KR102704883B1 - 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 mixture capable of improving the luminous efficiency, stability and lifespan of a device, and an organic electric device and an electronic device using the same.

Description

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

In general, the organic luminescence phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. An organic electric device utilizing the organic luminescence phenomenon usually has a structure including an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and can 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 electronic devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

In the case of bis-type ring compounds containing heteroatoms, the differences in properties depending on the material structure are very large, and thus they are applied to various layers as materials for organic electric devices. In particular, depending on the number of rings, fused positions, and the types and arrangements of heteroatoms, they have different characteristics such as band gaps (HOMO, LUMO), electrical properties, chemical properties, and physical properties, and thus, various applications for layers of organic electric devices have been developed using these.

In phosphorescent organic electroluminescent devices using phosphorescent dopant materials, the LUMO and HOMO levels of the host material are factors that greatly affect the efficiency and lifespan of the organic electroluminescent devices. Depending on whether electron and hole injection into the emitting layer can be efficiently controlled, the charge balance within the emitting layer can be controlled, and efficiency and lifespan reduction due to dopant quenching and luminescence at the hole transport layer interface can be prevented.

In the case of host materials for fluorescence and phosphorescence emission, research has been conducted recently to increase the efficiency and lifespan of organic electronic devices using TADF (Thermal activated delayed fluorescent), Exciplex, etc. In particular, much research is being conducted to elucidate the method of energy transfer from the host material to the dopant material.

There are several methods to elucidate the energy transfer within the emitting layer for TADF (Thermal activated delayed fluorescent), exciplex, but it can be easily confirmed using the PL lifetime (TRTP) measurement method.

The TRTP (Time resolved transient PL) measurement method is a method that observes the decrease in the spectrum over time (decay time) after irradiating a pulse light source to a host thin film, and is a measurement method that can elucidate the energy transfer method through observation of the energy transfer and luminescence delay time. The TRTP measurement is a measurement method that can distinguish between fluorescence and phosphorescence, and energy transfer methods in mixed host materials, exciplex energy transfer methods, and TADF energy transfer methods.

In this way, there are various factors that affect the efficiency and lifespan depending on the method of energy transfer from the host material to the dopant material, and since the method of energy transfer differs depending on the material, the development of stable and efficient host materials for organic electric devices has not yet been sufficiently achieved. 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.

KR 101170666 B1

The present invention has been proposed to solve the problems of the above-mentioned phosphorescent host material, and aims to provide a compound capable of controlling the charge balance in the light-emitting layer and improving the efficiency and lifespan through the HOMO level control of the host material of a phosphorescent light-emitting organic electric device including a phosphorescent dopant, and an organic electric device and an electronic device thereof using the same.

The present invention comprises a combination of a specific first host material and a specific second host material as main components to control efficient hole injection into a light-emitting layer of a phosphorescent organic electroluminescent device, thereby reducing the energy barrier between the light-emitting layer and the adjacent layer and maximizing the charge balance within the light-emitting layer, thereby providing high efficiency and long life to the organic electroluminescent device.

The present invention provides an organic electric device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer and includes a first host compound represented by chemical formula (1) and a second host compound represented by chemical formula (2).

Chemical formula (1) Chemical formula (2)

In addition, the present invention provides an organic electric element and an electronic device thereof using a compound represented by the chemical formulas above.

By using the mixture according to the present invention as a phosphorescent host material, high luminous efficiency and low operating voltage of an organic electric device can be achieved, and the lifespan of the device can also be greatly improved.

Figure 1 is an exemplary diagram of an organic light-emitting device 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 judged 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.

Also, in describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

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

The term "halo" or "halogen" as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and a cycloalkyl-substituted alkyl group.

The term “haloalkyl group” or “halogenalkyl group” as used in the present invention, unless otherwise specified, means an alkyl group substituted with a halogen.

The term "heteroalkyl group" used in the present invention means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.

The terms “alkenyl group,” “alkenyl group,” or “alkynyl group,” as used in the present invention, unless otherwise stated, include, but are not limited to, straight-chain or branched-chain groups each having a double bond or triple bond of 2 to 60 carbon atoms.

The term "cycloalkyl" as used in the present invention, unless otherwise stated, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” as used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

The terms “alkenoxyl group”, “alkenoxy group”, “alkenyloxy group”, or “alkenyloxy group” as used in the present invention mean an alkenyl group having an oxygen radical attached thereto, and unless otherwise stated, has from 2 to 60 carbon atoms, but is not limited thereto.

The term "aryloxyl group" or "aryloxy group" as used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise stated, has 6 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group can be a phenyl group, a biphenyl group, a fluorene group, a dimethylfluorene group, a diphenylfluorene group, or a 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 the aryl substituted radical has the number of carbon atoms described herein.

Also, when prefixes are named consecutively, it means that the substituents are listed in the order they were first described. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term "heteroalkyl" means an alkyl group containing one or more heteroatoms, unless otherwise stated. The term "heteroaryl group" or "heteroarylene group" as used in the present invention, unless otherwise stated, means an aryl group or arylene group having 2 to 60 carbon atoms, respectively, containing one or more heteroatoms, but is not limited thereto, and includes at least one of a single ring and multiple rings, and may be formed by bonding adjacent functional groups.

The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by bonding adjacent functional groups.

The term "heteroatom" as used herein, unless otherwise stated, represents N, O, S, P or Si.

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

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term "ring" as used in the present invention refers to a fused ring composed of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, and includes a saturated or unsaturated ring.

Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds contain one or more heteroatoms, but are not limited thereto.

Unless otherwise stated, the term "carbonyl" as used herein is represented by -COR', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise stated, the term "ether" as used in the present invention is represented by the formula -R-O-R', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

In addition, unless explicitly stated otherwise, the term "substituted or unsubstituted" used in the present invention means "substituted" with deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C 1 to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkylamine group, C ₁ to C ₂₀ alkylthiophene group, C ₆ to C ₂₀ arylthiophene group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl _group , C ₃ to C _{20 cycloalkyl} group, C ₆ to C 20 aryl group, C ₆ to C ₂₀ aryl group substituted with deuterium, C ₈ to C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and C ₂ to C It means being substituted with one or more substituents selected from the group consisting of ₂₀ heterocyclic groups, but is not limited to these substituents.

Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

Here, when a is an integer of 0, it means that the substituent R ¹ is absent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring. In this case, the indication of the hydrogen bonded to the carbon can be omitted and the chemical formula or compound can be described. 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, they are bonded as follows respectively, and in this case, R ¹ may be the same or different, and when a is an integer of 4 to 6, they are bonded to the carbons of the benzene ring in a similar manner, and on the other hand, the indication of the hydrogen bonded to the carbons forming the benzene ring is omitted.

Hereinafter, a compound according to one aspect of the present invention and an organic electric device comprising the same will be described.

The present invention provides an organic electric device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer and includes a first host compound represented by chemical formula (1) and a second host compound represented by chemical formula (2).

Chemical formula (1) Chemical formula (2)

{In the above chemical formulas (1) and (2),

1) X and Y are each independently O; S; CR'R"; SiR'R" or Se;,

2) a and b are each independently 0 or 1, provided that a+b is greater than or equal to 1,

3) R' and R" are each independently selected from the group consisting of hydrogen; an alkyl group having a carbon number of C ₁ to C ₅₀ ; an aryl group having a carbon number of C ₆ to C ₆₀ ; and a heteroaryl group having a carbon number of C ₂ to C ₆₀ ; or R' and R" form a ring with each other to form a spiro ring,

4) L ¹ , L ² and L' are each independently a single bond; an arylene group having C ₆ to C ₆₀ ; or a heteroarylene group having C ₂ to C ₆₀ ;

5) Ar ¹ and Ar ² are each independently selected from the group consisting of hydrogen; deuterium; a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; a C ₆ to C ₃₀ aryloxy group; and -L'-NR'R";

6) Z is NR', O, S, CR'R", SiR'R", or Se,

7) R ¹ to R ⁶ are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; a C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b );

The above R _a and R _b are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; and a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P.

When the above l, m, n, o, p and q are 2 or more, they are each plural and identical or different, and plural R ^1s , plural R ^2s , plural R ^3s , plural R ^4s , plural R ^5s and plural R ^6s can combine with each other to form aromatic and heteroaromatic rings,

8) The A and B rings are each independently a C ₆ to C ₆₀ aryl group or a C ₂ to C ₆₀ heteroaryl group, and one of A and B is a C ₁₀ to C ₆₀ aryl group,

9) n, l, p and q are any integers from 0 to 4, m is 0 or 1, o is any integer from 0 to 3,

10) One of X ¹ and X ² is N and the other is C-Ar ² ,

Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each independently selected from 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 alkynyl 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; It may be further substituted with one or more substituents selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group and a C ₈ -C ₂₀ arylalkenyl group; and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a fused ring formed of a C ₃ -C ₆₀ aliphatic ring, a C ₆ -C ₆₀ aromatic ring, a C ₂ -C ₆₀ heterocycle, or a combination thereof, and includes a saturated or unsaturated ring.

In the present invention, the compound represented by the chemical formula (1) provides an organic electric device including a compound represented by the following chemical formula (3) or (4).

Chemical formula (3) Chemical formula (4)

(In the chemical formulas (3) and (4) above, X, Y, Z, Ar ¹ , L ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , l, m, n, o, and p are the same as defined above.)

As another specific example, the present invention provides an organic electric device including a compound represented by the chemical formula (1) as defined above, wherein the compound is represented by any one of the chemical formulas (5) to (12).

Chemical formula (5) Chemical formula (6) Chemical formula (7) Chemical formula (8)

Chemical formula (9) Chemical formula (10) Chemical formula (11) Chemical formula (12)

(In the chemical formulas (5) to (12) above, X, Y, Z, Ar ¹ , L ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , l, m, n, o, and p are the same as defined above.)

In addition, the present invention provides an organic electric device including a compound in which l, m, n, o, and p in the chemical formula (1) are all 0.

As another example, the present invention provides an organic electric device including a compound in which any one of R ¹ , R ² , R ³ , R ⁴ and R ⁵ in the chemical formula (1) is a pair of adjacent pairs bonded to each other to form a ring.

In addition, the present invention provides an organic electric device including a compound in the chemical formula (1), wherein X or Y is S or O.

As a specific example, the chemical formula (1) in the present invention includes the following compound.

Meanwhile, the present invention provides an organic electric device comprising a compound represented by the chemical formula (2) and a compound represented by the chemical formula (13) or (14).

Chemical formula (13) Chemical formula (14)

(In the chemical formulas (13) and (14) above, A, B, L ² , Ar ² , R ⁶ and q are the same as defined above.)

The present invention provides an organic electric device including a compound in which rings A and B of the compound represented by the chemical formula (2) are represented by any one of the following (A-1) to (A-9).

(A-1) (A-2) (A-3) (A-4) (A-5) (A-6) (A-7)

(A-8) (A-9)

(In the above chemical formulas (A-1) to (A-9), R ¹⁰ is the same as R ¹ above,

* Indicates the bonding position of rings A and B.)

As another example, the present invention includes a compound represented by the above chemical formula (2) as well as a compound represented by any one of the following chemical formulas (15) to (28).

Chemical formula (15) Chemical formula (16) Chemical formula (17)

Chemical formula (18) Chemical formula (19) Chemical formula (20)

Chemical formula (21) Chemical formula (22) Chemical formula (23)

Chemical formula (24) Chemical formula (25) Chemical formula (26)

Chemical formula (27) Chemical formula (28)

(In the above chemical formulas (15) to (28),

L ² , X ¹ , X ² , R ⁶ and q are as defined above,

R ¹² and R ¹³ are identical to R ¹ defined above,

s and u are each independently an integer from 0 to 6,

t is an integer between 0 and 4,

v and w are each independently an integer from 0 to 8.)

In addition, the present invention provides an organic electric device including a compound represented by the chemical formula (2) in which R ⁶ is hydrogen.

As a specific example, the chemical formula (2) in the present invention includes the following compound.

Referring to FIG. 1, an organic electric element (100) according to the present invention comprises a first electrode (120), a second electrode (180) formed on a substrate (110), and an organic layer including compounds represented by chemical formulas 1 and 2 between the first electrode (120) and the second electrode (180). At this time, the first electrode (120) may be an anode, the second electrode (180) may be a cathode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer may sequentially include a hole injection layer (130), a hole transport layer (140), an emission layer (150), an emission auxiliary layer (151), an electron transport layer (160), and an electron injection layer (170) on the first electrode (120). At this time, the remaining layers except for the emission layer (150) may not be formed. A hole blocking layer, an electron blocking layer, an emission auxiliary layer (151), an electron transport auxiliary layer, a buffer layer (141), etc. may be further included, and the electron transport layer (160), etc. may also function as a hole blocking layer.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer formed on at least one surface of the first electrode and the second electrode, which is opposite to the organic layer. The compound including the chemical formula 1 of the present invention can be used as a material for a light efficiency improvement layer or a protective layer.

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

An organic light emitting device according to one embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, it can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer (130), a hole transport layer (140), an emission layer (150), an electron transport layer (160), and an electron injection layer (170) thereon, and then depositing a material that can be used as a cathode thereon. In addition, an emission auxiliary layer (151) can be additionally formed between the hole transport layer (140) and the emission layer (150), and an electron transport auxiliary layer can be additionally formed between the emission layer (150) and the electron transport layer (160).

Accordingly, the present invention provides an organic electric device in which the compounds represented by the chemical formula (1) and the chemical formula (2) are mixed in a ratio of any one of 1:9 to 9:1 and included in the light-emitting layer, preferably in a ratio of 1:9 to 5:5, more preferably in a ratio of 2:8 to 3:7 and included in the light-emitting layer.

The present invention provides an organic electric device further including a light efficiency improvement layer formed on at least one of the sides of the first electrode, which is opposite the organic layer, or the sides of the second electrode, which is opposite the organic layer.

In addition, in the present invention, the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a deep coating process, and a roll-to-roll process, and since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

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

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution, excellent processability, and being able to be manufactured using the color filter technology of existing LCDs. Various structures for white organic light emitting devices, mainly used as backlight devices, have been proposed and patented. Representative examples include a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in parallel with each other plane-wise, a stacking method in which R, G, and B light emitting layers are stacked vertically, and a color conversion material (CCM) method in which electroluminescence by a blue (B) organic light emitting layer and the light therefrom are utilized for self-luminescence (photoluminescence) of an inorganic phosphor. The present invention can also be applied to such WOLEDs.

In addition, the present invention provides an electronic device including a display device including the above-described organic electric element; and a control unit for driving the display device.

In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element. 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 systems, game consoles, various TVs, and various computers.

Hereinafter, examples of synthesis of compounds represented by the chemical formulas (1) and (2) of the present invention and examples of manufacturing organic electric devices of the present invention will be described in detail by way of examples, but the present invention is not limited to the following examples.

[Synthesis Example 1]

The compound (final product 1) represented by chemical formula (1) according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in the following reaction scheme 1.

<Reaction Formula 1>

1. Synthesis example of Sub 1

Sub 1 of reaction scheme 1 can be synthesized by the reaction path of reaction scheme 2 below, but is not limited thereto.

<Reaction Formula 2> (X'= I, Br, Cl)

Synthetic examples of compounds belonging to Sub 1 of the above reaction scheme 2 are as follows.

1. Synthesis example of Sub 1-1 (when a=1, b=0, X=S)

Synthesis of Sub 1-I-1

2-Chloroaniline (67.2 g, 525 mmol), 1,4-Dibromodibenzothiophene (150 g, 438 mmol), Pd ₂ (dba) ₃ (16.2 g, 17.4 mmol), P(t-Bu) ₃ (15 g, 43.8 mmol), NaO(t-Bu) (126 g, 1317 mmol), and toluene (1.5 L) were added to a round-bottomed flask. Then, the mixture was refluxed at 70 ℃ for 4 hours. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with methylene chloride and hexane to obtain the product Sub 1-I-1 (135 g, 79%).

Synthesis of Sub 1-II-1

Add Sub 1-I-1 (135 g, 348 mmol), PPh ₃ (228 g, 867 mmol), and o -Dichlorobenzene (900 mL) to a round-bottomed flask. Then, heat and reflux at 180 ℃ for 24 hours. After the reaction is complete, cool to room temperature and concentrate. The concentrated compound was purified by silica column and recrystallized to obtain the product Sub 1-II-1 (91.8 g, 75%).

Synthesis of Sub 1-1

Add Sub 1-II-1 (30.6 g 87 mmol), 1-Bromonaphthalene (21.5 g, 104 mmol), Pd ₂ (dba) ₃ (3.2 g, 3.5 mmol), P(t-Bu) ₃ (1.8 g, 8.7 mmol), NaO(t-Bu) (25 g, 261 mmol), and toluene (300 mL) to a round-bottomed flask. Then, heat and reflux at 110 ℃ for 8 hours. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. Dry the organic layer over MgSO ₄ and concentrate, and recrystallize the resulting compound with methylene chloride and hexane to obtain the product Sub 1-1 (31.6 g, 74%).

2. Synthesis example of Sub 1-2 (when a=1, b=0, X=S)

Synthesis of Sub 1-2

Sub 1-II-1 (30 g, 84 mmol), Iodobenzene (20.7 g, 102 mmol), Pd ₂ (dba) ₃ (3 g, 3.3 mmol), P(t-Bu) ₃ (1.8 g, 8.4 mmol), NaO(t-Bu) (24.6 g, 255 mmol), and toluene (240 mL) were placed in a round-bottomed flask and the product Sub 1-2 (28 g, 76%) was obtained using the synthetic method of Sub 1-1.

Synthesis example of Sub 1-3 (when a=1, b=0, X=S)

Synthesis of Sub 1-3

Sub 1-II-1 (30.6 g 87 mmol), 4-Iodo-1,1'-biphenyl (29.2 g, 104 mmol), Pd ₂ (dba) ₃ (3.2 g, 3.5 mmol), P(t-Bu) ₃ (1.8 g, 8.7 mmol), NaO(t-Bu) (25 g, 261 mmol), and toluene (300 mL) were placed in a round-bottomed flask and the product Sub 1-3 (32 g, 74%) was obtained using the synthetic method of Sub 1-1.

Synthesis example of Sub 1-5 (when a=1, b=0, X=S)

Synthesis of Sub 1-5

Sub 1-II-1 (30.6 g 87 mmol), 2-Bromonaphthalene (21.5 g, 104 mmol), Pd ₂ (dba) ₃ (3.2 g, 3.5 mmol), P(t-Bu) ₃ (1.8 g, 8.7 mmol), NaO(t-Bu) (25 g, 261 mmol), and toluene (300 mL) were placed in a round-bottomed flask and the product Sub 1-5 (29.1 g, 70%) was obtained using the synthetic method of Sub 1-1.

Sub 1-6 Synthesis Example (when a=1, b=0, X=S)

Synthesis of Sub 1-I-6 (when a=1, b=0, X=S)

2-Chloroaniline (22.4 g, 175 mmol), 2,4-Dibromodibenzothiophene (50 g, 146 mmol), Pd ₂ (dba) ₃ (5.4 g, 5.8 mmol), P(t-Bu) ₃ (5 g, 14.6 mmol), NaO(t-Bu) (42 g, 439 mmol), and toluene (500 mL) were placed in a round-bottomed flask and the product Sub 1-I-6 (46 g, 90%) was obtained using the synthetic method of Sub 1-I-1.

Synthesis of Sub 1-II-6

Sub 1-I-6 (45 g, 116 mmol), PPh ₃ (76 g, 289 mmol), o -Dichlorobenzene (300 mL) were added to a round-bottom flask, and the product Sub 1-II-6 (32.6 g, 80%) was obtained using the synthetic method of Sub 1-II-1.

Synthesis of Sub 1-6

Sub 1-II-6 (10 g, 28 mmol), Iodobenzene (6.9 g, 34 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P(t-Bu) ₃ (0.6 g, 2.8 mmol), NaO(t-Bu) (8.2 g, 85 mmol), and toluene (80 mL) were placed in a round-bottomed flask and the product Sub 1-6 (10 g, 84%) was obtained using the synthetic method of Sub 1-1.

Sub 1-7 Synthesis Example (when a=1, b=0, X=S)

Synthesis of Sub 1-7

Sub 1-II-6 (10 g, 28 mmol), 4-Iodo-1,1'-biphenyl (9.5 g, 34 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P(t-Bu) ₃ (0.6 g, 2.8 mmol), NaO(t-Bu) (8.2 g, 85 mmol), and toluene (80 mL) were placed in a round-bottomed flask and the product Sub 1-7 (10 g, 71%) was obtained using the synthetic method of Sub 1-1.

Sub 1-14 Synthesis Example (when a=1, b=0, X=S)

Synthesis of Sub 1-I-14

2-Chloronaphthalen-1-amine (31 g, 175 mmol), 2,4-Dibromodibenzothiophene (50 g, 146 mmol), Pd ₂ (dba) ₃ (5.4 g, 5.8 mmol), P(t-Bu) ₃ (5 g, 14.6 mmol), NaO(t-Bu) (42 g, 439 mmol), and toluene (500 mL) were placed in a round-bottomed flask and the product Sub 1-I-14 (48 g, 75%) was obtained using the synthetic method of Sub 1-I-1.

Synthesis of Sub 1-II-14

Add Sub 1-I-14 (30 g, 68 mmol), PPh ₃ (45 g, 171 mmol), and o -Dichlorobenzene (150 mL) to a round-bottomed flask. Then, heat and reflux at 180 °C for 24 hours. After the reaction is complete, cool to room temperature and concentrate. The concentrated compound was purified by silica column and recrystallized to obtain the product Sub 1-II-14 (25 g, 93%).

Synthesis of Sub 1-14

In a round-bottomed flask, add Sub 1-II-14 (25 g, 62 mmol), Iodobenzene (15 g 75 mmol), Pd ₂ (dba) ₃ (2. g, 2.5 mmol), P(t-Bu) ₃ (1.3 g (6.2 mmol), NaO(t-Bu) (18 g, 186 mmol), and Toluene (300 mL). Then, heat and reflux at 110 ℃ for 8 hours. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. Dry the organic layer over MgSO ₄ and concentrate, and recrystallize the resulting compound with methylene chloride and hexane to obtain the product Sub 1-14 (20 g, 67%).

Sub 1-29 Synthesis Example (when a=1, b=0, X=C)

Synthesis of Sub 1-I-29

2-Chloronaphthalen-1-amine (31 g, 175 mmol), 1,4-dibromo-9,9-dimethyl-9H-fluorene (51 g, 146 mmol), Pd ₂ (dba) ₃ (5.4 g, 5.8 mmol), P(t-Bu) ₃ (5 g, 14.6 mmol), NaO(t-Bu) (42 g, 439 mmol), toluene (500 mL) were placed in a round-bottomed flask to obtain the product Sub 1-I-29 (36 g, 63%) using the synthetic method of Sub 1-I-1.

Synthesis of Sub 1-II-29

Sub 1-I-29 (27 g, 68 mmol), PPh ₃ (45 g, 171 mmol), o -Dichlorobenzene (150 mL) were placed in a round-bottom flask and the product Sub 1-II-29 (22 g, 92%) was obtained using the synthetic method of Sub 1-II-1.

Synthesis of Sub 1-29

Sub 1-II-29 (22 g, 62 mmol), 2-Bromonaphthalene (15 g 74 mmol), Pd ₂ (dba) ₃ (2. g, 2.5 mmol), P(t-Bu) ₃ (1.3 g (6.2 mmol), NaO(t-Bu) (18 g, 186 mmol), toluene (300 mL) were placed in a round-bottomed flask to obtain the product Sub 1-29 (20 g, 67%) using the synthetic method of Sub 1-1.

Sub 1-25 Synthesis Example (when a= 1, b= 0, X= O)

Synthesis of Sub 1-I-25

In a round-bottomed flask, 2-Chloronaphthalen-1-amine (23.45 g, 183.85 mmol), 1,4-dibromodibenzo[b,d]furan (50 g, 153.4 mmol), Pd ₂ (dba) ₃ (5.58 g, 6.1 mmol), P(t-Bu) ₃ (3.1 g, 15.34 mmol), NaO(t-Bu) (44.32 g, 461.2 mmol), toluene (340 mL) were added. Using the synthetic method of Sub 1-I-1, the product Sub 1-I-25 (41.7 g, 73%) was obtained.

Synthesis of Sub 1-II-25

Sub 1-I-25 (47 g, 126.1 mmol), PPh ₃ (82.7 g, 315.3 mmol), o -Dichlorobenzene (505 mL) were added to a round-bottomed flask, and the product Sub 1-II-25 (35.62 g, 84%) was obtained using the synthetic method of Sub 1-II-1.

Synthesis of Sub 1-25

Sub 1-II-25 (47 g, 126.13 mmol), Bromobenzene (19.59 g 124.79 mmol), Pd ₂ (dba) ₃ (3.79 g, 4.14 mmol), P(t-Bu) ₃ (2.11 g, 10.4 mmol), NaO(t-Bu) (30.08 g, 313.045 mmol), Toluene (230 mL) were added to a round-bottomed flask, and the product Sub 1-25 (34.77 g, 82%) was obtained using the synthetic method of Sub 1-1.

Example of Sub 1

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

Compound FD-MS compound FD-MS Sub 1-1 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 1-2 m/z=427.00(C24HBrNS=428.34) Sub 1-3 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 1-4 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 1-5 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 1-6 m/z=427.00(C24HBrNS=428.34) Sub 1-7 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 1-8 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 1-9 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40)) Sub 1-10 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 1-11 m/z=605.06(C ₃₆ H ₂₀ BrN ₃ S=606.53) Sub 1-12 m/z=555.04(C ₃₂ H ₁₈ BrN ₃ S=556.47) Sub 1-13 m/z=603.07(C ₃₈ H ₂₂ BrNS=604.56) Sub 1-14 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 1-15 m/z=527.03(C ₃₂ H ₁₈ BrNS=528.46) Sub 1-16 m/z=629.08(C ₄₀ H ₂₄ BrNS=630.59) Sub 1-17 m/z=554.05C ₃₃ H ₁₉ BrN ₂ S=555.49) Sub 1-18 m/z=734.11(C ₄₅ H ₂₇ BrN ₄ S=735.69) Sub 1-19 m/z=721.08(C ₄₄ H ₂₄ BrN ₃ OS=722.65) Sub 1-20 m/z=629.08(C ₄₀ H ₂₄ BrNS=630.59) Sub 1-21 m/z=529.02(C ₃₀ H ₁₆ BrN ₃ S=530.44) Sub 1-22 m/z=555.04(C ₃₂ H ₁₈ BrN ₃ S=556.47) Sub 1-23 m/z=581.06(C ₃₄ H ₂₀ BrN ₃ S=582.51) Sub 1-24 m/z=600.06(C ₃₃ H ₂₁ BrN ₄ OS=601.52) Sub 1-25 m/z=411.03(C ₂₄ H ₁₄ BrNO=412.28) Sub 1-26 m/z=671.07(C ₄₀ H ₂₂ BrN ₃ OS=672.59) Sub 1-27 m/z=593.04(C ₃₆ H ₂₀ BrNOS=594.52) Sub 1-28 m/z=437.08(C ₂₇ H ₂₀ BrN=438.36) Sub 1-29 m/z=487.09(C ₃₁ H ₂₂ BrN=488.42) Sub 1-30 m/z=453.05(C ₂₆ H ₂₀ BrNSi=454.43) Sub 1-31 m/z=474.95(C ₂₄ H ₁₄ BrNSe=475.24)

2. Synthesis example of Sub 2

Sub 2 of reaction scheme 1 can be synthesized by the reaction path of reaction scheme 3 below, but is not limited thereto.

<Reaction Formula 3> (X'= I, Br, Cl)

Synthetic examples of compounds belonging to Sub 2 of the above reaction scheme 3 are as follows.

Sub 2-1 Synthesis Example (when a= 0, b=1, Y= S)

Synthesis of Sub 2-I-1

2-Bromodibenzothiophene (100 g, 380 mmol), 2-Nitrophenyl boronic acid (76 g, 456 mmol), Pd(PPh ₃ ) ₄ (18 g, 15 mmol), NaOH (46 g, 1140 mmol), THF (1.2 L)/H ₂ O (0.6 L) were added to a round-bottomed flask. Then, it was refluxed and heated at 70 ℃ for 4 hours. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with methylene chloride and hexane to obtain the product Sub 2-I-1 (99 g, 85%).

Synthesis of Sub 2-II-1

Add Sub 2-I-1 (99 g, 323 mmol), PPh ₃ (218 g, 808 mmol), and o -Dichlorobenzene (1.0 L) to a round-bottomed flask. Then, heat and reflux at 180 ℃ for 24 hours. After the reaction is complete, cool to room temperature and concentrate. The concentrated compound was purified by silica column and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).

Synthesis of Sub 2-III-1

Add Sub 2-II-1 (70 g, 293 mmol), N-Bromosuccinimide (52 g, 293 mmol), and methylene chloride (1 L) to a round-bottomed flask. Stir at room temperature for 4 hours. When the reaction is complete, add distilled water, and extract with methylene chloride and water. Dry the organic layer over MgSO ₄ and concentrate, and recrystallize the resulting compound with methylene chloride and hexane to obtain the product Sub 2-III-1 (86 g, 83%).

Synthesis method of Sub 2-1

Add Sub 2-III-1 (30 g, 84 mmol), Iodobenzene (20.7 g, 102 mmol), Pd ₂ (dba) ₃ (3 g, 3.3 mmol), P(t-Bu) ₃ (1.8 g, 8.4 mmol), NaO(t-Bu) (24.6 g, 255 mmol), and toluene (240 mL) to a round-bottomed flask. Then, heat and reflux at 110 ℃ for 8 hours. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. Dry the organic layer over MgSO ₄ and concentrate, and recrystallize the resulting compound with methylene chloride and hexane to obtain the product Sub 2-1 (28 g, 76%).

Sub 2-2 Synthesis Example (when a= 0, b=1, Y= S)

Synthesis method of Sub 2-2

Sub 2-III-1 (30 g, 84 mmol), 4-Iodo-1,1'-biphenyl (28.6 g, 102 mmol), Pd ₂ (dba) ₃ (3 g, 3.3 mmol), P(t-Bu) ₃ (1.8 g, 8.4 mmol), NaO(t-Bu) (24.6 g, 255 mmol), and toluene (240 mL) were placed in a round-bottom flask and the product Sub 2-2 (32 g, 76%) was obtained using the synthetic method of Sub 2-1.

Sub 2-3 Synthesis Example (when a= 0, b=1, Y= S)

Synthesis of Sub 2-3

Sub 2-III-1 (30 g, 84 mmol), 3-Bromo-1,1'-biphenyl (23.8 g, 102 mmol), Pd ₂ (dba) ₃ (3 g, 3.3 mmol), P(t-Bu) ₃ (1.8 g, 8.4 mmol), NaO(t-Bu) (24.6 g, 255 mmol), and toluene (240 mL) were placed in a round-bottom flask and the product Sub 2-3 (34 g, 80%) was obtained using the synthetic method of Sub 2-1.

Sub 2-37 Synthesis Example (when a= 0, b=1, Y= O)

Synthesis of Sub 2-I-37

2-Bromodibenzofuran (50 g, 202 mmol), 2-Nitrophenyl boronic acid (40.5 g, 242 mmol), Pd(PPh ₃ ) ₄ (9.3 g, 8 mmol), NaOH (24 g, 606 mmol), THF (600 mL)/H ₂ O (300 mL) were placed in a round-bottomed flask and the product Sub 2-I-37 (43 g, 74%) was obtained using the synthetic method of Sub 2-I-1.

Synthesis of Sub 2-II-37

Sub 2-I-37 (43 g, 110 mmol), PPh ₃ (72 g, 276 mmol), o -Dichlorobenzene (350 mL) were placed in a round-bottom flask and the product Sub 2-II-37 (23 g, 82%) was obtained using the synthetic method of Sub 2-II-1.

Synthesis of Sub 2-III-37

Sub 2-II-37 (23 g, 89 mmol), N-Bromosuccinimide (16 g, 89 mmol), and methylene chloride (300 mL) were placed in a round-bottom flask and the product Sub 2-III-37 (21 g, 70%) was obtained using the synthetic method of Sub 2-III-1.

Synthesis of Sub 2-37

Sub 2-III-37 (21 g, 62 mmol), Iodobenzene (15.3 g, 75 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), P(t-Bu) ₃ (1.3 g, 6.2 mmol), NaO(t-Bu) (18 g, 187 mmol), and toluene (200 mL) were placed in a round-bottomed flask and the product Sub 2-37 (16 g, 63%) was obtained using the synthetic method of Sub 2-1.

Synthesis example of Sub 2-144 (where a= 0, b=1, Y= C)

Synthesis of Sub 2-I-144

In a round-bottomed flask, 3-bromo-9,9-dimethyl-9H-fluorene (50 g, 183.04 mmol), 2-Nitrophenyl boronic acid (36.6 g, 219.28 mmol), Pd(PPh ₃ ) ₄ (8.4 g, 7.25 mmol), NaOH (22 g, 549.11 mmol), THF (805 mL)/H ₂ O (402 mL) were added. Using the above Sub 2-I-1 synthetic method, the product Sub 2-I-144 (47.72 g, 69%) was obtained.

Synthesis of Sub 2-II-144

Sub 2-I-144 (47 g, 149 mmol), PPh ₃ (97.7 g, 372.48 mmol), o -Dichlorobenzene (596 mL) were added to a round-bottomed flask, and the product Sub 2-II-144 (30.41 g, 72%) was obtained using the synthetic method of Sub 2-II-1.

Synthesis of Sub 2-III-144

Sub 2-II-144 (30 g, 89 mmol), N-Bromosuccinimide (18.8 g, 105.9 mmol), and methylene chloride (318 mL) were added to a round-bottomed flask, and the product Sub 2-III-144 (18.24 g, 53%) was obtained using the synthetic method of Sub 2-III-1.

Synthesis of Sub 2-144

Sub 2-III-144 (18 g, 49.7 mmol), Iodobenzene (12.26 g, 60.1 mmol), Pd ₂ (dba) ₃ (1.83 g, 2 mmol), P(t-Bu) ₃ (1.01 g, 4.97 mmol), NaO(t-Bu) (14.4 g, 149.9 mmol), toluene (109 mL) were added to a round-bottomed flask. The product Sub 2-144 (15.03 g, 69%) was obtained using the synthetic method of Sub 2-1.

Example of Sub 2

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

compound FD-MS compound FD-MS Sub 2-1 m/z=427.00(C24HBrNS=428.34) Sub 2-2 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-3 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-4 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 2-5 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 2-6 m/z=483.07(C ₂₈ H ₂₂ BrNS=484.45) Sub 2-7 m/z=507.03(C ₂₉ H ₁₈ BrNOS=508.43) Sub 2-8 m/z=467.03(C ₂₇ H ₁₈ BrNS=468.41) Sub 2-9 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-10 m/z=427.00(C24HBrNS=428.34) Sub 2-11 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-12 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-13 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 2-14 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 2-15 m/z=582.05(C ₃₃ H ₁₉ BrN ₄ S=583.50) Sub 2-16 m/z=581.06(C ₃₄ H ₂₀ BrN ₃ S=582.51) Sub 2-17 m/z=581.06(C ₃₄ H ₂₀ BrN ₃ S=582.51) Sub 2-18 m/z=581.06(C ₃₄ H ₂₀ BrN ₃ S=582.51) Sub 2-19 m/z=555.04(C ₃₂ H ₁₈ BrN ₃ S=556.47) Sub 2-20 m/z=611.01(C ₃₄ H ₁₈ BrN ₃ S ₂ =612.56) Sub 2-21 m/z=681.09(C ₄₂ H ₂₄ BrN ₃ S=682.63) Sub 2-22 m/z=542.05(C ₃₂ H ₁₉ BrN ₂ S=543.48) Sub 2-23 m/z=665.08(C ₄₃ H ₂₄ BrNS=666.63) Sub 2-24 m/z=599.11(C ₃₆ H ₁₈ D ₅ BrN ₂ S=600.58) Sub 2-25 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-26 m/z=502.01(C ₂₉ H ₁₅ BrN ₂ S=503.41) Sub 2-27 m/z=629.08(C ₄₀ H ₂₄ BrNS=630.59) Sub 2-28 m/z=605.06(C ₃₆ H ₂₀ BrN ₃ S =606.53) Sub 2-29 m/z=657.09(C ₄₀ H ₂₄ BrN ₃ S=658.61) Sub 2-30 m/z=631.07(C ₃₈ H ₂₂ BrN ₃ S=632.57) Sub 2-31 m/z=720.09(C ₄₅ H ₂₅ BrN ₂ OS=721.66) Sub 2-32 m/z=593.08(C ₃₇ H ₂₄ BrNS=594.56) Sub 2-33 m/z=471.99(C ₂₄ H ₁₃ BrN ₂ O ₂ S=473.34) Sub 2-34 m/z=503.03(C ₃₀ H ₁₈ BrNS=504.44) Sub 2-35 m/z=477.02(C ₂₈ H ₁₆ BrNS=478.40) Sub 2-36 m/z=508.07(C ₃₀ H ₁₃ D ₅ BrNS=509.47) Sub 2-37 m/z=411.03(C ₂₄ H ₁₄ BrNO=412.28) Sub 2-38 m/z=655.09(C ₄₀ H ₂₂ BrN ₃ O ₂ =656.53) Sub 2-39 m/z=539.06(C ₃₂ H ₁₈ BrN ₃ O=540.41) Sub 2-40 m/z=645.05(C ₃₈ H ₂₀ BrN ₃ OS=646.55) Sub 2-41 m/z=461.04(C ₂₈ H ₁₆ BrNO=462.34) Sub 2-42 m/z=487.06(C ₃₀ H ₁₈ BrNO=488.37) Sub 2-43 m/z=537.07(C ₃₄ H ₂₀ BrNO=538.43) Sub 2-44 m/z=437.08(C ₂₇ H ₂₀ BrN=438.36) Sub 2-45 m/z=453.05(C ₂₀ H ₂₀ BrNSi=453.43) Sub 2-46 m/z=474.95(C ₂₄ H ₁₄ BrNSi=478.24)

Example of Sub 3

Meanwhile, compounds belonging to Sub 3 may include, but are not limited to, the compounds below, and Table 3 shows the FD-MS values of compounds belonging to Sub 3.

compound FD-MS compound FD-MS Sub 3-1 m/z=287.11(C ₁₈ H ₁₄ BNO ₂ =287.12) Sub 3-2 m/z=287.11(C ₁₈ H ₁₄ BNO ₂ =287.12) Sub 3-3 m/z=287.11(C ₁₈ H ₁₄ BNO ₂ =287.12) Sub 3-4 m/z=287.11(C ₁₈ H ₁₄ BNO ₂ =287.12) Sub 3-5 m/z=337.13(C ₂₂ H ₁₆ BNO ₂ =337.18) Sub 3-6 m/z=337.13(C ₂₂ H ₁₆ BNO ₂ =337.18) Sub 3-7 m/z=337.13(C ₂₂ H ₁₆ BNO ₂ =337.18) Sub 3-8 m/z=337.13(C ₂₂ H ₁₆ BNO ₂ =337.18) Sub 3-9 m/z=337.13(C ₂₂ H ₁₆ BNO ₂ =337.18) Sub 3-10 m/z=363.14(C ₂₄ H ₁₈ BNO ₂ =363.22) Sub 3-11 m/z=363.14(C ₂₄ H ₁₈ BNO ₂ =363.22) Sub 3-12 m/z=368.17(C ₂₄ H ₁₃ D ₅ BNO ₂ =368.25) Sub 3-13 m/z=387.14(C ₂₆ H ₁₈ BNO ₂ =387.24) Sub 3-14 m/z=437.16(C ₃₀ H ₂₀ BNO ₂ =437.30) Sub 3-15 m/z=413.16(C ₂₈ H ₂₀ BNO ₂ =413.27) Sub 3-16 m/z=429.13(C ₂₈ H ₁₇ BFNO ₂ =429.25) Sub 3-17 m/z=368.17(C ₂₄ H ₁₃ D ₅ BNO ₂ =368.25) Sub 3-18 m/z=482.18(C ₃₁ H ₂₃ BNO ₃ =482.34) Sub 3-19 m/z=452.17(C ₃₀ H ₂₁ BN ₂ O ₂ =452.31) Sub 3-20 m/z=364.14(C ₂₃ H ₁₇ BN ₂ O ₂ =364.20) Sub 3-21 m/z=442.16(C ₂₇ H ₁₉ BN ₄ O ₂ =442.28) Sub 3-22 m/z=441.16(C ₂₈ H ₂₀ BN ₃ O ₂ =441.29) Sub 3-23 m/z=441.26(C ₂₈ H ₂₀ BN ₃ O ₂ =441.29) Sub 3-24 m/z=442.16(C ₂₇ H ₁₉ BN ₄ O ₂ =442.28) Sub 3-25 m/z=441.16(C ₂₈ H ₂₀ BN ₃ O ₂ =441.29) Sub 3-26 m/z=517.20(C ₃₄ H ₂₄ BN ₃ O ₂ =517.38) Sub 3-27 m/z=528.25(C ₃₃ H ₁₃ D ₁₀ BN ₄ O ₂ =528.43) Sub 3-28 m/z=455.14(C ₂₈ H ₁₈ BN ₃ O ₃ =455.27) Sub 3-29 m/z=505.16(C ₃₂ H ₂₀ BN ₃ O ₃ =505.33) Sub 3-30 m/z=444.11(C ₂₇ H ₁₇ BN ₂ O ₂ S=444.31) Sub 3-31 m/z=547.15(C ₃₄ H ₂₂ BN ₃ O ₂ S=547.43) Sub 3-32 m/z=415.15(C ₂₆ H ₁₈ BN ₃ O ₂ =415.25) Sub 3-33 m/z=465.16(C ₃₀ H ₂₀ BN ₃ O ₂ =465.31) Sub 3-34 m/z=565.20(C ₃₈ H ₂₄ BN ₃ O ₂ =565.43) Sub 3-35 m/z=465.16(C ₃₀ H ₂₀ BN ₃ O ₂ =465.31) Sub 3-36 m/z=228.04(C ₁₂ H ₉ BO ₂ S=228.07) Sub 3-37 m/z=228.04(C ₁₂ H ₉ BO ₂ S=228.07) Sub 3-38 m/z=228.04(C ₁₂ H ₉ BO ₂ S=228.07) Sub 3-39 m/z=278.06(C ₁₆ H ₁₁ BN ₂ S=278.13) Sub 3-40 m/z=278.06(C ₁₆ H ₁₁ BO ₂ S=278.13) Sub 3-41 m/z=278.06(C ₁₆ H ₁₁ BO ₂ S=278.13) Sub 3-42 m/z=305.07(C ₁₇ H ₁₂ BNO ₂ S=305.16) Sub 3-43 m/z=212.06(C ₁₂ H ₉ BO ₃ =212.01) Sub 3-44 m/z=212.06(C ₁₂ H ₉ BO ₃ =212.01) Sub 3-45 m/z=212.06(C ₁₂ H ₉ BO ₃ =212.01) Sub 3-46 m/z=262.08(C ₁₆ H ₁₁ BO ₃ =262.07) Sub 3-47 m/z=312.10(C ₂₀ H ₁₃ BO ₃ =312.13) Sub 3-48 m/z=289.09(C ₁₇ H ₁₂ BNO ₃ =289.09) Sub 3-49 m/z=238.12(C ₁₅ H ₁₅ BO ₂ =238.09) Sub 3-50 m/z=238.12(C ₁₅ H ₁₅ BO ₂ =238.09) Sub 3-51 m/z=266.15(C ₁₇ H ₁₉ BO ₂ =266.14) Sub 3-52 m/z=362.15(C ₂₅ H ₁₉ BO ₂ =362.23) Sub 3-53 m/z=438.18(C ₃₁ H ₂₃ BO ₂ =438.32) Sub 3-54 m/z=360.13(C ₂₄ H ₁₇ BO ₂ =360.21) Sub 3-55 m/z=410.15(C ₂₉ H ₁₉ BO ₂ =410.27) Sub 3-56 m/z=254.09(C ₁₄ H ₁₅ BO ₂ Si=254.16) Sub 3-57 m/z=254.09(C ₁₄ H ₁₅ BO ₂ Si=254.16) Sub 3-58 m/z=282.12(C ₁₆ H ₁₉ BO ₂ Si=282.22) Sub 3-59 m/z=378.12(C ₂₄ H ₁₉ BO ₂ Si=387.30) Sub 3-60 m/z=378.12(C ₂₄ H ₁₉ BO ₂ Si=378.30) Sub 3-61 m/z=376.11(C ₂₄ H ₁₇ BO ₂ Si=376.29) Sub 3-62 m/z=275.99(C ₁₂ H ₉ BO ₂ Se=274.97) Sub 3-63 m/z=275.99(C ₁₂ H ₉ BO ₂ Se=274.97) Sub 3-64 m/z=326.00(C ₁₆ H ₁₁ BO ₂ Se=325.03)

Synthesis method of product of chemical formula 1

Add Sub 1 or Sub 2 compound (1 equivalent) to a round bottom flask, and add Sub 3 compound (1 equivalent), Pd(PPh ₃ ) ₄ (0.03 to 0.05 equivalent), NaOH (3 equivalents), THF (3 mL / 1 mmol), and water (1.5 mL / 1 mmol). Then, heat and reflux at 80°C. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. Dry the organic layer with MgSO ₄ and concentrate, and recrystallize the resulting compound with toluene and acetone to obtain the product.

Synthesis of compound 1-2

Add Sub 1-2 (5 g, 11.5 mmol), Sub 3-3 (3.9 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) to a round-bottomed flask. Then, heat and reflux at 80 ℃ for 8 hours. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. Dry the organic layer over MgSO ₄ and concentrate, and recrystallize the resulting compound with toluene and acetone to obtain product 1-2 (5.4 g, 80%).

Synthesis of compounds 1-7

Sub 1-3 (10 g, 20 mmol), Sub 3-3 (5.7 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol), NaOH (2.4 g, 59 mmol), THF (40 mL)/H ₂ O (20 mL) were used to obtain product 1-7 (11.3 g, 85%) using the synthetic method of 1-2.

Synthesis of compounds 1-14

Sub 1-5 (10 g, 21 mmol), Sub 3-10 (7.6 g, 21 mmol), Pd(PPh ₃ ) ₄ (1 g, 0.8 mmol), NaOH (2.5 g, 63 mmol), THF (40 mL)/H ₂ O (20 mL) were used to obtain product 1-14 (12.3 g, 82%) using the synthetic method described in 1-2.

Synthesis of compounds 1-20

Sub 1-1 (10 g, 21 mmol), Sub 3-11 (7.6 g, 21 mmol), Pd(PPh ₃ ) ₄ (1 g, 0.8 mmol), NaOH (2.5 g, 63 mmol), THF (40 mL)/H ₂ O (20 mL) were used to obtain product 1-20 (12.5 g, 83%) using the synthetic method of 1-2 above.

Synthesis of compound 1-26

Sub 1-6 (5 g, 11.5 mmol), Sub 3-3 (3.9 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were used to obtain product 1-26 (4.9 g, 72%) using the synthetic method described in 1-2.

Synthesis of compound 1-27

Sub 1-6 (5 g, 11.5 mmol), Sub 3-10 (4.2 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were used to obtain product 1-27 (6.5 g, 85%) using the synthetic method described in 1-2.

Synthesis of compound 1-33

Sub 1-7 (10 g, 20 mmol), Sub 3-11 (7.3 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol), NaOH (2.4 g, 59 mmol), THF (40 mL)/H ₂ O (20 mL) were used to obtain product 1-33 (13.5 g, 91%) using the synthetic method described in 1-2.

Synthesis of compound 1-51

Sub 1-6 (5 g, 11.5 mmol), Sub 3-1 (3.9 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were used to obtain product 1-51 (3.5 g, 51%) using the synthetic method of 1-2.

Synthesis of compound 1-52

Sub 1-6 (5 g, 11.5 mmol), Sub 3-2 (3.9 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were used to obtain product 1-52 (3.8 g, 56%) using the synthetic method of 1-2.

Synthesis of compound 1-53

Sub 1-6 (5 g, 11.5 mmol), Sub 3-4 (3.9 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were used to obtain product 1-53 (4.2 g, 62%) using the synthetic method described in 1-2.

Synthesis of compound 1-66

Sub 1-14 (10 g, 21 mmol), Sub 3-3 (7.6 g, 21 mmol), Pd(PPh ₃ ) ₄ (1 g, 0.8 mmol), NaOH (2.5 g, 63 mmol), THF (40 mL)/H ₂ O (20 mL) were used to obtain product 1-66 (8.5 g, 63%) using the synthetic method of 1-2.

Synthesis of compound 1-71

Sub 1-1 (5 g, 11.5 mmol), Sub 3-46 (3.0 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were placed in a round-bottomed flask and the product 1-71 (4.7 g, 73%) was obtained using the synthetic method of 1-2.

Synthesis of compound 1-78

Sub 1-4 (5 g, 9.9 mmol), Sub 3-53 (4.3 g, 9.9 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 29.7 mmol), THF (40 mL)/H ₂ O (20 mL) were placed in a round-bottomed flask and the product 1-78 (5.3 g, 65%) was obtained using the synthetic method described in 1-2.

Synthesis of compound 1-90

Sub 1-39 (10 g, 20.5 mmol), Sub 3-38 (5.9 g, 20.5 mmol), Pd(PPh ₃ ) ₄ (1 g, 0.8 mmol), NaOH (2.5 g, 61 mmol), THF (40 mL)/H ₂ O (20 mL) were placed in a round-bottomed flask and the product 1-90 (5.8 g, 48%) was obtained using the synthetic method described in 1-2.

Synthesis of compound 2-1

Sub 2-1 (5 g, 11.5 mmol), Sub 3-3 (3.9 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were placed in a round-bottom flask and the product 2-1 (5.5 g, 81%) was obtained using the synthetic method described in 1-2.

Synthesis of compound 2-2

Sub 2-1 (5 g, 11.5 mmol), Sub 3-10 (4.2 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were placed in a round-bottom flask and the product 2-2 (6.1 g, 80%) was obtained using the synthetic method of 1-2.

Synthesis of compound 2-3

In a round-bottom flask, Sub 2-1 (5 g, 11.5 mmol), Sub 3-11 (4.2 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were placed, and the product 2-3 (5.8 g, 76%) was obtained using the synthetic method of 1-2.

Synthesis of compounds 2-6

Sub 2-2 (10 g, 20 mmol), Sub 3-3 (5.7 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol), NaOH (2.4 g, 59 mmol), THF (40 mL)/H ₂ O (20 mL) were placed in a round-bottom flask and the product 2-6 (10.3 g, 81%) was obtained using the synthetic method of 1-2.

Synthesis of compounds 2-7

Sub 2-2 (10 g, 20 mmol), Sub 3-10 (7.3 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol), NaOH (2.4 g, 59 mmol), THF (40 mL)/H ₂ O (20 mL) were placed in a round-bottom flask and the product 2-7 (11 g, 74%) was obtained using the synthetic method of 1-2.

Synthesis of compound 2-8

Sub 2-2 (10 g, 20 mmol), Sub 3-11 (7.3 g, 20 mmol), Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol), NaOH (2.4 g, 59 mmol), THF (40 mL)/H ₂ O (20 mL) were placed in a round-bottom flask and the product 2-8 (12 g, 81%) was obtained using the synthetic method of 1-2.

Synthesis of compound 2-33

Sub 2-1 (5 g, 11.5 mmol), Sub 3-38 (2.6 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were placed in a round-bottom flask and the product 2-1 (5.0 g, 82%) was obtained using the synthetic method described in 1-2.

Synthesis of compound 2-38

Sub 2-1 (5 g, 11.5 mmol), Sub 3-45 (2.4 g, 11.5 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol), NaOH (1.4 g, 35 mmol), THF (30 mL)/H ₂ O (15 mL) were placed in a round-bottom flask and the product 2-1 (4.4 g, 74%) was obtained using the synthetic method of 1-2 above.

Synthesis of compound 2-133

Sub 2-37 (5 g, 12 mmol), Sub 3-10 (4.4 g, 12 mmol), Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.5 g, 36 mmol), THF (30 mL)/H ₂ O (15 mL) were placed in a round-bottomed flask and the product 2-133 (5.6 g, 72%) was obtained using the synthetic method described in 1-2.

compound FD-MS compound FD-MS 1-1 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-2 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-3 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-4 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-5 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-6 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-7 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-8 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 1-9 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 1-10 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-11 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-12 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-13 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-14 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-15 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-16 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-17 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-18 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-19 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-20 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-21 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-22 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-23 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-24 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-25 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-26 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-27 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-28 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-29 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-30 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-31 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-32 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 1-33 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 1-34 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-35 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-36 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 1-37 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 1-38 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 1-39 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-40 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-41 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-42 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-43 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-44 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-45 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-46 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-47 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-48 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 1-49 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-50 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 1-51 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-52 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-53 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 1-54 m/z=531.11(C ₃₆ H ₂₁ NS ₂ =531.69) 1-55 m/z=531.11(C ₃₆ H ₂₁ NS ₂ =531.69) 1-56 m/z=515.13(C ₃₆ H ₂₁ NOS=515.62) 1-57 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=743.90) 1-58 m/z=870.28(C ₆₂ H ₃₈ N ₄ S=871.06) 1-59 m/z=768.23(C ₅₄ H ₃₂ N ₄ S=768.92) 1-60 m/z=718.22(C ₅₀ H ₃₀ N ₄ S=718.87) 1-61 m/z=931.30(C ₆₈ H ₄₁ N ₃ S=932.14) 1-62 m/z=808.23(C ₅₆ H ₃₂ N ₄ OS=808.94) 1-63 m/z=850.22(C ₅₈ H ₃₄ N ₄ S ₂ =851.05) 1-64 m/z=831.32(C ₅₇ H ₂₅ D ₁₀ N ₅ S=832.05) 1-65 m/z=768.23(C ₅₄ H ₃₂ N ₄ S=768.92) 1-66 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 1-67 m/z=531.11(C ₃₆ H ₂₁ NS ₂ =531.69) 1-68 m/z=708.17(C ₄₉ H ₂₈ N ₂ S ₂ =708.89) 1-69 m/z=733.19(C ₅₂ H ₃₁ NS ₂ =733.94) 1-70 m/z=708.17(C ₄₉ H ₂₈ N ₂ S ₂ =708.89) 1-71 m/z=565.15(C ₄₀ H ₂₃ NOS=565.68) 1-72 m/z=822.25(C ₅₇ H ₃₄ N ₄ OS=822.97) 1-73 m/z=809.21(C ₅₆ H ₃₁ N ₃ O ₂ S=809.93) 1-74 m/z=781.13(C ₅₂ H ₃₁ NSSe=780.83) 1-75 m/z=681.08(C4 ₂ H ₂₃ N ₃ SSe=680.68) 1-76 m/z=585.19(C ₄₀ H ₃₁ NSSi=585.83) 1-77 m/z=809.23(C ₅₆ H ₃₅ N ₃ SSi=810.05) 1-78 m/z=817.28(C ₆₁ H ₃₉ NS=818.03) 1-79 m/z=817.26(C ₅₉ H ₃₅ N ₃ S=817.99) 1-80 m/z=742.28(C ₅₀ H ₃₀ N ₄ OS=742.93) 1-81 m/z=574.20(C ₄₂ H ₂₆ N ₂ O=574.67) 1-82 m/z=624.22(C ₄₆ H ₂₈ N ₂ O=624.73) 1-83 m/z=852.29(C ₆₂ H ₃₆ N ₄ O=852.98) 1-84 m/z=834.25(C ₅₈ H ₃₄ N ₄ OS=834.98) 1-85 m/z=649.24(C ₄₉ H ₃₁ NO=649.78) 1-86 m/z=829.24(C ₆₁ H ₃₅ NOS=830.00) 1-87 m/z=665.22(C ₄₈ H ₃₁ NOSi=665.85) 1-88 m/z=563.08(C ₃₆ H ₂₁ NOSe=562.52) 1-89 m/z=600.26(C ₄₅ H ₃₂ N ₂ =600.75) 1-90 m/z=591.20(C ₄₃ H ₂₉ NS=591.76) 1-91 m/z=525.21(C ₃₉ H ₂₇ NO=525.64) 1-92 m/z=551.26(C ₄₂ H ₃₃ N=551.72) 1-93 m/z=616.23(C ₄₄ H ₃₂ N ₂ Si=616.82) 1-94 m/z=541.19(C ₃₈ H ₂₇ NOSi=541.71) 1-95 m/z=557.16(C ₃₈ H ₂₇ NSSi=557.78) 1-96 m/z=638.13(C ₄₂ H ₂₆ N ₂ Se=637.63) 1-97 m/z=563.08(C ₃₆ H ₂₁ NOSe=562.52) 1-98 m/z=589.13(C ₃₉ H ₂₇ NSe=588.60) 2-1 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-2 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-3 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-4 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-5 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-6 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-7 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-8 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-9 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-10 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-11 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-12 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-13 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-14 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-15 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-16 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-17 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-18 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-19 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-20 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-21 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-22 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-23 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-24 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-25 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-26 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-27 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-28 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-29 m/z=746.28(C ₅₄ H ₃₈ N ₂ S=746.96) 2-30 m/z=796.25(C ₅₇ H ₃₆ N ₂ OS=796.97) 2-31 m/z=780.26(C ₅₇ H ₃₆ N ₂ S=780.97) 2-32 m/z=743.24(C ₅₃ H ₃₃ N ₃ S=743.91) 2-33 m/z=531.11(C ₃₆ H ₂₁ NS ₂ =531.69) 2-34 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.78) 2-35 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.78) 2-36 m/z=581.13(C ₄₀ H ₂₃ NS ₂ =581.75) 2-37 m/z=581.13(C ₄₀ H ₂₃ NS ₂ =581.75) 2-38 m/z=515.13(C ₃₆ H ₂₁ NOS=515.62) 2-39 m/z=591.17(C ₄₂ H ₂₅ NOS=591.72) 2-40 m/z=591.17(C ₄₂ H ₂₅ NOS=591.72) 2-41 m/z=565.15(C ₄₀ H ₂₃ NOS=565.68) 2-42 m/z=565.15(C ₄₀ H ₂₃ NOS=565.68) 2-43 m/z=541.19(C ₃₉ H ₂₇ NS=541.70) 2-44 m/z=617.21(C ₄₅ H ₃₁ NS=617.80) 2-45 m/z=617.21(C ₄₅ H ₃₁ NS=617.80) 2-46 m/z=591.20(C ₄₃ H ₂₉ NS=591.76) 2-47 m/z=591.20(C ₄₃ H ₂₉ NS=591.76) 2-48 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-49 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-50 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-51 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-52 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-53 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-54 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-55 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-56 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-57 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-58 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-59 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-60 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-61 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-62 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-63 m/z=742.24(C ₅₄ H ₃₄ N ₂ S=742.93) 2-64 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-65 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-66 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-67 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-68 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-69 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-70 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-71 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-72 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-73 m/z=716.23(C ₅₂ H ₃₂ N ₂ S=716.89) 2-74 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-75 m/z=690.21(C ₅₀ H ₃₀ N ₂ S=690.85) 2-76 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-77 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-78 m/z=590.18(C ₄₂ H ₂₆ N ₂ S=590.73) 2-79 m/z=581.13(C ₄₀ H ₂₃ NS ₂ =581.75) 2-80 m/z=581.13(C ₄₀ H ₂₃ NS ₂ =581.75) 2-81 m/z=515.13(C ₃₆ H ₂₁ NOS=515.62) 2-82 m/z=591.17(C ₄₂ H ₂₅ NOS=591.72) 2-83 m/z=591.17(C ₄₂ H ₂₅ NOS=591.72) 2-84 m/z=565.15(C ₄₀ H ₂₃ NOS=565.68) 2-85 m/z=565.15(C ₄₀ H ₂₃ NOS=565.68) 2-86 m/z=541.19(C ₃₉ H ₂₇ NS=541.70) 2-87 m/z=617.21(C ₄₅ H ₃₁ NS=617.80) 2-88 m/z=617.21(C ₄₅ H ₃₁ NS=617.80) 2-89 m/z=531.11(C ₃₆ H ₂₁ NS ₂ =531.69) 2-90 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.78) 2-91 m/z=607.14(C ₄₂ H ₂₅ NS ₂ =607.78) 2-92 m/z=591.20(C ₄₃ H ₂₉ NS=591.76) 2-93 m/z=591.20(C ₄₃ H ₂₉ NS=591.76) 2-94 m/z=745.23(C ₅₁ H ₃₁ N ₅ S=745.89) 2-95 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=744.90) 2-96 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=744.90) 2-97 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=744.90) 2-98 m/z=718.22(C ₅₀ H ₃₀ N ₄ S=718.87) 2-99 m/z=745.23(C ₅₁ H ₃₁ N ₅ S=745.89) 2-100 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=744.90) 2-101 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=744.90) 2-102 m/z=744.23(C ₅₂ H ₃₂ N ₄ S=744.90) 2-103 m/z=718.22(C ₅₀ H ₃₀ N ₄ S=718.87) 2-104 m/z=768.24(C ₅₄ H ₃₂ N ₄ S=768.92) 2-105 m/z=834.25(C ₅₈ H ₃₄ N ₄ OS=834.98) 2-106 m/z=900.24(C ₆₂ H ₃₆ N ₄ S ₂ =901.11) 2-107 m/z=844.27(C ₆₀ H ₃₆ N ₄ S=845.02) 2-108 m/z=847.25(C ₆₀ H ₃ FN ₃ S=848.00) 2-109 m/z=745.23(C ₅₁ H ₃₁ N ₅ S=745.89) 2-110 m/z=909.32(C ₆₇ H ₃₅ D ₅ N ₂ S=910.14) 2-111 m/z=747.18(C ₅₁ H ₂₉ N ₃ S ₂ =747.93) 2-112 m/z=762.29(C ₅₄ H ₃₀ D ₅ N ₃ S=762.97) 2-113 m/z=789.25(C ₅₉ H ₃₅ NS=789.98) 2-114 m/z=860.26(C ₆₀ H ₃₆ N ₄ OS=861.02) 2-115 m/z=515.13(C ₃₆ H ₂₁ NOS=515.62) 2-116 m/z=717.21(C ₅₂ H ₃₁ NOS=717.87) 2-117 m/z=770.21(C ₅₃ H ₃₀ N ₄ S=770.90) 2-118 m/z=845.25(C ₆₀ H ₃₅ N ₃ OS=846.00) 2-119 m/z=699.14(C ₄₆ H ₂₅ N ₃ S ₂ =699.84) 2-120 m/z=581.13(C ₄₀ H ₂₃ NS ₂ =581.75) 2-121 m/z=785.20(C ₅₄ H ₃₁ N ₃ S ₂ =785.97) 2-122 m/z=824.20(C ₅₇ H ₃₂ N ₂ OS ₂ =825.01) 2-123 m/z=697.19(C ₄₉ H ₃₁ NS ₂ =697.91) 2-124 m/z=624.04(C ₃₆ H ₂₀ N ₂ O ₂ SSe=623.58) 2-125 m/z=666.21(C ₄₈ H ₃₀ N ₂ S=666.83) 2-126 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-127 m/z=640.20(C ₄₆ H ₂₈ N ₂ S=640.79) 2-128 m/z=671.24(C ₄₈ H ₂₅ D ₅ N ₂ S=671.86) 2-129 m/z=671.24(C ₄₈ H ₂₅ D ₅ N ₂ S=671.86) 2-130 m/z=557.16(C ₃₈ H ₂₇ NSSi=557.78) 2-131 m/z=579.06(C ₃₆ H ₂₁ NSSe=579.58) 2-132 m/z=681.19(C ₄₈ H ₃₁ NSSi=681.92) 2-133 m/z=574.20(C ₄₂ H ₂₆ N ₂ O=574.67) 2-134 m/z=650.24(C ₄₈ H ₃₀ N ₂ O=650.76) 2-135 m/z=664.22(C ₄₈ H ₂₈ N ₂ O ₂ =664.75) 2-136 m/z=818.27(C ₅₈ H ₃₄ N ₄ O ₂ =818.92) 2-137 m/z=758.21(C ₅₂ H ₃₀ N ₄ OS=758.89) 2-138 m/z=702.24(C ₅₀ H ₃₀ N ₄ O=702.80) 2-139 m/z=729.25(C ₅₁ H ₃₁ N ₅ O=729.82) 2-140 m/z=759.23(C ₅₃ H ₃₃ N ₃ OS=759.91) 2-141 m/z=697.24(C ₅₃ H ₃₁ NO=697.82) 2-142 m/z=739.23(C ₅₄ H ₃₃ NOSi=739.93) 2-143 m/z=739.14(C ₅₀ H ₂₉ NOSe=738.73) 2-144 m/z=650.27(C ₄₉ H ₃₄ N ₂ =650.81) 2-145 m/z=591.20(C ₄₃ H ₂₉ NO=591.76) 2-146 m/z=525.21(C ₃₉ H ₂₇ NO=525.64) 2-147 m/z=551.26(C ₄₂ H ₃₃ =551.72) 2-148 m/z=616.23(C ₄₄ H ₃₂ N ₂ Si=616.82) 2-149 m/z=557.16(C ₃₈ H ₂₇ NSSi=557.78) 2-150 m/z=541.19(C ₃₈ H ₂₇ NOSi=541.71) 2-151 m/z=583.22(C ₄₀ H ₃₃ NSi ₂ =583.87) 2-152 m/z=638.13(C ₄₂ H ₂₆ N ₂ Se=637.63) 2-153 m/z=579.06(C ₃₆ H ₂₁ NSSe=578.58) 2-154 m/z=589.13(C ₃₉ H ₂₇ NSe=588.60)

[Synthesis Example 2]

The compound (final product 2) represented by chemical formula (2) according to the present invention is prepared by reacting Sub 4 and Sub 5 as shown in the following reaction scheme 4.

<Reaction Formula 4>

Sub 4 Synthesis Example

Sub 4 of Scheme 4 can be synthesized by the reaction path of Scheme 5 below, but is not limited thereto. (A and B are as defined in Chemical Formula 2 above)

<Reaction Formula 5>

1. Sub 4-1 Synthesis Example

(1) Sub 4-a-1 Synthesis

1-bromonaphthalene (50.0 g, 241 mmol), bis(pinacolato)diboron (67.4 g, 266 mmol), KOAc (71 g, 724 mmol), PdCl ₂ (dppf) (5.30 g, 7.24 mmol) were dissolved in DMF (1 L) and refluxed at 120°C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic matter was recrystallized using CH ₂ Cl ₂ and methanol to obtain 45.4 g (yield: 74%) of the desired product.

(2) Sub 4-1b Synthesis

Sub 4-a-1 (45.4 g, 179 mmol), 1-bromo-2-nitrobenzene (36.1 g, 179 mmol), K ₂ CO ₃ (74.1 g, 536 mmol), Pd(PPh ₃ ) ₄ (12.4 g, 10.7 mmol) obtained above were placed in a round-bottomed flask, THF (800 mL) and water (400 mL) were added, and the mixture was dissolved and refluxed at 80 ℃ for 12 hours. After the reaction was completed, the temperature of the reaction product was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. The organic layer was dried over MgSO ₄ and concentrated. The generated organic matter was separated using a silica gel column to obtain 37.0 g (yield: 83%) of the desired product.

(3) Sub 4-1 Synthesis

Sub 4-b-1 (37.0 g, 148 mmol) and triphenylphosphine (97.3 g, 37.1 mmol) obtained above were dissolved in o -dichlorobenzene (800 mL) and refluxed at 200 ^o C for 24 hours. After the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was purified through a silica gel column and recrystallized to obtain 26.1 g (yield: 81%) of the desired product.

2. Sub 4-10 Synthesis Example

(1) Sub 4-a-10 Synthesis

3-bromo-1,1'-biphenyl (50.0 g, 214 mmol), bis(pinacolato)diboron (59.9 g, 236 mmol), KOAc (63.2 g, 643 mmol), PdCl ₂ (dppf) (4.71 g, 6.43 mmol) were reacted in the same manner as in Sub 4-a-1 to obtain 45.1 g of the product (yield: 75%).

(2) Sub 4-b-10 synthesis

Sub 4-a-10 (45.1 g, 161 mmol), 2-bromo-3-nitronaphthalene (40.6 g, 161 mmol), K ₂ CO ₃ (66.7 g, 483 mmol), Pd(PPh ₃ ) ₄ (11.2 g, 9.65 mmol) obtained above were prepared in the same manner as in Sub 4-b-1, to obtain 44.0 g of the product (yield: 84%).

(3) Sub 4-10 Synthesis

Sub 4-b-10 (44.0 g, 135 mmol) and triphenylphosphine (88.6 g, 338 mmol) obtained above were treated in the same manner as in the experimental method of Sub 4-1 to obtain 34.5 g of the product (yield: 87%).

3. Sub 4-12 Synthesis Example

(1) Sub 4-c-12 Synthesis

In a round-bottomed flask, 1-bromo-4-chlorobenzene (50.0 g, 261 mmol) was dissolved in toluene, and 3-bromonaphthalen-2-amine (58.0 g, 261 mmol), Pd ₂ (dba) ₃ (7.17 g, 7.83 mmol), P( t -Bu) ₃ (3.17 g, 15.7 mmol), and NaO t -Bu (50.2 g, 522 mmol) were added and stirred at 100°C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The resulting compound was recrystallized after applying a silica gel column to obtain 66.9 g of the product (yield: 77%).

(2) Sub 4-d-12 synthesis

Sub 4-c-12 (66.9 g, 201 mmol) was added to DMA (400 mL), followed by Pd(OAc) ₂ (1.35 g, 6.03 mmol), K ₂ CO ₃ (83.4 g, 603 mmol), P(t-Bu) ₃ H BF ₄ (15.1 mL, 12.1 mmol) and stirred at 90 °C. When the reaction was complete, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 43.0 g of the product (yield: 85%).

(3) Sub 4-12 Synthesis

Sub 4-d-12 (43.0 g, 171 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (63.1 g, 171 mmol), K ₂ CO ₃ (70.9 g, 513 mmol), Pd(PPh ₃ ) ₄ (11.9 g, 10.3 mmol) obtained above were prepared in the same manner as in Sub 4-b-1, obtaining 68.2 g of the product (yield: 87%).

4. Sub 4-18 Synthesis Example

(1) Sub 4-a-18 Synthesis

1-bromonaphthalene (50.0 g, 241 mmol), bis(pinacolato)diboron (67.4 g, 266 mmol), KOAc (71.1 g, 724 mmol), PdCl ₂ (dppf) (5.30 g, 7.24 mmol) were prepared in the same manner as in Sub 4-a-1, to obtain 44.2 g of the product (yield: 72%).

(2) Sub 4-b-18 synthesis

Sub 4-a-18 (44.2 g, 174 mmol), 1-bromo-2-nitronaphthalene (43.8 g, 174 mmol), K ₂ CO ₃ (72.1 g, 522 mmol), Pd(PPh ₃ ) ₄ (12.1 g, 10.4 mmol) obtained above were prepared in the same manner as in Sub 4-b-1, to obtain 42.2 g of the product (yield: 81%).

(3) Sub 4-18 Synthesis

Sub 4-b-18 (42.2 g, 141 mmol) and triphenylphosphine (92.3 g, 352 mmol) obtained above were prepared in the same manner as in the experimental method of Sub 4-1, to obtain 31.6 g of the product (yield: 84%).

5. Sub 4-35 Synthesis Example

(1) Sub 4-c-35 Synthesis

1-bromonaphthalene (50.0 g, 241 mmol), 2-chloronaphthalen-1-amine (42.9 g, 241 mmol), Pd ₂ (dba) ₃ (6.63 g, 7.24 mmol), P( t -Bu) ₃ (2.93 g, 14.5 mmol), NaO t -Bu (46.4 g, 483 mmol) were reacted in the same manner as in Sub 4-c-12 to obtain 52.1 g of the product (yield: 71%).

(2) Sub 4-35 Synthesis

Sub 4-c-35 (52.1 g, 171 mmol), Pd(OAc) ₂ (1.15 g, 5.14 mmol), K ₂ CO ₃ (71.1 g, 514 mmol), P(t-Bu) ₃ H BF ₄ (12.9 mL, 10.3 mmol) were prepared in the same manner as in Sub 4-d-12, to obtain 34.4 g of the product (yield: 75%).

6. Sub 4-36 Synthesis Example

(1) Sub 4-a-36 Synthesis

9-bromophenanthrene (50.0 g, 194 mmol), bis(pinacolato)diboron (54.3 g, 214 mmol), KOAc (57.3 g, 583 mmol), PdCl ₂ (dppf) (4.27 g, 5.83 mmol) were prepared in the same manner as in Sub 4-a-1, to obtain 46.9 g of the product (yield: 76%).

(2) Sub 4-b-36 synthesis

Sub 4-a-36 (46.9 g, 148 mmol), 1-bromo-2-nitronaphthalene (37.3 g, 148 mmol), K ₂ CO ₃ (61.2 g, 443 mmol), Pd(PPh ₃ ) ₄ (10.3 g, 8.88 mmol) obtained above were prepared in the same manner as in Sub 4-b-1, to obtain 41.9 g of the product (yield: 81%).

(3) Sub 4-36 Synthesis

Sub 4-b-36 (41.9 g, 120 mmol) and triphenylphosphine (78.6 g, 300 mmol) obtained above were treated in the same manner as in the experimental method of Sub 4-1 to obtain 28.2 g of the product (yield: 74%).

Examples of Sub 4 include, but are not limited to, the following, and Table 5 shows the FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 4.

compound FD-MS compound FD-MS Sub4-1 m/z=217.09(C ₁₆ H ₁₁ N=217.27) Sub4-2 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-3 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-4 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-5 m/z=369.15(C ₂₈ H ₁₉ N=369.47) Sub4-6 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-7 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-8 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-9 m/z=217.09(C ₁₆ H ₁₁ N=217.27) Sub4-10 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-11 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-12 m/z=458.18(C ₃₄ H ₂₂ N ₂ =458.56) Sub4-13 m/z=217.09(C ₁₆ H ₁₁ N=217.27) Sub4-14 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-15 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-16 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-17 m/z=293.12(C ₂₂ H ₁₅ N=293.37) Sub4-18 m/z=267.10(C ₂₀ H ₁₃ N=267.33) Sub4-19 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-20 m/z=419.17(C ₃₂ H ₂₁ N=419.53) Sub4-21 m/z=267.10(C ₂₀ H ₁₃ N=267.33) Sub4-22 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-23 m/z=267.10(C ₂₀ H ₁₃ N=267.33) Sub4-24 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-25 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-26 m/z=419.17(C ₃₂ H ₂₁ N=419.53) Sub4-27 m/z=267.10(C ₂₀ H ₁₃ N=267.33) Sub4-28 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-29 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-30 m/z=419.17(C ₃₂ H ₂₁ N=419.53) Sub4-31 m/z=267.10(C ₂₀ H ₁₃ N=267.33) Sub4-32 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-33 m/z=343.14(C ₂₆ H ₁₇ N=343.43) Sub4-34 m/z=449.12(C ₃₂ H ₁₉ NS=449.57) Sub4-35 m/z=267.10(C ₂₀ H ₁₃ N=267.33) Sub4-36 m/z=317.12(C ₂₄ H ₁₅ N=317.39) Sub4-37 m/z=317.12(C ₂₄ H ₁₅ N=317.39) Sub4-38 m/z=317.12(C ₂₄ H ₁₅ N=317.39) Sub4-39 m/z=367.14(C ₂₈ H ₁₇ N=367.45)

Example of Sub 5

Examples of Sub 5 of Scheme 4 include, but are not limited to, the following.

compound FD-MS compound FD-MS Sub 5-1 m/z=240.05(C ₁₄ H ₉ ClN ₂ =240.69) Sub 5-2 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-3 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-4 m/z=316.08(C ₂₀ H ₁₃ ClN ₂ =316.79) Sub 5-5 m/z=316.08(C ₂₀ H ₁₃ ClN ₂ =316.79) Sub 5-6 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-7 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-8 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-9 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-10 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-11 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-12 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-13 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-14 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-15 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-16 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-17 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-18 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-19 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-20 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-21 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-22 m/z=480.14(C ₃₃ H ₂₁ ClN ₂ =481.00) Sub 5-23 m/z=480.14(C ₃₃ H ₂₁ ClN ₂ =481.00) Sub 5-24 m/z=480.14(C ₃₃ H ₂₁ ClN ₂ =481.00) Sub 5-25 m/z=360.03(C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 5-26 m/z=360.03(C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 5-27 m/z=410.04(C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 5-28 m/z=410.04(C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 5-29 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-30 m/z=366.09(C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 5-31 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-32 m/z=366.09(C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 5-33 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-34 m/z=366.09(C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 5-35 m/z=240.05(C ₁₄ H ₉ ClN ₂ =240.69) Sub 5-36 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-37 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-38 m/z=316.08(C ₂₀ H ₁₃ ClN ₂ =316.79) Sub 5-39 m/z=316.08(C ₂₀ H ₁₃ ClN ₂ =316.79) Sub 5-40 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-41 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-42 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-43 m/z=346.03(C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 5-44 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-45 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-46 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-47 m/z=330.06(C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 5-48 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-49 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-50 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-51 m/z=405.10(C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 5-52 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-53 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-54 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-55 m/z=356.11(C ₂₃ H ₁₇ ClN ₂ =356.85) Sub 5-56 m/z=480.14(C ₃₃ H ₂₁ ClN ₂ =481.00) Sub 5-57 m/z=480.14(C ₃₃ H ₂₁ ClN ₂ =481.00) Sub 5-58 m/z=478.12(C ₃₃ H ₁₉ ClN ₂ =478.98) Sub 5-59 m/z=360.03(C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 5-60 m/z=360.03(C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 5-61 m/z=410.04(C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 5-62 m/z=410.04(C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 5-63 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-64 m/z=366.09(C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 5-65 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-66 m/z=366.09(C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 5-67 m/z=290.06(C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 5-68 m/z=366.09(C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 5-69 m/z=245.08(C ₁₄ H ₄ D ₅ ClN ₂ =245.72) Sub 5-70 m/z=245.08(C ₁₄ H ₄ D ₅ ClN ₂ =245.72)

Synthesis example of Final products 2

After dissolving Sub 4 (1 equivalent) in toluene in a round-bottomed flask, Sub 5 (1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P( t -Bu) ₃ (0.06 equivalent), and NaO t -Bu (2 equivalent) were added and stirred at 100°C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silica gel column and recrystallized to obtain the final product 2.

1. 3-1 Synthesis example

Sub 4-1 (26.1 g, 120 mmol), Toluene (300 mL), Sub 5-1 (28.9 g, 120 mmol), Pd ₂ (dba) ₃ (3.30 g, 3.60 mmol), P( t -Bu) ₃ (1.46 g, 7.21 mmol), NaO t -Bu (23.1 g, 240 mmol) were added and stirred at 100°C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silica gel column and recrystallized to obtain 40.0 g of the product (yield: 79%).

2. 3-18 Synthetic example

Sub 4-10 (34.5 g, 118 mmol), Sub 5-35 (28.3 g, 118 mmol), Pd ₂ (dba) ₃ (3.23 g, 3.53 mmol), P( t -Bu) ₃ (1.43 g, 7.06 mmol), NaO t -Bu (22.6 g, 235 mmol) were synthesized using the synthetic method of 3-1, obtaining the final product (42.7 g (yield: 73%).

3. 3-20 Synthesis Example

Sub 4-12 (68.2 g, 149 mmol), Sub 5-60 (53.7 g, 149 mmol), Pd ₂ (dba) ₃ (4.09 g, 4.46 mmol), P( t -Bu) ₃ (1.81 g, 8.92 mmol), NaO t -Bu (28.6 g, 297 mmol) were synthesized using the synthetic method of 3-1, obtaining the final product (83.5 g, yield: 76%).

4. 3-31 Synthesis example

Sub 4-18 (31.6 g, 118 mmol), Sub 5-7 (41.0 g, 118 mmol), Pd ₂ (dba) ₃ (3.25 g, 3.55 mmol), P( t -Bu) ₃ (1.43 g, 7.09 mmol), NaO t -Bu (22.7 g, 236 mmol) were synthesized using the synthetic method of 3-1, obtaining the final product (55.1 g (yield: 78%).

5. 3-69 Synthesis example

Sub 4-35 (34.4 g, 129 mmol), Sub 5-30 (47.2 g, 129 mmol), Pd ₂ (dba) ₃ (3.53 g, 3.86 mmol), P( t -Bu) ₃ (1.56 g, 7.72 mmol), NaO t -Bu (24.7 g, 257 mmol) were synthesized using the synthetic method of 3-1, thereby obtaining the final product (53.1 g (yield: 69%).

6. 3-73 Synthesis example

Sub 4-36 (28.2 g, 88.8 mmol), Sub 5-69 (21.8 g, 88.8 mmol), Pd ₂ (dba) ₃ (2.44 g, 2.67 mmol), P( t -Bu) ₃ (1.08 g, 5.33 mmol), NaO t -Bu (17.1 g, 178 mmol) were synthesized using the synthetic method of 3-1, obtaining the final product (33.2 g, 71%).

compound FD-MS compound FD-MS 3-1 m/z=421.16(C ₃₀ H ₁₉ N ₃ =421.50) 3-2 m/z=421.16(C ₃₀ H ₁₉ N ₃ =421.50) 3-3 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-4 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-5 m/z=573.22(C ₄₂ H ₂₇ N ₃ =573.70) 3-6 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-7 m/z=573.22(C ₄₂ H ₂₇ N ₃ =573.70) 3-8 m/z=573.22(C ₄₂ H ₂₇ N ₃ =573.70) 3-9 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-10 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-11 m/z=573.22(C ₄₂ H ₂₇ N ₃ =573.70) 3-12 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-13 m/z=421.16(C ₃₀ H ₁₉ N ₃ =421.50) 3-14 m/z=421.16(C ₃₀ H ₁₉ N ₃ =421.50) 3-15 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-16 m/z=603.18(C ₄₂ H ₂₅ N ₃ S=603.74) 3-17 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-18 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-19 m/z=573.22(C ₄₂ H ₂₇ N ₃ =573.70) 3-20 m/z=738.28(C ₅₄ H ₃₄ N ₄ =738.89) 3-21 m/z=421.16(C ₃₀ H ₁₉ N ₃ =421.50) 3-22 m/z=421.16(C ₃₀ H ₁₉ N ₃ =421.50) 3-23 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-24 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-25 m/z=587.20(C ₄₂ H ₂₅ N ₃ O=587.68) 3-26 m/z=497.19(C ₃₆ H ₂₃ N ₃ =497.60) 3-27 m/z=587.20(C ₄₂ H ₂₅ N ₃ O=587.68) 3-28 m/z=587.20(C ₄₂ H ₂₅ N ₃ O=587.68) 3-29 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-30 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-31 m/z=577.16(C ₄₀ H ₂₃ N ₃ S=577.71) 3-32 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-33 m/z=673.25(C ₅₀ H ₃₁ N ₃ =673.82) 3-34 m/z=653.19(C ₄₆ H ₂₇ N ₃ S=653.80) 3-35 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-36 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-37 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-38 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-39 m/z=577.16(C ₄₀ H ₂₃ N ₃ S=577.71) 3-40 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-41 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-42 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-43 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-44 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-45 m/z=663.27(C ₄₉ H ₃₃ N ₃ =663.82) 3-46 m/z=597.22(C ₄₄ H ₂₇ N ₃ =597.72) 3-47 m/z=673.25(C ₅₀ H ₃₁ N ₃ =673.82) 3-48 m/z=597.22(C ₄₄ H ₂₇ N ₃ =597.72) 3-49 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-50 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-51 m/z=597.22(C ₄₄ H ₂₇ N ₃ =597.72) 3-52 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-53 m/z=623.24(C ₄₆ H ₂₉ N ₃ =623.76) 3-54 m/z=712.26(C ₅₂ H ₃₂ N ₄ =712.86) 3-55 m/z=623.24(C ₄₆ H ₂₉ N ₃ =623.76) 3-56 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-57 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-58 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-59 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-60 m/z=597.22(C ₄₄ H ₂₇ N ₃ =597.72) 3-61 m/z=712.26(C ₅₂ H ₃₂ N ₄ =712.86) 3-62 m/z=785.28(C ₅₉ H ₃₅ N ₃ =785.95) 3-63 m/z=893.29(C ₆₅ H ₃₉ N ₃ S=894.11) 3-64 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-65 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-66 m/z=471.17(C ₃₄ H ₂₁ N ₃ =471.56) 3-67 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-68 m/z=577.16(C ₄₀ H ₂₃ N ₃ S=577.71) 3-69 m/z=597.22(C ₄₄ H ₂₇ N ₃ =597.72) 3-70 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-71 m/z=547.20(C ₄₀ H ₂₅ N ₃ =547.66) 3-72 m/z=597.22(C ₄₄ H ₂₇ N ₃ =597.72) 3-73 m/z=526.22(C ₃₈ H ₁₈ D ₅ N ₃ =526.65) 3-74 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-75 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-76 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-77 m/z=521.19(C ₃₈ H ₂₃ N ₃ =521.62) 3-78 m/z=526.22(C ₃₈ H ₁₈ D ₅ N ₃ =526.65) 3-79 m/z=571.20(C ₄₂ H ₂₅ N ₃ =571.68) 3-80 m/z=571.20(C ₄₂ H ₂₅ N ₃ =571.68)

Manufacturing and Evaluation of Organic Electronics

Example 1) Fabrication and testing of red organic light-emitting device

First, a N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to a thickness of 60 nm as a hole injection layer on an ITO layer (anode) formed on a glass substrate. Next, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. A mixture of the above-described inventive compounds represented by chemical formulas (1) and (2) in a 50:50 ratio was used as a host on the hole transport layer, and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate] was doped as a dopant in a 95:5 weight ratio, thereby depositing a 30 nm thick emitting layer on the hole transport layer. (1,1'-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a 10 nm thickness as a hole blocking layer, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was deposited to a 40 nm thickness as an electron transport layer. Afterwards, LiF, a halogenated alkali metal, was deposited as an electron injection layer with a thickness of 0.2 nm, and then Al was deposited with a thickness of 150 nm and used as a cathode to manufacture an organic light emitting device.

[Comparative examples 1-3]

An organic light-emitting device was manufactured in the same manner as in the above example, except that the compound represented by chemical formula 1 was used solely as a host.

[Comparative examples 4-7]

An organic light-emitting device was manufactured in the same manner as in the above example, except that the compound represented by chemical formula 2 was used solely as a host.

[Comparative Example 8]

An organic light-emitting device was manufactured in the same manner as in the above example, except that the compound represented by chemical formula 1 and comparative compound 1 were used as a mixture.

[Comparative Example 9, Comparative Example 10]

An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by chemical formula 2 and comparative compound 2 or comparative compound 3 were used as a mixture.

The electroluminescence (EL) characteristics were measured using PR-650 of Photoresearch by applying a forward bias DC voltage to the organic electroluminescence devices manufactured in this manner and the comparative examples, and the T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a standard luminance of 2500 cd/m2. The table below shows the results of device fabrication and evaluation.

Comparative compound 1 Comparative compound 2 Comparative compound

　 First host Second host Voltage Current Density Brightness
(cd/m2) Efficiency Lifetime
T(95) Comparative example (1) Compound (1-56) - 5.1 19.5 2500 12.8 90.7 Comparative example (2) Compound (2-43) - 5.2 22.1 2500 11.3 90.4 Comparative example (3) Compound (2-133) - 5.0 18.5 2500 13.5 95.0 Comparative example (4) Compound (3-6) - 4.6 13.0 2500 19.2 91.9 Comparative example (5) Compound (3-10) - 4.3 13.3 2500 18.8 83.1 Comparative example (6) Compound (3-25) - 4.3 14.5 2500 17.2 90.2 Comparative example (7) Compound (3-26) - 4.1 14.9 2500 16.8 80.5 Comparative example (8) Compound (2-133) Comparative compound 1 4.5 12.1 2500 20.7 102.5 Comparative example (9) Compound (3-25) Comparative compound 2 4.3 9.1 2500 27.5 110.7 Comparative example (10) Compound (3-25) Comparative compound 3 4.1 9.8 2500 25.4 105.3 Example (1) Compound (1-56) Compound (3-6) 4.2 6.2 2500 40.2 128.0 Example (2) Compound (2-43) Compound (3-6) 4.1 6.0 2500 42.0 128.8 Example (3) Compound (2-133) Compound (3-6) 4.0 5.9 2500 42.3 132.2 Example (4) Compound (1-56) Compound (3-10) 4.0 6.3 2500 40.0 116.7 Example (5) Compound (2-43) Compound (3-10) 4.0 6.0 2500 41.8 116.9 Example (6) Compound (2-133) Compound (3-10) 3.8 5.9 2500 42.1 119.1 Example (7) Compound (1-56) Compound (3-13) 4.1 6.7 2500 37.5 129.6 Example (8) Compound (2-43) Compound (3-13) 4.1 6.5 2500 38.5 130.5 Example (9) Compound (2-133) Compound (3-13) 3.9 6.2 2500 40.1 131.4 Example (10) Compound (1-56) Compound (3-18) 3.9 6.9 2500 36.1 114.9 Example (11) Compound (2-43) Compound (3-18) 3.7 6.7 2500 37.3 116.2 Example (12) Compound (2-133) Compound (3-18) 3.7 6.3 2500 39.4 118.8 Example (13) Compound (1-56) Compound (3-25) 4.0 6.8 2500 36.8 129.1 Example (14) Compound (2-43) Compound (3-25) 3.9 6.6 2500 37.7 130.7 Example (15) Compound (2-133) Compound (3-25) 3.9 6.6 2500 37.9 131.0 Example (16) Compound (1-56) Compound (3-26) 3.8 7.1 2500 35.4 115.8 Example (17) Compound (2-43) Compound (3-26) 3.8 6.7 2500 37.1 116.2 Example (18) Compound (2-133) Compound (3-26) 3.6 6.7 2500 37.5 119.4

As can be seen from the results in Table 8 above, when the materials for the organic electroluminescent device of the present invention represented by Chemical Formula 1 and Chemical Formula 2 are mixed and used as a phosphorescent host (Examples 1 to 18), it was confirmed that the driving voltage, efficiency, and lifespan were significantly improved compared to the devices using a single material (Comparative Examples 1 to 7) and the devices using a mixture of comparative compounds (Comparative Examples 8 to 10).

In other words, the results of Comparative Examples 8 to 10 in which Comparative Compound 1 or Comparative Compound 2 was mixed and used as a phosphorescent host were generally superior in terms of efficiency and lifespan to those in which the compounds of the present invention represented by Chemical Formulas 1 and 2 were used alone as a phosphorescent host (Comparative Examples 1 to 7), and it can be seen that Examples 1 to 18 in which the compounds of the present invention represented by Chemical Formulas 1 and 2 were mixed showed significantly superior effects in terms of operating voltage, efficiency, and lifespan.

Based on the experimental results above, the inventors of the present invention judged that a material mixed with a substance of Chemical Formula 1 and a substance of Chemical Formula 2 has novel properties other than the properties of each substance, and thus measured PL and PL lifetime using the substance of Chemical Formula 1, the substance of Chemical Formula 2, and the mixture of the present invention, respectively. As a result, it was confirmed that a new PL wavelength was formed when the compounds of Chemical Formula 1 and Chemical Formula 2 of the present invention were mixed, unlike when they were either compound alone, and it was confirmed that the decrease and disappearance time of the newly formed PL wavelength was longer than the decrease and disappearance times of the substances of Chemical Formula 1 and Chemical Formula 2, respectively. This suggests that when the compounds of the present invention are mixed and used, electrons and holes move through the energy levels of each substance, and the efficiency and lifetime increase due to electron and hole movement or energy transfer by a new region (exciplex) having a new energy level formed by the mixing. As a result, it can be said that this is an important example in which a mixed thin film exhibits an exciplex energy transfer and luminescence process when the mixture of the present invention is used.

Also, the reason why the combination of the present invention is superior to Comparative Examples 8 to 10 which used a phosphorescent host mixed with a comparative compound is that when a compound represented by Chemical Formula 1 having strong hole properties is mixed with a polycyclic compound represented by Chemical Formula 2 which has the characteristics of stability for not only electrons but also holes, high T1, etc., the electron blocking ability is improved due to the high T1 and high LUMO energy value, and more holes move quickly and easily to the emitting layer. Accordingly, the charge balance of holes and electrons in the emitting layer increases, so that light emission is well achieved inside the emitting layer rather than at the hole transport layer interface, and as a result, deterioration at the HTL interface is also reduced, which maximizes the driving voltage, efficiency, and lifespan of the entire device. That is, it is thought that the combination of Chemical Formula 1 and Chemical Formula 2 has an electrochemical synergistic effect to improve the performance of the entire device.

Example 2) Production and testing of red organic light-emitting devices according to mixing ratio

First host Second Host` Mixing ratio Voltage Current Density Brightness Efficiency Lifetime (1st host: 2nd host) (cd/m2) T(95) Example (19) Compound (1-56) Compound (3-6) 2:8 4.0 6.4 2500 38.9 115.1 Example (20) Compound (1-56) Compound (3-6) 3:7 4.1 6.4 2500 39.1 121.2 Example (21) Compound (1-56) Compound (3-6) 4:6 4.1 6.3 2500 39.4 126.1 Example (22) Compound (2-133) Compound (3-26) 2:8 3.4 6.9 2500 36.1 112.3 Example (23) Compound (2-133) Compound (3-26) 3:7 3.4 6.8 2500 36.5 117.7 Example (24) Compound (2-133) Compound (3-26) 4:6 3.6 6.7 2500 37.1 118.3

As shown in Table 9 above, devices were manufactured and measured using mixtures of compounds of the present invention at different ratios (2:8, 3:7, 4:6).

To elaborate on the results, it was confirmed that the driving voltage results improved as the second host ratio increased, but on the contrary, the efficiency and lifespan showed the opposite trend. Therefore, in the case of a mixture, it is judged that it is a very important task to derive a mixing ratio that maximizes the charge balance within the light-emitting layer because the amount of the mixing ratio affects the characteristics.

The above description is merely an example of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are not intended to limit the present invention, but rather to explain it, 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 by the claims below, and all technologies within a scope equivalent thereto should be interpreted as being included in the scope of the rights of the present invention.

100: Organic electronic device 110: Substrate
120: First electrode (anode) 130: Hole injection layer
140: Hole transport layer 141: Buffer layer
150: Emitting layer 151: Emitting auxiliary layer
160: Electron transport layer 170: Electron injection layer
180: Second electrode (cathode)

Claims (17)

An organic electric device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer and comprises a first host compound represented by chemical formula (1) and a second host compound represented by chemical formula (2).
Chemical formula (1) Chemical formula (2)

{In the above chemical formulas (1) and (2),
1) X and Y are each independently O; S; or CR'R";,
2) a and b are each independently 0 or 1, provided that a+b is greater than or equal to 1,
3) R' and R" are each independently selected from the group consisting of hydrogen; an alkyl group of C ₁ to C ₅₀ ; and an aryl group of C ₆ to C ₆₀ ; or R' and R" form a ring with each other to form a spiro ring,
4) L ¹ , L ² and L' are each independently a single bond; an arylene group having C ₆ to C ₆₀ ; or a heteroarylene group having C ₂ to C ₆₀ ;
5) Ar ¹ and Ar ² are each independently selected from the group consisting of hydrogen; deuterium; an aryl group of C ₆ to C ₆₀ ; a fluorenyl group; and a heterocyclic group of C ₂ to C ₆₀ containing at least one heteroatom of O, N, S, Si and P;
6) Z is NR', O, S, CR'R", SiR'R", or Se,
7) R ¹ to R ⁶ are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; a C ₁ to C ₅₀ alkyl group; and a C ₂ to C ₂₀ alkenyl group;
When the above l, m, n, o, p and q are 2 or more, each is plural and identical or different from each other, and plural R ^1s , plural R ^2s , plural R ^3s , plural R ^4s , plural R ^5s and plural R ^6s can combine with each other to form aromatic and heteroaromatic rings,
8) Rings A and B are each independently an aryl group having C ₆ to C ₆₀ , and one of A and B is an aryl group having C ₁₀ to C ₆₀ ,
9) n, l, p and q are any integers from 0 to 4, m is 0 or 1, o is any integer from 0 to 3,
10) One of X ¹ and X ² is N and the other is C-Ar ² ,
Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, alkyl group, and alkenyl group may be further substituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ -C ₂₀ heterocyclic group; and C ₃ -C ₂₀ cycloalkyl group.
In claim 1, an organic electric device characterized in that the compound represented by the chemical formula (1) is represented by the following chemical formula (3) or (4)
Chemical formula (3) Chemical formula (4)

(In the above chemical formulas (3) and (4), X, Y, Z, Ar ¹ , L ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , l, m, n, o, and p are the same as defined in claim 1.)
In claim 1, an organic electric device characterized in that the compound represented by the chemical formula (1) is represented by any one of the following chemical formulas (5) to (12).
Chemical formula (5) Chemical formula (6) Chemical formula (7) Chemical formula (8)

Chemical formula (9) Chemical formula (10) Chemical formula (11) Chemical formula (12)

(In the chemical formulas (5) to (12) above, X, Y, Z, Ar ¹ , L ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , l, m, n, o, and p are the same as defined in claim 1.)
An organic electric element characterized in that in claim 1, l, m, n, o and p are all 0 In the first paragraph, an organic electric element characterized in that any one of R ¹ , R ² , R ³ , R ⁴ and R ⁵ is a pair of adjacent ones bonded to each other to form a ring. An organic electric element characterized in that in claim 1, X or Y is S or O.
In the first paragraph, an organic electric device characterized in that the chemical formula (1) is any one of the following compounds

In the first paragraph, an organic electric device characterized in that the compound represented by the chemical formula (2) is represented by the following chemical formula (13) or (14)
Chemical formula (13) Chemical formula (14)

(In the above chemical formulas (13) and (14), A, B, L ² , Ar ² , R ⁶ and q are the same as defined in claim 1.)
An organic electric device characterized in that in claim 1, the A and B rings of the compound represented by the chemical formula (2) are any one of the following (A-1) to (A-9).
(A-1) (A-2) (A-3) (A-4) (A-5) (A-6) (A-7)

(A-8) (A-9)

(In the above chemical formulas (A-1) to (A-9), R ¹⁰ is the same as R ¹ of claim 1,
* Indicates the bonding position of rings A and B.)
In the first paragraph, an organic electric device characterized in that the compound represented by the chemical formula (2) is represented by any one of the following chemical formulas (15) to (28).
Chemical formula (15) Chemical formula (16) Chemical formula (17)

Chemical formula (18) Chemical formula (19) Chemical formula (20)

Chemical formula (21) Chemical formula (22) Chemical formula (23)

Chemical formula (24) Chemical formula (25) Chemical formula (26)

Chemical formula (27) Chemical formula (28)

(In the above chemical formulas (15) to (28),
L ² , X ¹ , X ² , R ⁶ and q are as defined in claim 1,
R ¹² and R ¹³ are identical to R ¹ defined in claim 1,
s and u are each independently an integer from 0 to 6,
t is an integer between 0 and 4,
v and w are each independently an integer from 0 to 8.)
An organic electric device characterized in that in claim 1, R ⁶ of the compound represented by the chemical formula (2) is hydrogen.
In the first paragraph, an organic electric device characterized in that the chemical formula (2) is one of the following compounds

An organic electric device characterized in that, in claim 1, the compounds represented by the chemical formula (1) and the chemical formula (2) are mixed in a weight ratio of any one of 1:9 to 9:1.
An organic electric device characterized in that, in claim 1, the compounds represented by the chemical formula (1) and the chemical formula (2) are mixed in a weight ratio of 1:9 to 5:5.
An organic electric device characterized in that, in claim 1, the compounds represented by the chemical formula (1) and the chemical formula (2) are mixed in a weight ratio of 2:8 to 3:7.
A display device including an organic electric element according to claim 1; and an electronic device including a control unit for driving the display device.
An electronic device according to claim 16, characterized in that the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element.