KR102585263B1 - Compound for organic electric element, organic electric element comprising the same and electronic device thereof - Google Patents

Abstract

The present invention relates to compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof. According to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and lifespan of the device can be improved. It can be improved.

Description

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

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

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

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

In addition, the light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the luminescence mechanism. You can. In addition, light-emitting materials can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to realize better natural colors.

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

Currently, the portable display market is increasing in size toward large-area displays. Since portable displays have batteries that provide limited power, more efficient power consumption is required than that required by existing portable displays. In addition, in addition to efficient power consumption, luminous efficiency and lifespan issues must also be resolved.

Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. It indicates a tendency for lifespan to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined. Therefore, there is a need to develop a light-emitting material that has high thermal stability and can efficiently achieve charge balance within the light-emitting layer.

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

The purpose of the present invention is to provide a compound that can improve the high luminous efficiency, low driving voltage, high heat resistance, color purity and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the formula below.

[Formula 1]

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

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 improved.

1 is a cross-sectional view of an organic light-emitting device according to an embodiment of the present invention.

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

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

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

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

The terms used in this specification and in the appended claims are as follows, unless otherwise noted.

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

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

The term “haloalkyl group” or “halogenalkyl group” used in the present invention refers to an alkyl group in which halogen is substituted, unless otherwise specified.

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

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

The term “alkoxy group” or “alkyloxy group” used in this specification refers to an alkyl group to which an oxygen radical is bonded, and unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

As used herein, the term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group”, or “alkenyloxy group” refers to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, refers to an alkenyl group having an oxygen radical attached thereto. It has a carbon number of, but is not limited to.

As used in the present invention, the term "fluorenyl group" or "fluorenylene group" refers to a monovalent or divalent functional group of fluorene, respectively, unless otherwise specified, and "substituted fluorenyl group" or "substituted fluorenyl group" "Orenylene group" means that at least one of the substituents R, R', R", and R''' is a functional group other than hydrogen, and R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. Includes one case.

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or arylene group includes a single ring type, a ring conjugate, a fused multiple ring system, a spiro compound, etc.

The term “heterocyclic group” used in the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, each carbon number containing one or more heteroatoms. It refers to a ring numbered from 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P, or Si, unless otherwise specified, and the heterocyclic group refers to a single ring containing heteroatoms, a ring conjugate, a fused multiple ring system, or a ring group. refers to compounds, etc.

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

The term “ring” used in the present invention includes single rings and polycyclic rings, includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" used in the present invention includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems, and spiro compounds, and includes not only aromatics but also non-aromatics, and hydrocarbons. Rings of course include heterocycles containing at least one heteroatom.

The term “ring assemblies” used in the present invention refers to two or more ring systems (single rings or fused ring systems) directly connected to each other through single or double bonds, and the direct connection between such rings. This means that the number of connections is one less than the total number of ring systems in this compound. In ring aggregates, the same or different ring systems may be directly connected to each other through single or double bonds.

The term "fused multiple ring system" as used in the present invention refers to a fused ring form sharing at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. This includes forms in which at least one heterocyclic ring is fused. This fused multiple ring system may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.

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

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

Also, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in the present invention, "substituted" means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, silane group, boron means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P. and is not limited to these substituents.

In this specification, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent, may be written as the 'name of the functional group reflecting the valence', but is written as the 'parent compound name'. You may. For example, in the case of 'phenanthrene', a type of aryl group, the monovalent 'group' is 'phenanthryl (group)', the divalent group is 'phenanthrylene (group)', etc., and the name of the group is written by dividing the valence. However, it can also be written as 'phenanthrene', which is the name of the parent compound, regardless of the valence. Similarly, in the case of pyrimidine, it may be written as 'pyrimidine' regardless of the valence, or the 'group' of the corresponding valence, such as pyrimidinyl (group) in the case of monovalent, pyrimidinylene (group) in the case of divalent, etc. It can also be written as ‘name’. Therefore, in this specification, when the type of substituent is described as the name of the parent compound, it may mean an n-valent 'group' formed by desorption of a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.

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

Here, when a is 0, the substituent R ¹ is absent, when a is 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is 2 or 3, each is as follows They are bonded together, and in this case, 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, and the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted. .

1 is an exemplary diagram of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode 180 formed on a substrate 110. ) and an organic material layer containing the compound according to the present invention is provided between them. At this time, the first electrode 120 may be an anode and the second electrode 180 may be a cathode. In the case of the inverted type, the first electrode may be the cathode and the second electrode may be the anode.

The organic material layer may sequentially include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120. At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, an emission auxiliary layer 151, a buffer layer 141, etc. may be further included, and an electron transport layer 160, etc. may serve as a hole blocking layer. You might be able to do it.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improvement layer (capping layer) formed on at least one side of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, a light efficiency improvement layer, a light emitting auxiliary layer, etc. It can be used as a material for For example, the compound of the present invention can be used as a material for the auxiliary light emitting layer 151 and/or the light emitting layer 150.

Meanwhile, even if it is the same core, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so the selection of the core and the combination of subsubstituents attached to it are very important, especially When the energy level and T ₁ value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

As already explained, in order to solve the problem of light emission from the hole transport layer in recent organic electroluminescent devices, it is desirable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, corresponding to each light emitting layer (R, G, and B). Therefore, it is necessary to form different light emitting auxiliary layers. In other words, the light emitting auxiliary layer includes a red light emitting auxiliary layer among the red light emitting layer, green light emitting layer, and blue light emitting layer corresponding to the red light emitting layer, green light emitting layer, and blue light emitting auxiliary layer. Meanwhile, in the case of the auxiliary light emitting layer, the interrelationship between the hole transport layer and the light emitting layer (host) must be identified, so even if a similar core is used, it will be very difficult to infer its characteristics if the organic material layer used is different.

Therefore, by forming a light-emitting layer and/or a light-emitting auxiliary layer using the compound according to Formula 1 of the present invention, the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimized. Thus, the lifespan and efficiency of organic electric devices can be improved at the same time.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD (Physical Vapor Deposition) or CVD (Chemical Vapor Deposition). For example, the anode 120 is formed by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate. After forming an organic material layer including a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, a cathode 180 is formed thereon. It can be manufactured by depositing any available material. Additionally, a light emitting auxiliary layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150.

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

The organic electric device according to the present invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to achieve high resolution and having excellent fairness, while being manufactured using the color filter technology of existing LCDs. Various structures for white organic light emitting devices, mainly used as backlight devices, are being proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in parallel with each other in a plane, and a stacking method in which R, G, and B light emitting layers are stacked top and bottom. There is a color conversion material (CCM) method that uses electroluminescence by a blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom, and the present invention. can be applied to these WOLEDs as well.

Additionally, the organic electric device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting.

Figure 2 is an exemplary diagram of an electronic device according to another embodiment of the present invention.

The electronic device 200 may include a display device 210 including the organic electric element 230 of the present invention described above, and an electronic device including a control unit 220 that controls the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

The control unit 220 applies a driving voltage and/or signal to the organic electric element, for example, a plurality of gate lines, a gate driving circuit for driving the gate line, a plurality of data lines, and the data line. It may include a data driving circuit that drives and a controller that controls the gate driving circuit and the data driving circuit.

The controller controls the data driving circuit and the gate driving circuit by supplying various control signals to the data driving circuit and the gate driving circuit.

Hereinafter, a compound according to one aspect of the present invention will be described. The compound according to one aspect of the present invention is represented by the following formula (1).

[Formula 1]

In Formula 1,

_X ^{1 and} _{_} ^{_ _} _{_} ^{_ _} NL ¹ -(Ar ¹ ) _n .

Wherein L ¹ is a single bond, an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and a divalent aliphatic hydrocarbon group of C ₁ to C ₂₀ ; where L ¹ is a single bond, X ¹ and/or X ² are N-Ar ¹ and L ¹ is not a single bond. In this case, L ¹ is replaced with n Ar ^1s .

Ar ¹ is a functional group other than hydrogen substituted on L ¹ , and Ar ¹ is each independently an aryl group having C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₂ ~ C ₂₀ alkoxy group; and C ₆ to C ₃₀ aryloxy groups.

When L ¹ is an aryl group, L ¹ is not a ring assembly and may be an aryl group of C ₆ to C ₁₈ , for example, benzene.

When L ¹ is a heterocyclic group, L ¹ is not a ring assembly and may be a C ₂ to C ₃₀ heterocyclic group, or a C ₂ to C ₁₅ heterocyclic group, for example, pyrimidine, triazine, It may be quinazoline, carbazole, dibenzofuran, isoquinoline, imidazole, or a substituent represented by the following formulas A to K.

[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

[Formula F]

[Formula G]

[Formula H]

[Formula I]

[Formula J]

[Formula K]

In each of the above formulas A to K, at least one * is bonded to Ar ¹ by a single bond, at least one * is bonded to N by a single bond, and * in which Ar ¹ is not substituted and is not bonded to N is Hydrogen or deuterium is combined by a single bond.

When Ar ¹ is an aryl group, it may be a C ₆ to C ₄₀ aryl group, or a C ₆ to C ₂₅ aryl group, for example, benzene, biphenyl, naphthalene, phenanthrene, fluorene, 9,9' -It may be spirobi[9H-fluorene], m-terphenyl, triphenylene, pyrene, or a substituent represented by the formula L below.

[Formula L]

In the formula L, * is bonded to hydrogen, deuterium, or L ¹ by a single bond, and at least one * is bonded to L ¹ by a single bond.

When Ar ¹ is a heterocyclic group, it may be a heterocyclic group of C ₆ to C ₄₀ , or a heterocyclic group of C ₆ to C ₁₈ , for example, dibenzofuran, carbazole, pyridine, dibenzothiophene, indole. It may be [3,2,1-jk]carbazole, or a substituent represented by formulas M to R.

[Formula M]

[Formula N]

[Formula O]

[Formula P]

[Formula Q]

[Formula R]

In each of the above formulas M to R, * is bonded to hydrogen, deuterium, or L ¹ by a single bond, and at least one * is bonded to L ¹ by a single bond.

The n is a positive integer other than 0.

R ¹ , R ² , and R ³ are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₁ ~ C ₅₀ alkyl group; Silane group; Cyano group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₂ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; It may be selected from the group consisting of -N(R')(R"), and a plurality of R ¹ , R ² , and R ³ may be bonded to each other to form an aromatic ring or heteroaromatic ring.

R' and R" are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₁ ~ C ₅₀ alkyl group; silane group; cyano group; O , N, S, Si, P, C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₂ to C ₂₀ alkoxyl group; C ₆ to C ₃₀ aryloxy group.

R' and R" may be, for example, a phenyl group.

Additionally, when neighboring R ¹ bonds with each other to form a ring, for example, a benzene ring can be formed.

When R ² is an aryl group, for example, it may be a phenyl group. When R ² is a heterocyclic group, for example, it may be pyridine.

When R ³ is an aryl group, for example, each R ³ may be a phenyl group or a deuterium-substituted phenyl group. When R ³ is a heterocyclic group, for example, it may be phenylcarbazole. When a plurality of neighboring R ³ bonds to each other to form a ring, a benzene ring can be formed.

a and c are 0 to 4, and b is 0 to 5.

For example, one of X ¹ and ^{X 2 may} be ^{NL 1} -(Ar ¹ ) _n . More specifically, X ¹ is NL ¹ -(Ar ¹ ) _n , and R ¹ may each independently be hydrogen or deuterium.

Here, the aliphatic hydrocarbon group, aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and silane group each have deuterium; nitro group; Nitrile group; halogen group; amino group; A silane group substituted or unsubstituted with a C ₁ to C ₂₀ alkyl group or a C ₆ to C ₂₀ aryl group; siloxane group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group, and these substituents may be combined with each other to form a ring, where 'ring ' refers to a fused ring including a saturated or unsaturated ring, a C ₃ to C ₆₀ aliphatic ring, a C ₆ to C ₆₀ aromatic ring, a C ₂ to C ₆₀ heterocycle, or a combination thereof.

When the compound of Formula 1 is used in the organic material layer of an organic electronic device, an organic electronic device with excellent luminous efficiency and lifespan can be manufactured.

The compound represented by Formula 1 may be represented by Formulas 2 and 3 below.

[Formula 2]

[Formula 3]

In Formulas 2 and 3, L ¹ , Ar ¹ , R ¹ to R ³ , a to c and n are the same as previously described.

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

.

As another example, the present invention provides an organic electric device containing the compound represented by Formula 1 above.

The organic electric device includes a first electrode; second electrode; and an organic material layer located between the first electrode and the second electrode, wherein the organic material layer may include a compound represented by Formula 1, and the compound represented by Formula 1 is a hole injection layer of the organic material layer, a hole injection layer, and a hole injection layer of the organic material layer. It may be contained in at least one of a transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In particular, the compound represented by Formula 1 may be included in the hole transport layer or the light emitting layer.

That is, the compound represented by Formula 1 can be used as a material for a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, or an electron injection layer. In particular, the compound represented by Formula 1 can be used as a host material for a hole transport layer or a light emitting layer. Specifically, an organic electric device is provided in which the organic material layer includes one of the compounds represented by Formula 1, and more specifically, the organic material layer includes a compound represented by the individual formulas (P-1 to P-70). Provides an organic electric device that

In another embodiment, the compound is contained alone in at least one layer of the hole injection layer, the hole transport layer, the auxiliary light emitting layer, the light emitting layer, the electron transport layer, and the electron injection layer of the organic material layer, or It provides an organic electric device characterized in that the compound is contained in a combination of two or more different types, or the compound is contained in a combination of two or more types with other compounds.

In another embodiment, the layer containing the compound alone, containing the compound in a combination of two or more different types, or containing the compound in a combination of two or more types of other compounds is at least one of a hole transport layer and a light emitting layer. It could be a layer.

In other words, each layer may contain a compound corresponding to Formula 1 alone or a mixture of two or more compounds of Formula 1, the compounds of claims 1 to 3, and compounds that do not correspond to the present invention. A mixture of and may be included. Here, the compound that does not fall under the present invention may be a single compound, or may be two or more types of compounds. At this time, when the compound is contained in a combination of two or more types of other compounds, the other compounds may be already known compounds of each organic layer, or may be compounds to be developed in the future. At this time, the compound contained in the organic layer may be composed of only the same type of compound, but may also be a mixture of two or more different types of compounds represented by Chemical Formula 1.

For example, the organic layer may be a mixture of two compounds with different structures at a molar ratio of 99:1 to 1:99.

In another embodiment of the present invention, the present invention provides a light efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device further comprising:

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

[Synthesis example]

The compound represented by Formula 1 is synthesized by reacting Sub 1 or Sub 1' with Sub 2 as shown in Scheme 1 below, but is not limited thereto. In Scheme 1 below, R ¹ to R ³ , Ar ¹ , L ¹ , a to c and n are the same as previously described in the section regarding Formula 1, and Pd ₂ (dba) ₃ described in the synthesis examples of the present specification is Tris ( It is dibenzylideneacetone)dipalladium(0).

[Scheme 1]

I. Synthesis of Sub 1 or Sub 1'

Sub 1 of Scheme 1 may be synthesized through the reaction route of Scheme 2 below, but is not limited thereto. DMA below is N,N-Dimethylacetamide, and MC below is Methylene chloride.

[Scheme 2]

1. Sub1-1 synthesis example

Among the Sub 1 compounds, the following Sub 1-1 compounds in which R ¹ to R ³ are all hydrogen can be synthesized according to Scheme 3 below. Those skilled in the art will understand that Scheme 3 below is one of several reactions belonging to Scheme 2 above.

[Scheme 3]

(1) Sub1-I-1 synthesis

1H-benzo[g]indole (50 g, 0.299 mol), 1-bromo-2-chlorobenzene (68.7 g, 0.358 mol), Cu powder (2 g, 0.03 mol), K ₂ CO ₃ (123 g, 0.897 mol) ), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 70 g (85%) of product Sub1-I-1.

(2) Sub1-II-1 synthesis

In Sub1-I-1 (70 g, 0.253 mol), Pd(OAc) ₂ (1.7 g, 0.007 mol), P(t-Bu) ₃ (6.1 g, 0.015 mol), K ₂ CO ₃ (104 g, 0.758 mol) mol), DMA (N,N-Dimethylacetamide) (170 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 44 g (72%) of product Sub1-II-1.

(3) Sub1-III-1 synthesis

Dissolve Sub1-II-1 (44 g, 0.253 mol) in MC (methylene chloride) (365mL) and then slowly add Br ₂ (29 g, 0.183 mol) dropwise. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 40 g (68%) of product Sub1-III-1.

(4) Sub1-IV-1 synthesis

Sub1-III-1 (40 g, 0.137 mol), 2-chloroaniline (17.5 g, 0.137 mol), Pd ₂ (dba) ₃ (3.8 g, 0.004 mol), 50% P( t -Bu) ₃ (3.3 ml , 0.008 mol), NaO t -Bu (40 g, 0.4 mol) were added to toluene (275ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 40 g (yield: 79%) of the product Sub 1-IV-1 was obtained.

(5) Sub1-1 synthesis

In Sub1-IV-1 (40 g, 0.11 mol), Pd(OAc) ₂ (0.7 g, 0.003 mol), P(t-Bu) ₃ (3 g, 0.008 mol), K ₂ CO ₃ (52 g, 0.338 mol) mol), DMA (N,N-Dimethylacetamide) (218 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 30 g (83%) of product Sub1-1.

2. Sub1-4 synthesis example

Among the Sub 1 compounds, the following Sub 1-4 compounds, in which adjacent R ^1s are bonded to each other to form a benzene ring, can be synthesized according to Scheme 4 below. Those skilled in the art will understand that Scheme 4 below is one of several reactions belonging to Scheme 2 above.

[Scheme 4]

(1) Sub1-I-4 synthesis

1H-benzo[g]indole (50 g, 0.299 mol), 2-bromo-3-chloronaphthalene (89 g, 0.358 mol), Cu powder (2 g, 0.03 mol), K ₂ CO ₃ (123 g, 0.897 mol) ), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 60 g (61%) of the product Sub1-I-4.

(2) Sub1-II-4 synthesis

In Sub1-I-4 (61 g, 0.186 mol), Pd(OAc) ₂ (1.2 g, 0.005 mol), P(t-Bu) ₃ (4.5 g, 0.005 mol), K ₂ CO ₃ (77 g, 0.55 mol) mol), DMA (N,N-Dimethylacetamide) (370 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 48 g (88.6%) of product Sub1-II-4.

(3) Sub1-III-4 synthesis

Dissolve Sub1-II-4 (48 g, 0.165 mol) in MC (methylene chloride) (330mL) and then slowly add Br ₂ (26 g, 0.165 mol) dropwise. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 50 g (82%) of product Sub1-III-4.

(4) Sub1-IV-4 synthesis

Sub1-III-4 (50 g, 0.135 mol), 2-chloroaniline (17.5 g, 0.137 mol), Pd ₂ (dba) ₃ (3.8 g, 0.004 mol), 50% P( t -Bu) ₃ (3.3 ml , 0.008 mol), NaO t -Bu (40 g, 0.4 mol) were added to toluene (275ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 49 g (yield: 87%) of the product Sub 1-IV-4 was obtained.

(5) Sub1-4 synthesis

Sub1-IV-4 (49 g, 0.11 mol) with Pd(OAc) ₂ (0.7 g, 0.003 mol), P(t-Bu) ₃ (3 g, 0.008 mol), K ₂ CO ₃ (52 g, 0.338 mol) mol), DMA (N,N-Dimethylacetamide) (218 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 33 g (74%) of product Sub1-4.

3. Sub1-5 synthesis example

Among the Sub 1 compounds, R ¹ and R ² are both hydrogen and either R ³ is N-phenyl carbazole. The following Sub 1-5 compounds were synthesized according to Scheme 5 below. Those skilled in the art will understand that Scheme 5 below is one of several reactions belonging to Scheme 2 above. Additionally, in the synthesis examples of this specification, THF is tetrahydrofuran, and Pd(PPh ₃ ) ₄ is Tetrakis(triphenylphosphine)palladium(0).

[Scheme 5]

(1) Sub1-I-5 synthesis

1H-benzo[g]indole (50 g, 0.299 mol), 1-bromo-2-chlorobenzene (68.7 g, 0.358 mol), Cu powder (2 g, 0.03 mol), K ₂ CO ₃ (123 g, 0.897 mol) ), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 70 g (85%) of product Sub1-I-5.

(2) Sub1-II-5 synthesis

In Sub1-I-5 (70 g, 0.253 mol), Pd(OAc) ₂ (1.7 g, 0.007 mol), P(t-Bu) ₃ (6.1 g, 0.015 mol), K ₂ CO ₃ (104 g, 0.758 mol) mol), DMA (N,N-Dimethylacetamide) (170 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 44 g (72%) of product Sub1-II-5.

(3) Sub1-III-5 synthesis

Dissolve Sub1-II-5 (44 g, 0.253 mol) in MC (methylene chloride) (365mL) and then slowly add Br ₂ (29 g, 0.183 mol) dropwise. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 40 g (68%) of product Sub1-III-5.

(4) Sub1-IV-5 synthesis

Sub1-III-5 (40 g, 0.137 mol), 2,4-dichloroaniline (20 g, 0.137 mol), Pd ₂ (dba) ₃ (3.8 g, 0.004 mol), 50% P( t -Bu) ₃ ( 3.3 ml, 0.008 mol) and NaO t -Bu (40 g, 0.4 mol) were added to toluene (275ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 38 g (yield: 75.8%) of the product Sub 1-IV-5 was obtained.

(5) Sub1-V-5 synthesis

Sub1-IV-5 (38 g, 0.10 mol) Pd(OAc) ₂ (0.7 g, 0.003 mol), P(t-Bu) ₃ (3 g, 0.008 mol), K ₂ CO ₃ (52 g, 0.338 mol) mol), DMA (N,N-Dimethylacetamide) (190 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 30 g (87%) of product Sub1-V-5.

(6) Sub1-5 synthesis

Sub1-V-5 (30 g, 0.82 mol) was dissolved in THF/H ₂ O (164/45 mL) in a round bottom flask, then (9-phenyl-9H-carbazol-3-yl)boronic acid (23.6 g) , 0.82 mol), Pd(pph ₃ ) ₄ (2.8 g, 0.002 mol), and NaOH (10 g, 0.247 mol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with MC (methylene chloride) and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 40 g of product Sub1-5 (yield: 85%).

4. Sub1-8 synthesis example

Among the Sub 1 compounds, the following compounds Sub 1-8, in which both R ¹ and R ² are hydrogen and adjacent R ³ are bonded to each other to form a benzene ring, were synthesized according to Scheme 6 below. Those skilled in the art will understand that Scheme 6 below is one of several reactions belonging to Scheme 2 above.

[Scheme 6]

(1) Sub1-I-8 synthesis

1H-benzo[g]indole (50 g, 0.299 mol), 1-bromo-2-chlorobenzene (68.7 g, 0.358 mol), Cu powder (2 g, 0.03 mol), K ₂ CO ₃ (123 g, 0.897 mol) ), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 70 g (85%) of the product Sub1-I-8.

(2) Sub1-II-8 synthesis

In Sub1-I-8 (70 g, 0.253 mol), Pd(OAc) ₂ (1.7 g, 0.007 mol), P(t-Bu) ₃ (6.1 g, 0.015 mol), K ₂ CO ₃ (104 g, 0.758 mol) mol), DMA (N,N-Dimethylacetamide) (170 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 44 g (72%) of product Sub1-II-8.

(3) Sub1-III-8 synthesis

Dissolve Sub1-II-8 (44 g, 0.253 mol) in MC (365 mL) and then slowly add Br ₂ (29 g, 0.183 mol) dropwise. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 40 g (68%) of product Sub1-III-8.

(4) Sub1-IV-8 synthesis

Sub1-III-8 (40 g, 0.125 mol), 2-chloronaphthalen-1-amine (22.1 g, 0.125 mol), Pd ₂ (dba) ₃ (3.4 g, 0.004 mol), 50% P( t -Bu) ₃ (3 ml, 0.008 mol) and NaO t -Bu (36 g, 0.4 mol) were added to toluene (250ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 40 g (yield: 76.8%) of the product Sub 1-IV-8 was obtained.

(5) Sub1-8 synthesis

In Sub1-IV-8 (40 g, 0.96 mol), Pd(OAc) ₂ (0.6 g, 0.003 mol), P(t-Bu) ₃ (2.8 g, 0.007 mol), K ₂ CO ₃ (48 g, 0.301 mol) mol), DMA (N,N-Dimethylacetamide) (190 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 31 g (83%) of product Sub1-8.

5. Sub1-10 synthesis example

Among the Sub 1' compounds, all R ¹ and R ² are hydrogen, and any one of R ³ is deuterium-substituted phenyl. The following Sub 1-10 compounds can be synthesized according to Scheme 7 below. Those skilled in the art will understand that Scheme 7 below is one of several reactions belonging to Scheme 2 above.

[Scheme 7]

(1) Sub1-I-10 synthesis

1H-benzo[g]indole (50 g, 0.299 mol), 1-bromo-2-chlorobenzene (68.7 g, 0.358 mol), Cu powder (2 g, 0.03 mol), K ₂ CO ₃ (123 g, 0.897 mol) ), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 70 g (85%) of product Sub1-I-10.

(2) Sub1-II-10 synthesis

In Sub1-I-10 (70 g, 0.253 mol), Pd(OAc) ₂ (1.7 g, 0.007 mol), P(t-Bu) ₃ (6.1 g, 0.015 mol), K ₂ CO ₃ (104 g, 0.758 mol) mol), DMA (N,N-Dimethylacetamide) (170 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 44 g (72%) of product Sub1-II-10.

(3) Sub1-III-10 synthesis

Dissolve Sub1-II-10 (44 g, 0.253 mol) in MC (methylene chloride) (365mL) and then slowly add Br ₂ (39 g, 0.253 mol) dropwise. Afterwards, the reaction temperature is raised to 50 ^o C. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 40 g (68%) of product Sub1-III-10.

(4) Sub1-IV-10 synthesis

Sub1-III-10 (40 g, 0.137 mol), 2,4-dichloroaniline (20 g, 0.137 mol), Pd ₂ (dba) ₃ (3.8 g, 0.004 mol), 50% P( t -Bu) ₃ ( 3.3 ml, 0.008 mol) and NaO t -Bu (40 g, 0.4 mol) were added to toluene (275ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 38 g (yield: 75.8%) of the product Sub 1-IV-10 was obtained.

(5) Sub1-V-10 synthesis

In Sub1-IV-10 (38 g, 0.10 mol), Pd(OAc) ₂ (0.7 g, 0.003 mol), P(t-Bu) ₃ (3 g, 0.008 mol), K ₂ CO ₃ (52 g, 0.338 mol) mol), DMA (N,N-Dimethylacetamide) (190 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 30 g (87%) of product Sub1-V-10.

(6) Sub1-10 synthesis

After dissolving Sub1-V-10 (30 g, 0.82 mol) in THF/H ₂ O (164/45 mL) in a round bottom flask, (phenyl-d5)boronic acid (10.4 g, 0.82 mol), Pd(pph) ₃ ) ₄ (2.8 g, 0.002 mol) and NaOH (10 g, 0.247 mol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with MC (methylene chloride) and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 29 g of product Sub1-10 (yield: 83%).

6. Sub1-13 synthesis example

Among the Sub 1' compounds, the following Sub 1-13 compounds in which R ¹ to R ³ are all hydrogen can be synthesized according to Scheme 8 below. Those skilled in the art will understand that Scheme 8 below is one of several reactions belonging to Scheme 2 above.

[Scheme 8]

(1) Sub1-I-13 synthesis

6-(Pyridin-3-yl)-1H-benzo[g]indole (70 g, 0.299 mol), 1-bromo-2-chlorobenzene (68.5 g, 0.358 mol), Cu powder (2 g, 0.03 mol), Add K ₂ CO ₃ (123 g, 0.897 mol), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) and reflux for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 80 g (75%) of product Sub1-I-13.

(2) Sub1-II-13 synthesis

In Sub1-I-13 (80 g, 0.225 mol), Pd(OAc) ₂ (1.5 g, 0.006 mol), P(t-Bu) ₃ (6 g, 0.015 mol), K ₂ CO ₃ (93 g, 0.734 mol) mol), DMA (N,N-Dimethylacetamide) (450 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 64 g (89%) of product Sub1-II-13.

(3) Sub1-III-13 synthesis

Dissolve Sub1-II-13 (80 g, 0.253 mol) in MC (methylene chloride) (365mL) and then slowly add Br ₂ (40 g, 0.253 mol) dropwise. Afterwards, the reaction temperature is raised to 50 ^o C. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 70 g (70%) of product Sub1-III-13.

(4) Sub1-IV-13 synthesis

Sub1-III-13 (55 g, 0.137 mol), 2-chloroaniline (21 g, 0.137 mol), Pd ₂ (dba) ₃ (3.8 g, 0.004 mol), 50% P( t -Bu) ₃ (3.3 ml , 0.008 mol), NaO t -Bu (40 g, 0.4 mol) were added to toluene (275ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 50 g (yield: 81%) of the product Sub 1-IV-13 was obtained.

(5) Sub1-13 synthesis

In Sub1-IV-13 (50 g, 0.11 mol), Pd(OAc) ₂ (0.8 g, 0.003 mol), P(t-Bu) ₃ (3 g, 0.008 mol), K ₂ CO ₃ (55 g, 0.338 mol) mol), DMA (N,N-Dimethylacetamide) (250 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 38 g (82%) of product Sub1-13.

7. Sub1-15 synthesis example

Among the Sub 1' compounds, the following Sub 1-15 compounds in which both R ¹ and R ² are hydrogen and adjacent R ³ are bonded to each other to form a benzene ring can be synthesized according to Scheme 9 below. Those skilled in the art will understand that Scheme 9 below is one of several reactions belonging to Scheme 2 above.

[Scheme 9]

(1) Sub1-I-15 synthesis

1H-benzo[g]indole (50 g, 0.299 mol), 1-bromo-2-chlorobenzene (68.7 g, 0.358 mol), Cu powder (2 g, 0.03 mol), K ₂ CO ₃ (123 g, 0.897 mol) ), 18-Crown-6 (3.1 g, 0.011 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and nitrobenzene is removed. It was extracted with MC (methylene chloride) and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 70 g (85%) of product Sub1-I-15.

(2) Sub1-II-15 synthesis

In Sub1-I-15 (70 g, 0.253 mol), Pd(OAc) ₂ (1.7 g, 0.007 mol), P(t-Bu) ₃ (6.1 g, 0.015 mol), K ₂ CO ₃ (104 g, 0.758 mol) mol), DMA (N,N-Dimethylacetamide) (170 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 48 g (76%) of product Sub1-II-15.

(3) Sub1-III-15 synthesis

Dissolve Sub1-II-15 (44 g, 0.253 mol) in MC (methylene chloride) (365mL) and then slowly add Br ₂ (29 g, 0.183 mol) dropwise. Afterwards, the reaction temperature is raised to 50 ^o C. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 42 g (70%) of product Sub1-III-15.

(4) Sub1-IV-15 synthesis

Sub1-III-15 (40 g, 0.125 mol), 1-chloronaphthalen-2-amine (22.1 g, 0.125 mol), Pd ₂ (dba) ₃ (3.4 g, 0.004 mol), 50% P( t -Bu) ₃ (3 ml, 0.008 mol) and NaO t -Bu (36 g, 0.4 mol) were added to toluene (250ml) and stirred at 90°C. Through the Sub1-I-1 synthesis method, 42 g (yield: 78%) of the product Sub 1-IV-15 was obtained.

(5) Sub1-15 synthesis

In Sub1-IV-15 (40 g, 0.96 mol), Pd(OAc) ₂ (0.6 g, 0.003 mol), P(t-Bu) ₃ (2.8 g, 0.007 mol), K ₂ CO ₃ (48 g, 0.301 mol) mol), DMA (N,N-Dimethylacetamide) (190 ml) and refluxed at 170°C for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 33 g (84%) of product Sub1-15.

Meanwhile, the compounds belonging to Sub 1 or Sub 1' may be, but are not limited to, the compounds below. Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub 1 or Sub 1'. It represents.

compound FD-MS compound FD-MS Sub1-1 m/z= 330.12 (C ₂₄ H ₁₄ N ₂ = 330.39) Sub1-2 m/z= 406.15 (C ₃₀ H ₁₈ N ₂ = 406.49) Sub1-3 m/z= 355.11 (C ₂₅ H ₁₃ N ₃ = 355.40) Sub1-4 m/z= 380.13 (C ₂₈ H ₁₆ N ₂ = 380.45) Sub1-5 m/z= 571.20 (C ₄₂ H ₂₅ N ₃ = 571.68) Sub1-6 m/z= 406.15 (C ₃₀ H ₁₈ N ₂ = 406.49) Sub1-7 m/z= 356.13 (C ₂₆ H ₁₆ N ₂ = 356.43) Sub1-8 m/z= 380.13 (C ₂₈ H ₁₆ N ₂ = 380.45) Sub1-9 m/z= 330.12 (C ₂₄ H ₁₄ N ₂ = 330.39) Sub1-10 m/z= 411.18 (C ₃₀ H ₁₃ D ₅ N ₂ = 411.52) Sub1-11 m/z= 406.15 (C ₃₀ H ₁₈ N ₂ = 406.49) Sub1-12 m/z= 380.13 (C ₂₈ H1 ₆ N ₂ = 380.45) Sub1-13 m/z= 407.14 (C ₂₉ H ₁₇ N ₃ = 407.48) Sub1-14 m/z= 380.13 (C ₂₈ H ₁₆ N ₂ = 380.45) Sub1-15 m/z= 380.13 (C ₂₈ H ₁₆ N ₂ = 380.45) Sub1-16 m/z= 497.19 (C ₃₆ H ₂₃ N ₃ = 497.60)

8. Sub 2 compounds

Specific examples of the Sub 2 compound of Scheme 2 used in this synthesis example are as follows, but are not limited thereto.

compound FD-MS compound FD-MS Sub2-1 m/z=155.96 (C ₆ H ₅ Br=157.01) Sub2-2 m/z=231.99 (C ₁₂ H ₉ Br=233.11) Sub2-3 m/z=245.97 (C ₁₂ H ₇ BrO=247.09) Sub2-4 m/z= 321.02 (C ₁₈ H ₁₂ BrN= 322.21) Sub2-5 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ =316.79) Sub2-6 m/z= 267.06 (C ₁₅ H ₁₀ ClN ₃ = 267.72) Sub2-7 m/z= 266.06 (C ₁₆ H ₁₁ ClN ₂ = 266.73) Sub2-8 m/z=442.12 (C ₃₀ H ₁₉ ClN ₂ = 442.95) Sub2-9 m/z= 240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub2-10 m/z= 290.06 (C ₁₈ H ₁₁ ClN ₂ =290.75) Sub2-11 m/z=416.11 (C ₂₈ H ₁₇ ClN ₂ =416.91) Sub2-12 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ =316.79) Sub2-13 m/z= 296.02 (C ₁₆ H ₉ ClN ₂ S= 296.77) Sub2-14 m/z= 330.06 (C ₂₀ H ₁₁ ClN ₂ O= 330.77) Sub2-15 m/z= 377.08 (C ₂₂ H ₈ D ₅ ClN ₂ S= 377.90) Sub2-16 m/z=356.11 (C ₂₃ H ₁₇ ClN ₂ =356.85) Sub2-17 m/z= 236.04 (C ₁₆ H ₉ Cl= 236.70) Sub2-18 m/z=365.10 ( _{C25H16ClN =} 365.86) Sub2-19 m/z= 372.05 (C ₂₂ H ₁₃ ClN ₂ S= 372.87) Sub2-20 m/z=346.03 (C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub2-21 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ = 316.79) Sub2-22 m/z= 240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub2-23 m/z= 386.03 (C ₂₂ H ₁₁ ClN ₂ OS= 386.85) Sub2-24 m/z=356.07 (C ₂₂ H ₁₃ ClN ₂ O=356.81) Sub2-25 m/z= 337.98 (C ₁₈ H ₁₁ BrS= 339.25) Sub2-26 m/z= 262.94 (C ₁₁ H ₆ BrNS= 264.14) Sub2-27 m/z= 319.00 (C ₁₈ H ₁₀ BrN= 320.19) Sub2-28 m/z= 247.09 (C ₁₄ H ₂ D ₇ ClN ₂ = 247.73) Sub2-29 m/z=366.09 (C ₂₄ H ₁₅ ClN ₂ = 366.85) Sub2-30 m/z= 346.03 (C ₂₀ H ₁₁ ClN ₂ S= 346.83) Sub2-31 m/z= 326.04 (C ₁₈ H ₉ ClF ₂ N ₂ = 326.73) Sub2-32 m/z=406.12 (C ₂₇ H ₁₉ ClN ₂ = 406.91) Sub2-33 m/z= 406.09 (C ₂₆ H ₁₅ ClN ₂ O= 406.87) Sub2-34 m/z= 372.05 (C ₂₂ H ₁₃ ClN ₂ S= 372.87) Sub2-35 m/z= 331.05 (C ₁₉ H ₁₀ ClN ₃ O= 331.76) Sub2-36 m/z= 372.05 (C ₂₂ H ₁₃ ClN ₂ S= 372.87) Sub2-37 m/z= 346.03 (C ₂₀ H ₁₁ ClN ₂ S= 346.83) Sub2-38 m/z= 468.02 (C ₂₆ H ₁₃ ClN ₂ OS ₂ = 468.97) Sub2-39 m/z= 355.09 (C ₂₂ H ₁₄ ClN ₃ = 355.83) Sub2-40 m/z= 237.02 (C ₁₂ H ₄ D ₅ Br= 238.14) Sub2-41 m/z= 394.04 (C ₂₅ H ₁₅ Br= 395.30) Sub2-42 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ = 316.79) Sub2-43 m/z=392.11 (C ₂₆ H ₁₇ ClN ₂ = 392.89) Sub2-44 m/z= 266.06 (C ₁₆ H ₁₁ ClN ₂ = 266.73) Sub2-45 m/z= 265.07 (C ₁₇ H ₁₂ ClN= 265.74) Sub2-46 m/z= 380.07 (C ₂₄ H ₁₃ ClN ₂ O= 380.83) Sub2-47 m/z= 346.03 (C ₂₀ H ₁₁ ClN ₂ S= 346.83) Sub2-48 m/z= 317.07 (C ₁₉ H ₁₂ ClN ₃ = 317.78) Sub2-49 m/z= 422.06 (C ₂₆ H ₁₅ ClN ₂ S= 422.93) Sub2-50 m/z= 382.04 (C ₂₄ H ₁₅ Br= 383.29) Sub2-51 m/z= 301.05 (C ₁₆ H ₄ D ₅ ClN2S= 301.80) Sub2-52 m/z= 239.05 (C ₁₅ H ₁₀ ClN= 239.70) Sub2-53 m/z= 205.97 (C ₁₀ H ₇ Br= 207.07) Sub2-54 m/z= 291.06 (C ₁₇ H ₁₀ ClN ₃ = 291.74) Sub2-55 m/z= 280.04 (C ₁₆ H ₉ ClN ₂ O= 280.71) Sub2-56 m/z= 402.01 (C ₂₂ H ₁₁ ClN ₂ S ₂ = 402.91) Sub2-57 m/z= 356.07 (C ₂₂ H ₁₃ ClN ₂ O= 356.81) Sub2-58 m/z= 346.03 (C ₂₀ H ₁₁ ClN ₂ S= 346.83) Sub2-59 m/z= 254.06 (C ₁₅ H ₁₁ ClN ₂ = 254.72) Sub2-60 m/z= 317.07 (C ₁₉ H ₁₂ ClN ₃ = 317.78)

II. Product synthesis

1. P-2 synthesis example

[Scheme 10]

Sub1-1 (10 g, 0.03 mol), Sub2-2 (7 g, 0.03 mol), Pd ₂ (dba) ₃ (0.8 g, 0.0009 mol), t-BuONa (8.3 g, 0.09 mmol), P(t -bu) ₃ (0.7 g, 0.002 mmol) and toluene (60 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic matter was separated using a silicagel filter, and 10 g (68.5%) of product P-2 was obtained.

2. P-6 synthesis example

[Scheme 11]

Sub1-1 (10 g, 0.03 mol), Sub2-6 (8 g, 0.03 mol), Pd ₂ (dba) ₃ (0.8 g, 0.0009 mol), t-BuONa (8.3 g, 0.09 mmol), P(t -bu) ₃ (0.7 g, 0.002 mmol) and toluene (60 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic matter was separated using a silicagel filter, and 14 g (82.4%) of product P-6 was obtained.

3. P-21 synthesis example

[Scheme 12]

Sub1-5 (15 g, 0.026 mol), Sub2-1 (4 g, 0.026 mol), Pd ₂ (dba) ₃ (0.7 g, 0.0009 mol), t-BuONa (7.5 g, 0.009 mmol), P(t -bu) ₃ (0.75 g, 0.002 mmol) and toluene (50 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic matter was separated using a silicagel filter, and 15 g (88%) of product P-21 was obtained.

4. P-23 synthesis example

[Scheme 13]

Sub1-1 (11 g, 0.03 mol), Sub2-22 (8 g, 0.03 mol), Pd ₂ (dba) ₃ (0.7 g, 0.0009 mol), t-BuONa (9.6 g, 0.009 mmol), P(t -bu) ₃ (0.8 g, 0.002 mmol) and toluene (60 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic matter was separated using a silicagel filter, and 13 g (73%) of product P-23 was obtained.

5. P-54 synthesis example

[Scheme 14]

Sub1-10 (10 g, 0.025 mol), Sub2-53 (5 g, 0.025 mol), Pd ₂ (dba) ₃ (0.7 g, 0.0009 mol), t-BuONa (7 g, 0.009 mmol), P(t -bu) ₃ (0.8 g, 0.002 mmol) and toluene (60 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic matter was separated using a silicagel filter, and 10 g (76.6%) of product P-54 was obtained.

6. P-65 synthesis example

[Scheme 15]

Sub1-12 (13 g, 0.034 mol), Sub2-63 (9.1 g, 0.034 mol), Pd ₂ (dba) ₃ (0.8 g, 0.001 mol), t-BuONa (9.8 g, 0.01 mmol), P(t -bu) ₃ (0.75 g, 0.003 mmol) and toluene (80 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC (methylene chloride), and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic matter was separated using a silicagel filter, and 12 g (57.5%) of product P-65 was obtained.

P-1, P-3 to P-5, P-7 to P-20, P-22, P-24 to P-53, P-55 to P-64 and P-66 to P-70 also in the table below It can be synthesized using a method similar to the above synthesis method using the Sub 1, Sub 1', and Sub 2 compounds described in 3. When each compound described in column 1 of Table 3 below is reacted with the compound described in column 2, the compound described in the product column can be synthesized.

Sub1 and Sub 1' Sub2 product Sub 1-1 Sub 2-1 P-1 Sub 2-3 P-3 Sub 2-4 P-4 Sub 2-5 P-5 Sub 2-7 P-7 Sub 2-8 P-8 Sub 2-9 P-9 Sub 2-10 P-10 Sub 2-11 P-11 Sub 2-12 P-12 Sub 2-13 P-13 Sub 2-14 P-14 Sub 2-15 P-15 Sub 2-16 P-16 Sub 2-17 P-17 Sub 2-18 P-18 Sub 2-20 P-20 Sub 2-22 P-24 Sub 2-25 P-26 Sub 2-26 P-27 Sub 2-27 P-28 Sub 2-28 P-29 Sub 2-29 P-30 Sub 2-30 P-31 Sub 2-31 P-32 Sub 2-32 P-33 Sub 2-33 P-34 Sub 2-34 P-35 Sub 2-35 P-36 Sub 2-36 P-37 Sub 2-37 P-38 Sub 2-38 P-39 Sub 2-39 P-40 Sub 1-2 Sub 2-19 P-19 Sub 1-6 Sub 2-21 P-22 Sub 1-7 Sub 2-24 P-25 Sub 1-11 Sub 2-59 P-61 Sub 1-12 Sub 2-9 P-55 Sub 2-13 P-64 Sub 2-22 P-66 Sub 2-41 P-42 Sub 2-42 P-43 Sub 2-43 P-44 Sub 2-44 P-45 Sub 2-45 P-46 Sub 2-46 P-47 Sub 2-47 P-48 Sub 2-48 P-49 Sub 2-49 P-50 Sub 2-50 P-51 Sub 2-51 P-52 Sub 2-52 P-53 Sub 2-54 P-56 Sub 2-56 P-58 Sub 2-57 P-59 Sub 2-58 P-60 Sub 2-60 P-62 Sub 2-61 P-63 Sub 2-64 P-67 Sub 2-65 P-57 Sub 2-65 P-68 Sub 1-13 Sub 2-40 P-41 Sub 1-15 Sub 2-55 P-69 Sub 1-16 Sub 2-62 P-70

Meanwhile, the FD-MS (Field Desorption-Mass Spectrometry) values of compounds P-1 to P-72 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

compound FD-MS compound FD-MS P-1 m/z= 406.15 (C ₃₀ H ₁₈ N ₂ =406.49) P-2 m/z= 482.18 (C ₃₆ H ₂₂ N ₂ =482.59) P-3 m/z= 496.16 (C ₃₆ H ₂₀ N ₂ O=496.57) P-4 m/z= 571.20 (C ₄₂ H ₂₅ N ₃ =571.68) P-5 m/z=610.22 (C ₄₄ H ₂₆ N ₄ =610.72) P-6 m/z= 561.20 (C ₃₉ H ₂₃ N ₅ =561.65) P-7 m/z= 560.20 (C ₄₀ H ₂₄ N ₄ =560.66) P-8 m/z=6736.26 (C ₅₄ H ₃₂ N ₄ =736.88) P-9 m/z= 534.18 (C ₃₈ H ₂₂ N ₄ =534.62) P-10 m/z=584.20 (C ₄₂ H ₂₄ N ₄ =584.68) P-11 m/z= 710.25 (C ₅₂ H ₃₀ N ₄ =710.84) P-12 m/z=610.22 (C ₄₄ H ₂₆ N ₄ =610.72) P-13 m/z=590.16 (C ₄₀ H ₂₂ N ₄ S=590.70) P-14 m/z=624.20 (C ₄₄ H ₂₄ N ₄ O=624.70) P-15 m/z=671.22 (C ₄₆ H ₂₁ D ₅ N ₄ S=671.83) P-16 m/z=650.25 (C ₄₇ H ₃₀ N ₄ =650.79) P-17 m/z= 530.18 (C ₄₀ H ₂₂ N ₂ =530.63) P-18 m/z=659.24 (C ₄₉ H ₂₉ N ₃ =659.79) P-19 m/z= 742.22 (C ₅₂ H ₃₀ N ₄ S= 742.90) P-20 m/z= 640.17 (C ₄₄ H ₂₄ N ₄ S= 640.76) P-21 m/z=647.24 (C ₄₈ H ₂₉ N ₃ =647.78) P-22 m/z=686.25 (C ₅₀ H ₃₀ N ₄ =686.82) P-23 m/z= 534.18 (C ₃₈ H ₂₂ N ₄ =534.62) P-24 m/z= 680.17 (C ₄₆ H ₂₄ N ₄ OS= 680.79) P-25 m/z=676.23 (C ₄₈ H ₂₈ N ₄ O=676.78) P-26 m/z= 588.17 (C ₄₂ H ₂₄ N ₂ S= 588.73) P-27 m/z= 513.13 (C ₃₅ H ₁₉ N ₃ S= 513.62) P-28 m/z= 569.19 (C ₄₂ H ₂₃ N ₃ = 569.67) P-29 m/z= 591.24 (C ₄₂ H ₁₇ D ₇ N ₄ =591.72) P-30 m/z= 660.23 (C ₄₈ H ₂₈ N ₄ = 660.78) P-31 m/z= 640.17 (C ₄₄ H ₂₄ N ₄ S= 640.76) P-32 m/z= 670.20 (C ₄₆ H ₂₄ F ₂ N ₄ = 670.72) P-33 m/z= 700.26 (C ₅₁ H ₃₂ N ₄ = 700.85) P-34 m/z= 700.23 (C ₅₀ H ₂₈ N ₄ O= 700.80) P-35 m/z=666.19 (C ₄₆ H ₂₆ N ₄ S=666.80) P-36 m/z= 625.19 (C ₄₃ H ₂₃ N ₅ O= 625.69) P-37 m/z=691.18 (C ₄₇ H ₂₅ N ₅ S= 691.81) P-38 m/z= 640.17 (C ₄₄ H ₂₄ N ₄ S= 640.76) P-39 m/z= 762.15 (C ₅₀ H ₂₆ N ₄ OS ₂ = 762.91) P-40 m/z=649.23 (C ₄₆ H ₂₇ N ₅ = 649.76) P-41 m/z= 564.24 (C ₄₁ H ₂₀ D ₅ N ₃ = 564.70) P-42 m/z=644.23 (C ₄₉ H ₂₈ N ₂ = 644.78) P-43 m/z=610.22 (C ₄₄ H ₂₆ N ₄ = 610.72) P-44 m/z=686.25 (C ₅₀ H ₃₀ N ₄ = 686.82) P-45 m/z= 560.20 (C ₄₀ H ₂₄ N ₄ = 560.66) P-46 m/z= 559.20 (C ₄₁ H ₂₅ N ₃ = 559.67) P-47 m/z= 674.21 (C ₄₈ H ₂₆ N ₄ O= 674.76) P-48 m/z= 640.17 (C ₄₄ H ₂₄ N ₄ S= 640.76) P-49 m/z=611.21 (C ₄₃ H ₂₅ N ₅ = 611.71) P-50 m/z= 716.20 (C ₅₀ H ₂₈ N ₄ S= 716.86) P-51 m/z=632.23 (C ₄₈ H ₂₈ N ₂ = 632.77) P-52 m/z= 595.19 (C ₄₀ H ₁₇ D ₅ N ₄ S= 595.73) P-53 m/z= 533.19 (C ₃₉ H ₂₃ N ₃ = 533.63) P-54 m/z= 537.23 (C ₄₀ H ₁₉ D ₅ N ₂ = 537.68) P-55 m/z= 534.18 (C ₃₈ H ₂₂ N ₄ = 534.62) P-56 m/z= 585.20 (C ₄₁ H ₂₃ N ₅ = 585.67) P-57 m/z= 584.20 (C ₄₂ H ₂₄ N ₄ = 584.68) P-58 m/z=696.14 (C ₄₆ H ₂₄ N ₄ S ₂ = 696.85) P-59 m/z= 650.21 (C ₄₆ H ₂₆ N ₄ O= 650.74) P-60 m/z= 640.17 (C ₄₄ H ₂₄ N ₄ S= 640.76) P-61 m/z=624.23 (C ₄₅ H ₂₈ N ₄ = 624.75) P-65 m/z=610.22 (C ₄₄ H ₂₆ N ₄ = 610.72)

Meanwhile, in the above, exemplary synthesis examples of the present invention represented by Formula 1 have been described, but these are all BuchwaldHartwig cross coupling reaction, Suzuki cross-coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, and intramolecular acid-induced cyclization reaction ( J. mater. Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), based on ^Grignard reaction and Cyclic Dehydration reaction ^, etc. ^In addition to the substituents specified ⁱⁿ the specific synthesis examples ^, other substituents defined in Formula ¹ (X ¹ , ) will be easily understood by those skilled in the art that the above reaction proceeds even if it is combined.

Manufacturing evaluation of organic electric devices

Example) Production and testing of red organic light emitting device

First, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl( A phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a 60 nm thick film. Next, 4,4-bis[ N -(1-naphthyl)- N -phenylamino] biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum deposited on this film to a thickness of 60 nm to form a hole transport layer. formed. The above invention compound represented by Chemical Formula (1) was used as a host on the upper part of the hole transport layer, and as a dopant, (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate] was used at 95:5 weight. A 30 nm thick light emitting layer was deposited on the hole transport layer by doping with . (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinoline oleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole-blocking layer, and the electron transport layer Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a 40 nm thick film. Afterwards, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

A forward bias direct current voltage was applied to the organic electroluminescent devices of Examples and Comparative Examples manufactured in this way, and the electroluminescence (EL) characteristics were measured with PR-650 from Photoresearch, and the measurement results showed a luminance of 2500 cd/m ² . The T95 lifespan was measured using a lifespan measuring device manufactured by McScience. The table below shows the results of device fabrication and evaluation.

[Comparative Examples 1, 2, 3]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that comparative compounds A, B, and C were used as hosts.

compound driving voltage
(V) electric current
(mA/ ^cm2 ) Luminance
(cd/ ^m2 ) efficiency
(cd/A) T95 lifespan
(hr) CIE x y Comparative example (1) Comparative compound (A) 7.0 32.9 2500.0 7.6 60.7 0.62 0.34 Comparative example (2) Comparative compound (B) 6.5 22.9 2500.0 10.9 98.2 0.62 0.30 Comparative example (3) Comparative compound (C) 6.6 24.0 2500.0 10.4 100.4 0.64 0.31 Example (1) Compound (P-9) 5.8 12.8 2500.0 19.5 112.7 0.62 0.33 Example (2) Compound (P-10) 6.0 13.2 2500.0 18.9 113.5 0.65 0.34 Example (3) Compound (P-11) 5.9 12.5 2500.0 20.0 116.0 0.62 0.30 Example (4) Compound (P-12) 5.8 13.1 2500.0 19.1 112.1 0.64 0.31 Example (5) Compound (P-13) 5.9 12.9 2500.0 19.4 117.1 0.62 0.31 Example (6) Compound (P-14) 5.9 12.5 2500.0 20.0 114.1 0.60 0.31 Example (7) Compound (P-15) 5.9 13.2 2500.0 18.9 115.3 0.65 0.33 Example (8) Compound (P-16) 5.8 13.2 2500.0 18.9 112.2 0.63 0.31 Example (9) Compound (P-20) 5.8 13.1 2500.0 19.1 112.8 0.62 0.35 Example (10) Compound (P-23) 5.9 13.0 2500.0 19.3 114.4 0.64 0.31 Example (11) Compound (P-55) 5.9 14.8 2500.0 16.9 124.8 0.60 0.33 Example (12) Compound (P-57) 5.9 15.4 2500.0 16.2 123.7 0.62 0.31 Example (13) Compound (P-58) 6.0 15.0 2500.0 16.7 122.3 0.61 0.31 Example (14) Compound (P-59) 5.9 13.9 2500.0 18.0 122.9 0.61 0.33 Example (15) Compound (P-64) 5.9 14.8 2500.0 16.9 124.1 0.61 0.31 Example (16) Compound (P-66) 5.9 14.7 2500.0 17.0 120.3 0.60 0.33

As can be seen from the results in the table above, when a red organic electroluminescent device was manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, the organic electroluminescence was higher than that of the comparative examples using Comparative Compounds A to Comparative Compounds C. It can be seen that not only can the driving voltage of the device be lowered, but also the luminous efficiency and lifespan can be significantly improved.

In order to examine the effect of the compounds of the present invention, compounds with relatively high structural similarity were set as comparison groups. However, in conclusion, Comparative Compounds A to C are structurally different from the compounds of the present invention, so their chemical and physical properties are significantly different. As a result, the compound of the present invention produced remarkably excellent device results that were completely unexpected by those skilled in the art.

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

200: Electronic device
210: Display device
220: control unit
230: Organic electric device

Claims (9)

Compounds represented by the following formula 2 or 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
Wherein L ¹ is a single bond, an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and a C ₁ to C ₂₀ divalent aliphatic hydrocarbon group;
Ar ¹ is a functional group other than hydrogen substituted on L ¹ , and Ar ¹ is each independently an aryl group having C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₂ ~ C ₂₀ alkoxy group; and an aryloxy group from C ₆ to C ₃₀ ,
where n is a positive integer other than 0,
R ¹ , R ² , and R ³ are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₁ ~ C ₅₀ alkyl group; Silane group; Cyano group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₂ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; -N(R')(R"), and a plurality of R ¹ , R ² , and R ³ may be combined with each other to form an aromatic ring or heteroaromatic ring,
R' and R" are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₁ ~ C ₅₀ alkyl group; silane group; cyano group; O , N, S, Si, P, C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₂ ~C ₂₀ alkenyl group; C ₂ ~C ₂₀ alkynyl group; C ₂ ~C ₂₀ alkoxyl group; C ₆ ~C ₃₀ aryloxy group;
a and c are 0 to 4, and b is 0 to 5,
The aliphatic hydrocarbon group, aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and silane group each contain deuterium; nitro group; Nitrile group; halogen group; amino group; A silane group unsubstituted or substituted with a C ₁ to C ₂₀ alkyl group or a C ₆ to C ₂₀ aryl group; siloxane group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group, and these substituents may be combined with each other to form a ring, where 'ring ' refers to a fused ring including a saturated or unsaturated ring, a C ₃ to C ₆₀ aliphatic ring, a C ₆ to C ₆₀ aromatic ring, a C ₂ to C ₆₀ heterocycle, or a combination thereof. delete According to clause 1,
The compound represented by Formula 1 is characterized in that it is one of the following compounds:


. first electrode; second electrode; And an organic material layer located between the first electrode and the second electrode. In the organic electric device comprising,
The organic material layer is an organic electric device containing the compound of claim 1. According to clause 4,
The organic layer includes at least one of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an auxiliary electron transport layer, an electron transport layer, and an electron injection layer,
The compound is a single compound of any one of claims 1 or 3 in at least one of the hole injection layer, hole transport layer, auxiliary light emitting layer, light emitting layer, electron transport auxiliary layer, electron transport layer, and electron injection layer. Or an organic electric device characterized in that it is included as a mixture of two or more compounds. According to clause 4,
The organic layer includes at least one of a hole transport layer and a light emitting layer,
The compound is an organic electronic device characterized in that it is included in at least one of the hole transport layer and the light emitting layer as a single compound or a mixture of two or more compounds of any one of claims 1 or 3. According to clause 4,
The organic material layer is an organic electric device formed by at least one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process. A display device including the organic electric element of claim 4; and
An electronic device comprising a control unit that controls the display device. According to clause 8,
The organic electric device is an electronic device that is one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.