KR20230005021A - An organic electronic element comprising compound for organic electronic element and an electronic device thereof - Google Patents

Abstract

The present invention provides organic electric elements containing an anode, a cathode, and an organic material layer between the anode and the cathode, and electronic devices including the organic electric elements. Since an organic material layer contains each compound represented by chemical formulas (1) and (2) of the present invention, the driving voltage of the organic electric elements can be lowered and the luminous efficiency and lifespan can be improved.

Description

Organic electric element and electronic device containing a compound for organic electric element

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as organic layers in organic electric devices may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

Lifespan and efficiency are the most problematic issues in organic light emitting devices, and as displays become larger, these efficiency and lifespan problems must be solved. Efficiency, lifespan, driving voltage, etc. are related to each other. As the efficiency increases, the driving voltage relatively decreases. indicates a tendency to increase life expectancy.

However, efficiency cannot be maximized by simply improving the organic layer. This is because long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interfacial property, etc.) of the material is achieved.

In addition, in order to solve the light emission problem in the hole transport layer in recent organic light emitting devices, an auxiliary light emitting layer must be present between the hole transport layer and the light emitting layer, and different light emission auxiliary layers according to each light emitting layer (R, G, B) It is time to develop the layer.

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

However, since the material used in the hole transport layer must have a low HOMO value, most of them have a low T1 value, and as a result, excitons generated in the light emitting layer are transferred to the hole transport layer, resulting in charge unbalance in the light emitting layer resulting in light emission at the interface of the hole transport layer.

When light is emitted from the interface of the hole transport layer, the color purity and efficiency of the organic electric element are lowered and the lifetime is shortened. Therefore, there is an urgent need to develop a light emitting auxiliary layer having a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer.

On the other hand, it delays the penetration and diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of life shortening of organic electric devices, and has stable characteristics against Joule heating generated during device operation, that is, high glass transition. It is necessary to develop a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has a property of reducing the uniformity of the surface of the thin film when the device is driven, which is reported to have a great effect on the lifespan of the device. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop materials that can endure for a long time during deposition, that is, materials with strong heat resistance.

That is, in order to fully exhibit the excellent characteristics of organic electric devices, materials constituting the organic material layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and light emitting auxiliary layer materials, etc. are stable and efficient. Although supporting by materials should precede, the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently achieved. Therefore, the development of new materials continues to be required.

An object of the present invention is to provide an organic electric device and an electronic device containing a compound capable of lowering the driving voltage of the device and improving the light emitting efficiency, color purity, stability and lifespan of the device.

In one aspect, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is phosphorescent. An organic electric device including compounds represented by Chemical Formulas 1 and 2 below as an active light emitting layer is provided.

Formula 1 Formula 2

Formula 3

In another aspect, the present invention provides an electronic device including the organic electric element.

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

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.

Hereinafter, it will be described in detail with reference to embodiments of the present invention. In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

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

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

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

As used herein, unless otherwise specified, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, and includes a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and the like. A radical of a saturated aliphatic functional group, including an alkyl group, a cycloalkyl-substituted alkyl group.

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

As used herein, unless otherwise specified, the term "cycloalkyl" refers to an alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms, unless otherwise specified, and is limited thereto. It is not.

As used herein, the term "aryloxyl group" or "aryloxy group" refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

The terms "aryl group" and "arylene group" used herein have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, an aryl group or an arylene group refers to a single-ring or multi-ring aromatic ring, and includes an aromatic ring formed by bonding or reacting with adjacent substituents. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene 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 a radical substituted with an aryl group has carbon atoms described herein.

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

As used herein, the term "heterocyclic group" includes at least one heteroatom, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes a heteroaliphatic ring and a heterocyclic group, unless otherwise specified. Contains an aromatic ring. It may also be formed by combining adjacent functional groups.

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

In addition, the "heterocyclic group" may include a ring containing SO ₂ instead of carbon forming the ring. For example, "heterocyclic group" includes the following compounds.

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

As used herein, the term "spiro compound" has a 'spiro union', which means a connection formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called 'spiro atoms', and according to the number of spiro atoms in a compound, they are called 'monospiro-', 'dispiro-', and 'trispiro-', respectively. ' It's called a compound.

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

Unless otherwise specified, the term "ring" used herein 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, Contains saturated or unsaturated rings.

Other hetero compounds or heteroradicals other than the aforementioned hetero compounds include, but are not limited to, one or more heteroatoms.

In addition, unless explicitly stated otherwise, “substituted” in the term “substituted or unsubstituted” as used herein means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ arylthiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, deuterium-substituted C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and C ₂ ~ C ₂₀ means substituted with one or more substituents selected from the group consisting of heterocyclic groups, but is not limited to these substituents.

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

Here, when a is an integer of 0, substituent R ¹ does not exist, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbon atoms forming the benzene ring, and when a is an integer of 2 or 3 Each is combined as follows, wherein R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while indicating the hydrogen bonded to the carbon forming the benzene ring. is omitted.

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

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

1 to 3 are exemplary views of an organic electric element according to an embodiment of the present invention.

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

The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (negative electrode), 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 material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 and an electron injection layer 160 . Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.

Preferably, the light efficiency improvement layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the light efficiency improvement layer 180 is formed Light efficiency of the organic electric element may be improved.

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

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

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

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

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

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

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

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

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

When a plurality of light emitting layers are formed by a multi-layer stack structure method as shown in FIG. 3, it is possible to manufacture an organic light emitting device that emits white light by a mixing effect of light emitted from each light emitting layer, as well as to emit light of various colors. An organic electroluminescent device that emits light can also be manufactured.

Compounds represented by Formula 1 and Formula 2 of the present invention are hole injection layers (120, 320, 420), hole transport layers (130, 330, 430), buffer layer 210, light emitting auxiliary layer 220, electron transport layer ( 150, 350, 450), may be used as a material for the electron injection layer 160, the light emitting layer 140, 340, 440 or the light efficiency improvement layer 180, but preferably represented by the formulas (1) and (2) of the present invention. A compound may be used as a host of the light emitting layer (140, 340, 440).

Since the band gap, electrical properties, interface properties, etc. may vary depending on which substituent is attached to which position even in the same or similar core, selection of the core and research on the combination of sub-substituents bound thereto In particular, long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial property, etc.) is achieved.

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

In addition, the organic material layer is formed by a solution process or a solvent process other than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, and a doctor blading process. It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the forming method.

In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and an device for quantum dot display.

Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention and a control unit controlling the display device. At this time, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, and various computers.

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

An organic electric device according to an embodiment of the present invention includes a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer. And, the light emitting layer is a phosphorescent light emitting layer and includes compounds represented by Formulas 1 and 2 below.

Formula 1 Formula 2

Formula 3

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

1) R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~C ₆₀ Alkenyl group; C ₂ ~C ₆₀ alkynyl group; C ₁ ~ C ₆₀ alkoxy group; And C ₆ ~ C ₆₀ aryloxy group; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are aryl groups, preferably C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₂₅ aryl groups such as phenyl It may be rene, biphenyl, naphthalene, terphenyl, etc.

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups. pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, It may be benzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

When the above R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are fused ring groups, preferably C ₃ ~ C ₃₀ aliphatic ring and C ₆ ~ C ₃₀ aromatic ring fused ring group; Preferably, it may be a fused ring group of a C ₃ ~ C ₂₄ aliphatic ring and a C ₆ ~ C ₂₄ aromatic ring,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, more preferably C ₁ to C ₂₄ alkyl groups,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are alkenyl groups, they are preferably C ₂ to C ₃₀ alkenyl groups, more preferably C ₂ to C ₂₄ alkenyl groups. there is,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are alkynyl groups, they are preferably C ₂ to C ₃₀ alkenyl groups, more preferably C ₂ to C ₂₄ alkynyl groups. there is,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are alkoxy groups, they may be preferably C ₁ to C ₃₀ alkoxy groups, more preferably C ₁ to C ₂₄ alkoxy groups,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are aryloxy groups, they are preferably C ₁ to C ₃₀ aryloxy groups, more preferably C ₁ to C ₂₄ aryloxy groups. can,

2) A is a substituent represented by Formula 3,

3) X, Y and Z independently of each other are O, S or CR'R”;

4) L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And C ₃ ~ C ₆₀ It is selected from the group consisting of; aliphatic ring group,

When L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are arylene groups, they are preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₂₄ arylene groups. It may be, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

When L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are aliphatic cyclic groups, preferably C ₃ -C ₃₀ aliphatic cyclic groups, more preferably C ₃ -C ₂₄ aliphatic cyclic groups. can,

When L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups. pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, It may be benzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

5) Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently a C ₆ to C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; and C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; is selected from the group consisting of;

When Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are aryl groups, preferably C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₂₅ aryl groups such as phenylene, biphenyl, naphthalene , terphenyl, etc.,

When Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are heterocyclic groups, they may be preferably C ₂ ~ C ₃₀ heterocyclic groups, more preferably C ₂ ~ C ₂₄ heterocyclic groups, and exemplarily Pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothione It may be nopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

When Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are fused ring groups, preferably C ₃ ~ C ₃₀ aliphatic ring and C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably C ₃ ~ It may be a fused ring group of C ₂₄ aliphatic ring and C ₆ ~ C ₂₄ aromatic ring,

6) X ¹ , X ² and X ³ are each independently CR ^a or N, provided that at least one of X ¹ , X ² and X ³ is N;

7) R', R” and R ^a are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ Alkyl group; A C ₂ ~C ₂₀ alkenyl group; A C ₂ ~C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxy group; And a C ₆ ~ C ₃₀ aryloxy group; It is selected from the group consisting of, or R' and R” may be bonded to each other to form a spy ring,

When R', R” and R ^a are aryl groups, preferably C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₂₅ aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl etc.,

When R', R” and R ^a are heterocyclic groups, they may be preferably C ₂ ~ C ₃₀ heterocyclic groups, more preferably C ₂ ~ C ₂₄ heterocyclic groups, and examples include pyrazine, Opene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine , Benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.,

When R', R” and R ^a are fused ring groups, preferably C ₃ ~ C ₃₀ aliphatic ring and C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably C ₃ ~ C ₂₄ It may be a fused ring group of an aliphatic ring and a C ₆ ~ C ₂₄ aromatic ring,

When R', R” and R ^a are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, more preferably C ₁ to C ₂₄ alkyl groups,

When R', R” and R ^a are alkoxy groups, they may be preferably C ₁ to C ₂₄ alkoxy groups,

When R', R” and R ^a are aryloxy groups, they may be preferably C ₆ to C ₂₄ aryloxy groups;

8) a and f are independently integers from 0 to 4, b, c, d and e are independently integers from 0 to 3;

는 결합위치를 의미하고,9)

denotes a binding position,

10) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group are each 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; A C ₂ ~C ₂₀ alkenyl group; A C ₂ ~C ₂₀ alkynyl group; C ₆ ~ C ₂₀ aryl group; A deuterium-substituted C ₆ ~C ₂₀ aryl group; fluorenyl group; C ₂ ~C ₂₀ heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And a C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may combine with each other to form a ring, wherein 'ring' means C ₃ ~C ₆₀ It refers to an aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring or a C ₂ ~ C ₆₀ hetero ring or a fused ring composed of a combination thereof, and includes a saturated or unsaturated ring.

In addition, the present invention provides an organic electric device in which the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-12 below.

Formula 1-1 Formula 1-2

Formula 1-3 Formula 1-4

Formula 1-5 Formula 1-6

Formula 1-7 Formula 1-8

Formula 1-9 Formula 1-10

Formula 1-11 Formula 1-12

{In Formula 1-1 to Formula 1-12, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a, b, c, d , e, f, R' and R” are as defined above.}

In addition, the present invention provides an organic electric device in which the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-13 to 1-16 below.

Formula 1-13 Formula 1-14

Formula 1-15 Formula 1-16

{In Formula 1-13 to Formula 1-16, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a, b, c, d , e, f, X, Y and Z are as defined above.}

In addition, the present invention provides an organic electric device in which the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-17 to 1-24.

Formula 1-17 Formula 1-18

Formula 1-19 Formula 1-20

Formula 1-21 Formula 1-22

Formula 1-23 Formula 1-24

{In Formula 1-17 to Formula 1-24,

1) R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a, b, c, d, e, f, X, Y and Z are As defined above,

2) a' and f' are independently integers from 0 to 3, b', c', d' and e' are independently integers from 0 to 2, g is an integer from 0 to 5, and h Is an integer from 0 to 3, i is an integer from 0 to 4,

3) R ⁷ , R ⁸ and R ⁹ are the same as the definition of R ¹ above,

4) X' is the same as the definition of X above.}

In addition, the present invention provides an organic electric device in which the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 1-25 to 1-117 below.

Formula 1-25 Formula 1-26 Formula 1-27

Formula 1-28 Formula 1-29 Formula 1-30

Formula 1-31 Formula 1-32 Formula 1-33

Formula 1-34 Formula 1-35 Formula 1-36

Formula 1-37 Formula 1-38 Formula 1-39

Formula 1-40 Formula 1-41 Formula 1-42

Formula 1-43 Formula 1-44 Formula 1-45

Formula 1-46 Formula 1-47 Formula 1-48

Formula 1-49 Formula 1-50 Formula 1-51

Formula 1-52 Formula 1-53 Formula 1-54

Formula 1-55 Formula 1-56 Formula 1-57

Formula 1-58 Formula 1-59 Formula 1-60

Formula 1-61 Formula 1-62 Formula 1-63

Formula 1-64 Formula 1-65 Formula 1-66

Formula 1-67 Formula 1-68 Formula 1-69

Formula 1-70 Formula 1-71 Formula 1-72

Formula 1-73 Formula 1-74 Formula 1-75

Formula 1-76 Formula 1-77 Formula 1-78

Formula 1-79 Formula 1-80 Formula 1-81

Formula 1-82 Formula 1-83 Formula 1-84

Formula 1-85 Formula 1-86 Formula 1-87

Formula 1-88 Formula 1-89 Formula 1-90

Formula 1-91 Formula 1-92 Formula 1-93

Formula 1-94 Formula 1-95 Formula 1-96

Formula 1-97 Formula 1-98 Formula 1-99

Formula 1-100 Formula 1-101 Formula 1-102

Formula 1-103 Formula 1-104 Formula 1-105

Formula 1-106 Formula 1-107 Formula 1-108

Formula 1-109 Formula 1-110 Formula 1-111

Formula 1-112 Formula 1-113 Formula 1-114

Formula 1-115 Formula 1-116 Formula 1-117

{In Formula 1-25 to Formula 1-117, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a , b, c, d, e, and f are as defined above.}

In addition, the present invention provides an organic electric element in which at least one of Ar ² , Ar ³ and Ar ⁴ is represented by any one of Chemical Formula Ar-1 to Chemical Formula Ar-8.

Formula Ar-1 Formula Ar-2 Formula Ar-3

Formula Ar-4 Formula Ar-5 Formula Ar-6

Formula Ar-7 Formula Ar-8

{In Formula Ar-1 to Formula Ar-8,

1) X ²¹ and X ²² are each independently NAr ⁵ , O, S or C(R ¹⁵ )(R ¹⁶ );

2) ta, tb and td are each independently an integer from 0 to 4, tc is an integer from 0 to 6, te is an integer from 0 to 7, tf is an integer from 0 to 5,

3) Ar ⁵ is the same as the definition of Ar ¹ above,

4) R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are the same as the definition of R ¹ above,

는 결합위치를 의미한다.}5)

means the binding position.}

In addition, the present invention provides an organic electric device in which the compound represented by Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-8 below.

Formula 2-1 Formula 2-2

Formula 2-3 Formula 2-4

Formula 2-5 Formula 2-6

Formula 2-7 Formula 2-8

{In Formulas 2-1 to 2-8,

1) X ²¹ , X ²³ and X ²⁵ are each independently NAr ⁶ , O, S or C(R ¹⁷ )(R ¹⁸ );

2) X ²² , X ²⁴ and X ²⁶ are each independently NAr ⁷ , O, S, C(R ¹⁹ )(R ²⁰ ) or a single bond;

3) a”, d” and f” are independently integers from 0 to 4, b”, c” and e” are integers from 0 to 3,

4) Ar ⁶ and Ar ⁷ are the same as the definition of Ar ¹ above,

5) ta, tb, te, tf, R ¹⁰ , R ¹¹ , R ¹³ and R ¹⁴ are as defined above;

6) L ⁴ , L ⁵ and L ⁶ are as defined above;

7) R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ have the same definition as R ¹ }

In addition, the present invention provides an organic electric device in which L ¹ to L ⁶ are represented by any one of Chemical Formulas (b-1) to (b-13) below.

Formula b-1 Formula b-2 Formula b-3 Formula b-4 Formula b-5 Formula b-6

Formula b-7 Formula b-8 Formula b-9 Formula b-10

Formula b-11 Formula b-12 Formula b-13

{In the formula b-1 to formula b-13,

1) Z ¹⁰ is O, S, NL ⁷ -Ar ⁸ or C(R ³⁰ )(R ³¹ );

2) L ⁷ is the same as the definition of L ¹ above,

3) Ar ⁸ is the same as the definition of Ar ¹ above,

4) aa, cc, dd, and ee are independently integers from 0 to 4, bb is an integer from 0 to 6, ff and gg are independently integers from 0 to 3, and hh is an integer from 0 to 2 , ii is 0 or 1,

5) Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ are independently CR ³² or N, provided that at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,

6) R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² have the same definition as R ¹ above,

는 결합위치를 의미한다.}7)

means the binding position.}

Specifically, the compound represented by Formula 1 may be any one of the following compounds.

Specifically, the compound represented by Formula 2 may be any one of the following compounds.

The present invention may further include a light efficiency improving layer formed on at least one surface opposite to the organic material layer among surfaces of the first electrode and the second electrode.

In the present invention, the compound represented by Chemical Formula 1 may be included in the light efficiency improving layer.

In addition, the organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on an anode, and the organic material layer may further include a charge generation layer formed between the two or more stacks.

In another aspect, the present invention provides a display device including the organic electric element; and a controller for driving the display device. In this case, the organic electric element may be at least one of an organic light emitting element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white lighting.

Hereinafter, a synthesis example of a compound represented by the chemical formula according to the present invention and a manufacturing example of an organic electric device will be described in detail with examples, but the present invention is not limited to the following examples.

[ synthesis example One]

The compound represented by Formula 1 according to the present invention (Final Product) is synthesized as shown in Reaction Scheme 1 below, but is not limited thereto. Hal is I, Br or Cl.

<Scheme 1>

I. Sub- Synthesis of 1

Sub-1 of Reaction Scheme 1 is synthesized by the reaction pathway of Reaction Scheme 2 below, but is not limited thereto. Hal is I, Br or Cl.

<Scheme 2>

1. Sub-1-11 synthesis example

In a round bottom flask, Sub-1-a-11 (20.0 g, 80.9 mmol), Sub-1-b-11 (14.3 g, 80.9 mmol), Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol), P( After adding t-Bu) ₃ (1.0 g, 4.9 mmol), NaOt-Bu (15.6 g, 161.9 mmol), and toluene (405 mL), the reaction proceeds at 80 °C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ , concentrated, and the organic material was recrystallized using a silica gel column to obtain 22.6 g of the product. (Yield: 80%)

2. Sub-1-56 synthesis example

In a round bottom flask, Sub-1-a-56 (20.0 g, 61.9 mmol), Sub-1-b-56 (11.0 g, 61.9 mmol), Pd ₂ (dba) ₃ (1.7 g, 1.9 mmol), P( t-Bu) ₃ (0.8 g, 3.7 mmol), NaOt-Bu (11.9 g, 123.8 mmol), and toluene (309 mL) were tested in the same manner as in Sub-1-11 to obtain 20.8 g of the product. (Yield: 79%)

3. Sub-1-72 synthesis example

In a round bottom flask, Sub-1-a-72 (20.0 g, 44.8 mmol), Sub-1-b-56 (7.9 g, 44.8 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.3 mmol), P( t-Bu) ₃ (0.5 g, 2.7 mmol), NaOt-Bu (8.6 g, 89.6 mmol), and toluene (224 mL) were tested in the same manner as in Sub-1-11 to obtain 19.9 g of a product. (Yield: 81%)

4. Sub-1-73 synthesis example

In a round bottom flask, Sub-1-a-73 (20.0 g, 61.9 mmol), Sub-1-b-73 (5.6 g, 61.9 mmol), Pd ₂ (dba) ₃ (5.6 g, 61.9 mmol), P( t-Bu) ₃ (0.8 g, 3.7 mmol), NaOt-Bu (11.9 g, 123.8 mmol), and toluene (309 mL) were tested in the same manner as in Sub-1-11 to obtain 17.0 g of product. (Yield: 82%)

5. Sub-1-79 synthesis example

In a round bottom flask, Sub-1-a-79 (20.0 g, 44.9 mmol), Sub-1-b-79 (4.0 g, 44.9 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.4 mmol), P( t-Bu) ₃ (0.6 g, 2.7 mmol), NaOt-Bu (8.6 g, 89.8 mmol), and toluene (225 mL) were tested in the same manner as in Sub-1-11 to obtain 18.7 g of a product. (Yield: 78%)

6. Sub-1-94 synthesis example

In a round bottom flask, Sub-1-a-94 (20.0 g, 48.4 mmol), Sub-1-b-73 (4.4 g, 48.4 mmol), Pd ₂ (dba) ₃ (1.3 g, 1.5 mmol), P( t-Bu) ₃ (0.6 g, 2.9 mmol), NaOt-Bu (9.3 g, 96.8 mmol), and toluene (242 mL) were tested in the same manner as in Sub-1-11 to obtain 16.3 g of a product. (Yield: 79%)

The compound belonging to Sub-1 may be the following compounds, but is not limited thereto, and Table 1 below shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub-1.

compound FD-MS compound FD-MS Sub-1-1 m/z=259.10 (C ₁₈ H ₁₃ NO=259.31) Sub-1-2 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub-1-3 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub-1-4 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub-1-5 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub-1-6 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub-1-7 m/z=411.16 (C ₃₀ H ₂₁ NO=411.50) Sub-1-8 m/z=411.16 (C ₃₀ H ₂₁ NO=411.50) Sub-1-9 m/z=411.16 (C ₃₀ H ₂₁ NO=411.50) Sub-1-10 m/z=259.10 (C ₁₈ H ₁₃ NO=259.31) Sub-1-11 m/z=349.11 (C ₂₄ H ₁₅ NO ₂ =349.39) Sub-1-12 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub-1-13 m/z=375.16 (C ₂₇ H ₂₁ NO=375.47) Sub-1-14 m/z=401.12 (C ₂₈ H ₁₉ NS=401.53) Sub-1-15 m/z=424.16 (C ₃₀ H ₂₀ N ₂ O=424.50) Sub-1-16 m/z=497.18 (C ₃₇ H ₂₃ NO=497.60) Sub-1-17 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub-1-18 m/z=529.15 (C ₃₇ H ₂₃ NOS=529.66) Sub-1-19 m/z = 513.17 (C ₃₇ H ₂₃ NO ₂ =513.60) Sub-1-20 m/z=602.24 (C ₄₄ H ₃₀ N ₂ O=602.74) Sub-1-21 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) Sub-1-22 m/z=499.19 (C ₃₇ H ₂₅ NO=499.61) Sub-1-23 m/z=381.08 (C ₂₄ H ₁₅ NO ₂ S=381.45) Sub-1-24 m/z = 365.11 (C ₂₄ H ₁₅ NO ₃ =365.39) Sub-1-25 m/z=397.06 (C ₂₄ H ₁₅ NOS ₂ =397.51) Sub-1-26 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub-1-27 m/z=391.16 (C ₂₇ H ₂₁ NO ₂ =391.47) Sub-1-28 m/z=425.12 (C ₃₀ H ₁₉ NS=425.55) Sub-1-29 m/z=466.20 (C ₃₃ H ₂₆ N ₂ O=466.58) Sub-1-30 m/z=264.13 (C ₁₈ H ₈ D ₅ NO=264.34) Sub-1-31 m/z=399.13 (C ₂₈ H ₁₇ NO ₂ =399.45) Sub-1-32 m/z=547.19 (C ₄₁ H ₂₅ NO=547.66) Sub-1-33 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub-1-34 m/z = 501.17 (C ₃₆ H ₂₃ NO ₂ =501.59) Sub-1-35 m/z=517.15 (C ₃₆ H ₂₃ NOS=517.65) Sub-1-36 m/z=527.22 (C ₃₉ H ₂₉ NO=527.67) Sub-1-37 m/z=381.16 (C ₂₆ H ₂₃ NS=381.54) Sub-1-38 m/z=325.09 (C ₂₂ H ₁₅ NS=325.43) Sub-1-39 m/z=440.13 (C ₃₀ H ₂₀ N ₂ S=440.56) Sub-1-40 m/z=503.17 (C ₃₆ H ₂₅ NS=503.66) Sub-1-41 m/z = 643.23 (C ₄₇ H ₃₃ NS = 643.85) Sub-1-42 m/z=719.26 (C ₅₃ H ₃₇ NS=719.95) Sub-1-43 m/z=273.12 (C ₁₉ H ₁₅ NO=273.34) Sub-1-44 m/z = 637.28 (C ₄₉ H ₃₅ N = 637.83) Sub-1-45 m/z=550.20 (C ₄₀ H ₂₆ N ₂ O=550.66) Sub-1-46 m/z=474.17 (C ₃₄ H ₂₂ N ₂ O=474.56) Sub-1-47 m/z=474.17 (C ₃₄ H ₂₂ N ₂ O=474.56) Sub-1-48 m/z=477.16 (C ₃₄ H ₂₃ NS=477.63) Sub-1-49 m/z=467.22 (C ₃₄ H ₂₉ NO=467.61) Sub-1-50 m/z=490.18 (C ₃₃ H ₂₂ N ₄ O=490.57) Sub-1-51 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub-1-52 m/z=376.12 (C ₂₅ H ₁₆ N ₂ O ₂ =376.42) Sub-1-53 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub-1-54 m/z=435.16 (C ₃₂ H ₂₁ NO=435.53) Sub-1-55 m/z=435.16 (C ₃₂ H ₂₁ NO=435.53) Sub-1-56 m/z=425.14 (C ₃₀ H ₁₉ NO ₂ =425.49) Sub-1-57 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub-1-58 m/z=435.16 (C ₃₂ H ₂₁ NO=435.53) Sub-1-59 m/z=531.13 (C ₃₆ H ₂₁ NO ₂ S=531.63) Sub-1-60 m/z=531.13 (C ₃₆ H ₂₁ NO ₂ S=531.63) Sub-1-61 m/z=401.21 (C ₃₀ H ₂₇ N=401.55) Sub-1-62 m/z=435.16 (C ₃₂ H ₂₁ NO=435.53) Sub-1-63 m/z=738.27 (C ₅₅ H ₃₄ N ₂ O=738.89) Sub-1-64 m/z=487.19 (C ₃₆ H ₂₅ NO=487.60) Sub-1-65 m/z=359.13 (C ₂₆ H ₁₇ NO=359.43) Sub-1-66 m/z=555.20 (C ₄₀ H ₂₉ NS=555.74) Sub-1-67 m/z = 661.24 (C ₅₀ H ₃₁ NO = 661.80) Sub-1-68 m/z=588.22 (C ₄₃ H ₂₈ N ₂ O=588.71) Sub-1-69 m/z=587.22 (C ₄₄ H ₂₉ NO=587.72) Sub-1-70 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub-1-71 m/z = 713.15 (C ₄₈ H ₂₇ NO ₂ S ₂ =713.87) Sub-1-72 m/z = 548.25 (C ₃₉ H ₂₀ D ₇ NO ₂ =548.69) Sub-1-73 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub-1-74 m/z=411.16 (C ₃₀ H ₂₁ NO=411.50) Sub-1-75 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub-1-76 m/z=550.24 (C ₄₁ H ₃₀ N ₂ =550.71) Sub-1-77 m/z=517.15 (C ₃₆ H ₂₃ NOS=517.65) Sub-1-78 m/z = 727.29 (C ₅₅ H ₃₇ NO = 727.91) Sub-1-79 m/z = 533.14 (C ₃₆ H ₂₃ NO ₂ S = 533.65) Sub-1-80 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub-1-81 m/z=415.10 (C ₂₈ H ₁₇ NOS=415.51) Sub-1-82 m/z=591.17 (C ₄₂ H ₂₅ NOS=591.73) Sub-1-83 m/z=401.12 (C ₂₈ H ₁₉ NS=401.53) Sub-1-84 m/z = 575.22 (C ₄₃ H ₂₉ NO = 575.71) Sub-1-85 m/z=513.25 (C ₃₉ H ₃₁ N=513.68) Sub-1-86 m/z=411.16 (C ₃₀ H ₂₁ NO=411.50) Sub-1-87 m/z = 537.21 (C ₄₀ H ₂₇ NO = 537.66) Sub-1-88 m/z=414.15 (C ₂₇ H ₁₈ N ₄ O=414.47) Sub-1-89 m/z=573.21 (C ₄₃ H ₂₇ NO=573.70) Sub-1-90 m/z=415.10 (C ₂₈ H ₁₇ NOS=415.51) Sub-1-91 m/z=451.19 (C ₃₃ H ₂₅ NO=451.57) Sub-1-92 m/z=401.21 (C ₃₀ H ₂₇ N=401.55) Sub-1-93 m/z=587.22 (C ₄₄ H ₂₉ NO=587.72) Sub-1-94 m/z=425.14 (C ₃₀ H ₁₉ NO ₂ =425.49) Sub-1-95 m/z=617.18 (C ₄₄ H ₂₇ NOS=617.77) Sub-1-96 m/z=471.26 (C ₃₄ H ₃₃ NO=471.64) Sub-1-97 m/z=397.28 (C ₂₉ H ₃₅ N=397.61) Sub-1-98 m/z=336.13 (C ₂₃ H ₁₆ N ₂ O=336.39) Sub-1-99 m/z=474.17 (C ₃₄ H ₂₂ N ₂ O=474.56) Sub-1-100 m/z = 507.21 (C ₃₆ H ₁₇ D ₆ NO ₂ =507.62) Sub-1-101 m/z=549.30 (C ₄₀ H ₃₉ NO=549.76)

II. Synthesis of Sub-2

Sub-2 of Reaction Scheme 1 is synthesized by the reaction pathway of Reaction Scheme 3 below, but is not limited thereto. Hal is I, Br or Cl.

<Scheme 3>

1. Sub-2-11 synthesis example

After dissolving Sub-2-a-11 (20.0 g, 71.0 mmol) in THF (355 mL) in a round bottom flask, Sub-2-b-11 (16.2 g, 71.0 mmol), Pd(PPh ₃ ) ₄ ( 4.9 g, 4.3 mmol), NaOH (8.5 g, 213.1 mmol), H ₂ O (178 mL) and stirred at 80 °C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ , concentrated, and the resulting compound was recrystallized using a Silicagel column to obtain 21.3 g of the product. (Yield: 78%)

2. Sub-2-56 synthesis example

In a round bottom flask, Sub-2-a-56 (20.0 g, 67.2 mmol), THF (336 mL), Sub-2-b-56 (14.2 g, 67.2 mmol), Pd(PPh ₃ ) ₄ (4.7 g, 4.0 mmol), NaOH (8.1 g, 201.6 mmol), and H ₂ O (168 mL) were added thereto, and 20.2 g of the product was obtained at 80° C. in the same manner as in Sub-2-11. (Yield: 78%)

3. Sub-2-72 synthesis example

In a round bottom flask, Sub-2-a-72 (20.0 g, 67.2 mmol), THF (336 mL), Sub-2-b-72 (14.5 g, 67.2 mmol), Pd(PPh ₃ ) ₄ (4.7 g, 4.0 mmol), NaOH (8.1 g, 201.6 mmol), and H ₂ O (168 mL) were added thereto, and 20.6 g of the product was obtained at 80° C. in the same manner as in Sub-2-11. (Yield: 79%)

4. Sub-2-73 synthesis example

In a round bottom flask, Sub-2-a-73 (20.0 g, 71.0 mmol), THF (355 mL), Sub-2-b-56 (15.1 g, 71.0 mmol), Pd(PPh ₃ ) ₄ (4.9 g, 4.3 mmol), NaOH (8.5 g, 213.1 mmol), and H ₂ O (178 mL) were added thereto, and 20.2 g of the product was obtained at 80° C. in the same manner as in Sub-2-11. (Yield: 77%)

5. Sub-2-79 synthesis example

In a round bottom flask, Sub-2-a-79 (20.0 g, 67.2 mmol), THF (336 mL), Sub-2-b-11 (15.3 g, 67.2 mmol), Pd(PPh ₃ ) ₄ (4.7 g, 4.0 mmol), NaOH (8.1 g, 201.6 mmol), and H ₂ O (168 mL) were added thereto, and 21.8 g of the product was obtained at 80° C. in the same manner as in Sub-2-11. (Yield: 81%)

6. Sub-2-94 synthesis example

In a round bottom flask, Sub-2-a-94 (20.0 g, 53.5 mmol), THF (268 mL), Sub-2-b-94 (11.3 g, 53.5 mmol), Pd(PPh ₃ ) ₄ (3.7 g, 3.2 mmol), NaOH (6.4 g, 160.6 mmol), and H ₂ O (134 mL) were added thereto, and 19.0 g of the product was obtained at 80° C. in the same manner as in Sub-2-94. (Yield: 77%)

The compound belonging to Sub-2 may be the following compounds, but is not limited thereto, and Table 2 below shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub-2.

compound FD-MS compound FD-MS Sub-2-1 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-2 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-3 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-4 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-5 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-6 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-7 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-8 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-9 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-10 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-11 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-12 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-13 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-14 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-15 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-16 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-17 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-18 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-19 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-20 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-21 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-22 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-23 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-24 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-25 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-26 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-27 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-28 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-29 m/z=552.08 (C ₃₆ H ₂₁ ClS ₂ =553.13) Sub-2-30 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-31 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-32 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-33 m/z=368.06 (C ₂₄ H ₁₃ ClO ₂ =368.82) Sub-2-34 m/z=612.13 (C ₄₂ H ₂₅ ClOS=613.17) Sub-2-35 m/z=400.01 (C ₂₄ H ₁₃ ClS ₂ =400.94) Sub-2-36 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-37 m/z=510.08 (C ₃₄ H ₁₉ ClOS=511.04) Sub-2-38 m/z=494.09 (C ₃₁ H ₂₃ ClS ₂ =495.10) Sub-2-39 m/z=410.05 (C ₂₆ H ₁₅ ClOS=410.92) Sub-2-40 m/z=368.06 (C ₂₄ H ₁₃ ClO ₂ =368.82) Sub-2-41 m/z=510.08 (C ₃₄ H ₁₉ ClOS=511.04) Sub-2-42 m/z=536.10 (C ₃₆ H ₂₁ ClOS=537.07) Sub-2-43 m/z=551.11 (C ₃₆ H ₂₂ ClNOS=552.09) Sub-2-44 m/z=536.10 (C ₃₆ H ₂₁ ClOS=537.07) Sub-2-45 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-46 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub-2-47 m/z=520.12 (C ₃₆ H ₂₁ ClO ₂ =521.01) Sub-2-48 m/z=414.05 (C ₂₅ H ₁₅ ClO ₂ S=414.90) Sub-2-49 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-50 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-51 m/z=409.03 (C ₂₅ H ₁₂ ClNOS=409.89) Sub-2-52 m/z=566.06 (C ₃₆ H ₁₉ ClOS ₂ =567.12) Sub-2-53 m/z=486.12 (C ₃₃ H ₂₃ ClS=487.06) Sub-2-54 m/z=560.10 (C ₃₈ H ₂₁ ClOS=561.10) Sub-2-55 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub-2-56 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-57 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-58 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-59 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-60 m/z = 394.11 (C ₂₇ H ₁₉ ClO = 394.90) Sub-2-61 m/z = 394.11 (C ₂₇ H ₁₉ ClO = 394.90) Sub-2-62 m/z=534.12 (C ₃₇ H ₂₃ ClS=535.10) Sub-2-63 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-64 m/z=576.13 (C ₃₉ H ₂₅ ClOS=577.14) Sub-2-65 m/z = 420.16 (C ₃₀ H ₂₅ Cl = 420.98) Sub-2-66 m/z=486.12 (C ₃₃ H ₂₃ ClS=487.06) Sub-2-67 m/z=548.10 (C ₃₇ H ₂₁ ClOS=549.08) Sub-2-68 m/z = 394.11 (C ₂₇ H ₁₉ ClO = 394.90) Sub-2-69 m/z=510.08 (C ₃₄ H ₁₉ ClOS=511.04) Sub-2-70 m/z=510.08 (C ₃₄ H ₁₉ ClOS=511.04) Sub-2-71 m/z = 394.11 (C ₂₇ H ₁₉ ClO = 394.90) Sub-2-72 m/z=388.06 (C ₂₄ H ₉ D ₄ ClOS=388.90) Sub-2-73 m/z=368.06 (C ₂₄ H ₁₃ ClO ₂ =368.82) Sub-2-74 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-75 m/z=534.10 (C ₃₆ H ₁₉ ClO ₃ =535.00) Sub-2-76 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub-2-77 m/z=690.12 (C ₄₇ H ₂₇ ClS ₂ =691.30) Sub-2-78 m/z=410.09 (C ₂₇ H ₁₉ ClS=410.96) Sub-2-79 m/z=400.01 (C ₂₄ H ₁₃ ClS ₂ =400.94) Sub-2-80 m/z=450.03 (C ₂₈ H ₁₅ ClS ₂ =451.00) Sub-2-81 m/z=460.11 (C ₃₁ H ₂₁ ClS=461.02) Sub-2-82 m/z=476.05 (C ₃₀ H ₁₇ ClS ₂ =477.04) Sub-2-83 m/z=526.06 (C ₃₄ H ₁₉ ClS ₂ =527.10) Sub-2-84 m/z=562.15 (C ₃₉ H ₂₇ ClS=563.16) Sub-2-85 m/z=552.08 (C ₃₆ H ₂₁ ClS ₂ =553.13) Sub-2-86 m/z=612.13 (C ₄₂ H ₂₅ ClOS=613.17) Sub-2-87 m/z = 618.21 (C ₄₆ H ₃₁ Cl = 619.20) Sub-2-88 m/z = 618.21 (C ₄₆ H ₃₁ Cl = 619.20) Sub-2-89 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-90 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-91 m/z=510.08 (C ₃₄ H ₁₉ ClOS=511.04) Sub-2-92 m/z = 618.21 (C ₄₆ H ₃₁ Cl = 619.20) Sub-2-93 m/z=456.13 (C ₃₂ H ₂₁ ClO=456.97) Sub-2-94 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-95 m/z=614.01 (C ₃₆ H ₁₉ ClS ₄ =615.24) Sub-2-96 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-97 m/z=699.18 (C ₄₉ H ₃₀ ClNS=700.30) Sub-2-98 m/z=444.09 (C ₃₀ H ₁₇ ClO ₂ =444.91) Sub-2-99 m/z=400.01 (C ₂₄ H ₁₃ ClS ₂ =400.94) Sub-2-100 m/z=625.13 (C ₄₂ H ₂₄ ClNOS=626.17) Sub-2-101 m/z=486.12 (C ₃₃ H ₂₃ ClS=487.06) Sub-2-102 m/z=472.12 (C ₃₂ H ₂₁ ClO ₂ =472.97) Sub-2-103 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-104 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub-2-105 m/z=576.13 (C ₃₉ H ₂₅ ClOS=577.14) Sub-2-106 m/z=536.10 (C ₃₆ H ₂₁ ClOS=537.07) Sub-2-107 m/z=368.06 (C ₂₄ H ₁₃ ClO ₂ =368.82) Sub-2-108 m/z=560.10 (C ₃₈ H ₂₁ ClOS=561.10) Sub-2-109 m/z=625.13 (C ₄₂ H ₂₄ ClNOS=626.17) Sub-2-110 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub-2-111 m/z=470.14 (C ₃₃ H ₂₃ ClO=471.00)

III. Synthesis of Final Product

1.P-11 synthesis example

In a round bottom flask, Sub-1-11 (10.0 g, 28.6 mmol), Sub-2-11 (10.6 g, 28.6 mmol), Pd ₂ (dba) ₃ (0.8 g, 0.9 mmol), P(t-Bu) After adding ₃ (0.4 g, 1.7 mmol), NaOt-Bu (5.5 g, 57.2 mmol), and toluene (143 mL), the reaction proceeds at 80 °C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ , concentrated, and the organic material was recrystallized using a silica gel column to obtain 14.0 g of the product. (Yield: 70%)

2. P-56 synthesis example

In a round bottom flask, Sub-1-56 (10.0 g, 23.5 mmol), Sub-2-56 (8.7 g, 23.5 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.7 mmol), P(t-Bu) After adding No. ₃ (0.3 g, 1.4 mmol), NaOt-Bu (4.5 g, 47.0 mmol), and toluene (118 mL), 12.4 g of the product was obtained by performing the experiment at 80 ° C in the same manner as in P-11. (Yield: 68%)

3. P-72 synthesis example

In a round bottom flask, Sub-1-72 (10.0 g, 18.2 mmol), Sub-2-72 (6.8 g, 18.2 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P(t-Bu) After adding No. ₃ (0.2 g, 1.1 mmol), NaOt-Bu (3.5 g, 36.5 mmol), and toluene (91 mL), 11.7 g of product was obtained by conducting the same experiment as in P-11 at 80 ° C. (Yield: 71%)

4. P-73 synthesis example

In a round bottom flask, Sub-1-73 (10.0 g, 29.8 mmol), Sub-2-17 (11.1 g, 29.8 mmol), Pd ₂ (dba) ₃ (0.8 g, 0.9 mmol), P(t-Bu) After adding No. ₃ (0.4 g, 1.8 mmol), NaOt-Bu (5.7 g, 59.6 mmol), and toluene (149 mL), 13.7 g of the product was obtained by performing the experiment at 80 ° C in the same manner as in P-11. (Yield: 67%)

5. P-79 synthesis example

In a round bottom flask, Sub-1-79 (10.0 g, 18.7 mmol), Sub-2-79 (7.3 g, 18.7 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P(t-Bu) After adding No. ₃ (0.2 g, 1.1 mmol), NaOt-Bu (3.6 g, 37.5 mmol), and toluene (94 mL), 12.1 g of product was obtained by conducting the same experiment as in P-11 at 80 ° C. (Yield: 72%)

6. P-94 synthesis example

In a round bottom flask, Sub-1-94 (10.0 g, 23.5 mmol), Sub-2-94 (10.5 g, 23.5 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.7 mmol), P(t-Bu) After adding No. ₃ (0.3 g, 1.4 mmol), NaOt-Bu (4.5 g, 47.0 mmol), and toluene (118 mL), 14.2 g of product was obtained by conducting the same experiment as in P-11 at 80 ° C. (Yield: 71%)

On the other hand, the FD-MS values of the compounds P-1 to P-120 of the present invention prepared according to the Synthesis Example as described above are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z = 607.16 (C ₄₂ H ₂₅ NO ₂ S = 607.73) P-2 m/z = 683.19 (C ₄₈ H ₂₉ NO ₂ S = 683.83) P-3 m/z = 683.19 (C ₄₈ H ₂₉ NO ₂ S = 683.83) P-4 m/z = 683.19 (C ₄₈ H ₂₉ NO ₂ S = 683.83) P-5 m/z = 657.18 (C ₄₆ H ₂₇ NO ₂ S = 657.79) P-6 m/z = 657.18 (C ₄₆ H ₂₇ NO ₂ S = 657.79) P-7 m/z = 759.22 (C ₅₄ H ₃₃ NO ₂ S = 759.92) P-8 m/z = 759.22 (C ₅₄ H ₃₃ NO ₂ S = 759.92) P-9 m/z = 759.22 (C ₅₄ H ₃₃ NO ₂ S = 759.92) P-10 m/z = 607.16 (C ₄₂ H ₂₅ NO ₂ S = 607.73) P-11 m/z = 697.17 (C ₄₈ H ₂₇ NO ₃ S = 697.81) P-12 m/z = 713.15 (C ₄₈ H ₂₇ NO ₂ S ₂ =713.87) P-13 m/z = 723.22 (C ₅₁ H ₃₃ NO ₂ S = 723.89) P-14 m/z = 607.16 (C ₄₂ H ₂₅ NO ₂ S = 607.73) P-15 m/z=772.22 (C ₅₄ H ₃₂ N ₂ O ₂ S=772.92) P-16 m/z = 845.24 (C ₆₁ H ₃₅ NO ₂ S = 846.02) P-17 m/z = 683.19 (C ₄₈ H ₂₉ NO ₂ S = 683.83) P-18 m/z = 877.21 (C ₆₁ H ₃₅ NO ₂ S ₂ =878.08) P-19 m/z = 861.23 (C ₆₁ H ₃₅ NO ₃ S = 862.02) P-20 m/z = 950.30 (C ₆₈ H ₄₂ N ₂ O ₂ S = 951.16) P-21 m/z = 847.25 (C ₆₁ H ₃₇ NO ₂ S = 848.03) P-22 m/z = 847.25 (C ₆₁ H ₃₇ NO ₂ S = 848.03) P-23 m/z = 729.14 (C ₄₈ H ₂₇ NO ₃ S ₂ =729.87) P-24 m/z = 713.17 (C ₄₈ H ₂₇ NO ₄ S = 713.81) P-25 m/z = 745.12 (C ₄₈ H ₂₇ NO ₂ S ₃ =745.93) P-26 m/z = 733.21 (C ₅₂ H ₃₁ NO ₂ S = 733.89) P-27 m/z = 739.22 (C ₅₁ H ₃₃ NO ₃ S = 739.89) P-28 m/z = 773.18 (C ₅₄ H ₃₁ NOS ₂ =773.97) P-29 m/z=814.27 (C ₅₇ H ₃₈ N ₂ O ₂ S=815.00) P-30 m/z = 612.19 (C ₄₂ H ₂₀ D ₅ NO ₂ S = 612.76) P-31 m/z = 747.19 (C ₅₂ H ₂₉ NO ₃ S = 747.87) P-32 m/z = 895.25 (C ₆₅ H ₃₇ NO ₂ S = 896.08) P-33 m/z = 667.21 (C ₄₈ H ₂₉ NO ₃ =667.76) P-34 m/z = 849.23 (C ₆₀ H ₃₅ NO ₃ S = 850.00) P-35 m/z = 881.19 (C ₆₀ H ₃₅ NOS ₃ =882.13) P-36 m/z = 875.29 (C ₆₃ H ₄₁ NO ₂ S = 876.09) P-37 m/z = 729.22 (C ₅₀ H ₃₅ NOS ₂ =729.96) P-38 m/z = 783.21 (C ₅₃ H ₃₇ NS ₃ =784.07) P-39 m/z=814.21 (C ₅₆ H ₃₄ N ₂ OS ₂ =815.02) P-40 m/z = 835.25 (C ₆₀ H ₃₇ NO ₂ S = 836.02) P-41 m/z = 885.27 (C ₆₄ H ₃₉ NO ₂ S = 886.08) P-42 m/z = 759.22 (C ₅₄ H ₃₃ NO ₂ S = 759.92) P-43 m/z = 864.24 (C ₆₀ H ₃₆ N ₂ O ₃ S = 865.02) P-44 m/z = 865.21 (C ₆₀ H ₃₅ NO ₂ S ₂ =866.07) P-45 m/z = 799.25 (C ₅₇ H ₃₇ NO ₂ S = 799.99) P-46 m/z = 657.18 (C ₄₆ H ₂₇ NO ₂ S = 657.79) P-47 m/z=822.23 (C ₅₈ H ₃₄ N ₂ O ₂ S=822.98) P-48 m/z = 875.25 (C ₆₂ H ₃₇ NO ₃ S = 876.04) P-49 m/z = 815.29 (C ₅₈ H ₄₁ NO ₂ S = 816.03) P-50 m/z=856.23 (C ₅₇ H ₃₃ FN ₄ O ₂ S=856.98) P-51 m/z=758.20 (C ₅₃ H ₃₀ N ₂ O ₂ S=758.90) P-52 m/z = 906.20 (C ₆₁ H ₃₄ N ₂ O ₃ S ₂ =907.07) P-53 m/z = 733.21 (C ₅₂ H ₃₁ NO ₂ S = 733.89) P-54 m/z = 783.22 (C ₅₆ H ₃₃ NO ₂ S = 783.95) P-55 m/z = 833.24 (C ₆₀ H ₃₅ NO ₂ S = 834.01) P-56 m/z = 773.20 (C ₅₄ H ₃₁ NO ₃ S = 773.91) P-57 m/z = 759.22 (C ₅₄ H ₃₃ NO ₂ S = 759.92) P-58 m/z = 683.19 (C ₄₈ H ₂₉ NO ₂ S = 683.83) P-59 m/z = 879.19 (C ₆₀ H ₃₃ NO ₃ S ₂ =880.05) P-60 m/z = 889.27 (C ₆₃ H ₃₉ NO ₃ S = 890.07) P-61 m/z=759.35 (C ₅₇ H ₄₅ NO=759.99) P-62 m/z=757.24 (C ₅₅ H ₃₅ NOS=757.95) P-63 m/z=1086.33 (C ₇₉ H ₄₆ N ₂ O ₂ S=1087.31) P-64 m/z = 1037.33 (C ₇₆ H ₄₇ NO ₂ S = 1038.28) P-65 m/z=719.32 (C ₅₄ H ₄₁ NO=719.93) P-66 m/z = 1005.35 (C ₇₃ H ₅₁ NS ₂ =1006.34) P-67 m/z = 1173.36 (C ₈₇ H ₅₁ NO ₂ S = 1174.43) P-68 m/z=946.36 (C ₇₀ H ₄₆ N ₂ O ₂ =947.15) P-69 m/z = 809.24 (C ₅₈ H ₃₅ NO ₂ S = 809.98) P-70 m/z = 859.25 (C ₆₂ H ₃₇ NO ₂ S = 860.04) P-71 m/z = 1071.28 (C ₇₅ H ₄₅ NO ₃ S ₂ =1072.31) P-72 m/z = 900.33 (C ₆₃ H ₂₈ D ₁₁ NO ₃ S = 901.14) P-73 m/z = 683.19 (C ₄₈ H ₂₉ NO ₂ S = 683.83) P-74 m/z = 835.25 (C ₆₀ H ₃₇ NO ₂ S = 836.02) P-75 m/z = 807.24 (C ₅₈ H ₃₃ NO ₄ =807.91) P-76 m/z=898.30 (C ₆₅ H ₄₂ N ₂ OS=899.12) P-77 m/z = 913.25 (C ₆₅ H ₃₉ NOS ₂ =914.15) P-78 m/z=1101.40 (C ₈₂ H ₅₅ NOS=1102.41) P-79 m/z = 897.18 (C ₆₀ H ₃₅ NO ₂ S ₃ =898.13) P-80 m/z = 723.17 (C ₅₀ H ₂₉ NOS ₂ =723.91) P-81 m/z = 839.23 (C ₅₉ H ₃₇ NOS ₂ =840.07) P-82 m/z = 1031.24 (C ₇₂ H ₄₁ NOS ₃ =1032.31) P-83 m/z = 891.21 (C ₆₂ H ₃₇ NS ₃ =892.17) P-84 m/z=1101.40 (C ₈₂ H ₅₅ NOS=1102.41) P-85 m/z = 1029.35 (C ₇₅ H ₅₁ NS ₂ =1030.36) P-86 m/z = 987.32 (C ₇₂ H ₄₅ NO ₂ S = 988.22) P-87 m/z=1119.44 (C ₈₆ H ₅₇ NO=1120.41) P-88 m/z=838.24 (C ₅₇ H ₃₄ N ₄ O ₂ S=838.99) P-89 m/z = 997.30 (C ₇₃ H ₄₃ NO ₂ S = 998.21) P-90 m/z = 839.20 (C ₅₈ H ₃₃ NO ₂ S ₂ =840.03) P-91 m/z = 925.30 (C ₆₇ H ₄₃ NO ₂ S = 926.15) P-92 m/z = 983.45 (C ₇₆ H ₅₇ N = 984.30) P-93 m/z = 1007.38 (C ₇₆ H ₄₉ NO ₂ =1008.23) P-94 m/z = 849.23 (C ₆₀ H ₃₅ NO ₃ S = 850.00) P-95 m/z = 837.13 (C ₅₄ H ₃₁ NOS ₄ =838.09) P-96 m/z = 895.35 (C ₆₄ H ₄₉ NO ₂ S = 896.16) P-97 m/z=1060.48 (C ₇₈ H ₆₄ N ₂ S=1061.44) P-98 m/z = 744.24 (C ₅₃ H ₃₂ N ₂ O ₃ =744.85) P-99 m/z=838.21 (C ₅₈ H ₃₄ N ₂ OS ₂ =839.04) P-100 m/z=848.25 (C ₆₀ H ₃₆ N ₂ O ₂ S=849.02) P-101 m/z=999.45 (C ₇₃ H ₆₁ NOS=1000.36) P-102 m/z = 837.27 (C ₆₀ H ₃₉ NO ₂ S = 838.04) P-103 m/z = 1067.33 (C ₇₇ H ₄₉ NOS ₂ =1068.37) P-104 m/z=1143.36 (C ₈₃ H ₅₃ NOS ₂ =1144.46) P-105 m/z = 875.29 (C ₆₃ H ₄₁ NO ₂ S = 876.09) P-106 m/z = 773.24 (C ₅₅ H ₃₅ NO ₂ S = 773.95) P-107 m/z = 969.36 (C ₇₃ H ₄₇ NO ₂ =970.18) P-108 m/z = 833.24 (C ₆₀ H ₃₅ NO ₂ S = 834.01) P-109 m/z=1139.35 (C ₈₂ H ₄₉ N ₃ O ₂ S=1140.37) P-110 m/z=872.25 (C ₆₂ H ₃₆ N ₂ O ₂ S=873.04) P-111 m/z = 993.26 (C ₇₀ H ₄₃ NS ₃ =994.30) P-112 m/z = 961.30 (C ₇₀ H ₄₃ NO ₂ S = 962.18) P-113 m/z = 909.27 (C ₆₆ H ₃₉ NO ₂ S = 910.10) P-114 m/z = 919.31 (C ₆₈ H ₄₁ NO ₃ =920.08) P-115 m/z = 937.34 (C ₆₉ H ₄₇ NOS = 938.20) P-116 m/z = 883.25 (C ₆₄ H ₃₇ NO ₂ S = 884.07) P-117 m/z = 1021.39 (C ₇₇ H ₅₁ NO ₂ =1022.26) P-118 m/z = 941.24 (C ₆₆ H ₃₉ NO ₂ S ₂ =942.16) P-119 m/z = 1041.27 (C ₇₄ H ₄₃ NO ₂ S ₂ =1042.28) P-120 m/z = 839.29 (C ₆₀ H ₂₉ D ₆ NO ₄ =839.98)

[ synthesis example 2]

The compound represented by Formula 2 according to the present invention (final product 2) is synthesized as shown in Reaction Scheme 4 below, but is not limited thereto.

In Scheme 4 below, G ¹ is L ⁵ or L ⁶ , G ² is Ar ³ or Ar ⁴ , and X ¹ to X ³ , L ⁴ to L ⁶ , and Ar ² to Ar ⁴ are the same as defined in Formula 1 above. Do.

<Scheme 4> (Hal ³ and Hal ⁴ are independently I, Br or Cl.)

I. Synthesis Example of Sub 7

1. Sub 7-1 synthesis example

4 in 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (CAS Registry Number: 10202-45-6) (20 g, 66.19 mmol) -Biphenylboronic acid (CAS Registry Number: 5122-94-1) (13.1 g, 66.19 mmol) was dissolved in THF (370 ml), Pd(PPh ₃ ) ₄ (3.8 g, 3.31 mmol), K ₂ CO ₃ ( 27.4 g, 198.57 mmol) and water (165 ml) are added and stirred at reflux. Upon completion of the reaction, after extraction with ether and water, the organic layer is concentrated. The concentrated organic layer was dried over MgSO ₄ and concentrated once more. The final concentrate was passed through a silica gel column and recrystallized to obtain 20.8 g of product. (75% yield)

2. Subs 7-8 synthesis example

(3-(pyridin-2-yl)phenyl)boronic acid (14.3 g, 72.43 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv.), K ₂ CO ₃ (3 equiv.), anhydrous THF and a small amount of water were added, and 20.3 g of the product was synthesized in the same manner as in the synthesis of Sub 7-1. (Yield 71%)

3. Sub 7-19 synthesis example

2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (15 g, 49.64 mmol) in (9,9-dimethyl-9H-fluoren-3 -yl)boronic acid (11.8 g, 49.64 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv.), K ₂ CO ₃ (3 equiv.), anhydrous THF and a small amount of water were added, and the same method as in the synthesis of Sub 7-1 was added. 15.7 g of the product was synthesized by the method. (yield 69%)

4. Sub 7-35 synthesis example

2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol) in dibenzo[b,d]furan-2-ylboronic acid (28.1 g, 132.71 mmol), Pd(PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq.), anhydrous THF and a small amount of water were added, and 30.8 g of the product was synthesized in the same manner as in the synthesis of Sub 7-1. (yield 65%)

The compounds belonging to Sub 7 may be the following compounds, but are not limited thereto, and Table 4 below shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 7.

compound FD-MS compound FD-MS Sub 7-1 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 7-2 m/z=469.13 (C ₃₁ H ₂₀ ClN ₃ =469.97) Sub 7-3 m/z=393.10 (C ₂₅ H ₁₆ ClN ₃ =393.87) Sub 7-4 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 7-5 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 7-6 m/z=421.11 (C ₂₅ H ₁₆ ClN ₅ =421.89) Sub 7-7 m/z=575.16 (C ₃₅ H ₂₂ ClN ₇ =576.06) Sub 7-8 m/z=394.10 (C ₂₄ H ₁₅ ClN ₄ =394.86) Sub 7-9 m/z=421.11 (C ₂₅ H ₁₆ ClN ₅ =421.89) Sub 7-10 m/z=469.13 (C ₃₁ H ₂₀ ClN ₃ =469.97) Sub 7-11 m/z=503.21 (C ₃₃ H ₃₀ ClN ₃ =504.07) Sub 7-12 m/z=525.11 (C ₃₃ H ₂₀ ClN ₃ S=526.05) Sub 7-13 m/z=433.10 (C ₂₇ H ₁₆ ClN ₃ O=433.90) Sub 7-14 m/z=568.17 (C ₄₀ H ₂₅ ClN ₂ =569.10) Sub 7-15 m/z=569.17 (C ₃₉ H ₂₄ ClN ₃ =570.09) Sub 7-16 m/z=469.13 (C ₃₁ H ₂₀ ClN ₃ =469.97) Sub 7-17 m/z=433.10 (C ₂₇ H ₁₆ ClN ₃ O=433.90) Sub 7-18 m/z=583.18 (C ₄₀ H ₂₆ ClN ₃ =584.12) Sub 7-19 m/z=461.17 (C ₃₀ H ₂₄ ClN ₃ =461.99) Sub 7-20 m/z=418.12 (C ₂₈ H ₁₉ ClN ₂ =418.92) Sub 7-21 m/z=420.11 (C ₂₆ H ₁₇ ClN ₄ =420.90) Sub 7-22 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.80) Sub 7-23 m/z=459.15 (C ₃₀ H ₂₂ ClN ₃ =459.98) Sub 7-24 m/z=507.15 (C ₃₄ H ₂₂ ClN ₃ =508.02) Sub 7-25 m/z=519.15 (C ₃₅ H ₂₂ ClN ₃ =520.03) Sub 7-26 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 7-27 m/z=266.06 (C ₁₆ H ₁₁ ClN ₂ =266.73) Sub 7-28 m/z=433.10 (C ₂₇ H ₁₆ ClN ₃ O=433.90) Sub 7-29 m/z=355.09 (C ₂₂ H ₁₄ ClN ₃ =355.83) Sub 7-30 m/z=470.13 (C ₃₀ H ₁₉ ClN ₄ =470.96) Sub 7-31 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 7-32 m/z=545.17 (C ₃₇ H ₂₄ ClN ₃ =546.07) Sub 7-33 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 7-34 m/z=269.05 (C ₁₃ H ₈ ClN ₅ =269.69) Sub 7-35 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.80) Sub 7-36 m/z=420.11 (C ₂₆ H ₁₇ ClN ₄ =420.90) Sub 7-37 m/z=433.10 (C ₂₇ H ₁₆ ClN ₃ O=433.90) Sub 7-38 m/z=368.08 (C ₂₂ H ₁₃ ClN ₄ =368.82) Sub 7-39 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 7-40 m/z=395.09 (C ₂₃ H ₁₄ ClN ₅ =395.85) Sub 7-41 m/z=267.06 (C ₁₅ H ₁₀ ClN ₃ =267.72) Sub 7-42 m/z=369.08 (C ₂₁ H ₁₂ ClN ₅ =369.81) Sub 7-43 m/z=469.11 (C ₂₉ H ₁₆ ClN ₅ =469.93) Sub 7-44 m/z=581.17 (C ₄₀ H ₂₄ ClN ₃ =582.10) Sub 7-45 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub 7-46 m/z=449.08 (C ₂₇ H ₁₆ ClN ₃ S=449.96) Sub 7-47 m/z=495.15 (C ₃₃ H ₂₂ ClN ₃ =496.01) Sub 7-48 m/z=449.08 (C ₂₇ H ₁₆ ClN ₃ S=449.96) Sub 7-49 m/z = 803.29 (C ₅₉ H ₃₇ N ₃ O = 803.97)

II. Synthesis example of Sub 6

Sub 6 of Reaction Scheme 4 may be synthesized by the reaction pathway of Reaction Scheme 5 below, but is not limited thereto.

<Scheme 5> (Hal ⁵ is I, Br or Cl.)

1. Sub 6-2 synthesis example

bis(pinacolato)diboron (7.1 g, 27.89 mmol), PdCl ₂ (dppf) _, (0.78 g, 1.07 mmol), KOAc (6.3 g, 64.35 mmol) and DMF (270 ml), and stirred and refluxed at 120°C. When the reaction is completed, the reactant is cooled to room temperature, extracted with MC, and washed with water. After drying the organic layer with MgSO ₄ and concentrating, the resulting organic material was separated using a silica gel column to obtain 3.4 g (80%) of Sub 6-2.

2. Subs 6-37 synthesis example

Add 2-bromodibenzo[b,d]furan (10 g, 40.47 mmol) bis(pinacolato)diboron (13.3 g, 52.61 mmol), PdCl ₂ (dppf) _, (0.05 equiv.), KOAc (3 equiv.), anhydrous DMF and 7 g of the product was synthesized in the same manner as in the synthesis of Sub 6-2. (Yield 82%)

The compound belonging to Sub 6 may be the following compounds, but is not limited thereto, and Table 5 below shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 6.

compound FD-MS compound FD-MS Sub 6-1 m/z=122.05 (C ₆ H ₇ BO ₂ =121.93) Sub 6-2 m/z=198.09 (C ₁₂ H ₁₁ BO ₂ =198.03) Sub 6-3 m/z=172.07 (C ₁₀ H ₉ BO ₂ =171.99) Sub 6-4 m/z=172.07 (C ₁₀ H ₉ BO ₂ =171.99) Sub 6-5 m/z=274.12 (C ₁₈ H ₁₅ BO ₂ =274.13) Sub 6-6 m/z=198.09 (C ₁₂ H ₁₁ BO ₂ =198.03) Sub 6-7 m/z=248.10 (C ₁₆ H ₁₃ BO ₂ =248.09) Sub 6-8 m/z=222.09 (C ₁₄ H ₁₁ BO ₂ =222.05) Sub 6-9 m/z=246.09 (C ₁₆ H ₁₁ BO ₂ =246.07) Sub 6-10 m/z=399.14 (C ₂₇ H ₁₈ BNO ₂ =399.26) Sub 6-11 m/z=123.05 (C ₅ H ₆ BNO ₂ =122.92) Sub 6-12 m/z=123.05 (C ₅ H ₆ BNO ₂ =122.92) Sub 6-13 m/z=123.05 (C ₅ H ₆ BNO ₂ =122.92) Sub 6-14 m/z=199.08 (C ₁₁ H ₁₀ BNO ₂ =199.02) Sub 6-15 m/z=199.08 (C ₁₁ H ₁₀ BNO ₂ =199.02) Sub 6-16 m/z=240.13 (C ₁₅ H ₁₇ BO ₂ =240.11) Sub 6-17 m/z=248.10 (C ₁₆ H ₁₃ BO ₂ =248.09) Sub 6-18 m/z=222.09 (C ₁₄ H ₁₁ BO ₂ =222.05) Sub 6-19 m/z=224.08 (C ₁₂ H ₉ BN ₂ O ₂ =224.03) Sub 6-20 m/z=224.08 (C ₁₂ H ₉ BN ₂ O ₂ =224.03) Sub 6-21 m/z=350.15 (C ₂₄ H ₁₉ BO ₂ =350.22) Sub 6-22 m/z=374.15 (C ₂₆ H ₁₉ BO ₂ =374.25) Sub 6-23 m/z=272.10 (C ₁₈ H ₁₃ BO ₂ =272.11) Sub 6-24 m/z=174.06 (C ₈ H ₇ BN ₂ O ₂ =173.97) Sub 6-25 m/z=174.06 (C ₈ H ₇ BN ₂ O ₂ =173.97) Sub 6-26 m/z=223.08 (C ₁₃ H ₁₀ BNO ₂ =223.04) Sub 6-27 m/z=238.12 (C ₁₅ H ₁₅ BO ₂ =238.09) Sub 6-28 m/z=238.12 (C ₁₅ H ₁₅ BO ₂ =238.09) Sub 6-29 m/z=362.15 (C ₂₅ H ₁₉ BO ₂ =362.24) Sub 6-30 m/z=360.13 (C ₂₅ H ₁₇ BO ₂ =360.22) Sub 6-31 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 6-32 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 6-33 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 6-34 m/z=228.04 (C ₁₂ H ₉ BO ₂ S=228.07) Sub 6-35 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 6-36 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 6-37 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 6-38 m/z=212.06 (C ₁₂ H ₉ BO ₃ =212.01) Sub 6-39 m/z=306.06 (C ₁₆ H ₁₁ BN ₂ O ₂ S=306.15) Sub 6-40 m/z=290.09 (C ₁₆ H ₁₁ BN ₂ O ₃ =290.09) Sub 6-41 m/z=443.14 (C ₂₇ H ₁₈ BN ₃ O ₃ =443.27) Sub 6-42 m/z=288.10 (C ₁₈ H ₁₃ BO ₃ =288.11) Sub 6-43 m/z=304.07 (C ₁₈ H ₁₃ BO ₂ S=304.17) Sub 6-44 m/z=304.07 (C ₁₈ H ₁₃ BO ₂ S=304.17) Sub 6-45 m/z=578.24 (C ₄₂ H ₃₁ BO ₂ =578.52) Sub 6-46 m/z=424.16 (C ₃₀ H ₂₁ BO ₂ =424.31) Sub 6-47 m/z=378.11 (C ₂₄ H ₁₅ BO ₄ =378.19) Sub 6-48 m/z=256.07 (C ₁₂ H ₁₀ B ₂ O ₅ =255.83) Sub 6-49 m/z=424.16 (C ₃₀ H ₂₁ BO ₂ =424.31) Sub 6-50 m/z=288.10 (C ₁₈ H ₁₃ BO ₃ =288.11) Sub 6-51 m/z=376.13 (C ₂₅ H ₁₇ BO ₃ =376.22) Sub 6-52 m/z=362.15 (C ₂₅ H ₁₉ BO ₂ =362.24) Sub 6-53 m/z=262.08 (C ₁₆ H ₁₁ BO ₃ =262.07) Sub 6-54 m/z=392.10 (C ₂₅ H ₁₇ BO ₂ S=392.28) Sub 6-55 m/z=424.16 (C ₃₀ H ₂₁ BO ₂ =424.31)

III. Synthesis of Final Product 2

Sub 7 (1 equivalent) and Sub 6 (1-2 equivalents) were put in a round flask, dissolved in THF, and Pd(PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq.) and water were added and stirred and refluxed. After the reaction was completed, after extraction with ether and water, the organic layer was dried with MgSO ₄ , concentrated, and the resulting compound was recrystallized using a silica gel column to obtain Final product 2.

1. Synthesis example of 6-9

Sub 7-1 (5 g, 11.91 mmol) was dissolved in Sub 6-36 (2.8 g, 13.1 mmol) in THF (70 ml), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol), K ₂ CO ₃ (5 g, 35.73 mmol) and water (30 ml) were added and stirred at reflux. Upon completion of the reaction, after extraction with ether and water, the organic layer is concentrated. The concentrated organic layer was dried over MgSO ₄ and concentrated once more. The final concentrate was passed through a silica gel column and recrystallized to obtain 5.4 g of product. (Yield 71%)

2. Synthesis example of 6-29

Sub 7-39 (4 g, 14.94 mmol) with Sub 6-47 (6.2 g, 16.43 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water was added, and 8.1 g of the product was synthesized in the same manner as in the above synthesis method 6-9. (yield 84%)

3. Synthesis example of 6-62

Sub 7-33 (4 g, 10.7 mmol) Sub 6-32 (2.7 g, 11.8 mmol), Pd(PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and a small amount of water was added, and 4.4 g of the product was synthesized in the same manner as in the above synthesis method 6-9. (yield 80%)

4. Synthesis example of 6-115

Sub 7-41 (10 g, 37.35 mmol) Sub 6-48 (4.7 g, 18.5 mmol), Pd(PPh ₃ ) ₄ (0.1 equiv), K ₂ CO ₃ (6 equiv), anhydrous THF and a small amount of water was added, and 9.1 g of the product was synthesized in the same manner as in the above synthesis method 6-9. (Yield 78%)

5. N-19 synthesis example

2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (12.6 g, 30 mmol) and (5-phenylnaphthalen-2-yl)boronic acid (8.2 g, 33 mmol) was obtained by using the synthesis method of 6-9 above to obtain 15.5 g (yield: 88%) of the product.

6. N-86 synthesis example

2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (11 g, 30 mmol) and (6-phenylnaphthalen-2-yl)boronic acid (8.2 g, 33 mmol) 10.8 g of the product (yield: 67%) was obtained using the synthesis method of 6-9 above.

On the other hand, the FD-MS values of the compounds of the present invention prepared according to the Synthesis Example as described above are shown in Table 6 below.

compound FD-MS compound FD-MS 6-1 m/z=399.14 (C ₂₇ H ₁₇ N ₃ O=399.45) 6-2 m/z=415.11 (C ₂₇ H ₁₇ N ₃ S=415.51) 6-3 m/z=474.18 (C ₃₃ H ₂₂ N ₄ =474.57) 6-4 m/z=449.15 (C ₃₁ H ₁₉ N ₃ O=449.51) 6-5 m/z=449.15 (C ₃₁ H ₁₉ N ₃ O=449.51) 6-6 m/z=515.15 (C ₃₅ H ₂₁ N ₃ S=515.63) 6-7 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 6-8 m/z=499.17 (C ₃₅ H ₂₁ N ₃ O=499.57) 6-9 m/z=551.20 (C ₃₉ H ₂₅ N ₃ O=551.65) 6-10 m/z=567.18 (C ₃₉ H ₂₅ N ₃ S=567.71) 6-11 m/z=702.28 (C ₅₁ H ₃₄ N ₄ =702.86) 6-12 m/z=657.22 (C ₄₆ H ₃₁ N ₃ S=657.84) 6-13 m/z=551.20 (C ₃₉ H ₂₅ N ₃ O=551.65) 6-14 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 6-15 m/z = 700.26 (C ₅₁ H ₃₂ N ₄ =700.85) 6-16 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 6-17 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 6-18 m/z=591.18 (C ₄₁ H ₂₅ N ₃ S=591.73) 6-19 m/z=627.24 (C ₄₄ H ₂₉ N ₅ =627.75) 6-20 m/z=524.20 (C ₃₇ H ₂₄ N ₄ =524.63) 6-21 m/z=551.20 (C ₃₉ H ₂₅ N ₃ O=551.65) 6-22 m/z=567.18 (C ₃₉ H ₂₅ N ₃ S=567.71) 6-23 m/z=702.28 (C ₅₁ H ₃₄ N ₄ =702.86) 6-24 m/z=474.18 (C ₃₃ H ₂₂ N ₄ =474.57) 6-25 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.94) 6-26 m/z=731.24 (C ₅₂ H ₃₃ N ₃ S=731.92) 6-27 m/z=601.23 (C ₄₂ H ₂₇ N ₅ =601.71) 6-28 m/z=475.17 (C ₃₃ H ₂₁ N ₃ O=475.55) 6-29 m/z=641.21 (C ₄₅ H ₂₇ N ₃ O ₂ =641.73) 6-30 m/z=746.21 (C ₅₁ H ₃₀ N ₄ OS=746.89) 6-31 m/z=716.26 (C ₅₁ H ₃₂ N ₄ O=716.84) 6-32 m/z=681.19 (C ₄₇ H ₂₇ N ₃ OS=681.81) 6-33 m/z=475.17 (C ₃₃ H ₂₁ N ₃ O=475.55) 6-34 m/z=491.15 (C ₃₃ H ₂₁ N ₃ S=491.61) 6-35 m/z=550.22 (C ₃₉ H ₂₆ N ₄ =550.67) 6-36 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 6-37 m/z=475.17 (C ₃₃ H ₂₁ N ₃ O=475.55) 6-38 m/z=491.15 (C ₃₃ H ₂₁ N ₃ S=491.61) 6-39 m/z = 704.27 (C ₄₉ H ₃₂ N ₆ =704.84) 6-40 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 6-41 m/z=551.20 (C ₃₉ H ₂₅ N ₃ O=551.65) 6-42 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 6-43 m/z=626.25 (C ₄₅ H ₃₀ N ₄ =626.76) 6-44 m/z = 676.26 (C ₄₉ H ₃₂ N ₄ =676.82) 6-45 m/z=551.20 (C ₃₉ H ₂₅ N ₃ O=551.65) 6-46 m/z=567.18 (C ₃₉ H ₂₅ N ₃ S=567.71) 6-47 m/z=614.25 (C ₄₄ H ₃₀ N ₄ =614.75) 6-48 m/z=575.17 (C ₃₉ H ₂₁ N ₅ O=575.63) 6-49 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 6-50 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) 6-51 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 6-52 m/z=625.22 (C ₄₅ H ₂₇ N ₃ O=625.73) 6-53 m/z=525.18 (C ₃₇ H ₂₃ N ₃ O=525.61) 6-54 m/z=591.18 (C ₄₁ H ₂₅ N ₃ S=591.73) 6-55 m/z=600.23 (C ₄₃ H ₂₈ N ₄ =600.73) 6-56 m/z=693.22 (C ₄₉ H ₃₁ N ₃ S=693.87) 6-57 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.60) 6-58 m/z=641.21 (C ₄₅ H ₂₇ N ₃ O ₂ =641.73) 6-59 m/z=571.12 (C ₃₇ H ₂₁ N ₃ S ₂ =571.72) 6-60 m/z=564.20 (C ₃₉ H ₂₄ N ₄ O=564.65) 6-61 m/z=581.16 (C ₃₉ H ₂₃ N ₃ OS=581.69) 6-62 m/z=521.10 (C ₃₃ H ₁₉ N ₃ S ₂ =521.66) 6-63 m/z=489.15 (C ₃₃ H ₁₉ N ₃ O ₂ =489.53) 6-64 m/z=640.23 (C ₄₅ H ₂₈ N ₄ O=640.75) 6-65 m/z=489.15 (C ₃₃ H ₁₉ N ₃ O ₂ =489.53) 6-66 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.60) 6-67 m/z=580.17 (C ₃₉ H ₂₄ N ₄ S=580.71) 6-68 m/z=564.20 (C ₃₉ H ₂₄ N ₄ O=564.65) 6-69 m/z=489.15 (C ₃₃ H ₁₉ N ₃ O ₂ =489.53) 6-70 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.60) 6-71 m/z=505.12 (C ₃₃ H ₁₉ N ₃ OS=505.60) 6-72 m/z=639.24 (C ₄₅ H ₂₉ N ₅ =639.76) 6-73 m/z=607.21 (C ₄₂ H ₂₉ N ₃ S=607.78) 6-74 m/z=715.26 (C ₅₂ H ₃₃ N ₃ O=715.86) 6-75 m/z=640.23 (C ₄₅ H ₂₈ N ₄ O=640.75) 6-76 m/z=707.20 (C ₄₉ H ₂₉ N ₃ OS=707.85) 6-77 m/z=591.23 (C ₄₂ H ₂₉ N ₃ O=591.71) 6-78 m/z = 617.28 (C ₄₅ H ₃₅ N ₃ =617.80) 6-79 m/z=653.25 (C ₄₇ H ₃₁ N ₃ O=653.79) 6-80 m/z=733.22 (C ₅₁ H ₃₁ N ₃ OS=733.89) 6-81 m/z = 615.19 (C ₄₃ H ₂₅ N ₃ O ₂ =615.69) 6-82 m/z=681.19 (C ₄₇ H ₂₇ N ₃ OS=681.81) 6-83 m/z = 716.29 (C ₅₂ H ₃₆ N ₄ =716.89) 6-84 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 6-85 m/z=641.25 (C ₄₆ H ₃₁ N ₃ O=641.77) 6-86 m/z=693.22 (C ₄₉ H ₃₁ N ₃ S=693.87) 6-87 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81) 6-88 m/z=631.17 (C ₄₃ H ₂₅ N ₃ OS=631.75) 6-89 m/z=595.14 (C ₃₉ H ₂₁ N ₃ O ₂ S=595.68) 6-90 m/z = 659.24 (C ₄₅ H ₂₁ D ₅ N ₄ O ₂ =659.76) 6-91 m/z = 637.16 (C ₄₂ H ₂₇ N ₃ S ₂ =637.82) 6-92 m/z=729.25 (C ₅₁ H ₃₁ N ₅ O=729.84) 6-93 m/z=578.17 (C ₃₉ H ₂₂ N ₄ O ₂ =578.63) 6-94 m/z=746.21 (C ₅₁ H ₃₀ N ₄ OS=746.89) 6-95 m/z = 681.24 (C ₄₈ H ₃₁ N ₃ O ₂ =681.80) 6-96 m/z = 762.19 (C ₅₁ H ₃₀ N ₄ S ₂ =762.95) 6-97 m/z=436.17 (C ₃₀ H ₂₀ N ₄ =436.52) 6-98 m/z=437.16 (C ₂₉ H ₁₉ N ₅ =437.51) 6-99 m/z=513.20 (C ₃₅ H ₂₃ N ₅ =513.60) 6-100 m/z=589.23 (C ₄₁ H ₂₇ N ₅ =589.70) 6-101 m/z=486.18 (C ₃₄ H ₂₂ N ₄ =486.58) 6-102 m/z=527.17 (C ₃₅ H ₂₁ N ₅ O=527.59) 6-103 m/z=589.23 (C ₄₁ H ₂₇ N ₅ =589.70) 6-104 m/z=502.18 (C ₃₄ H ₂₂ N ₄ O=502.58) 6-105 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) 6-106 m/z=563.21 (C ₃₉ H ₂₅ N ₅ =563.66) 6-107 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) 6-108 m/z=589.23 (C ₄₁ H ₂₇ N ₅ =589.70) 6-109 m/z=513.20 (C ₃₅ H ₂₃ N ₅ =513.60) 6-110 m/z=462.16 (C ₃₀ H ₁₈ N ₆ =462.52) 6-111 m/z=612.21 (C ₄₂ H ₂₄ N ₆ =612.70) 6-112 m/z=499.20 (C ₃₆ H ₂₅ N ₃ =499.62) 6-113 m/z=569.17 (C ₃₇ H ₂₃ N ₅ S=569.69) 6-114 m/z=629.22 (C ₄₃ H ₂₇ N ₅ O=629.72) 6-115 m/z=629.22 (C ₄₃ H ₂₇ N ₅ O=629.72) 6-116 m/z=563.21 (C ₃₉ H ₂₅ N ₅ =563.66) 6-117 m/z=565.20 (C ₃₇ H ₂₃ N ₇ =565.64) 6-118 m/z = 630.22 (C ₄₂ H ₂₆ N ₆ O = 630.71) 6-119 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) 6-120 m/z = 803.29 (C ₅₉ H ₃₇ N ₃ O = 803.97) 6-121 m/z=563.20 (C ₄₀ H ₂₅ N ₃ O=563.66) 6-122 m/z=549.22 (C ₄₀ H ₂₇ N ₃ =549.68) 6-123 m/z=449.15 (C ₃₁ H ₁₉ N ₃ O=449.51) 6-124 m/z=579.18 (C ₄₀ H ₂₅ N ₃ S=579.72) N-1 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-2 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-3 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-4 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-5 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-6 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-7 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-8 m/z=434.18 (C ₃₂ H ₂₂ N ₂ =434.54) N-9 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-10 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-11 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-12 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-13 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-14 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-15 m/z=434.18 (C ₃₂ H ₂₂ N ₂ =434.54) N-16 m/z=434.18 (C ₃₂ H ₂₂ N ₂ =434.54) N-17 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-18 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-19 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-20 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-21 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-22 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-23 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-24 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-25 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-26 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-27 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-28 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-29 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-30 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-31 m/z=435.17 (C ₃₁ H ₂₁ N ₃ =435.53) N-32 m/z=434.18 (C ₃₂ H ₂₂ N ₂ =434.54) N-33 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-34 m/z=511.2 (C ₃₇ H ₂₅ N ₃ =511.63) N-35 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-36 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-37 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-38 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-39 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-40 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-41 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-42 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-43 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-44 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-45 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-46 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-47 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-48 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-49 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-50 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-51 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-52 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-53 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-54 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) N-55 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-56 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-57 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-58 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-59 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-60 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) N-61 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-62 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-63 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) N-64 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) N-65 m/z=637.25 (C ₄₇ H ₃₁ N ₃ =637.79) N-66 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-67 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-68 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-69 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-70 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-71 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-72 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-73 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-74 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-75 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-76 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-77 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-78 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-79 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-80 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-81 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-82 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) N-83 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) N-84 m/z=535.2 (C ₃₉ H ₂₅ N ₃ =535.65) N-85 m/z=585.22 (C ₄₃ H ₂₇ N ₃ =585.71) N-86 m/z=535.2 (C ₃₉ H ₂₅ N ₃ =535.65) N-87 m/z=585.22 (C ₄₃ H ₂₇ N ₃ =585.71) N-88 m/z=585.22 (C ₄₃ H ₂₇ N ₃ =585.71) N-89 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-90 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-91 m/z=585.22 (C ₄₃ H ₂₇ N ₃ =585.71) N-92 m/z=611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-93 m/z = 687.27 (C ₅₁ H ₃₃ N ₃ =687.85) N-94 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-95 m/z=511.20 (C ₃₇ H ₂₅ N ₃ =511.63) N-96 m/z = 611.24 (C ₄₅ H ₂₉ N ₃ =611.75) N-97 m/z=561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-98 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-99 m/z = 663.27 (C ₄₉ H ₃₃ N ₃ =663.82) N-100 m/z = 713.28 (C ₅₃ H ₃₅ N ₃ =713.88) N-101 m/z=575.20 (C ₄₁ H ₂₅ N ₃ O=575.67) N-102 m/z = 601.22 (C ₄₃ H ₂₇ N ₃ O = 601.71) N-103 m/z = 700.26 (C ₅₁ H ₃₂ N ₄ =700.85) N-104 m/z=701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) N-105 m/z=667.21 (C ₄₇ H ₂₉ N ₃ S=667.83) N-106 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) N-107 m/z=612.23 (C ₄₄ H ₂₈ N ₄ =612.74) N-108 m/z = 562.22 (C ₄₀ H ₂₆ N ₄ =562.68) N-109 m/z=689.26 (C ₄₉ H ₃₁ N ₅ =689.82) N-110 m/z=639.24 (C ₄₅ H ₂₉ N ₅ =639.76) N-111 m/z=701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) N-112 m/z=631.17 (C ₄₃ H ₂₅ N ₃ OS=631.75) N-113 m/z=625.22 (C ₄₅ H ₂₇ N ₃ O=625.73) N-114 m/z=591.18 (C ₄₁ H ₂₅ N ₃ S=591.73) N-115 m/z = 687.27 (C ₅₁ H ₃₃ N ₃ =687.85) N-116 m/z=701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) N-117 m/z=619.30 (C ₄₅ H ₃₇ N ₃ =619.81) N-118 m/z=601.25 (C ₄₄ H ₃₁ N ₃ =601.75) N-119 m/z=667.23 (C ₄₇ H ₂₉ N ₃ O ₂ =667.77) N-120 m/z = 540.24 (C ₃₉ H ₂₀ D ₅ N ₃ =540.68) N-121 m/z = 521.17 (C ₃₅ H ₂₁ F ₂ N ₃ =521.57) N-122 m/z=510.18 (C ₃₆ H ₂₂ N ₄ =510.60) N-123 m/z=652.23 (C ₄₆ H ₂₈ N ₄ O=652.76) N-124 m/z=527.24 (C ₃₈ H ₂₉ N ₃ =527.67) N-125 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) N-126 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) N-127 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) N-128 m/z=535.20 (C ₃₉ H ₂₅ N ₃ =535.65) N-129 m/z=587.24 (C ₄₃ H ₂₉ N ₃ =587.73) N-130 m/z=612.23 (C ₄₄ H ₂₈ N ₄ =612.74) N-131 m/z = 561.22 (C ₄₁ H ₂₇ N ₃ =561.69) N-132 m/z = 687.27 (C ₅₁ H ₃₃ N ₃ =687.85) N-133 m/z = 663.27 (C ₄₉ H ₃₃ N ₃ =663.82) N-134 m/z = 601.22 (C ₄₃ H ₂₇ N ₃ O = 601.71) N-135 m/z=617.19 (C ₄₃ H ₂₇ N ₃ S=617.77) N-136 m/z = 752.29 (C ₅₅ H ₃₆ N ₄ =752.92) N-137 m/z=651.23 (C ₄₇ H ₂₉ N ₃ O=651.77) N-138 m/z = 677.25 (C ₄₉ H ₃₁ N ₃ O = 677.81) N-139 m/z=541.16 (C ₃₇ H ₂₃ N ₃ S=541.67) N-140 m/z = 750.28 (C ₅₅ H ₃₄ N ₄ =750.91) N-141 m/z = 707.24 (C ₅₀ H ₃₃ N ₃ S = 707.90) N-142 m/z=651.23 (C ₄₇ H ₂₉ N ₃ O=651.77) N-143 m/z=617.19 (C ₄₃ H ₂₇ N ₃ S=617.77) N-144 m/z=667.21 (C ₄₇ H ₂₉ N ₃ S=667.83) N-145 m/z=631.17 (C ₄₃ H ₂₅ N ₃ OS=631.75) N-146 m/z = 767.26 (C ₅₅ H ₃₃ N ₃ O ₂ =767.89) N-147 m/z = 647.15 (C ₄₃ H ₂₅ N ₃ S ₂ =647.81) N-148 m/z=690.24 (C ₄₉ H ₃₀ N ₄ O=690.81)

Manufacturing evaluation of organic electric devices

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

[ Example 1] to [ Example 30] red organic light emitting device ( light emitting layer mixed phosphorescent host)

After vacuum deposition of 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (abbreviated as 2-TNATA) on the ITO layer (anode) to a thickness of 60 nm to form a hole injection layer, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) is vacuum deposited to a thickness of 60 nm Next, as shown in Table 7 below, on the hole transport layer, the compound represented by Formula 1 (first host) and the compound represented by Formula 2 (second host) were mixed in a 3:7 ratio , and used as a host, and using bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as (piq)2Ir(acac)) as a dopant so that the host and dopant have a weight ratio of 95:5. Then, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was formed on the light emitting layer with a thickness of 30 nm. A hole blocking layer was formed by vacuum deposition to a thickness of 10 nm, and an electron transport layer was formed by vacuum deposition of tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as "Alq3") to a thickness of 40 nm on the hole blocking layer. Then, an organic light emitting device was manufactured by depositing LiF to a thickness of 0.2 nm and depositing Al to a thickness of 150 nm to form a cathode.

[ comparative example 1] to [ comparative example 3]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound represented by Formula 1, Formula 2 or Comparative Compound A of the present invention was used alone as the host material of the light emitting layer, as shown in Table 7 below. produced.

[Comparative Compound A]

[ comparative example 4] to [ comparative example 9]

An organic light emitting device was manufactured in the same manner as in Example 1, except that a mixture of Comparative Compound 1 and the compound represented by Formula 2 was used as a host.

A forward bias DC voltage was applied to the organic electroluminescent devices of Examples and Comparative Examples prepared as described above to measure electroluminescence (EL) characteristics with PR-650 of Photoresearch, and as a result of the measurement, 2500cd/m ² standard luminance T95 life was measured through life measurement equipment manufactured by McScience. Table 7 below shows the device fabrication and evaluation results.

1st host 2nd host drive voltage electric current
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) Comparative Example 1 Comparative Compound A - 6.5 20.0 2500.0 12.5 79.0 Comparative Example 2 - N-79 6.4 17.9 2500.0 14.0 77.7 Comparative Example 3 P-11 - 6.3 21.0 2500.0 11.9 80.2 Comparative Example 4 Comparative Compound A 6-5 6.0 13.0 2500.0 19.3 115.0 Comparative Example 5 6-6 6.0 11.9 2500.0 21.0 111.7 Comparative Example 6 6-71 5.9 12.1 2500.0 20.7 114.2 Comparative Example 7 N-4 5.9 12.5 2500.0 20.0 113.5 Comparative Example 8 N-79 5.8 12.6 2500.0 19.8 112.6 Comparative Example 9 N-86 5.8 12.3 2500.0 20.3 110.9 Example 1 P-11 6-5 5.1 9.8 2500.0 25.5 138.4 Example 2 6-6 5.0 7.9 2500.0 31.6 123.3 Example 3 6-71 5.3 8.2 2500.0 30.4 136.8 Example 4 N-4 5.1 9.6 2500.0 26.1 125.4 Example 5 N-79 5.0 9.0 2500.0 27.8 130.5 Example 6 N-86 5.0 8.8 2500.0 28.5 133.0 Example 7 P-17 6-5 5.1 9.7 2500.0 25.8 138.8 Example 8 6-6 5.1 8.1 2500.0 30.9 123.6 Example 9 6-71 5.2 8.5 2500.0 29.5 136.1 Example 10 N-4 5.0 9.4 2500.0 26.6 127.4 Example 11 N-79 5.0 9.1 2500.0 27.4 130.1 Example 12 N-86 4.9 8.5 2500.0 29.5 134.4 Example 13 P-65 6-5 5.1 10.0 2500.0 25.0 138.5 Example 14 6-6 5.0 8.1 2500.0 30.8 125.5 Example 15 6-71 5.3 8.4 2500.0 29.7 136.2 Example 16 N-4 5.0 9.3 2500.0 26.8 125.4 Example 17 N-79 5.1 9.0 2500.0 27.7 129.1 Example 18 N-86 5.0 8.8 2500.0 28.6 134.6 Example 19 P-73 6-5 5.2 9.7 2500.0 25.8 135.9 Example 20 6-6 5.1 7.8 2500.0 30.2 124.0 Example 21 6-71 5.3 8.5 2500.0 29.6 136.9 Example 22 N-4 5.0 9.6 2500.0 26.1 126.7 Example 23 N-79 5.0 9.1 2500.0 27.5 128.2 Example 24 N-86 4.9 8.7 2500.0 31.5 138.7 Example 25 P-94 6-5 5.2 9.8 2500.0 25.4 137.9 Example 26 6-6 5.0 8.1 2500.0 30.8 120.4 Example 27 6-71 5.3 8.3 2500.0 30.0 137.8 Example 28 N-4 5.0 9.3 2500.0 26.7 125.8 Example 29 N-79 5.1 9.1 2500.0 27.5 129.2 Example 30 N-86 5.0 8.4 2500.0 29.9 135.5

As can be seen from Table 7, when the organic electroluminescent device materials of the present invention represented by Formulas 1 and 2 are mixed and used as a phosphorescent host (Examples 1 to 30), a device using a single material (comparison It was confirmed that the driving voltage, efficiency and lifetime were significantly improved compared to the devices (Comparative Examples 4 to 9) using a mixture of Examples 1 to 3) and the comparative compound.

In other words, Comparative Examples 4 to 9 in which Comparative Compound A was mixed and used as a phosphorescent host rather than when the compounds of the present invention represented by Formulas 1 and 2 were used alone as a phosphorescent host (Comparative Example 2 and Comparative Example 3). The results were generally excellent in terms of efficiency and lifespan, and Examples 1 to 30, in which the compounds of the present invention represented by Formulas 1 and 2 were mixed, showed significantly superior effects in terms of driving voltage, efficiency and lifespan. indication can be seen.

The reason why the device characteristics of the embodiments of the present invention are the best is that the conjugation length is longer than that of the comparative compound by using the compound in which the 3-condensed cyclic ring is introduced into the 3-condensed cyclic ring. When the tertiary amine compound is mixed with the compound represented by Chemical Formula 2, which has strong electron characteristics, the electron blocking ability is improved due to the high LUMO energy value of Chemical Formula 1, and more holes move quickly and easily in the light emitting layer, thereby increasing the driving voltage of the entire device. , efficiency, and life are improved.

That is, when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 of the present invention are mixed, the ability to inject/transport holes and electrons toward the light emitting layer is improved and stability is increased, and as a result, the driving of the entire device is improved. improvement, the charge balance of holes and electrons in the light emitting layer is increased, and the light emission is well made inside the light emitting layer, not at the interface of the hole transport layer, resulting in an increase in efficiency, and as a result, the degradation of the HTL interface is also reduced, which seems to maximize the lifetime of the entire device. .

Example 2) mixing ratio ( equivalent weight ) Fabrication and testing of star red organic light emitting device

1st host 2nd host ratio drive voltage electric current
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) Example 31 P-65 6-6 7:3 5.0 7.9 2500.0 30.8 122.7 Example 32 5:5 5.1 8.1 2500.0 30.2 123.2 Example 33 3:7 5.0 7.9 2500.0 29.3 125.5 Example 34 P-73 N-86 7:3 4.9 8.7 2500.0 31.5 138.7 Example 35 5:5 5.0 8.4 2500.0 30.8 139.2 Example 36 3:7 4.9 8.6 2500.0 30.0 140.2

As shown in Table 8, the mixture of the compound of the present invention was measured by manufacturing a device at a ratio (7:3, 5:5, 3:7). In detail, it was confirmed that as the red organic second host ratio increased, the results of driving voltage and efficiency were further improved. It is believed that this is because the charge balance in the light emitting layer is maximized when an appropriate amount of the compound represented by Chemical Formula 1 having strong hole characteristics, such as 7:3, is mixed.

The above description is only illustrative of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are intended to explain the present invention, not to limit it, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed according to the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric element 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: 1st stack ST2: 2nd stack

Claims (15)

An organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer represented by Chemical Formula 1 and An organic electric device comprising a compound represented by Formula 2
Formula 1 Formula 2

Formula 3

{In Formula 1 to Formula 3,
1) R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~C ₆₀ Alkenyl group; C ₂ ~C ₆₀ alkynyl group; C ₁ ~ C ₆₀ alkoxy group; And C ₆ ~ C ₆₀ aryloxy group; selected from the group consisting of, or adjacent groups may be bonded to each other to form a ring,
2) A is a substituent represented by Formula 3,
3) X, Y and Z independently of each other are O, S or CR'R”;
4) L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And C ₃ ~ C ₆₀ It is selected from the group consisting of; aliphatic ring group,
5) Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently a C ₆ to C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; and C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; is selected from the group consisting of;
6) X ¹ , X ² and X ³ are each independently CR ^a or N, provided that at least one of X ¹ , X ² and X ³ is N;
7) R', R” and R ^a are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₆₀ Alkyl group; A C ₂ ~C ₂₀ alkenyl group; A C ₂ ~C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxy group; And a C ₆ ~ C ₃₀ aryloxy group; It is selected from the group consisting of, or R' and R” may be bonded to each other to form a spy ring,
8) a and f are independently integers from 0 to 4, b, c, d and e are independently integers from 0 to 3;
9)

denotes a binding position,
10) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group are each 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; A 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; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And a C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may combine with each other to form a ring, wherein 'ring' means C ₃ ~C ₆₀ It refers to an aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring or a C ₂ ~ C ₆₀ hetero ring or a fused ring composed of a combination thereof, and includes a saturated or unsaturated ring.}
The organic electric device according to claim 1, wherein Formula 1 is represented by any one of Formulas 1-1 to 1-12 below.
Formula 1-1 Formula 1-2

Formula 1-3 Formula 1-4

Formula 1-5 Formula 1-6

Formula 1-7 Formula 1-8

Formula 1-9 Formula 1-10

Formula 1-11 Formula 1-12

{In Formula 1-1 to Formula 1-12, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a, b, c, d , e, f, R' and R” are as defined in claim 1 above.}
The organic electric device according to claim 1, wherein Formula 1 is represented by any one of Formulas 1-13 to 1-16 below.
Formula 1-13 Formula 1-14

Formula 1-15 Formula 1-16

{In Formula 1-13 to Formula 1-16, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a, b, c, d , e, f, X, Y and Z are as defined in claim 1 above.}
The organic electric device according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-17 to 1-24.
Formula 1-17 Formula 1-18

Formula 1-19 Formula 1-20

Formula 1-21 Formula 1-22

Formula 1-23 Formula 1-24

{In Formula 1-17 to Formula 1-24,
1) R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ¹ , L ² , L ³ , Ar ¹ , a, b, c, d, e, f, X, Y and Z are As defined in claim 1 above,
2) a' and f' are independently integers from 0 to 3, b', c', d' and e' are independently integers from 0 to 2, g is an integer from 0 to 5, and h Is an integer from 0 to 3, i is an integer from 0 to 4,
3) R ⁷ , R ⁸ and R ⁹ are the same as the definition of R ¹ in claim 1,
4) X' is the same as the definition of X in claim 1.}
The organic electric device according to claim 1, wherein at least one of Ar ² , Ar ³ and Ar ⁴ is represented by one of the following formulas Ar-1 to Ar-8
Formula Ar-1 Formula Ar-2 Formula Ar-3

Formula Ar-4 Formula Ar-5 Formula Ar-6

Formula Ar-7 Formula Ar-8

{In Formula Ar-1 to Formula Ar-8,
1) X ²¹ and X ²² are each independently NAr ⁵ , O, S or C(R ¹⁵ )(R ¹⁶ );
2) ta, tb and td are each independently an integer from 0 to 4, tc is an integer from 0 to 6, te is an integer from 0 to 7, tf is an integer from 0 to 5,
3) Ar ⁵ is the same as the definition of Ar ¹ in claim 1,
4) R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are the same as the definition of R ¹ in claim 1,
5)

means the binding position.}
The organic electric device according to claim 1, wherein Formula 2 is represented by any one of Formulas 2-1 to 2-8 below.
Formula 2-1 Formula 2-2

Formula 2-3 Formula 2-4

Formula 2-5 Formula 2-6

Formula 2-7 Formula 2-8

{In Formulas 2-1 to 2-8,
1) X ²¹ , X ²³ and X ²⁵ are each independently NAr ⁶ , O, S or C(R ¹⁷ )(R ¹⁸ );
2) X ²² , X ²⁴ and X ²⁶ are each independently NAr ⁷ , O, S, C(R ¹⁹ )(R ²⁰ ) or a single bond;
3) a”, d” and f” are independently integers from 0 to 4, b”, c” and e” are integers from 0 to 3,
4) Ar ⁶ and Ar ⁷ are the same as the definition of Ar ¹ in claim 1,
5) ta, tb, te, tf, R ¹⁰ , R ¹¹ , R ¹³ and R ¹⁴ are as defined in claim 5 above,
6) L ⁴ , L ⁵ and L ⁶ are the same as defined in claim 1 above,
7) R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are the same as the definition of R ¹ in claim 1.}
The organic electric device according to claim 1, wherein L ¹ to L ⁶ are represented by any one of the following formulas b-1 to b-13
Formula b-1 Formula b-2 Formula b-3 Formula b-4 Formula b-5 Formula b-6

Formula b-7 Formula b-8 Formula b-9 Formula b-10

Formula b-11 Formula b-12 Formula b-13

{In the formula b-1 to formula b-13,
1) Z ¹⁰ is O, S, NL ⁷ -Ar ⁸ or C(R ³⁰ )(R ³¹ );
2) L ⁷ is the same as the definition of L ¹ in claim 1,
3) Ar ⁸ is the same as the definition of Ar ¹ in claim 1,
4) aa, cc, dd, and ee are independently integers from 0 to 4, bb is an integer from 0 to 6, ff and gg are independently integers from 0 to 3, and hh is an integer from 0 to 2 , ii is 0 or 1,
5) Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ are independently CR ³² or N, provided that at least one of Z ⁴⁹ , Z ⁵⁰ and Z ⁵¹ is N,
6) R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² are the same as the definition of R ¹ in claim 1,
7)

means the binding position.}
The organic electric device according to claim 1, wherein the compound represented by Formula 1 is any one of the following compounds

The organic electric device according to claim 1, wherein the compound represented by Chemical Formula 2 is any one of the following compounds

The organic electric device of claim 1 , further comprising a light efficiency improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
The organic electric device according to claim 1, wherein the compound represented by Chemical Formula 1 is included in the light efficiency improving layer.
The organic electric device according to claim 1, wherein the organic material layer includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode.
The organic electric device according to claim 1, wherein the organic material layer further comprises a charge generation layer formed between the two or more stacks.
A display device comprising the organic electric element of claim 1; and a controller for driving the display device.
15. The electronic device of claim 14, wherein the organic electric element is at least one of an organic light emitting element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white light.

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