mmol), NaOH (1.3 g, 32.9 mmol), Pd(PPh ₃ ) ₄ (0.76 g, 0.66 mmol) and water (27 mL) were added, and then 4.8 g of product was obtained using the same method as P-1. (yield 78%)

12. P-121 synthesis example

After dissolving Sub1-58 (5.0 g, 9.9 mmol) in THF (49 mL) in a round bottom flask, Sub2-1 (2.6 g, 9.9 mmol), NaOH (1.2 g, 29.6 mmol), Pd(PPh ₃ ) ₄ (0.68 g, 0.59 mmol) and water (25 mL) were added, and then 4.8 g of product was obtained using the same method as P-1. (yield 79%)

Meanwhile, the FD-MS values of compounds P-1 to P-130 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=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-3 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-4 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-5 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-6 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-7 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-8 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-9 m/z=568.26(C ₄₁ H ₂₀ D ₇ N ₃ =568.73) P-10 m/z=564.24(C ₄₁ H ₂₄ D ₃ N ₃ =564.71) P-11 m/z=567.26(C ₄₁ H ₂₁ D ₆ N ₃ =567.72) P-12 m/z=577.32(C ₄₁ H ₁₁ D ₁₆ N ₃ =577.79) P-13 m/z=571.28(C ₄₁ H ₁₇ D ₁₀ N ₃ =571.75) P-14 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-15 m/z=641.28(C ₄₇ H ₂₇ D ₄ N ₃ =641.81) P-16 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-17 m/z=617.28(C ₄₅ H ₃₅ N ₃ =617.8) P-18 m/z=687.15(C ₄₁ H ₂₀ F ₇ N ₃ =687.62) P-19 m/z=617.28(C ₄₅ H ₃₅ N ₃ =617.8) P-20 m/z=655.3(C ₄₈ H ₃₇ N ₃ =655.85) P-21 m/z=667.21(C ₄₇ H ₂₉ N ₃ S=667.83) P-22 m/z=651.23(C ₄₇ H ₂₉ N ₃ O=651.77) P-23 m/z=667.21(C ₄₇ H ₂₉ N ₃ S=667.83) P-24 m/z=651.23(C ₄₇ H ₂₉ N ₃ O=651.77) P-25 m/z=717.22(C ₅₁ H ₃₁ N ₃ S=717.89) P-26 m/z=701.25(C ₅₁ H ₃₁ N ₃ O=701.83) P-27 m/z=717.22(C ₅₁ H ₃₁ N ₃ S=717.89) P-28 m/z=701.25(C ₅₁ H ₃₁ N ₃ O=701.83) P-29 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-30 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-31 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) 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=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-36 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-37 m/z=561.22(C ₄₁ H ₂₇ N ₃ =561.69) P-38 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-39 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-40 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-41 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-42 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-43 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-44 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-45 m/z=568.26(C ₄₁ H ₂₀ D ₇ N ₃ =568.73) P-46 m/z=567.26(C ₄₁ H ₂₁ D ₆ N ₃ =567.72) P-47 m/z=577.32(C ₄₁ H ₁₁ D ₁₆ N ₃ =577.79) P-48 m/z=587.38(C ₄₁ HD ₂₆ N ₃ =587.85) P-49 m/z=617.28(C ₄₅ H ₃₅ N ₃ =617.8) P-50 m/z=687.15(C ₄₁ H ₂₀ F ₇ N ₃ =687.62) P-51 m/z=643.3(C ₄₇ H ₃₇ N ₃ =643.83) P-52 m/z=741.13(C ₄₁ H ₁₇ F ₁₀ N ₃ =741.59) P-53 m/z=651.23(C ₄₇ H ₂₉ N ₃ O=651.77) P-54 m/z=727.26(C ₅₃ H ₃₃ N ₃ O=727.87) P-55 m/z=667.21(C ₄₇ H ₂₉ N ₃ S=667.83) P-56 m/z=717.22(C ₅₁ H ₃₁ N ₃ S=717.89) P-57 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-58 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-59 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-60 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-61 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-62 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-63 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-64 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-65 m/z=561.22(C ₄₁ H ₂₇ N ₃ =561.69) P-66 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-67 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-68 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-69 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-70 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-71 m/z=661.25(C ₄₉ H ₃₁ N ₃ =661.81) P-72 m/z=661.25(C ₄₉ H ₃₁ N ₃ =661.81) P-73 m/z=568.26(C ₄₁ H ₂₀ D ₇ N ₃ =568.73) P-74 m/z=567.26(C ₄₁ H ₂₁ D ₆ N ₃ =567.72) P-75 m/z=566.25(C ₄₁ H ₂₂ D ₅ N ₃ =566.72) P-76 m/z=641.28(C ₄₇ H ₂₇ D ₄ N ₃ =641.81) P-77 m/z=617.28(C ₄₅ H ₃₅ N ₃ =617.8) P-78 m/z=617.28(C ₄₅ H ₃₅ N ₃ =617.8) P-79 m/z=651.17(C ₄₁ H ₂₂ F ₅ N ₃ =651.64) P-80 m/z=695.33(C ₅₁ H ₄₁ N ₃ =695.91) P-81 m/z=667.21(C ₄₇ H ₂₉ N ₃ S=667.83) P-82 m/z=727.26(C ₅₃ H ₃₃ N ₃ O=727.87) P-83 m/z=777.28(C ₅₇ H ₃₅ N ₃ O=777.93) P-84 m/z=667.21(C ₄₇ H ₂₉ N ₃ S=667.83) P-85 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-86 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-87 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-88 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-89 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-90 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-91 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-92 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-93 m/z=561.22(C ₄₁ H ₂₇ N ₃ =561.69) P-94 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-95 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-96 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-97 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-98 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-99 m/z=661.25(C ₄₉ H ₃₁ N ₃ =661.81) P-100 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-101 m/z=568.26(C ₄₁ H ₂₀ D ₇ N ₃ =568.73) P-102 m/z=567.26(C ₄₁ H ₂₁ D ₆ N ₃ =567.72) P-103 m/z=566.25(C ₄₁ H ₂₂ D ₅ N ₃ =566.72) P-104 m/z=716.3(C ₅₃ H ₃₂ D ₃ N ₃ =716.9) P-105 m/z=617.28(C ₄₅ H ₃₅ N ₃ =617.8) P-106 m/z=643.3(C ₄₇ H ₃₇ N ₃ =643.83) P-107 m/z=687.15(C ₄₁ H ₂₀ F ₇ N ₃ =687.62) P-108 m/z=651.17(C ₄₁ H ₂₂ F ₅ N ₃ =651.64) P-109 m/z=743.24(C ₅₃ H ₃₃ N ₃ S=743.93) P-110 m/z=651.23(C ₄₇ H ₂₉ N ₃ O=651.77) P-111 m/z=717.22(C ₅₁ H ₃₁ N ₃ S=717.89) P-112 m/z=701.25(C ₅₁ H ₃₁ N ₃ O=701.83) P-113 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-114 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-115 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-116 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-117 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-118 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-119 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-120 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-121 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-122 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-123 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-124 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-125 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-126 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-127 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-128 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-129 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75) P-130 m/z=611.24(C ₄₅ H ₂₉ N ₃ =611.75)

[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 (170 mL) 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 (260 mL) 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 (80 mL) 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 (120 mL) 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. Upon completion of the reaction, 60 g (81.5%) of product S-104 was obtained using the separation method of P-1 indicated 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)

[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 20 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 Formula 1 as a host as a host and the compound N-2 represented by Formula 3 or Formula 4 as a first host compound were mixed in a weight ratio (5:5) ), and (piq) ₂ Ir(acac) was doped as a dopant material at a weight ratio of 95:5 to deposit a light emitting layer with a thickness of 30 nm. 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 BeBq2) was formed into a film with a thickness of 30 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 75]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that the compounds of the present invention shown in Table 6 below were used as host materials for the light emitting layer instead of the compounds P-1 and N-2 of the present invention.

[Comparative Example 1] to [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>

Forward bias direct current voltage was applied to the organic electric devices prepared in Examples 1 to 75 and Comparative Examples 1 to 2, producing electroluminescence (EL) using PR-650 from Photo Research. The characteristics were measured, and as a result of the measurement, the T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience at a standard luminance of 2500 cd/m ² . Table 6 below shows the results of device fabrication and evaluation.

first compound second compound driving voltage electric current
(mA/ ^cm2 ) Luminance
(cd/ ^m2 ) efficiency
(cd/A) T(95) Comparative Example 1 Comparative compound A Compound (N-2) 5.2 8.8 2500 28.3 103.3 Comparative example 2 Comparative compound B Compound (N-2) 5.1 8.5 2500 29.5 107.1 Example 1 Compound (P-1) Compound (N-2) 4.7 7.7 2500 32.7 131.2 Example 2 Compound (P-9) Compound (N-2) 4.7 7.5 2500 33.2 136.8 Example 3 Compound (P-17) Compound (N-2) 4.7 7.6 2500 32.7 131.6 Example 4 Compound (P-20) Compound (N-2) 4.8 7.9 2500 31.6 127.7 Example 5 Compound (P-24) Compound (N-2) 4.7 7.5 2500 33.3 130.5 Example 6 Compound (P-28) Compound (N-2) 4.7 7.4 2500 33.8 128.5 Example 7 Compound (P-29) Compound (N-2) 4.8 7.9 2500 31.6 128.7 Example 8 Compound (P-37) Compound (N-2) 4.8 8.0 2500 31.4 126.7 Example 9 Compound (P-45) Compound (N-2) 4.8 7.8 2500 32.0 131.2 Example 10 Compound (P-58) Compound (N-2) 4.8 8.2 2500 30.4 122.3 Example 11 Compound (P-65) Compound (N-2) 4.9 7.5 2500 33.3 120.3 Example 12 Compound (P-73) Compound (N-2) 4.9 7.4 2500 33.9 124.1 Example 13 Compound (P-93) Compound (N-2) 4.9 7.8 2500 32.0 115.4 Example 14 Compound (P-103) Compound (N-2) 4.9 7.7 2500 32.6 120.0 Example 15 Compound (P-121) Compound (N-2) 4.8 7.6 2500 33.1 124.1 Example 16 Compound (P-1) Compound (N-12) 4.7 7.9 2500 31.7 127.4 Example 17 Compound (P-9) Compound (N-12) 4.6 7.8 2500 32.2 132.8 Example 18 Compound (P-17) Compound (N-12) 4.7 7.9 2500 31.8 127.8 Example 19 Compound (P-20) Compound (N-12) 4.8 8.1 2500 30.7 124.0 Example 20 Compound (P-24) Compound (N-12) 4.6 7.7 2500 32.3 126.7 Example 21 Compound (P-28) Compound (N-12) 4.6 7.6 2500 32.8 124.8 Example 22 Compound (P-29) Compound (N-12) 4.7 8.1 2500 30.7 124.9 Example 23 Compound (P-37) Compound (N-12) 4.7 8.2 2500 30.5 123.0 Example 24 Compound (P-45) Compound (N-12) 4.7 8.1 2500 31.1 127.4 Example 25 Compound (P-58) Compound (N-12) 4.7 8.5 2500 29.5 118.8 Example 26 Compound (P-65) Compound (N-12) 4.8 7.7 2500 32.3 116.8 Example 27 Compound (P-73) Compound (N-12) 4.8 7.6 2500 32.9 120.5 Example 28 Compound (P-93) Compound (N-12) 4.8 8.1 2500 31.0 112.1 Example 29 Compound (P-103) Compound (N-12) 4.8 7.9 2500 31.6 116.5 Example 30 Compound (P-121) Compound (N-12) 4.7 7.8 2500 32.1 120.5 Example 31 Compound (P-1) Compound (N-19) 4.7 7.5 2500 33.3 135.0 Example 32 Compound (P-9) Compound (N-19) 4.7 7.4 2500 33.8 140.7 Example 33 Compound (P-17) Compound (N-19) 4.7 7.5 2500 33.4 135.4 Example 34 Compound (P-20) Compound (N-19) 4.8 7.8 2500 32.2 131.4 Example 35 Compound (P-24) Compound (N-19) 4.7 7.4 2500 33.9 134.3 Example 36 Compound (P-28) Compound (N-19) 4.7 7.3 2500 34.4 132.2 Example 37 Compound (P-29) Compound (N-19) 4.8 7.8 2500 32.2 132.4 Example 38 Compound (P-37) Compound (N-19) 4.8 7.8 2500 32.0 130.4 Example 39 Compound (P-45) Compound (N-19) 4.8 7.7 2500 32.6 135.1 Example 40 Compound (P-58) Compound (N-19) 4.8 8.1 2500 31.0 125.9 Example 41 Compound (P-65) Compound (N-19) 4.9 7.4 2500 33.9 123.8 Example 42 Compound (P-73) Compound (N-19) 4.9 7.2 2500 34.6 127.7 Example 43 Compound (P-93) Compound (N-19) 4.9 7.7 2500 32.6 118.8 Example 44 Compound (P-103) Compound (N-19) 4.9 7.5 2500 33.2 123.5 Example 45 Compound (P-121) Compound (N-19) 4.8 7.4 2500 33.7 127.7 Example 46 Compound (P-1) Compound (S-32) 4.8 7.4 2500 33.9 140.1 Example 47 Compound (P-9) Compound (S-32) 4.8 7.2 2500 34.5 146.1 Example 48 Compound (P-17) Compound (S-32) 4.8 7.4 2500 34.0 140.5 Example 49 Compound (P-20) Compound (S-32) 4.9 7.6 2500 32.8 136.4 Example 50 Compound (P-24) Compound (S-32) 4.7 7.2 2500 34.5 139.3 Example 51 Compound (P-28) Compound (S-32) 4.7 7.1 2500 35.1 137.2 Example 52 Compound (P-29) Compound (S-32) 4.8 7.6 2500 32.8 137.4 Example 53 Compound (P-37) Compound (S-32) 4.8 7.7 2500 32.6 135.3 Example 54 Compound (P-45) Compound (S-32) 4.8 7.5 2500 33.2 140.2 Example 55 Compound (P-58) Compound (S-32) 4.8 7.9 2500 31.6 130.6 Example 56 Compound (P-65) Compound (S-32) 4.9 7.2 2500 34.5 128.5 Example 57 Compound (P-73) Compound (S-32) 4.9 7.1 2500 35.2 132.5 Example 58 Compound (P-93) Compound (S-32) 5.0 7.5 2500 33.2 123.3 Example 59 Compound (P-103) Compound (S-32) 4.9 7.4 2500 33.8 128.1 Example 60 Compound (P-121) Compound (S-32) 4.8 7.3 2500 34.4 132.5 Example 61 Compound (P-1) Compound (S-104) 4.8 7.3 2500 34.3 142.6 Example 62 Compound (P-9) Compound (S-104) 4.8 7.2 2500 34.8 148.7 Example 63 Compound (P-17) Compound (S-104) 4.8 7.3 2500 34.3 143.1 Example 64 Compound (P-20) Compound (S-104) 4.9 7.5 2500 33.1 138.9 Example 65 Compound (P-24) Compound (S-104) 4.8 7.2 2500 34.9 141.9 Example 66 Compound (P-28) Compound (S-104) 4.8 7.1 2500 35.4 139.7 Example 67 Compound (P-29) Compound (S-104) 4.9 7.5 2500 33.1 139.9 Example 68 Compound (P-37) Compound (S-104) 4.9 7.6 2500 32.9 137.8 Example 69 Compound (P-45) Compound (S-104) 4.9 7.5 2500 33.5 142.7 Example 70 Compound (P-58) Compound (S-104) 4.9 7.8 2500 31.9 133.0 Example 71 Compound (P-65) Compound (S-104) 5.0 7.2 2500 34.9 130.9 Example 72 Compound (P-73) Compound (S-104) 5.0 7.0 2500 35.6 134.9 Example 73 Compound (P-93) Compound (S-104) 5.0 7.5 2500 33.5 125.5 Example 74 Compound (P-103) Compound (S-104) 5.0 7.3 2500 34.2 130.5 Example 75 Compound (P-121) Compound (S-104) 4.9 7.2 2500 34.7 134.9

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

Comparing Comparative Compound A or Comparative Compound B with the compound of the present invention, the point is that the naphthyl group is further substituted with a substituent of the -naphthyl-phenyl group, but in the case of Comparative Compound A or Comparative Compound B, the naphthyl group is para (para) of the phenyl group. The difference is that it is bound to the para) position, and in the case of the compound of the present invention, it is bound to the meta or ortho position. In other words, the planarity of the molecule is reduced by bonding a naphthyl group to the meta or ortho position. As the planarity of the molecule decreases, the thermal stability of the molecule becomes excellent, which can affect the characteristics of the device.

As the position of the substituent of the compound changes, the value of the energy level changes and the physical properties of the compound change. Therefore, it is believed to be a major factor in improving device performance during device deposition. That is, as a result of the comparative compounds and the compounds of the present invention, it can be confirmed that compounds with a naphthyl group introduced at the meta or ortho position have superior effects compared to compounds with a naphthyl group introduced at the para position.

The above description is merely an exemplary 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 (18)

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

<Formula 2>

{In Formula 1 and Formula 2 above,
1) R ¹ , R ² and R ³ are each the same or different and are independently hydrogen; heavy hydrogen; halogen; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkyne group; C ₁ ~ C ₆₀ alkoxyl group; and a cycloalkyl group of C ₃ to C ₆₀ ; or a plurality of adjacent R ³ groups may be bonded to each other to form a ring;
2) a is an integer from 0 to 3, b is an integer from 0 to 6, c is an integer from 0 to 7,
3) L ¹ , L ² and L ³ are independently single bonds; or an arylene group of C ₆ to C ₆₀ ;
4) Ar ¹ and Ar ² are independently C ₆ to C ₆₀ aryl groups; or a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
5) A is a substituent represented by Formula 2 above,
6)

means the binding position,
7) Here, the aryl group, arylene group, heterocyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and cycloalkyl group are each hydrogen; 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 1, wherein Formula 2 is represented by the following Formula 2-1 or Formula 2-2:
<Formula 2-1><Formula2-2>

{In Formula 2-1 and Formula 2-2, R ³ , c and is as defined in claim 1 above.}
The compound according to claim 1, wherein Formula 1 is represented by the following Formula 1-1 or Formula 1-2:
<Formula 1-1><Formula1-2>

{In Formula 1-1 and Formula 1-2, A, R ¹ , R ² , L ¹ , L ² , L ³ , Ar ¹ , Ar ² , a and b are as defined in claim 1.}
The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-3 to 1-6:
<Formula 1-3><Formula1-4>

<Formula 1-5><Formula1-6>

{In Formulas 1-3 to 1-6, R ¹ , R ² , R ³ , L ¹ , L ² , L ³ , Ar ¹ , Ar ² , a, b and c are as defined in claim 1 same.}
The compound according to claim 1, wherein L ¹ is a single bond.
The compound according to claim 1, wherein L ¹ to L ³ are represented by any one of the following formulas L1 to L3:
<Formula L1><FormulaL2><FormulaL3>

{In Formula L1 to Formula L3,
1) R ⁴ , R ⁵ , R ⁶ and R ⁷ are each the same or different and, independently of each other, hydrogen; heavy hydrogen; 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; C ₈ ~ C ₂₀ arylalkenyl group; and a fused ring group of an aliphatic ring from C ₃ to C ₂₀ and an aromatic ring from C ₆ to C ₂₀ ; selected from the group consisting of,
2) d, e and f are integers from 0 to 4, g is an integer from 0 to 6,
3) * means the part that is combined.}
The compound according to claim 1, wherein Formula 1 contains at least one deuterium.
The compound according to claim 1, wherein at least one of R ¹ and R ² contains deuterium.
The compound according to claim 1, wherein R ³ contains at least one deuterium.
The compound according to claim 1, wherein the compound represented by Formula 1 is any one of the following compounds P-1 to compound P-130:

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 having the chemical formula of claim 1 An organic electric device comprising a first host compound represented by 1 and a second host compound represented by Formula 3 or Formula 4 below:
<Formula 3><Formula4>

{In Formula 3 and Formula 4 above,
1) 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 from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ;
2) 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'-NR ^b R ^c ;,
3) L ⁴ , L ⁵ , L ⁶ , L ⁷ and L' are each independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; And C ₃ ~ C ₆₀ aliphatic ring; selected from the group consisting of,
4) Y is O, S, CR'R" or NR ^a ,
5) Ring B is an aryl group from C ₆ to C ₂₀ ,
6) R ⁸ , R ⁹ , R' and R" are each the same or different, and independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom among N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkynyl group; C ₁ ~ C ₆₀ alkoxy group; and C ₆ ~ C ₆₀ aryloxy group; selected from the group consisting of , or a plurality of adjacent R ^8s or a plurality of R ^9s may combine with each other to form a ring, or R' and R" may combine with each other to form a spiro ring,
7) R ^a 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;
8) R ^b and R ^c are each independently 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; And C ₃ ~ C ₆₀ aliphatic ring; selected from the group consisting of,
9) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl 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 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.}
The organic electric device according to claim 11, wherein the compound represented by Formula 3 is any one of the following compounds N-1 to N-96:

The organic electric device according to claim 11, wherein the compound represented by Formula 4 is any one of the following compounds S-1 to S-108.

The organic electric device of claim 11, 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 according to claim 11, 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 15, wherein the organic material layer further includes a charge generation layer formed between the two or more stacks.
A display device including the organic electric element of claim 11; and a control unit that drives the display device.
The electronic device of claim 17, 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.