KR102644211B1 - 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.

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.
Figure 2 is an exemplary diagram of an electronic 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.

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

As used herein, the term "alkenyl" or "alkynyl", unless otherwise specified, has a double bond or triple bond, includes a straight or branched chain group, and has a carbon number of 2 to 60, 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 herein, 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" refers to a monovalent or divalent functional group of substituted fluorene, and "substituted fluorene" refers to a group in which at least one of the following substituents R, R', R", and R''' is a functional group other than hydrogen. This means that R and R' are combined with each other to form a spiro compound with the carbon to which they are connected.

In addition, R, R', R" and R''' are each independently selected from an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 It may be a heterocyclic group having a carbon number of 30 to 30. For example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene, or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, or imidazole. , triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline.

As used herein, the terms “aryl group” and “arylene group” each have 6 to 60 carbon atoms unless otherwise specified, but are not limited thereto. In the present invention, an aryl group or arylene group includes a single ring type, a ring aggregate, a multiple ring system fused, a compound, etc. For example, the aryl group may refer to a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group.

As used herein, the term “ring assemblies” 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.

In the present specification, since the aryl group includes a ring assembly, the aryl group includes biphenyl and terphenyl in which a benzene ring, which is a single aromatic ring, is linked by a single bond. In addition, the aryl group also includes compounds in which an aromatic ring system bonded to an aromatic single ring is connected by a single bond, so for example, fluorene, an aromatic ring system bonded to a benzene ring, which is an aromatic single ring, forms a conjugated pi electronic system ( It also includes compounds linked to form a conjugated pi electron system.

As used herein, the term “multiple fused ring system” 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 herein 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.

The term "heterocyclic group" used herein includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as 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 aggregate, 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.

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, intrinsic properties of the material (mobility, interface properties, etc.), etc. By optimizing, the lifespan and efficiency of organic electric devices can be improved simultaneously.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD (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).

Hereinafter, X. L, Ar ₁ , R ₁ to R ₄ and m to q described in the above formula (1) will be described.

The X is O, S or Se.

By using the above-mentioned Group 16 element as

Wherein L is a single bond, C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ .

When L is an aryl group, L may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group. For example, L is benzene, naphthalene, anthracene, It may be phenanthrene, tetracene, benzoanthracene or triphenylene.

When L is a heterocyclic group, L may be a C ₂ ~ C ₃₀ heterocyclic group or a C ₂ ~ C ₁₅ heterocyclic group, for example, pyrrole, pyrazole, imidazole, triazole, furan, ti. It may be ophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene or dibenzofuran.

When L is a pyrimidine, for example, L, which is a pyrimidine, may be represented by the following formula (A).

[Formula A]

In the above formula A, 1 is the carbon to which L is bonded to N by a single bond in NL-(Ar ₁ ) _q of formula (1), and 2 and 3 are Ar ₁ in NL-(Ar ₁ ) _q . It is a carbon that can be substituted for L. When L is the same as Formula A, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is pyridine, for example, L, which is pyridine, may be represented by the following formula (B).

[Formula B]

In the above formula B, 1 is the carbon to which L is bonded to N by a single bond in NL-(Ar ₁ ) _q of formula (1), and 2 and 3 are Ar ₁ in NL-(Ar ₁ ) _q . It is a carbon that can be substituted for L. When L is the same as Formula B, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is quinazoline or quinoxaline, for example, L, which is quinazoline or quinoxaline, may be represented by the following formula C.

[Formula C]

In the formula C, 1 is a carbon to which L is bonded to the N by a single bond in NL-(Ar ₁ ) _q of formula (1), one of A and B is N and the other is Ar ₁ It is a substituted carbon. When L is the same as Formula C, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocyclic group, for example, L may be represented by the following formula E.

[Formula D]

In the formula D, 1 is a carbon to which L is bonded to the N by a single bond in NL-(Ar ₁ ) _q of formula (1), and R ₅ and R ₆ are between adjacent R ₅ or between adjacent R ₆ They combine with each other to form a benzene ring, and either R ₅ or R ₆ is hydrogen. Therefore, Formula D is a three-ring heterocyclic compound and has a structure in which benzene rings formed by bonding adjacent R ₅ or adjacent R ₆ are condensed (benzofused). When L is the same as Formula D, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocyclic group, for example, L may be represented by the following formula E.

[Formula E]

In the formula E, 1 is a carbon to which L is bonded to the N by a single bond in NL-(Ar ₁ ) _q of formula (1), one of C and D is N and the other is Ar ₁ is a substituted carbon, and Y is S or O. When L is the same as Formula E, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocycle, for example, L may be represented by the following formula F.

[Formula F]

In the formula F, 1 is the carbon to which L is bonded to the N by a single bond in NL-(Ar ₁ ) _q of the formula (1). When L is the same as Formula F, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocycle, for example, L may be represented by the following formula G.

[Formula G]

In the formula G, 1 is a carbon to which L in NL-(Ar ₁ ) _q of formula (1) is bonded to N by a single bond, and 2 is a carbon in NL-(Ar ₁ ) _q where Ar ₁ is L It is a carbon that can be substituted for. When L is the same as Formula G, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocycle, for example, L may be represented by the following formula H.

[Formula H]

In the formula H, 1 is the carbon where L in NL-(Ar ₁ ) _q of formula (1) is bonded to the N by a single bond, and 2 is the carbon in NL-(Ar ₁ ) _q where Ar ₁ is L It is a carbon that can be substituted for. When L is the same as Chemical Formula H, the compound of Chemical Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocycle, for example, L may be represented by the following formula (I).

[Formula I]

In the formula (I), 1 is a carbon to which L in NL-(Ar ₁ ) _q of formula (1) is bonded to N by a single bond, and 2 is a carbon in NL-(Ar ₁ ) _q where Ar ₁ is L It is a carbon that can be substituted for. When L is the same as Formula I, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocycle, for example, L may be represented by the following formula (J).

[Formula J]

In the formula J, 1 is a carbon where L in NL-(Ar ₁ ) _q of formula (1) is bonded to the N by a single bond, and 2 is a carbon in NL-(Ar ₁ ) _q where Ar ₁ is L It is a carbon that can be substituted for. When L is the same as Formula J, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When L is a heterocycle, for example, L may be represented by the following formula (K).

[Formula K]

In the formula K, 1 is a carbon to which L is bonded to the N by a single bond in NL-(Ar ₁ ) _q of the formula (1), and in N of the formula K, Ar ₁ substituted for L is a single bond are combined by When L is the same as Chemical Formula K, the compound of Chemical Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

Ar ₁ is a functional group other than hydrogen substituted on L, or is a functional group bonded to N of Formula (1) by a single bond, L, and Ar ₁ is each independently an aryl group of C ₆ to C ₆₀ ; 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 group; and -L'-N(R _a )(R _b );

L' is a single bond; C ₆ ~ C ₆₀ arylene group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of.

More specifically, L' may be a single bond or phenylene.

When Ar ₁ is an aryl group, Ar ₁ may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group. For example, Ar ₁ may be each independently It may be selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, triphenylene, biphenyl, terphenyl, and substituted or unsubstituted fluorene.

When Ar ₁ is a heterocyclic group, Ar ₁ may be a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group. For example, Ar ₁ is each independently pyrrole, pyrazole, or It may be selected from the group consisting of dazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, dibenzothiophene and dibenzofuran.

When Ar ₁ is a heterocyclic group, for example, Ar ₁ may be represented by the following formula L.

[Formula L]

In the above formula L, 1 is the carbon to which Ar ₁ is bonded to L by a single bond in NL-(Ar ₁ ) _q of formula (1). When Ar ₁ is the same as Formula L, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When Ar ₁ is a heterocyclic group, for example, Ar ₁ may be represented by the following formula M.

[Formula M]

In the above formula M, Z is S or O, 1 to 3 are carbons at which Ar ₁ can be bonded to L by a single bond in NL-(Ar ₁ ) _q of formula (1), and 1 to 3 carbons Any one of them is bonded to L by a single bond.

In the formula M, for example, when Z is S, either 2 or 3 carbons may be bonded to L by a single bond.

When Ar ₁ is the same as Formula M, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When Ar ₁ is a heterocyclic group, for example, Ar ₁ may be represented by the following formula N.

[Formula N]

In the above formula N, 1 is the carbon to which Ar ₁ is bonded to L by a single bond in NL-(Ar ₁ ) _q of formula (1). When Ar ₁ is the same as Formula N, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When Ar ₁ is a heterocyclic group, for example, Ar ₁ may be represented by the following formula O.

[Formula O]

In the above formula O, 1 is the carbon to which Ar ₁ is bonded to L by a single bond in NL-(Ar ₁ ) _q of formula (1). When Ar ₁ is the same as Formula O, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When Ar ₁ is a heterocyclic group, for example, Ar ₁ may be represented by the following formula P.

[Formula P]

In the above formula P, 1 is the carbon to which Ar ₁ is bonded to L by a single bond in NL-(Ar ₁ ) _q of formula (1). When Ar ₁ is the same as Formula P, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; 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 ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

When R _a and R _b are aryl groups, R _a and R _b may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group, for example, R _a and R _b may each independently be benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, triphenylene, biphenyl, or terphenyl.

The q is a positive integer other than 0.

Since q refers to the number of Ar ₁ substituted for L, for example, when L is a single bond, q is 1, and when L is phenylene, it may be an integer of 1 to 5.

The m, n, o and p are independently integers from 0 to 4.

The R ₁ , R ₂ , R ₃ and R ₄ are the same as or different from each other, and are each independently deuterium; halogen; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; and -L ¹ -N(R')(R"), and may be selected from the group consisting of a plurality of adjacent R ₁ , a plurality of adjacent R ₂ , a plurality of adjacent R ₃ , and a plurality of adjacent R ₄ . They can combine with each other to form saturated or unsaturated rings.

When a plurality of adjacent R _1s are combined with each other to form a saturated or unsaturated ring, a C ₄ to C ₂₀ saturated or unsaturated ring, a C ₄ to C ₁₂ saturated or unsaturated ring, or a C ₄ to C ₆ unsaturated ring can be formed. and may form, for example, cyclobutane, cyclopentane, cyclohexane, benzene, naphthalene, anthracene, phenanthrene, pyrrole, pyrazole, imidazole, indole, quinazoline or quinoxaline.

When a plurality of adjacent R ₂ bonds to each other to form a saturated or unsaturated ring, a C ₄ to C ₂₀ saturated or unsaturated ring, a C ₄ to C ₁₂ saturated or unsaturated ring, or a C ₄ to C ₆ unsaturated ring can be formed. and may form, for example, cyclobutane, cyclopentane, cyclohexane, benzene, naphthalene, anthracene, phenanthrene, pyrrole, pyrazole, imidazole, indole, quinazoline or quinoxaline.

When a plurality of adjacent R ₃ bonds to each other to form a saturated or unsaturated ring, a C ₄ to C ₂₀ saturated or unsaturated ring, a C ₄ to C ₁₂ saturated or unsaturated ring, or a C ₄ to C ₆ unsaturated ring can be formed. and may form, for example, cyclobutane, cyclopentane, cyclohexane, benzene, naphthalene, anthracene, phenanthrene, pyrrole, pyrazole, imidazole, indole, quinazoline or quinoxaline.

When a plurality of adjacent R ₄ bonds together to form a saturated or unsaturated ring, a C ₄ to C ₂₀ saturated or unsaturated ring, a C ₄ to C ₁₂ saturated or unsaturated ring, or a C ₄ to C ₆ unsaturated ring can be formed. and may form, for example, cyclobutane, cyclopentane, cyclohexane, benzene, naphthalene, anthracene, phenanthrene, pyrrole, pyrazole, imidazole, indole, quinazoline or quinoxaline.

R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl 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; may be selected from the group consisting of.

When at least one of R' and R" is an aryl group, the aryl groups R' and R" may be a C ₆ to C ₄₀ aryl group, a C ₆ to C ₃₀ aryl group, or a C ₆ to C ₂₀ aryl group, , for example, each independently benzene, naphthalene, anthracene, phenanthrene, tetracene, benzoanthracene, triphenylene and biphenyl, terphenyl, fluorene, 9,9-dimethylfluorene, 9,9-diphenyl. It may be selected from the group consisting of fluorene and 9,9'-spirobi[9H-fluorene].

When at least one of R' and R" is a heterocyclic group, the heterocyclic groups R' and R" are a C ₂ to C ₄₀ heterocyclic group, a C ₂ to C ₃₀ heterocyclic group, or a C ₂ to C ₂₀ heterocyclic group. It may be a heterocyclic group, for example, each independently pyrrole, pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, It may be selected from the group consisting of dibenzothiophene and dibenzofuran.

When at least one of R ₁ to R ₄ is a heterocyclic group, R ₁ to R ₄ may be a C ₂ to C ₃₀ heterocyclic group or a C ₂ to C ₁₅ heterocyclic group, for example, Heterocyclic groups R ₁ to R ₄ are pyrrole, pyrazole, imidazole, triazole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, quinazoline, quinoxaline, and dibenzothiophene. and dibenzofuran.

When at least one of R ₁ to R ₄ is a heterocyclic group, the heterocyclic groups R ₁ to R ₄ may be represented by the following formula Q.

[Formula Q]

In the above formula Q, 1 means the carbon bonded to the 8-ring parent nucleus of formula (1) when R ₁ to R ₄ are substituted. The 8-ring parent nucleus of the formula (1) refers to the central structure of the formula (1) in which -L-(Ar ₁ ) _q and R ₁ to R ₄ are substituted. When the heterocyclic groups R ₁ to R ₄ are the same as Chemical Formula Q, the compound of Chemical Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When at least one of R ₁ to R ₄ is a heterocyclic group, the heterocyclic groups R ₁ to R ₄ may be represented by the following formula R.

[Formula R]

In the formula R, 1 refers to the carbon bonded to the 8-ring parent nucleus of formula (1) when R ₁ to R ₄ are substituted, one of E and F is N, and the other is a phenyl group substituted It is carbon. The 8-ring parent nucleus of the formula (1) refers to the central structure of the formula (1) in which -L-(Ar ₁ ) _q and R ₁ to R ₄ are substituted. When the heterocyclic groups R ₁ to R ₄ are the same as the above formula R, the compound of formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When at least one of R ₁ to R ₄ is a heterocyclic group, the heterocyclic groups R ₁ to R ₄ may be represented by the following formula S.

[Formula S]

In the above formula S, 1 means the carbon bonded to the 8-ring parent nucleus of formula (1) when R ₁ to R ₄ are substituted. The 8-ring parent nucleus of the formula (1) refers to the central structure of the formula (1) in which -L-(Ar ₁ ) _q and R ₁ to R ₄ are substituted. When the heterocyclic groups R ₁ to R ₄ are the same as Chemical Formula S, the compound of Chemical Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

When at least one of R ₁ to R ₄ is a heterocyclic group, the heterocyclic groups R ₁ to R ₄ may be represented by the following formula T.

[Formula T]

In the above formula T, 1 means the carbon bonded to the 8-ring parent nucleus of formula (1) when R ₁ to R ₄ are substituted. The 8-ring parent nucleus of the formula (1) refers to the central structure of the formula (1) in which -L-(Ar ₁ ) _q and R ₁ to R ₄ are substituted. When the heterocyclic groups R ₁ to R ₄ are the same as Formula T, the compound of Formula (1) can provide a device that achieves high luminous efficiency, low driving voltage, high heat resistance, excellent color purity, and long lifespan.

In Ar ₁ , R ₁ to R ₄ , R _a , R _b , R' and R", an aliphatic hydrocarbon group, an aryl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, Aryloxy group and silane group are each deuterium; nitro group; nitrile group; halogen group; amino group; silane group substituted or unsubstituted with C ₁ ~ C ₂₀ alkyl group or C ₆ ~ 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 alkynyl group; C ₆ ~ C ₂₀ aryl group ; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkene It may be further substituted with one or more substituents selected from the group consisting of a single group, and these substituents may be combined with each other to form a ring, where 'ring' includes a saturated or unsaturated ring, and an aliphatic group of C ₃ to C ₆₀ It is a fused ring consisting of a ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , 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 the formula (1) may be represented by the following formulas (2) to (4).

Chemical formula (2)

Chemical formula (3)

Chemical formula (4)

In the formulas (2) to (4), L, Ar ₁ , R ₁ to R ₄ and q are the same as described above, m to p are independently integers of 0 to 4, and the formula (2) ), at least three of m, n, o, and p are 0, and in Formula (3), at least one of m and o is 0.

delete

Specifically, the compound represented by Formula (1) may be any one of the following compounds, but is not limited thereto.

As another example, the present invention provides an organic electric device containing the compound represented by the formula (1).

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 Chemical Formula (1), and the compound represented by Chemical Formula (1) is a hole of the organic material layer. It may be contained in at least one of an injection layer, a hole transport layer, an auxiliary light emitting 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, providing an organic electric device containing one of the compounds represented by the formula (1) in the organic material layer, and more specifically, a compound represented by the individual formulas (1-1 to 1-150) in the organic material layer It provides an organic electric device containing a.

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 the formula (1) alone or a mixture of two or more compounds of the formula (1), the compounds of claims 1 to 3, and the compounds of the present invention. Mixtures with non-applicable compounds 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, examples of synthesis of the compound represented by formula (1) and examples of manufacturing organic electric devices according to the present invention will be described in detail through examples, but the present invention is not limited to the following examples.

[Synthesis example]

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

_{In Scheme 1 below ,} (dibenzylideneacetone)dipalladium(0).

I. Example of synthesis of Sub 1

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

DMF below is N,N-Dimethylformamide, and DMA below is N,N-Dimethylacetamide.

1. Sub1-1 synthesis example

(1) Sub 1-1a synthesis

6,12-dibromochrysene (40g, 103.6mmol), 2-iodobenzenethiol (26.9g, 114.0mmol), CuI (4.74g, 5.2mmol), L-proline (2.1g, 10.4mmol), K ₃ PO ₄ (24.89g , 259.0 mmol) was dissolved in EtOH/Water (2:3) (1 L) and refluxed at 80°C for 6 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the desired product (54.95 g, 98%).

(2) Sub 1-1b synthesis

Sub 1-1a (54.95g, 101.5mmol), Pd ₂ (dba) ₃ (4.98g, 20.3mmol), Cu(OAc) ₂ (18.59g, 20.3mmol), PivONa·H ₂ O (20.54g) obtained above. , 101.5 mmol) was placed in a round bottom flask, dissolved in DMF (N,N-Dimethylformamide) (600 mL), and refluxed at 150°C for 5 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ 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 the desired product (34.41 g, 82%).

(3) Sub 1-1c synthesis

Sub 1-1b (34.41g, 83.3mmol), 2-chloroaniline (9.56g, 74.9mmol), Pd(OAc) ₂ (0.56g, 2.5mmol), and P(t-Bu) ₃ (2.4ml) obtained above. , NaOt-Bu (24.0g, 249.8mmol) was placed in a round bottom flask, dissolved in toluene (800mL), and refluxed at 70°C for 3 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (29.1 g, 76%).

(4) Sub 1-1 synthesis

Sub 1-1c (29.1g, 63.3mmol), Pd(OAc) ₂ (0.71g, 3.2mmol), P(t-Bu) ₃ ·HBF ₄ (1.84g, 6.3mmol), K ₂ CO ₃ obtained above. (26.23g, 189.8mmol) was dissolved in DMA (N,N-Dimethylacetamide) (300mL) and refluxed at 150 ^o C for 24 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (21.7 g, 81%).

2. Sub1-3 synthesis example

(1) Sub 1-3a synthesis

6,12-dibromochrysene (43g, 111.4mmol), 2,5-diiodobenzenethiol (44.35g, 122.5mmol), CuI (5.1g, 5.6mmol), L-proline (2.25g, 11.1mmol), K ₃ PO ₄ ( 26.76g, 278.4mmol) was dissolved in EtOH/Water (2:3) (1.1L) and refluxed at 80°C for 6 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the desired product (63.9 g, 86%).

(2) Sub 1-3b synthesis

Sub 1-3a (63.9g, 95.8mmol), Pd ₂ (dba) ₃ (4.7g, 19.2mmol), Cu(OAc) ₂ (17.54g, 19.2mmol), PivONa·H ₂ O (19.38g) obtained above. , 95.8mmol) was placed in a round bottom flask, dissolved in DMF (N,N-Dimethylformamide) (600mL), and refluxed at 150°C for 5 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ 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 the desired product (41.84 g, 81%).

(3) Sub 1-3c synthesis

Sub 1-3b (41.84g, 77.6mmol), N-phenyl-[1,1'-biphenyl]-4-amine (17.13g, 69.8mmol), and Pd ₂ (dba) ₃ (2.13g, 2.3) obtained above. mmol), P(t-Bu) ₃ (2.3ml), and NaOt-Bu (22.37g, 232.8mmol) were placed in a round bottom flask, dissolved in toluene (700mL), and refluxed at 80°C for 6 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (40.25 g, 79%).

(4) Sub 1-3d synthesis

Sub 1-3c (40.25g, 61.3mmol), 2-chloroaniline (7.04g, 55.2mmol), Pd(OAc) ₂ (0.41g, 1.8mmol), and P(t-Bu) ₃ (1.8ml) obtained above. , NaOt-Bu (17.67g, 183.9mmol) was added to a round bottom flask, dissolved in toluene (600mL), and refluxed at 70°C for 3 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (30.18 g, 70%).

(5) Sub 1-3 synthesis

Sub 1-3c (30.18g, 42.9mmol), Pd(OAc) ₂ (0.48g, 2.1mmol), P(t-Bu) ₃ ·HBF ₄ (1.25g, 4.3mmol), K ₂ CO ₃ obtained above. (17.79g, 128.7mmol) was dissolved in DMA (N,N-Dimethylacetamide) (200mL) and refluxed at 150 ^o C for 24 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (22.61 g, 79%).

3. Sub1-15 synthesis example

(1) Sub 1-15a synthesis

6,12-dibromochrysene (35g, 90.7mmol), 3-iodonaphthalene-2-thiol (28.53g, 99.7mmol), CuI (4.15g, 4.5mmol), L-proline (1.83g, 9.1mmol), K ₃ PO ₄ (21.78g, 226.6mmol) was dissolved in EtOH/Water (2:3) (1L) and refluxed at 80°C for 6 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the desired product (47.17 g, 88%).

(2) Sub 1-15b synthesis

Sub 1-15a (47.17g, 79.8mmol), Pd ₂ (dba) ₃ (3.91g, 16.0mmol), Cu(OAc) ₂ (14.61g, 16.0mmol), PivONa·H ₂ O (16.14g) obtained above. , 79.8mmol) was placed in a round bottom flask, dissolved in DMF (N,N-Dimethylformamide) (500mL), and refluxed at 150°C for 5 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ 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 the desired product (27.72 g, 75%).

(3) Sub 1-15c synthesis

Sub 1-15b (27.72g, 59.8mmol), 2-chloroaniline (6.87g, 53.8mmol), Pd(OAc) ₂ (0.4g, 1.8mmol), and P(t-Bu) ₃ (1.7ml) obtained above. , NaOt-Bu (17.25g, 179.5mmol) was added to a round bottom flask, dissolved in toluene (800mL), and refluxed at 70°C for 3 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized on a silicagel column to obtain the desired product (23.8 g, 78%).

(4) Sub 1-15 synthesis

Sub 1-15c (23.8g, 46.7mmol), Pd(OAc) ₂ (0.52g, 2.3mmol), P(t-Bu) ₃ ·HBF ₄ (1.35g, 4.7mmol), K ₂ CO ₃ obtained above. (19.35g, 140.0mmol) was dissolved in DMA (N,N-Dimethylacetamide) (250mL) and refluxed at 150 ^o C for 24 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (16.57 g, 75%).

4. Sub1-19 synthesis example

(1) Sub 1-19a synthesis

6,12-dibromochrysene (60g, 155.4mmol), 2-iodophenol (37.61g, 170.9mmol), and KOtBu (52.31g, 466.2mmol) were dissolved in DMSO (1.6L) solvent and refluxed at 50°C for 8 hours. . When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and washed with water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the desired product (48.97 g, 60%).

(2) Sub 1-19b synthesis

Sub 1-19a (48.97g, 93.2mmol), Pd/C (10 wt%) (2.98g, 28.0mmol), and NaOAc (22.95g, 279.7mmol) obtained above were added to a round bottom flask and then added to DMF (N, N-Dimethylformamide (600mL) was added and dissolved, and then refluxed at 140°C for 16 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ 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 the desired product (31.49 g, 85%).

(3) Sub 1-19c synthesis

Sub 1-19b (31.49g, 79.3mmol), 2-chloroaniline (9.1g, 71.3mmol), Pd(OAc) ₂ (0.53g, 2.4mmol), and P(t-Bu) ₃ (2.3ml) obtained above. , NaOt-Bu (22.85g, 237.8mmol) was added to a round bottom flask, dissolved in toluene (750mL), and refluxed at 70°C for 3 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (27.1 g, 77%).

(4) Sub 1-19 synthesis

Sub 1-19c (35.19g, 79.3mmol), Pd(OAc) ₂ (0.89g, 4.0mmol), P(t-Bu) ₃ ·HBF ₄ (2.3g, 7.9mmol), K ₂ CO ₃ obtained above. (32.87g, 237.8mmol) was dissolved in DMA (N,N-Dimethylacetamide) (400mL) and refluxed at 150 ^o C for 24 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation, and the concentrated product was recrystallized using a silicagel column to obtain the desired product (23.58 g, 73%).

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

compound FD-MS compound FD-MS Sub 1-1 m/z=423.11 (C ₃₀ H ₁₇ NS=423.53) Sub 1-2 m/z=590.18 (C ₄₂ H ₂₆ N ₂ S=590.74) Sub 1-3 m/z=666.21 (C ₄₈ H ₃₀ N ₂ S=666.84) Sub 1-4 m/z=690.21 (C ₅₀ H ₃₀ N ₂ S=690.86) Sub 1-5 m/z=706.24 (C ₅₁ H ₃₄ N ₂ S=706.91) Sub 1-6 m/z=742.24 (C ₅₄ H ₃₄ N ₂ S=742.94) Sub 1-7 m/z=906.31 (C ₆₇ H ₄₂ N ₂ S=907.15) Sub 1-8 m/z=904.29 (C ₆₇ H ₄₀ N ₂ S=905.13) Sub 1-9 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) Sub 1-10 m/z=704.20 (C ₄₉ H ₂₈ N ₄ S=704.85) Sub 1-11 m/z=627.18 (C ₄₄ H ₂₅ N ₃ S=627.77) Sub 1-12 m/z=683.15 (C ₄₆ H ₂₅ N ₃ S ₂ =683.85) Sub 1-13 m/z=611.20 (C ₄₄ H ₂₅ N ₃ O=611.70) Sub 1-14 m/z=661.22 (C ₄₈ H ₂₇ N ₃ O=661.76) Sub 1-15 m/z=473.12 (C ₃₄ H ₁₉ NS=473.59) Sub 1-16 m/z=473.12 (C ₃₄ H ₁₉ NS=473.59) Sub 1-17 m/z=457.15 (C ₃₄ H ₁₉ NO=457.53) Sub 1-18 m/z=521.07 (C ₃₄ H ₁₉ NSe=520.49) Sub 1-19 m/z=407.13 (C ₃₀ H ₁₇ NO=407.47) Sub 1-20 m/z=574.20 (C ₄₂ H ₂₆ N ₂ O=574.68) Sub 1-21 m/z=664.22 (C ₄₈ H ₂₈ N ₂ O ₂ =664.76) Sub 1-22 m/z=471.05 (C ₃₀ H ₁₇ NSe=470.43) Sub 1-23 m/z=463.14 (C ₃₃ H ₂₁ NS=463.60)

Ⅱ. Synthesis example of Sub 2

Sub 2 of Scheme 1 can be synthesized through the reaction route of Scheme 3 below, but the method of synthesizing Sub 2 is not limited thereto.

In Scheme 3 below, Hal ¹ is I, Br or Cl, Hal ² is Br or Cl, and L is the same as previously described in the section regarding Chemical Formula (1).

In this specification, THF is Tetrahydrofuran.

1. Sub 2-52 Synthesis Example

(1) Sub 2-52a synthesis

The starting material, 1-amino-2-naphthoic acid (CAS Registry Number: 4919-43-1) (75.11 g, 401.25 mmol), was added to a round bottom flask with urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol) and stirred at 160°C. After confirming the reaction by TLC, the mixture was cooled to 100°C, water (200ml) was added, and stirred for 1 hour. When the reaction was completed, the resulting solid was filtered under reduced pressure, washed with water, and dried to obtain 63.86 g of product (yield: 75%).

(2) Sub 2-52b synthesis

Sub 2-52a (63.86 g, 300.94 mmol) obtained in the above synthesis was dissolved in POCl ₃ (200ml) in a round bottom flask at room temperature, then N , N -Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise, and then dissolved in POCl 3 (200ml) at room temperature. Stirred at °C. When the reaction was completed, it was concentrated, then ice water (500ml) was added and stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 67.47 g of product (yield: 90%).

(3) Sub 2-52 synthesis

Sub 2-52b (67.47 g, 270.86 mmol) obtained in the above synthesis was added to a round bottom flask with THF (950ml).

After dissolving, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (CAS Registry Number: 24388-23-6) (60.80 g, 297.94 mmol), Pd(PPh ₃ ) ₄ ( 12.52 g, 10.83 mmol), K ₂ CO ₃ (112.30 g, 812.57 mmol), and water (475 ml) were added and stirred at 90°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 44.89 g of product (yield: 57%).

2. Sub 2-53 Synthesis Example

Sub 2-53b (19g, 76.28mmol), the starting material, was added to 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS Registry) Number: 947770-80-1) (22.44g, 76.28mmol), Pd(PPh ₃ ) ₄ (1.32g, 1.14mmol), K ₂ CO ₃ (15.81g, 114.42mmol), THF (336ml), water (168ml) ) was added and 15.69 g of product (yield: 54%) was obtained using the Sub 2-35 synthesis method.

3. Sub 2-56 synthesis example

4,4,5,5-tetramethyl was added to the starting material, 2,4-dichlorobenzo[4,5]thieno[3,2- d ]pyrimidine (CAS Registry Number: 160199-05-3) (32.01 g, 125.47 mmol). -2-(naphthalen-1-yl)-1,3,2-dioxaborolane (CAS Registry Number: 68716-52-9) (35.07 g, 138.02 mmol), Pd(PPh ₃ ) ₄ (5.80 g, 5.02 mmol) , K ₂ CO ₃ (52.02 g, 376.41 mmol), THF (440ml), and water (220ml) were added and 19.58 g of product (yield: 45%) was obtained using the Sub 2-35 synthesis method.

Compounds belonging to Sub 2 that can produce the compound represented by Chemical Formula (1) by Sub 1 and Reaction Scheme 1 may be the following compounds, but are not limited thereto.

Those skilled in the art will be able to synthesize the Sub 2 compound by referring to the above-described synthesis examples of Sub 2-52, Sub 2-53, and Sub 2-56 and Scheme 3.

Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 2.

compound FD-MS compound FD-MS Sub 2-1 m/z=311.01 (C ₁₅ H ₁₀ BrN ₃ =312.17) Sub 2-2 m/z=361.02(C ₁₉ H ₁₂ BrN ₃ =362.23) Sub 2-3 m/z=361.02 (C ₁₉ H ₁₂ BrN ₃ =362.23) Sub 2-4 m/z=411.04(C ₂₃ H ₁₄ BrN ₃ =412.29) Sub 2-5 m/z=411.04 (C ₂₃ H ₁₄ BrN ₃ =412.29) Sub 2-6 m/z=411.04(C ₂₃ H ₁₄ BrN ₃ =412.29) Sub 2-7 m/z=387.04 (C ₂₁ H ₁₄ BrN ₃ =388.27) Sub 2-8 m/z=463.07 (C ₂₇ H ₁₈ BrN ₃ =464.37) Sub 2-9 m/z=387.04 (C ₂₁ H ₁₄ BrN ₃ =388.27) Sub 2-10 m/z=387.04 (C ₂₁ H ₁₄ BrN ₃ =388.27) Sub 2-11 m/z=312.00 (C ₁₄ H ₉ BrN ₄ =313.16) Sub 2-12 m/z=388.03 (C ₂₀ H ₁₃ BrN ₄ =389.26) Sub 2-13 m/z=438.05 (C ₂₄ H ₁₅ BrN ₄ =439.32) Sub 2-14 m/z=313.00 (C ₁₃ H ₈ BrN ₅ =314.15) Sub 2-15 m/z=313.00 (C ₁₃ H ₈ BrN ₅ =314.15) Sub 2-16 m/z=310.01 (C ₁₆ H ₁₁ BrN ₂ =311.18) Sub 2-17 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-18 m/z=410.04 (C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 2-19 m/z=410.04 (C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 2-20 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-21 m/z=410.04 (C ₂₄ H ₁₅ BrN ₂ =411.30) Sub 2-22 m/z=386.04 (C ₂₂ H ₁₅ BrN ₂ =387.28) Sub 2-23 m/z=462.07 (C ₂₈ H ₁₉ BrN ₂ =463.38) Sub 2-24 m/z=386.04 (C ₂₂ H ₁₅ BrN ₂ =387.28) Sub 2-25 m/z=386.04 (C ₂₂ H ₁₅ BrN ₂ =387.28) Sub 2-26 m/z=311.01 (C ₁₅ H ₁₀ BrN ₃ =312.17) Sub 2-27 m/z=311.01 (C ₁₅ H ₁₀ BrN ₃ =312.17) Sub 2-28 m/z=311.01 (C ₁₅ H ₁₀ BrN ₃ =312.17) Sub 2-29 m/z=312.00 (C ₁₄ H ₉ BrN ₄ =313.16) Sub 2-30 m/z=312.00 (C ₁₄ H ₉ BrN ₄ =313.16) Sub 2-31 m/z=283.99 (C ₁₄ H ₉ BrN ₂ =285.14) Sub 2-32 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-33 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-34 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-35 m/z=334.01 (C ₁₈ H ₁₁ BrN ₂ =335.20) Sub 2-36 m/z=334.01 (C ₁₈ H ₁₁ BrN ₂ =335.20) Sub 2-37 m/z=375.04 (C ₂₀ H ₁₄ BrN ₃ =376.26) Sub 2-38 m/z=449.05 (C ₂₆ H ₁₆ BrN ₃ =450.34) Sub 2-39 m/z=389.98 (C ₂₀ H ₁₁ BrN ₂ S=391.29) Sub 2-40 m/z=374.01 (C ₂₀ H ₁₁ BrN ₂ O=375.23) Sub 2-41 m/z=340.06 (C ₁₈ H ₁₇ BrN ₂ =341.25) Sub 2-42 m/z=289.03 (C ₁₄ H ₄ D ₅ BrN ₂ =290.17) Sub 2-43 m/z=384.03 (C ₂₂ H ₁₃ BrN ₂ =385.26) Sub 2-44 m/z=387.04 (C ₂₁ H ₁₄ BrN ₃ =388.27) Sub 2-45 m/z=348.03 (C ₁₉ H ₁₃ BrN ₂ =349.23) Sub 2-46 m/z=334.01 (C ₁₈ H ₁₁ BrN ₂ =335.20) Sub 2-47 m/z=450.07 (C ₂₇ H ₁₉ BrN ₂ =451.37) Sub 2-48 m/z=384.03 (C ₂₂ H ₁₃ BrN ₂ =385.26) Sub 2-49 m/z=415.07 (C ₂₄ H ₁₀ D ₅ BrN ₂ =416.33) Sub 2-50 m/z=440.00 (C ₂₄ H ₁₃ BrN ₂ S=441.35) Sub 2-51 m/z=384.03 (C ₂₂ H ₁₃ BrN ₂ =385.26) Sub 2-52 m/z=290.06 (C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 2-53 m/z=380.07 (C ₂₄ H ₁₃ ClN ₂ O=380.83) Sub 2-54 m/z=157.95 (C ₄ H ₃ BrN ₂ =158.99) Sub 2-55 m/z=339.97 (C ₁₆ H ₉ BrN ₂ S=341.23) Sub 2-56 m/z=346.03 (C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 2-57 m/z=416.00 (C ₂₂ H ₁₃ BrN ₂ S=417.32) Sub 2-58 m/z=476.05 (C ₂₈ H ₁₇ BrN ₂ O=477.36) Sub 2-59 m/z=402.04 (C ₂₂ H ₁₅ BrN ₂ O=403.28) Sub 2-60 m/z=323.99 (C ₁₆ H ₉ BrN ₂ O=325.17) Sub 2-61 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-62 m/z=460.06 (C ₂₈ H ₁₇ BrN ₂ =461.36) Sub 2-63 m/z=416.00 (C ₂₂ H ₁₃ BrN ₂ S=417.32) Sub 2-64 m/z=516.03 (C ₃₀ H ₁₇ BrN ₂ S=517.44) Sub 2-65 m/z=283.99 (C ₁₄ H ₉ BrN ₂ =285.14) Sub 2-66 m/z=298.01 (C ₁₅ H ₁₁ BrN ₂ =299.17) Sub 2-67 m/z=360.03 (C ₂₀ H ₁₃ BrN ₂ =361.24) Sub 2-68 m/z=375.00 (C ₁₉ H ₁₀ BrN ₃ O=376.21) Sub 2-69 m/z=389.98 (C ₂₀ H ₁₁ BrN ₂ S=391.29) Sub 2-70 m/z=384.03 (C ₂₂ H ₁₃ BrN ₂ =385.26) Sub 2-71 m/z=339.97 (C ₁₆ H ₉ BrN ₂ S=341.23) Sub 2-72 m/z=323.99 (C ₁₆ H ₉ BrN ₂ O=325.17) Sub 2-73 m/z=416.00 (C ₂₂ H ₁₃ BrN ₂ S=417.32) Sub 2-74 m/z=461.08 (C ₂₉ H ₂₀ BrN=462.39) Sub 2-75 m/z=409.05 (C ₂₅ H ₁₆ BrN=410.31) Sub 2-76 m/z=359.03 (C ₂₁ H ₁₄ BrN=360.25) Sub 2-77 m/z=359.03 (C ₂₁ H ₁₄ BrN=360.25) Sub 2-78 m/z=409.05 (C ₂₅ H ₁₆ BrN=410.31) Sub 2-79 m/z=409.05 (C ₂₅ H ₁₆ BrN=410.31) Sub 2-80 m/z=385.05 (C ₂₃ H ₁₆ BrN=386.29) Sub 2-81 m/z=156.95 (C ₅ H ₄ BrN=158.00) Sub 2-82 m/z=309.02 (C ₁₇ H ₁₂ BrN=310.19) Sub 2-83 m/z=385.05 (C ₂₃ H ₁₆ BrN=386.29) Sub 2-84 m/z=385.05 (C ₂₃ H ₁₆ BrN=386.29) Sub 2-85 m/z=310.01 (C ₁₆ H ₁₁ BrN ₂ =311.18) Sub 2-86 m/z=310.01 (C ₁₆ H ₁₁ BrN ₂ =311.18) Sub 2-87 m/z=310.01 (C ₁₆ H ₁₁ BrN ₂ =311.18) Sub 2-88 m/z=311.01 (C ₁₅ H ₁₀ BrN ₃ =312.17) Sub 2-89 m/z=311.01 (C ₁₅ H ₁₀ BrN ₃ =312.17) Sub 2-90 m/z=155.96 (C ₆ H ₅ Br=157.01) Sub 2-91 m/z=323.03 (C ₁₈ H ₁₄ BrN=324.22) Sub 2-92 m/z=205.97 (C ₁₀ H ₇ Br=207.07) Sub 2-93 m/z=205.97 (C ₁₀ H ₇ Br=207.07) Sub 2-94 m/z=231.99 (C ₁₂ H ₉ Br=233.11) Sub 2-95 m/z=255.99 (C ₁₄ H ₉ Br=257.13) Sub 2-96 m/z=231.99 (C ₁₂ H ₉ Br=233.11) Sub 2-97 m/z=308.02 (C ₁₈ H ₁₃ Br=309.21) Sub 2-98 m/z=306.00 (C ₁₈ H ₁₁ Br=307.19) Sub 2-99 m/z=272.02 (C ₁₅ H ₁₃ Br=273.17) Sub 2-100 m/z=321.02 (C ₁₈ H ₁₂ BrN=322.21) Sub 2-101 m/z=261.95 (C ₁₂ H ₇ BrS=263.15) Sub 2-102 m/z=245.97 (C ₁₂ H ₇ BrO=247.09) Sub 2-103 m/z=271.00 (C ₁₄ H ₁₀ BrN=272.15) Sub 2-104 m/z=337.00 (C ₁₅ H ₈ BrN ₅ =338.17) Sub 2-105 m/z=323.99 (C ₁₆ H ₉ BrN ₂ O=325.17) Sub 2-106 m/z=401.02 (C ₂₁ H ₁₂ BrN ₃ O=402.25) Sub 2-107 m/z=323.99 (C ₁₆ H ₉ BrN ₂ O=325.17) Sub 2-108 m/z=463.07 (C ₂₇ H ₁₈ BrN ₃ =464.37) Sub 2-109 m/z=358.04 (C ₂₂ H ₁₅ Br=359.27) Sub 2-110 m/z=272.02 (C ₁₅ H ₁₃ Br=273.17) Sub 2-111 m/z=308.99 (C ₁₅ H ₈ BrN ₃ =310.15) Sub 2-112 m/z=416.99 (C ₂₁ H ₁₂ BrN ₃ S=418.31) Sub 2-113 m/z=258.00 (C ₁₄ H ₁₁ Br=259.15) Sub 2-114 m/z=339.03 (C ₁₈ H ₁₄ BrNO=340.22) Sub 2-115 m/z=352.00 (C ₁₈ H ₁₀ BrFN ₂ =353.19) Sub 2-116 m/z=367.07 (C ₁₉ H ₁₈ BrN ₃ =368.28) Sub 2-117 m/z=416.99 (C ₂₁ H ₁₂ BrN ₃ S=418.31)

Ⅲ. Final product synthesis example

After dissolving Sub 1 (1 equivalent) in toluene in a round bottom flask, Sub 2 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P( t -Bu) ₃ (0.1 equivalent), NaO t -Bu (3 equivalents) was added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain the final product.

1. 1-55 Synthesis example

Place Sub 1-1 (10g, 23.6mmol) in a round bottom flask, dissolve in toluene (250 mL), and then add Sub 2-55 (8.86g, 26.0mmol), Pd ₂ (dba) ₃ (0.65g, 0.7mmol) ), P( t -Bu) ₃ (1.2ml), NaO t -Bu (6.81g, 70.8mmol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 10.66 g of product (yield: 66%).

2. 1-121 Synthesis example

Sub 1-15 (8.0g, 16.9mmol) was placed in a round bottom flask, dissolved in toluene (180 mL), then Sub 2-1 (5.80g, 18.6mmol), Pd ₂ (dba) ₃ (0.46g, 0.5 mmol), P( t -Bu) ₃ (0.8ml), and NaO t -Bu (4.87g, 50.7mmol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 8.45 g of product (yield: 71%).

3. 1-123 Synthesis example

Sub 1-17 (7.7g, 16.8mmol) was placed in a round bottom flask, dissolved in toluene (180 mL), then Sub 2-20 (5.28g, 18.5mmol), Pd ₂ (dba) ₃ (0.46g, 0.5 mmol), P( t -Bu) ₃ (0.8ml), and NaO t -Bu (4.85g, 50.5mmol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 7.13 g of product (yield: 64%).

4. 1-131 Synthesis example

Sub 1-19 (8.3g, 20.4mmol) was placed in a round bottom flask and dissolved in toluene (210 mL), then Sub 2-65 (6.39g, 22.4mmol), Pd ₂ (dba) ₃ (0.56g, 0.6 mmol), P( t -Bu) ₃ (1.0ml), and NaO t -Bu (5.87g, 61.1mmol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 9.22 g of product (yield: 74%).

5. 1-137 Synthesis example

Sub 1-20 (9.1g, 15.8mmol) was placed in a round bottom flask, dissolved in toluene (170 mL), then Sub 2-90 (2.73g, 17.4mmol), Pd ₂ (dba) ₃ (0.44g, 0.5 mmol), P( t -Bu) ₃ (0.8ml), and NaO t -Bu (4.57g, 47.5mmol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 8.35 g of product (yield: 81%).

6. 1-139 Synthesis example

Sub 1-22 (5.7g, 12.1mmol) was placed in a round bottom flask, dissolved in toluene (130 mL), then Sub 2-1 (4.16g, 13.3mmol), Pd ₂ (dba) ₃ (0.33g, 0.4 mmol), P( t -Bu) ₃ (0.6ml), and NaO t -Bu (3.49g, 36.3mmol) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 5.36 g of product (yield: 63%).

1-1 to 1-54, 1-56 to 1-120, 1-122, 1-124 to 1-130, 1-132 to 1-136, 1-138 and 1-140 to 1-150 also in the table below It can be synthesized using a method similar to the above synthesis method using the Sub 1 and Sub 2 compounds described in 3. The compounds described in the product column can be synthesized by reacting each compound described in the Sub 1 column of Table 3 below with the compound described in the Sub 2 column, but the synthesis method is not limited thereto.

The above synthesis examples are for exemplary compounds of some of the compounds represented by formula (1), and the reactions include 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. Those skilled in the art will _easily understand that the above reaction proceeds even if other substituents _{( such} as .

Meanwhile, the FD-MS values of compounds 1-1 to 1-150 of the present invention prepared according to the above synthesis example are shown in Table 4 below.

compound FD-MS compound FD-MS 1-1 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-2 m/z=704.20 (C ₄₉ H ₂₈ N ₄ S=704.85) 1-3 m/z=704.20 (C ₄₉ H ₂₈ N ₄ S=704.85) 1-4 m/z=754.22 (C ₅₃ H ₃₀ N ₄ S=754.91) 1-5 m/z=754.22 (C ₅₃ H ₃₀ N ₄ S=754.91) 1-6 m/z=754.22 (C ₅₃ H ₃₀ N ₄ S=754.91) 1-7 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-8 m/z=806.25 (C ₅₇ H ₃₄ N ₄ S=806.99) 1-9 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-10 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-11 m/z=655.18 (C ₄₄ H ₂₅ N ₅ S=655.78) 1-12 m/z=731.21 (C ₅₀ H ₂₉ N ₅ S=731.88) 1-13 m/z=781.23 (C ₅₄ H ₃₁ N ₅ S=781.94) 1-14 m/z=656.18 (C ₄₃ H ₂₄ N ₆ S=656.77) 1-15 m/z=656.18 (C ₄₃ H ₂₄ N ₆ S=656.77) 1-16 m/z=653.19 (C ₄₆ H ₂₇ N ₃ S=653.80) 1-17 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-18 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-19 m/z=753.22 (C ₅₄ H ₃₁ N ₃ S=753.92) 1-20 m/z=753.22 (C ₅₄ H ₃₁ N ₃ S=753.92) 1-21 m/z=753.22 (C ₅₄ H ₃₁ N ₃ S=753.92) 1-22 m/z=729.22 (C ₅₂ H ₃₁ N ₃ S=729.90) 1-23 m/z=805.26 (C ₅₈ H ₃₅ N ₃ S=806.00) 1-24 m/z=729.22 (C ₅₂ H ₃₁ N ₃ S=729.90) 1-25 m/z=729.22 (C ₅₂ H ₃₁ N ₃ S=729.90) 1-26 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-27 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-28 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-29 m/z=655.18 (C ₄₄ H ₂₅ N ₅ S=655.78) 1-30 m/z=655.18 (C ₄₄ H ₂₅ N ₅ S=655.78) 1-31 m/z=627.18 (C ₄₄ H ₂₅ N ₃ S=627.77) 1-32 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-33 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-34 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-35 m/z=677.19 (C ₄₈ H ₂₇ N ₃ S=677.83) 1-36 m/z=677.19 (C ₄₈ H ₂₇ N ₃ S=677.83) 1-37 m/z=718.22 (C ₅₀ H ₃₀ N ₄ S=718.88) 1-38 m/z=792.23 (C ₅₆ H ₃₂ N ₄ S=792.96) 1-39 m/z=733.16 (C ₅₀ H ₂₇ N ₃ S ₂ =733.91) 1-40 m/z=717.19 (C ₅₀ H ₂₇ N ₃ OS=717.85) 1-41 m/z=683.24 (C ₄₈ H ₃₃ N ₃ S=683.87) 1-42 m/z=632.21 (C ₄₄ H ₂₀ D ₅ N ₃ S=632.80) 1-43 m/z=727.21 (C ₅₂ H ₂₉ N ₃ S=727.89) 1-44 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-45 m/z=691.21 (C ₄₉ H ₂₉ N ₃ S=691.85) 1-46 m/z=677.19 (C ₄₈ H ₂₇ N ₃ S=677.83) 1-47 m/z=793.26 (C ₅₇ H ₃₅ N ₃ S=793.99) 1-48 m/z=727.21 (C ₅₂ H ₂₉ N ₃ S=727.89) 1-49 m/z=758.26 (C ₅₄ H ₂₆ D ₅ N ₃ S=758.95) 1-50 m/z=783.18 (C ₅₄ H ₂₉ N ₃ S ₂ =783.97) 1-51 m/z=727.21 (C ₅₂ H ₂₉ N ₃ S=727.89) 1-52 m/z=677.19 (C ₄₈ H ₂₇ N ₃ S=677.83) 1-53 m/z=767.20 (C ₅₄ H ₂₉ N ₃ OS=767.91) 1-54 m/z=501.13 (C ₃₄ H ₁₉ N ₃ S=501.61) 1-55 m/z=683.15 (C ₄₆ H ₂₅ N ₃ S ₂ =683.85) 1-56 m/z=733.16 (C ₅₀ H ₂₇ N ₃ S ₂ =733.91) 1-57 m/z=759.18 (C ₅₂ H ₂₉ N ₃ S ₂ =759.95) 1-58 m/z=819.23 (C ₅₈ H ₃₃ N ₃ OS=819.98) 1-59 m/z=745.22 (C ₅₂ H ₃₁ N ₃ OS=745.90) 1-60 m/z=667.17 (C ₄₆ H ₂₅ N ₃ OS=667.79) 1-61 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-62 m/z=803.24 (C ₅₈ H ₃₃ N ₃ S=803.98) 1-63 m/z=759.18 (C ₅₂ H ₂₉ N ₃ S ₂ =759.95) 1-64 m/z=859.21 (C ₆₀ H ₃₃ N ₃ S ₂ =860.07) 1-65 m/z=627.18 (C ₄₄ H ₂₅ N ₃ S=627.77) 1-66 m/z=641.19 (C ₄₅ H ₂₇ N ₃ S=641.79) 1-67 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-68 m/z=718.18 (C ₄₉ H ₂₆ N ₄ OS=718.83) 1-69 m/z=733.16 (C ₅₀ H ₂₇ N ₃ S ₂ =733.91) 1-70 m/z=727.21 (C ₅₂ H ₂₉ N ₃ S=727.89) 1-71 m/z=683.15 (C ₄₆ H ₂₅ N ₃ S ₂ =683.85) 1-72 m/z=667.17 (C ₄₆ H ₂₅ N ₃ OS=667.79) 1-73 m/z=759.18 (C ₅₂ H ₂₉ N ₃ S ₂ =759.95) 1-74 m/z=500.13 (C ₃₅ H ₂₀ N ₂ S=500.62) 1-75 m/z=652.20 (C ₄₇ H ₂₈ N ₂ S=652.82) 1-76 m/z=702.21 (C ₅₁ H ₃₀ N ₂ S=702.88) 1-77 m/z=702.21 (C ₅₁ H ₃₀ N ₂ S=702.88) 1-78 m/z=752.23 (C ₅₅ H ₃₂ N ₂ S=752.94) 1-79 m/z=752.23 (C ₅₅ H ₃₂ N ₂ S=752.94) 1-80 m/z=752.23 (C ₅₅ H ₃₂ N ₂ S=752.94) 1-81 m/z=728.23 (C ₅₃ H ₃₂ N ₂ S=728.91) 1-82 m/z=804.26 (C ₅₉ H ₃₆ N ₂ S=805.01) 1-83 m/z=728.23 (C ₅₃ H ₃₂ N ₂ S=728.91) 1-84 m/z=728.23 (C ₅₃ H ₃₂ N ₂ S=728.91) 1-85 m/z=653.19 (C ₄₆ H ₂₇ N ₃ S=653.80) 1-86 m/z=653.19 (C ₄₆ H ₂₇ N ₃ S=653.80) 1-87 m/z=653.19 (C ₄₆ H ₂₇ N ₃ S=653.80) 1-88 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-89 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) 1-90 m/z=499.14 (C ₃₆ H ₂₁ NS=499.63) 1-91 m/z=666.21 (C ₄₈ H ₃₀ N ₂ S=666.84) 1-92 m/z=549.16 (C ₄₀ H ₂₃ NS=549.69) 1-93 m/z=549.16 (C ₄₀ H ₂₃ NS=549.69) 1-94 m/z=575.17 (C ₄₂ H ₂₅ NS=575.73) 1-95 m/z=575.17 (C ₄₂ H ₂₅ NS=575.73) 1-96 m/z=651.20 (C ₄₈ H ₂₉ NS=651.83) 1-97 m/z=599.17 (C ₄₄ H ₂₅ NS=599.75) 1-98 m/z=649.19 C ₄₈ H ₂₇ NS=649.81) 1-99 m/z=615.20 (C ₄₅ H ₂₉ NS=615.79) 1-100 m/z=664.20 (C ₄₈ H ₂₈ N ₂ S=664.83) 1-101 m/z=605.13 (C ₄₂ H ₂₃ NS ₂ =605.77) 1-102 m/z=589.15 (C ₄₂ H ₂₃ NOS=589.71) 1-103 m/z=614.18 (C ₄₄ H ₂₆ N ₂ S=614.77) 1-104 m/z=666.21 (C ₄₈ H ₃₀ N ₂ S=666.84) 1-105 m/z=742.24 (C ₅₄ H ₃₄ N ₂ S=742.94) 1-106 m/z=766.24 (C ₅₆ H ₃₄ N ₂ S=766.96) 1-107 m/z=782.28 (C ₅₇ H ₃₈ N ₂ S=783.28) 1-108 m/z=818.28 (C ₆₀ H ₃₈ N ₂ S=819.04) 1-109 m/z=982.34 (C ₇₃ H ₄₆ N ₂ S=983.25) 1-110 m/z=980.32 (C ₇₃ H ₄₄ N ₂ S=981.23) 1-111 m/z=680.18 (C ₄₅ H ₂₄ N ₆ S=680.79) 1-112 m/z=667.17 (C ₄₆ H ₂₅ N ₃ OS=667.79) 1-113 m/z=760.18 (C ₅₁ H ₂₈ N ₄ S ₂ =760.93) 1-114 m/z=744.20 (C ₅₁ H ₂₈ N ₄ OS=744.87) 1-115 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) 1-116 m/z=780.23 (C ₅₅ H ₃₂ N ₄ S=780.95) 1-117 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-118 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) 1-119 m/z=687.23 (C ₅₀ H ₂₉ N ₃ O=687.80) 1-120 m/z=737.25 (C ₅₄ H ₃₁ N ₃ O=737.86) 1-121 m/z=704.20 (C ₄₉ H ₂₈ N ₄ S=704.85) 1-122 m/z=754.22 (C ₅₃ H ₃₀ N ₄ S=754.91) 1-123 m/z=661.22 (C ₄₈ H ₂₇ N ₃ O=661.76) 1-124 m/z=781.11 (C ₅₀ H ₂₇ N ₃ SSe=780.81) 1-125 m/z=638.21 (C ₄₅ H ₂₆ N ₄ O=638.73) 1-126 m/z=688.23 (C ₄₉ H ₂₈ N ₄ O=688.79) 1-127 m/z=611.20 (C ₄₄ H ₂₅ N ₃ O=611.70) 1-128 m/z=661.22 (C ₄₈ H ₂₇ N ₃ O=661.76) 1-129 m/z=667.17 (C ₄₆ H ₂₅ N ₃ OS=667.79) 1-130 m/z=651.19 (C ₄₆ H ₂₅ N ₃ O ₂ =651.73) 1-131 m/z=611.20 (C ₄₄ H ₂₅ N ₃ O=611.70) 1-132 m/z=744.20 (C ₅₁ H ₂₈ N ₄ OS=744.87) 1-133 m/z=790.27 (C ₅₇ H ₃₄ N ₄ O=790.93) 1-134 m/z=661.22(C ₄₈ H ₂₇ N ₃ O=661.76) 1-134 m/z=685.24 (C ₅₂ H ₃₁ NO=685.83) 1-136 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) 1-137 m/z=650.24 (C ₄₈ H ₃₀ N ₂ O=650.78) 1-138 m/z=740.25 (C ₅₄ H ₃₂ N ₂ O ₂ =740.86) 1-139 m/z=702.13 (C ₄₅ H ₂₆ N ₄ Se=701.69) 1-140 m/z=752.15 (C ₄₉ H ₂₈ N ₄ Se=751.75) 1-141 m/z=675.12 (C ₄₄ H ₂₅ N ₃ Se=674.67) 1-142 m/z=725.14 (C ₄₈ H ₂₇ N ₃ Se=724.73) 1-143 m/z=731.09 (C ₄₆ H ₂₅ N ₃ SSe=730.75) 1-144 m/z=675.12 (C ₄₄ H ₂₅ N ₃ Se=674.67) 1-145 m/z=792.14 (C ₅₁ H ₂₈ N ₄ OSe=791.77) 1-146 m/z=700.12 (C ₄₅ H ₂₄ N ₄ Se=699.68) 1-147 m/z=601.19 (C ₄₄ H ₂₇ NS=601.77) 1-148 m/z=666.23 (C ₄₈ H ₃₀ N ₂ O ₂ =666.78) 1-149 m/z=695.18 (C ₄₈ H ₂₆ FN ₃ S=695.82) 1-150 m/z=750.28 (C ₅₂ H ₃₈ N ₄ S=750.96)

Manufacturing evaluation of organic electric devices

[Example 1] Fabrication and testing of red organic light-emitting device (phosphorescent host)

2-TNATA (N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)) on the ITO (indium tin oxide) layer (anode) formed on the glass substrate After forming a 60 nm thick hole injection layer by vacuum depositing an amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine) film, NPD (N,N′-Di(1-naphthyl)) was applied on the hole injection layer. -N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Thereafter, Compound 1-1 of the present invention was placed on the top of the hole transport layer as a host material, and [bis-(1-phenylisoquinolyl) iridium(Ⅲ)acetylacetonate] (hereinafter abbreviated as “(piq) ₂ Ir(acac)”) as a dopant. The light-emitting layer was deposited to a thickness of 30 nm by doping the material at a weight ratio of 95:5.

Next, BAlq was vacuum deposited to a thickness of 10 nm on the emitting layer to form a hole blocking layer, and Alq3 was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.

Afterwards, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[Example 2] to [Example 23] Red organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 5 below was used as the host material of the light emitting layer instead of Compound 1-1.

[Comparative Example 1] to [Comparative Example 3]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that Comparative Compounds 1 to 3 shown in Table 5 below were used instead of Compound 1-1 of the present invention as the host material of the light-emitting layer.

Electroluminescence (EL) characteristics were measured using PR-650 manufactured by Photoresearch by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured in Examples 1 to 23 and Comparative Examples 1 to 3 of the present invention. was measured, and the T95 lifespan was measured using McScience's lifespan measuring equipment at a standard luminance of 2500 cd/m ² , and the measurement results are shown in Table 5 below.

compound driving voltage
(V) electric current
(mA/cm2) Luminance
(cd/m2) efficiency
(cd/A) T95
(hr) CIE X Y Comparative example (1) Comparative compound 1 6.2 34.7 2500 7.2 69.1 0.66 0.32 Comparative example (2) Comparative compound 2 5.5 33.3 2500 7.5 78.4 0.66 0.34 Comparative example (3) Comparative compound 3 5.4 31.6 2500 7.9 79.1 0.66 0.34 Example (1) Compound 1-1 4.8 14.6 2500 17.1 140.3 0.66 0.33 Example (2) Compound 1-31 4.8 14.5 2500 17.3 141.5 0.66 0.34 Example (3) Compound 1-49 4.9 16.0 2500 15.6 135.4 0.66 0.33 Example (4) Compound 1-55 4.8 14.2 2500 17.6 142.7 0.66 0.34 Example (5) Compound 1-61 4.9 15.7 2500 15.9 138.1 0.66 0.33 Example (6) Compound 1-65 4.8 14.4 2500 17.4 142.2 0.66 0.34 Example (7) Compound 1-86 4.9 16.4 2500 15.2 133.0 0.66 0.34 Example (8) Compound 1-91 5.1 21.4 2500 11.7 118.8 0.66 0.34 Example (9) Compound 1-96 5.0 18.0 2500 13.9 126.4 0.66 0.33 Example (10) Compound 1-99 5.0 18.2 2500 13.7 124.9 0.66 0.33 Example (11) Compound 1-100 4.9 16.8 2500 14.9 131.6 0.66 0.34 Example (12) Compound 1-106 5.2 24.0 2500 10.4 112.2 0.66 0.33 Example (13) Compound 1-118 5.2 22.9 2500 10.9 114.3 0.66 0.34 Example (14) Compound 1-119 5.2 23.6 2500 10.6 115.8 0.66 0.34 Example (15) Compound 1-121 5.1 19.2 2500 13.0 122.1 0.66 0.34 Example (16) Compound 1-123 5.1 19.7 2500 12.7 123.8 0.66 0.33 Example (17) Compound 1-126 4.8 15.5 2500 16.1 143.4 0.66 0.33 Example (18) Compound 1-129 4.8 15.0 2500 16.7 145.8 0.66 0.34 Example (19) Compound 1-131 4.8 15.2 2500 16.4 144.9 0.66 0.34 Example (20) Compound 1-135 5.0 18.9 2500 13.2 128.7 0.66 0.34 Example (21) Compound 1-139 5.1 20.3 2500 12.3 120.5 0.66 0.34 Example (22) Compound 1-146 5.2 22.5 2500 11.1 117.0 0.66 0.33 Example (23) Compound 1-149 5.0 17.5 2500 14.3 129.8 0.66 0.34

As can be seen from the results in Table 5, the device using the compound according to an embodiment of the present invention as the phosphorescent host material of the light-emitting layer has significantly better electrical properties than the device using Comparative Compounds 1 to 3 as the phosphorescent host material of the light-emitting layer. You can see the improvement.

In more detail, CBP (4,4'-Bis(N-carbazolyl)-1,1'-biphenyl, which is generally used as a host material, has an 8-ring polycyclic structure rather than Comparative Compound 1, Comparative Compound 2 and Comparative Compound 3 When used as a host material, the device characteristics were excellent, and when the compound of the present invention, which has a similar skeleton or different hetero elements from Comparative Compounds 2 and 3, was used as a host material, the driving voltage, efficiency, and lifespan were higher than those of Comparative Examples 2 and 3. In this respect, it showed better results.

As can be seen from Table 6 below, this is because the compound of the present invention has a different heteroatom (O, S, Se) where at least one of the heteroatoms is not N, and the physical properties of the compound are significantly different. That is, when comparing the physical properties of Comparative Compound 2 and Comparative Compound 1-1 of the present invention, and Comparative Compound 3 and Compound 1-31 of the present invention, differences can be confirmed in the molecular weight and energy level of the compounds, especially the HOMO level and T1 level.

This means that, in the case of compounds with heteroatom heteroatoms, the packing structure of the molecules faces in the opposite direction compared to compounds with heteroatom heteroatoms. Accordingly, the arrangement order between molecules is made in a face-to-face form, and the steric effect of Ar ¹ of the asymmetrically arranged heteroatom N, which is the cause of this stacked structure, causes significantly higher carrier mobility and is believed to have high efficiency. It is believed that the lifespan is significantly increased because it has high oxidation stability.

In addition, the compound of the present invention has a lower molecular weight than Comparative Compound 2 and Comparative Compound 3 because it has heteroatoms. Accordingly, it can be seen that the thermal stability of the compound increases and the electrical properties of the device increase.

Table 6 below specifically compares the molecular weight and energy level of the compounds of the present invention and comparative compounds.

Comparative compound 2 Comparative compound 3 Compound 1-1 Compound 1-31 structure MW 713.84 686.82 704.85 627.77 HOMO (eV) -4.78 -4.63 -5.03 -4.87 LUMO (eV) -1.82 -1.98 -1.90 -2.06 Eg (eV) 2.96 2.65 3.13 2.81 T1 (eV) 2.24 2.11 2.00 2.16

In Table 6, only Compound 1-1 and Compound 1-31 were compared with the comparative compounds, but those skilled in the art can understand that the above description also applies to the remaining compounds that were used in the organic electric devices of the examples and achieved better effects than the comparative compounds. There will be.

The above description is merely an illustrative description of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. For example, in the examples of this specification, the compound of formula (1) was used as a host for the light-emitting layer, but depending on the application, it may be used as a hole injection layer, hole transport layer, light-emitting auxiliary layer, electron transport auxiliary layer, or electron transport layer of an organic electronic device. And it may also be used as a material for an electron injection layer. 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)

Compound represented by the following formula (1):

In the above formula (1),
X is O, S or Se,
Wherein L is a single bond, C ₆ ~ C ₆₀ aryl group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
Ar ₁ is a functional group other than hydrogen substituted on L, or a functional group bonded to N through L, which is a single bond, and Ar ¹ is each independently an aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and -L'-N(R _a )(R _b );
L' is a single bond; C ₆ ~ C ₆₀ arylene group; And C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of,
R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; 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 ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
where q is an integer of 1 to 2,
where m, n, o and p are independently integers from 0 to 4,
The R ₁ , R ₂ , R ₃ and R ₄ are the same or different from each other, and are each independently deuterium; and a C ₂ to C ₃₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P, and may be selected from the group consisting of a plurality of adjacent R ₁ groups, a plurality of adjacent R ₂ groups, A plurality of adjacent R ₃ and a plurality of adjacent R ₄ may be bonded to each other to form a saturated or unsaturated ring,
In Ar ₁ , R ₁ to R ₄ , R _a and R _b , the aryl group, heterocyclic group, fused ring group, and alkyl group are each hydrogen; Nitrile group; halogen group; amino 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; 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. According to clause 1,
Compounds characterized in that the compound represented by formula (1) is represented by the following formulas (2) to (4):


Chemical formula (2)

Chemical formula (3)

Chemical formula (4)
In the formulas (2) to (4), L, Ar ₁ , R ₁ to R ₄ and q are the same as defined in claim 1, and m to p are independently integers of 0 to 4,
In the formula (2), at least three of m, n, o and p are 0,
In the above formula (3), at least one of m and o is 0. According to clause 1,
The compound represented by the 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 or a mixture of two or more compounds of claim 1 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. An organic electric device characterized in that it is included as a mixture. According to clause 4,
The organic layer includes at least one of a hole transport layer and a light emitting layer,
An organic electronic device characterized in that the compound is included as a single compound of claim 1 or a mixture of two or more compounds of claim 1 in at least one layer of the hole transport layer and the light emitting layer. 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.