KR20220060358A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention relates to a compound for an organic electric element, the organic electric element using the same, and an electronic device including the organic electric element. According to the present invention, it is possible to provide the organic electric element having high luminous efficiency, low driving voltage, and high heat resistance, and it is possible to improve color purity and lifetime of the organic electric element.

Description

A compound for an organic electric device, an organic electric device using the same, and an electronic device thereof

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

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

Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these problems of efficiency and lifespan must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.

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

In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.

However, most of the materials used for the hole transport layer have a low T1 value because they should have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. ) and emit light at the hole transport layer interface. When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened.

In order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emitting auxiliary layers are formed according to each light emitting layer (R, G, B). is being developed

In order to fully exhibit the excellent characteristics of an organic electric device, the materials constituting the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc., are stable and efficient materials. It should be supported by this, and in particular, it is necessary to develop materials for the light emitting layer and the light emitting auxiliary layer.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifespan of the device, an organic electric device using the same, and an electronic device including the organic electric device.

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

<Formula 1>

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

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

1 to 3 schematically show an organic electric device according to embodiments of the present invention.
4 shows a chemical formula according to an aspect of the present invention.

Hereinafter, preferred embodiments of the present invention will be described with reference to the accompanying drawings.

In order to describe the present embodiments, it should be noted that, in adding reference numerals to components of each drawing, the same components are given the same reference numerals as much as possible even though they are indicated in different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted. In the drawings referenced below, no scale ratio applies.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms.

When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may also be “connected,” “coupled,” or “connected.”

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

Terms used in this specification and the appended claims are as follows, unless otherwise stated, without departing from the spirit of the present invention.

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

The term "alkyl" or "alkyl group" as used in this application, unless otherwise specified, has 1 to 60 carbons linked by a single bond, straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted means a radical 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 substituted with halogen unless otherwise specified.

The term "alkenyl" or "alkynyl" as used in this application, unless otherwise specified, has a double bond or a triple bond, respectively, includes a straight or branched chain group, and has 2 to 60 carbon atoms, but is limited thereto it is not going to be

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

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

As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" refer to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 has a carbon number of, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present application have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present application, the aryl group or the arylene group includes a single ring type, a ring aggregate, a fused multiple ring-based compound, and the like. For example, the aryl group may include a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, and a substituted fluorenyl group, and the arylene group may include a fluorenylene group, a substituted fluorenylene group. may include a group.

As used herein, the term "ring assemblies" refers to two or more ring systems (single or fused ring systems) directly connected to each other through a single bond or a double bond, and between such rings It means that the number of direct links is one less than the total number of ring systems in the compound. In a ring aggregate, the same or different ring systems may be directly linked to each other through single or double bonds.

Since the aryl group in the present application includes a ring aggregate, the aryl group includes biphenyl and terphenyl in which a single aromatic benzene ring is connected by a single bond. In addition, since the aryl group includes compounds in which an aromatic single ring and a fused aromatic ring system are connected by a single bond, for example, a compound in which a benzene ring, which is an aromatic single ring, and a fluorene, a fused aromatic ring system, are connected by a single bond are also included. do.

As used herein, the term "fused multiple ring system" refers to a fused ring type that shares at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. and a form in which at least one heterocyclic system is fused. The fused multiple ring system may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings. For example, in the case of an aryl group, it may be a naphthalenyl group, a phenanthrenyl group, a fluorenyl group, etc., but is not limited thereto.

The term "spiro compound" as used in the present application has a 'spiro union', and the spiro linkage means a connection formed by sharing only one atom in two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

As used herein, the terms "fluorenyl group", "fluorenylene group", and "fluorentriyl group" are, unless otherwise specified, in the following structures, R, R', R" and R'" are all hydrogen. It refers to a monovalent, divalent or trivalent functional group, and “substituted fluorenyl group”, “substituted fluorenylene group” or “substituted fluorentriyl group” is a substituent R, R', R", R' "means that at least one of " is a substituent other than hydrogen, and includes cases in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In the present specification, the fluorenyl group, the fluorenylene group, and the fluorentriyl group may all be referred to as fluorene groups regardless of valences such as monovalent, divalent, trivalent, and the like.

In addition, the R, R', R" and R'" are each independently 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 to It may be a heterocyclic group having 30 carbon atoms, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, imidazole, triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline. For example, the substituted fluorenyl group and the fluorenylene group are monovalent to 9,9-dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spirobi[9H-fluorene], respectively. It may be a functional group or a divalent functional group.

The term "heterocyclic group" used in this application includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, each carbon number including at least one heteroatom It means a ring of 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 is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.

For example, the “heterocyclic group” may include a compound including a heteroatom group such as SO ₂ , P=O, etc., such as the following compounds instead of carbon forming a ring.

As used herein, the term "ring" includes monocyclic and polycyclic rings, and includes hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems and spiro compounds, and includes aromatic as well as non-aromatic, hydrocarbon Rings include, of course, heterocycles containing at least one heteroatom.

The term "aliphatic ring group" used in the present application refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

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

In addition, unless there is an explicit explanation, the term "substituted" in the term "substituted or unsubstituted" used in this application means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₃₀ alkyl group, C ₁ ~ C ₃₀ Alkoxy group, C ₁ ~ C ₃₀ Alkylamine group, C ₁ ~ C ₃₀ Alkylthiophene group, C ₆ ~ C ₃₀ Arylthiophene group, C ₂ ~ C ₃₀ Alkenyl group, C ₂ ~ C ₃₀ alkynyl group, C ₃ ~ C ₃₀ cycloalkyl group, C ₆ ~ C ₃₀ aryl group, C ₆ ~ C ₃₀ aryl group substituted with deuterium, C ₈ ~ C ₃₀ arylalkenyl group, silane group, boron A group, a germanium group, and O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₃₀ It means substituted with one or more substituents selected from the group consisting of a heterocyclic group and is not limited to these substituents.

In the present application, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the functional group reflecting the valence', but it is described as 'the name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl (group)', and the divalent group is 'phenanthrylene (group)', etc. It can be described, but it can also be described as 'phenanthrene', which is the name of the parent compound, regardless of the valence.

Similarly, in the case of pyrimidine, regardless of the valence, it is described as 'pyrimidine', or if it is monovalent, it is pyrimidinyl (group), and if it is divalent, the 'group of the valence, such as pyrimidinylene (group), etc. It can also be written in the name of '. Therefore, in the present application, when the type of the substituent is described as the name of the parent compound, it may mean an n-valent 'group' formed by the detachment of a hydrogen atom bonding to a carbon atom and/or a hetero atom of the parent compound.

In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in the present application is the same as the definition of the substituent by the exponent definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the display of hydrogen bonded to carbon It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same as or different from each other.

Unless otherwise stated in the present application, forming a ring means that adjacent groups combine with each other to form a single ring or fused multiple rings, and the single ring and the formed fused multiple rings are at least one hydrocarbon ring as well as a hydrocarbon ring. It includes heterocycles containing heteroatoms, and may include aromatic and non-aromatic rings.

In addition, unless otherwise specified in the present specification, when representing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.

Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown); An organic material layer including the compound according to the present invention is included between the second electrodes 170 .

The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 . Specifically, the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .

Preferably, the capping layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer. The light efficiency of the device may be improved.

For example, a capping layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the capping layer 180 is formed on the second electrode 170 . It is possible to reduce optical energy loss due to surface plasmon polaritons (SPPs) of SPPs, and in the case of a bottom emission organic light emitting device, the capping layer 180 may serve as a buffer for the second electrode 170 . .

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

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

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

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

Referring to FIG. 3 , in the organic electric device 300 according to another embodiment of the present invention, there are two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, the organic electric device according to an embodiment of the present invention includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode. 170 and a capping layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer ( 350) may be included.

The second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 .

As described above, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.

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

The first light emitting layer 340 may include a light emitting material including a blue fluorescent dopant in a blue host, and in the second light emitting layer 440 a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.

In this case, the second hole transport layer 430 includes the second stack ST2 in which the energy level is set higher than the triplet excited state energy level of the second light emitting layer 440 .

Since the energy level of the second hole transport layer 430 is higher than that of the second light emitting layer 440 , triplet excitons of the second light emitting layer 440 pass to the second hole transport layer 430 and the luminous efficiency is lowered. it can be prevented That is, the second hole transport layer 430 functions as an exciton blocking layer for preventing triplet excitons from crossing while performing a function of transporting holes from the inherent second light emitting layer 440. .

In addition, for the function of the exciton blocking layer, the first hole transport layer 330 may also be set to an energy level higher than the triplet excitation energy level of the first light emitting layer 340 . In addition, the first electron transport layer 350 is also set to an energy level higher than the energy level of the triplet excited state of the first light emitting layer 340 , and the second electron transport layer 450 is also triplet excited by the second light emitting layer 440 . It is preferably set to an energy level higher than the energy level of the state.

In FIG. 3 , n may be an integer of 1 to 5. When n is 2, the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .

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

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer 210, a light emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material of the capping layer 180, preferably the hole transport layer (130, 330, 430), the light emission auxiliary layer 220 ), the light emitting layers 140 , 340 , 440 , and/or the capping layer 180 may be used as a material.

The organic electric device according to FIGS. 1 to 3 may further include a protective layer (not shown) and an encapsulation layer (not shown). The protective layer may be disposed on the capping layer, and the encapsulation layer is disposed on the capping layer, and a side portion of at least one of the first electrode, the second electrode, and the organic material layer to protect the first electrode, the second electrode, and the organic material layer may be formed to cover the

The protective layer may provide a planarized surface so that the encapsulation layer is uniformly formed, and may serve to protect the first electrode, the second electrode, and the organic material layer during the manufacturing process of the encapsulation layer.

The encapsulation layer may serve to prevent the penetration of external oxygen and moisture into the organic electric device.

On the other hand, even with the same and similar core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of the sub-substituents coupled thereto In particular, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

Therefore, in the present invention, by using the compound represented by Chemical Formula 1 as a material of the light-emitting auxiliary layer 220, the light-emitting layer 140, 340, 440, and/or the capping layer 180, the energy level and T1 value between each organic material layer, By optimizing the intrinsic properties (mobility, interfacial properties, etc.) of the material, the lifetime and efficiency of the organic electric device could be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120, 320, 420), the hole transport layers 130, 330, 430, the light emitting layers 140, 340, 440, the electron transport layers 150, 350, 450 and the electron injection layer 160 after forming the organic material layer including the It may be manufactured by depositing a material that can be used as the cathode 170 thereon. In addition, a light-emitting auxiliary layer 220 between the hole transport layers 130 , 330 , 430 and the light emitting layers 140 , 340 , 440 , and an electron transport auxiliary layer between the light emitting layer 140 and the electron transport layer 150 (not shown) may be further formed or may be formed in a stack structure as described above.

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

The organic electric device according to an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on a material used.

The organic electric device according to an embodiment of the present invention may include an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, a device for a quantum dot display, and the like.

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

Hereinafter, the compound according to one aspect of the present invention will be described.

The compound according to one aspect of the present invention is represented by the following formula (1).

<Formula 1>

In Formula 1,

1) X and Y are each independently O, S or -NL ₁ -Ar ₃ ,

2) a is an integer from 0 to 5; b is an integer from 0 to 3,

3) L ₁ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; or a combination thereof,

4) Ar ₃ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or C ₃ ~ C ₆₀ An aliphatic ring and C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; amine group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or a combination thereof,

5) R ¹ and R ² are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,

6) the R ¹ to R ² , Ar ₃ , L ₁ and the rings formed by bonding adjacent groups to each other are deuterium; halogen; C ₁ ~ C ₃₀ Alkyl group or C ₆ ~ C ₃₀ A silane group unsubstituted or substituted with an aryl group; siloxane group; boron group; germanium group; cyano group; amino group; nitro group; C ₁ ~ C ₃₀ Alkylthio group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Arylalkoxy group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ Aryl group substituted with deuterium; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₃₀ A heterocyclic group; C ₃ ~ C ₃₀ of an aliphatic ring; C ₇ ~ C ₃₀ Arylalkyl group; C ₈ ~ C ₃₀ Aryl alkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof, and adjacent substituents may form a ring.

When R ¹ to R ² and Ar ₃ are aryl groups, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, biphenyl, naphthyl, terphenyl etc.

Wherein R ¹ to R ² , Ar ₃ and L ₁ are a heterocyclic group, Preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, such as dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, etc. .

When R ¹ to R ² and Ar ₃ are a fluorenyl group, preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl group, 9,9′-spi It may be robifluorene or the like.

When L ₁ is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₈ arylene group, such as phenyl, biphenyl, naphthyl, terphenyl, and the like.

When R ¹ to R ² and Ar ₃ are alkyl groups, they may be preferably C ₁ to C ₁₀ alkyl groups, for example, methyl, t-butyl, or the like.

When R ¹ to R ² and Ar ₃ are an alkoxyl group, preferably a C ₁ to C ₂₀ alkoxyl group, more preferably a C ₁ to C ₁₀ alkoxyl group, such as methoxy, t-butoxy, etc. there is.

The ring formed by bonding adjacent groups of R ¹ to R ² , Ar ₃ and L ₁ to each other is a C ₆ to C ₆₀ aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or it may be a C ₃ ~ C ₆₀ aliphatic ring group, for example, when adjacent groups are bonded to each other to form an aromatic ring, preferably a C ₆ ~ C ₂₀ aromatic ring, more preferably C ₆ ~ C ₁₄ of aromatic rings, such as benzene, naphthalene, phenanthrene, and the like.

Preferably, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-10, but is not limited thereto.

(Formula 1-1) (Formula 1-2) (Formula 1-3) (Formula 1-4)

(Formula 1-5) (Formula 1-6) (Formula 1-7) (Formula 1-8)

(Formula 1-9) (Formula 1-10)

In Formulas 1-1 to 1-10,

1) The R ¹ to R ² , Ar ₃ , L ₁ and a to b are the same as defined in Formula 1,

2) Ar ₄ is the same as Ar ₃ in Formula 1 above.

Also preferably, R ¹ , R ² and Ar ₃ of Formula 1 may be each independently represented by Formula 2-1 or Formula 2-2, but are not limited thereto.

(Formula 2-1) (Formula 2-2)

In Formulas 2-1 to 2-2,

1) L ₁ is the same as defined in Formula 1,

2) Z ¹ to Z ⁵ are each independently C(R ₁ ) or N; At least one of Z ¹ to Z ⁵ is N,

3) Z ⁶ ~Z ⁸ are each independently C(R ₁ ) or N; At least one of Z ⁶ to Z ⁸ is N,

4) R ₁ is hydrogen; heavy hydrogen; halogen; C ₁ ~ C ₂₀ Alkyl group or C ₆ ~ C ₂₀ A silane group unsubstituted or substituted with an aryl group; cyano group; nitro group; C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy 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; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic ring group; C ₇ ~ C ₂₀ Arylalkyl group; And C ₈ ~ C ₂₀ It is selected from the group consisting of an aryl alkenyl group; Or it may combine with a neighboring group to form a ring,

5) C ring is a C ₆ ~ C ₃₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₃₀ A heterocyclic group; C ₃ ~ C ₃₀ of an aliphatic ring; C ₇ ~ C ₃₀ Arylalkyl group; C ₈ ~ C ₃₀ Aryl alkenyl group; or a combination thereof; Alternatively, it may combine with a neighboring group to form a ring.

Also preferably, Formula 1 may be represented by any one of Formulas 2-3 to 2-8, but is not limited thereto.

(Formula 2-3) (Formula 2-4) (Formula 2-5)

(Formula 2-6) (Formula 2-7) (Formula 2-8)

In Formula 2-3 to Formula 2-8,

1) The R ¹ to R ² , L ₁ , Ar ₃ and a to b are the same as defined in Formula 1,

2) Ar ₁ to Ar ₂ are the same as defined for Ar ₃ in Formula 1,

3) X ₁ to X ₃ are each independently N or CH; At least one of X ₁ to X ₃ is N.

Also preferably, Chemical Formula 1 may be represented by the following Chemical Formula 1-11 or Chemical Formula 1-12, but is not limited thereto.

(Formula 1-11) (Formula 1-12)

In Formulas 1-11 to 1-12,

1) R ¹ to R ² , X, Y and a to b are the same as defined in Formula 1 above,

2) L ₂ ~ L ₄ is the same as the definition of L ₁ in Formula 1,

3) Ar ₄ to Ar ₅ are the same as defined for Ar ₃ in Formula 1 above.

Also preferably, Chemical Formula 1 may be represented by the following Chemical Formula 1-13 or Chemical Formula 1-14, but is not limited thereto.

(Formula 1-13) (Formula 1-14)

In Formulas 1-13 to 1-14,

1) R ¹ to R ² , X, Y and a to b are the same as defined in Formula 1 above,

2) L ₂ ~ L ₄ is the same as the definition of L ₁ in Formula 1,

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

4) Z is substituted or unsubstituted C, O, S or N.

Meanwhile, The compound represented by Formula 1 may be one of the following P-1 to P-219, but is not limited thereto.

In another embodiment of the present invention, the present invention provides a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Formula 1 alone or in combination.

As another embodiment of the present invention, the present invention provides a first electrode; a second electrode; an organic material layer formed between the first electrode and the second electrode; and a capping layer, wherein the capping layer is formed on one side of both surfaces of the first electrode and the second electrode that is not in contact with the organic material layer, and the organic material layer or the capping layer is represented by Formula 1 The compounds used alone or in combination are included.

In another embodiment of the present invention, it is preferable that the organic layer further includes a compound of Formula 3 below as a dopant material.

(Formula 3)

In Formula 3,

1) M is a metal with an atomic weight of 40 or more,

2) L is an auxiliary ligand,

3) m is the oxidation number of M,

4) n is greater than or equal to 1,

5) R ⁷ and R ⁸ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,

6) c and d are each independently an integer of 0-4.

Preferably, Chemical Formula 3 may be represented by any one of Chemical Formulas 3-1 to 3-6, but is not limited thereto.

(Formula 3-1) (Formula 3-2) (Formula 3-3)

(Formula 3-4) (Formula 3-5) (Formula 3-6)

In Formulas 3-1 to 3-6,

1) M, L, m, n, d, R ⁷ and R ⁸ are the same as defined in Formula 3 above,

2) In Formulas 3-1 to 3-3, c is an integer of 0 to 6,

3) In Formulas 3-4 to 3-6, c is an integer of 0 to 8.

Also preferably, Chemical Formula 3 may be represented by the following Chemical Formula 3-7, but is not limited thereto.

(Formula 3-7)

In Formula 3-7,

1) R ⁷ and R ⁸ are as defined in Formula 3 above,

2) c is an integer from 0 to 8; d is an integer from 0 to 4,

3) Ar ₆ to Ar ₈ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; Alternatively, adjacent groups may be bonded to each other to form a ring.

Also preferably, L may be selected from a ligand represented by the following Chemical Formula 3A to a ligand represented by the following Chemical Formula 3D, but is not limited thereto.

(Formula 3A) (Formula 3B)

(Formula 3C) (Formula 3D)

In Formulas 3A to 3D,

1) Y ₁₁ ~ Y ₁₆ are each independently C or N,

2) CY ₃ ~CY ₄ are each independently a C ₂ ~ C ₂₀ alkynyl group; C ₆ ~ C ₂₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic ring group; C ₇ ~ C ₂₀ Arylalkyl group; And C ₈ ~ C ₂₀ It is selected from the group consisting of an aryl alkenyl group; Or it may combine with a neighboring group to form a ring,

3) C1~C2 are each independently an integer of 0~6,

4) X ₁₁ to X14 are each independently N, O, NR ₄₀ or PR ₄₁ R ₄₂ ,

5) Z ₂₁ , Z ₂₂ and R ₃₃ to R ₄₂ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,

6) * and *1 represent bonding positions.

Meanwhile, the compound represented by Formula 3 may be one of the following D-1 to D-28, but is not limited thereto.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. That is, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer included in the organic material layer may include a compound represented by Formula (1). .

Preferably, the organic material layer includes at least one of the hole transport layer, the light emitting auxiliary layer and the light emitting layer. That is, the compound may be included in at least one of the hole transport layer, the light emitting auxiliary layer, and the light emitting layer.

The organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode.

Preferably, the organic material layer further includes a charge generating layer formed between the two or more stacks.

Another aspect of the present invention is to provide an electronic device including a display device including an organic electric device including the compound represented by Chemical Formula 1 and a controller for driving the display device.

In an embodiment of the present invention, the compound of Formula 1 may be included alone, the compound may be included in a combination of two or more different types, or the compound may be included in a combination of two or more other compounds.

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

<Synthesis example>

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

<Scheme 1>

<Scheme 2>

I. Synthesis of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction route of Schemes 3,4, but is not limited thereto.

<Scheme 3>

<Scheme 4>

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

Synthesis example of Sub 1-1

(1) Sub 1-1-1 synthesis

After dissolving 8-bromonaphthalen-1-ol (60.0 g, 269.0 mmol) in 675 mL of THF in a round bottom flask, (2-chloro-6-nitrophenyl)boronic acid (59.6 g, 295.9 mmol), Pd(PPh ₃ ) ₄ (9.3 g, 8.1 mmol), K ₂ CO ₃ (111.5 g, 806.9 mmol) and 225 mL of water were added and stirred at 75°C. After the reaction was completed, the mixture was extracted with an organic solvent and water was removed with MgSO ₄ . After concentration of the solvent, the resulting compound was subjected to column chromatography and recrystallization to obtain a product (45.7 g, yield: 60 %).

(2) Sub 1-1-2 synthesis

Sub 1-1-1 (45.7 g, 152.5 mmol) obtained by the above synthesis, K ₂ CO ₃ (10.5 g, 76.2 mmol) and 510 mL of DMF were added and dissolved, followed by refluxing for 12 hours. After the reaction was completed, the mixture was extracted with an organic solvent and water was removed with MgSO ₄ . After concentration of the solvent, the resulting compound was subjected to column chromatography and recrystallization to obtain a product (24.8 g, yield: 62 %).

(3) Sub 1-1 synthesis

Sub 1-1-2 (24.8 g, 94.2 mmol) obtained by the above synthesis, PPh ₃ (74.1 g, 282.6 mmol) and 320 mL of o-DCB were added and dissolved, followed by refluxing for 12 hours. After the reaction was completed, the mixture was extracted with an organic solvent and water was removed with MgSO ₄ . After concentration of the solvent, the resulting compound was subjected to column chromatography and recrystallization to obtain a product (18.0 g, yield: 83 %).

Synthesis example of Sub 1-3

(1) Sub 1-3-1 synthesis

1-bromo-8-nitronaphthalene (50.0 g, 198.4 mmol), (2-(methylthio)phenyl)boronic acid (36.7 g, 218.2 mmol), Pd(PPh ₃ ) ₄ (6.9 g, 6.0 mmol) in a round bottom flask And K ₂ CO ₃ (82.3 g, 595.1 mmol) was obtained by using the synthesis method of Sub 1-1-1 above to obtain a product (38.0 g, yield: 65 %).

(2) Sub 1-3-2 synthesis

Sub 1-3-1 (38.0 g, 128.7 mmol) and PPh ₃ (101.2 g, 386.0 mmol) obtained by the above synthesis were used for the synthesis of Sub 1-1 as a product (25.0 g, yield: 74%) got it

(3) Sub 1-3-3 synthesis

Sub 1-3-2 (25.0 g, 94.9 mmol) obtained by the above synthesis was dissolved in 320 mL of AcOH, and then H ₂ O ₂ (2.3ml, 94.9 mmol) was slowly added at 0 ° C., followed by stirring at room temperature for 24 hours. . After the reaction was completed, the mixture was extracted with an organic solvent and water was removed with MgSO ₄ . After concentration of the solvent, the resulting compound was subjected to column chromatography and recrystallization to obtain a product (20.1 g, yield: 76 %).

(4) Sub 1-3 synthesis

After adding triflic acid (30.1 ml, 179.0 mmol) to Sub 1-3-3 (20.1 g, 89.5 mmol) obtained by the above synthesis, and stirring at room temperature for 24 hours, an aqueous solution of pyridine (300 ml, pyridine: H 2 O = 1 : 5) was slowly added, heated and refluxed for 30 minutes. After the reaction was completed, the mixture was extracted with an organic solvent and water was removed with MgSO ₄ . After concentration of the solvent, the resulting compound was subjected to column chromatography and recrystallization to obtain a product (14.3 g, yield: 65 %).

Synthesis example of Sub 1-5

(1) Sub 1-5-1 synthesis

1-bromo-8-nitronaphthalene (50.0 g, 198.4 mmol), (2-nitrophenyl)boronic acid (36.4 g, 218.2 mmol), Pd(PPh ₃ ) ₄ (6.9 g, 6.0 mmol) and K ₂ in a round bottom flask CO ₃ (82.3 g, 595.1 mmol) was used for the synthesis of Sub 1-1-1 to obtain a product (44.9 g, yield: 77 %).

(2) Sub 1-5 synthesis

Sub 1-5-1 (44.9 g, 152.6 mmol) and PPh ₃ (120.1 g, 457.7 mmol) obtained by the above synthesis were used for the synthesis of Sub 1-1 as a product (20.0 g, yield: 57%) got it

Synthesis example of Sub 1-7

Sub 1-7-1 (15.0 g, 56.5 mmol), triphenylen-2-ylboronic acid (16.9 g, 62.1 mmol), Pd(PPh ₃ ) ₄ (2.0 g, 1.7 mmol) and K ₂ CO ₃ in a round bottom flask (23.4 g, 235.8 mmol) was obtained by using the synthesis method of Sub 1-1-1 above to obtain a product (15.4 g, yield: 60 %).

Synthesis example of Sub 1-15

Sub 1-15-1 (10.0 g, 30.1 mmol), (9-(9,9'-spirobi[fluoren]-2-yl)-9H-carbazol-2-yl)boronic acid (17.4 g) in a round bottom flask , 33.1 mmol), Pd(PPh ₃ ) ₄ (1.0 g, 0.9 mmol) and K ₂ CO ₃ (12.5 g, 90.4 mmol) were prepared using the synthesis method of Sub 1-1-1 above for the product (12.8 g, yield) : 55%) was obtained.

Synthesis example of Sub 1-16

Sub 1-16-1 (10.0 g, 28.3 mmol), (3-(dibenzo[b,d]furan-3-yl(phenyl)amino)phenyl)boronic acid (11.8 g, 31.1 mmol) in a round bottom flask, Pd(PPh ₃ ) ₄ (1.0 g, 0.8 mmol) and K ₂ CO ₃ (11.7 g, 84.8 mmol) were prepared by using the synthesis method of Sub 1-1-1 above to prepare the product (7.9 g, yield: 43%) got it

Synthesis example of Sub 1-17

에서 교반하였다. 반응이 완료되면, 유기용매와 물로 추출한 후, 유기층을 MgSO₄로 건조하고 농축한 후, 생성된 화합물을 컬럼크로마토그래피 및 재결정을 통해 생성물 (23.9 g, 수율: 74%)를 얻었다.After dissolving Sub 1-17-1 (15.0 g, 53.2 mmol) in toluene (200 ml) in a round bottom flask, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl- 9H-fluoren-2-amine (21.2 g, 58.6 mmol), Pd ₂ (dba) ₃ (1.5 g, 1.6 mmol), 50% P(t-Bu) ₃ (1.3 ml, 3.2 mmol) and NaOt-Bu ( 7.7 g, 79.9 mmol) and 110

stirred in. Upon completion of the reaction, after extraction with an organic solvent and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was subjected to column chromatography and recrystallization to obtain a product (23.9 g, yield: 74%).

Synthesis example of Sub 1-31

Sub 1-31-1 (13 g, 28.1 mmol), 1-bromonaphthalene (6.4 g, 30.9 mmol), Pd ₂ (dba) ₃ (0.8 g, 0.8 mmol), 50% P(t-Bu) in a round bottom flask ) ₃ (0.7 ml, 1.7 mmol) and NaOt-Bu (4.1 g, 42.2 mmol) were synthesized using the method of Sub 1-17 above to obtain a product (13.5 g, yield: 82%).

Synthesis example of Sub 1-32

Sub 1-5 (12.0 g, 52.1 mmol), 2-bromodibenzo[b,d]furan (14.2 g, 57.3 mmol), Pd ₂ (dba) ₃ (1.4 g, 1.6 mmol), 50% P in a round bottom flask (t-Bu) ₃ (1.3 ml, 3.1 mmol) and NaOt-Bu (7.5 g, 78.2 mmol) were obtained using the synthesis method of Sub 1-17 above to obtain a product (12.3 g, yield: 60%).

Synthesis example of Sub 1-47

Sub 1-5 (13.5 g, 58.6 mmol), 3-bromo-9-phenyl-9H-carbazole (20.8 g, 64.5 mmol), Pd ₂ (dba) ₃ (1.6 g, 1.8 mmol), 50 in a round bottom flask % P(t-Bu) ₃ (1.5 ml, 3.5 mmol) and NaOt-Bu (8.5 g, 87.9 mmol) were obtained by using the synthesis method of Sub 1-17 above to obtain a product (15.2 g, yield: 55%) .

Synthesis example of Sub 1-48

Sub 1-5 (12.0 g, 52.1 mmol), 3-chloro-N,N-diphenylaniline (16.1 g, 57.3 mmol), Pd ₂ (dba) ₃ (1.4 g, 1.6 mmol), 50% P in a round bottom flask (t-Bu) ₃ (1.3 ml, 3.1 mmol) and NaOt-Bu (7.5 g, 78.2 mmol) were obtained using the synthesis method of Sub 1-17 above to obtain a product (12.0 g, yield: 49%).

Synthesis example of Sub 1-51

Sub 1-51-1 (13.5 g, 40.9 mmol), 2-(benzo[b]naphtho[2,3-d]thiophen-2-yl)-4-chlorodibenzo[b,d]furan ( 19.6 g, 44.9 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), 50% P(t-Bu) ₃ (1.0 ml, 2.5 mmol) and NaOt-Bu (5.9 g, 61.3 mmol) above The product (8.3 g, yield: 28%) was obtained by using the synthesis method of Sub 1-17.

Synthesis example of Sub 1-65

Sub 1-65-1 (20.0 g, 39.8 mmol), bromobenzene (6.9 g, 43.8 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), 50% P(t-Bu) ₃ in a round bottom flask (1.0 ml, 2.4 mmol) and NaOt-Bu (5.8 g, 59.8 mmol) were used for the synthesis of Sub 1-17 to obtain a product (6.9 g, yield: 30%).

Synthesis example of Sub 1-70

Sub 1-70-1 (21.0 g, 67.5 mmol), 4-chlorophenyl boronic acid (11.6 g, 74.2 mmol), Pd(PPh ₃ ) ₄ (2.3 g, 2.0 mmol) and K ₂ CO ₃ ( 28.0 g, 202.5 mmol) was used for the synthesis of Sub 1-1-1 above to obtain a product (16.4 g, yield: 71 %).

On the other hand, the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.

Table 1 below shows FD-MS values of compounds belonging to Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z=231.07 (C ₁₆ H ₉ NO=231.25) Sub 1-2 m/z=231.07 (C ₁₆ H ₉ NO=231.25) Sub 1-3 m/z=247.05 (C ₁₆ H ₉ NS=247.32) Sub 1-4 m/z=247.05 (C ₁₆ H ₉ NS=247.32) Sub 1-5 m/z=230.08 (C ₁₆ H ₁₀ N ₂ =230.27) Sub 1-6 m/z=399.11 (C ₂₈ H ₁₇ NS=399.51) Sub 1-7 m/z=457.15 (C ₃₄ H ₁₉ NO=457.53) Sub 1-8 m/z=347.08 (C ₂₄ H ₁₃ NS=347.44) Sub 1-9 m/z=335.08 (C ₂₃ H ₁₃ NS=335.42) Sub 1-10 m/z=331.1 (C ₂₄ H ₁₃ NO=331.37) Sub 1-11 m/z=639.17 (C ₄₆ H ₂₅ NOS=639.77) Sub 1-12 m/z=572.19 (C ₄₂ H ₂₄ N ₂ O=572.67) Sub 1-13 m/z=680.23 (C ₄₉ H ₃₂ N ₂ S=680.87) Sub 1-14 m/z=548.19 (C ₄₀ H ₂₄ N ₂ O=548.65) Sub 1-15 m/z=776.23 (C ₅₇ H ₃₂ N ₂ S=776.96) Sub 1-16 m/z=652.22 (C ₄₇ H ₂₈ N ₂ O ₂ =652.75) Sub 1-17 m/z=606.21 (C ₄₃ H ₃₀ N ₂ S=606.79) Sub 1-18 m/z=655.26 (C ₄₇ H ₃₃ N ₃ O=655.8) Sub 1-19 m/z=580.16 (C ₄₀ H ₂₄ N ₂ OS=580.71) Sub 1-20 m/z=778.26 (C ₅₇ H ₃₄ N ₂ O ₂ =778.91) Sub 1-21 m/z=281.08 (C ₂₀ H ₁₁ NO=281.31) Sub 1-22 m/z=719.21 (C ₄₉ H ₂₉ N ₅ S=719.87) Sub 1-23 m/z=269.08 (C ₁₉ H ₁₁ NO=269.3) Sub 1-24 m/z=331.1 (C ₂₄ H ₁₃ NO=331.37) Sub 1-25 m/z=307.1 (C ₂₂ H ₁₃ NO=307.35) Sub 1-26 m/z=597.1 (C ₃₈ H ₁₉ N ₃ OS ₂ =597.71) Sub 1-27 m/z=578.16 (C ₃₉ H ₂₂ N ₄ S=578.69) Sub 1-28 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-29 m/z=473.19 (C ₃₄ H ₂₃ N ₃ =473.58) Sub 1-30 m/z=471.17 (C ₃₄ H ₂₁ N ₃ =471.56) Sub 1-31 m/z=588.17 (C ₄₂ H ₂₄ N ₂ S=588.73) Sub 1-32 m/z=396.13 (C ₂₈ H ₁₆ N ₂ O=396.45) Sub 1-33 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-34 m/z=544.19 (C ₄₁ H ₂₄ N ₂ =544.66) Sub 1-35 m/z=406.15 (C ₃₀ H ₁₈ N ₂ =406.49) Sub 1-36 m/z=306.12 (C ₂₂ H ₁₄ N ₂ =306.37) Sub 1-37 m/z=382.15 (C ₂₈ H ₁₈ N ₂ =382.47) Sub 1-38 m/z=473.19 (C ₃₄ H ₂₃ N ₃ =473.58) Sub 1-39 m/z=432.16 (C ₃₂ H ₂₀ N ₂ =432.53) Sub 1-40 m/z=589.25 (C ₄₃ H ₃₁ N ₃ =589.74) Sub 1-41 m/z=369.13 (C ₂₆ H ₁₅ N ₃ =369.43) Sub 1-42 m/z=412.1 (C ₂₈ H ₁₆ N ₂ S=412.51) Sub 1-43 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-44 m/z=406.15 (C ₃₀ H ₁₈ N ₂ =406.49) Sub 1-45 m/z=432.16 (C ₃₂ H ₂₀ N ₂ =432.53) Sub 1-46 m/z=458.18 (C ₃₄ H ₂₂ N ₂ =458.56) Sub 1-47 m/z=471.17 (C ₃₄ H ₂₁ N ₃ =471.56) Sub 1-48 m/z=473.19 (C ₃₄ H ₂₃ N ₃ =473.58) Sub 1-49 m/z=396.13 (C ₂₈ H ₁₆ N ₂ O=396.45) Sub 1-50 m/z=690.28 (C ₅₀ H ₃₄ N ₄ =690.85) Sub 1-51 m/z=728.19 (C ₅₂ H ₂₈ N ₂ OS=728.87) Sub 1-52 m/z=647.22 (C ₄₉ H ₂₉ NO=647.78) Sub 1-53 m/z=613.22 (C ₄₄ H ₂₇ N ₃ O=613.72) Sub 1-54 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-55 m/z=324.11 (C ₂₂ H ₁₃ FN ₂ =324.36) Sub 1-56 m/z=382.15 (C ₂₈ H ₁₈ N ₂ =382.47) Sub 1-57 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-58 m/z=382.15 (C ₂₈ H ₁₈ N ₂ =382.47) Sub 1-59 m/z=471.17 (C ₃₄ H ₂₁ N ₃ =471.56) Sub 1-60 m/z=412.1 (C ₂₈ H ₁₆ N ₂ S=412.51) Sub 1-61 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-62 m/z=544.19 (C ₄₁ H ₂₄ N ₂ =544.66) Sub 1-63 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) Sub 1-64 m/z=651.24 (C ₄₆ H ₂₉ N ₅ =651.77) Sub 1-65 m/z=578.19 (C ₃₈ H ₂₂ N ₆ O=578.64) Sub 1-66 m/z=356.13 (C ₂₆ H ₁₆ N ₂ =356.43) Sub 1-67 m/z=676.23 (C ₄₈ H ₂₈ N ₄ O=676.78) Sub 1-68 m/z=406.15 (C ₃₀ H ₁₈ N ₂ =406.49) Sub 1-69 m/z=390.09 (C ₂₂ H ₁₉ BO ₂ S ₂ =390.32) Sub 1-70 m/z=342.04 (C ₂₂ H ₁₁ ClO ₂ =342.78) Sub 1-71 m/z=374.11 (C ₂₂ H ₁₉ BO ₃ S=374.26) Sub 1-72 m/z=374.11 (C ₂₂ H ₁₉ BO ₃ S=374.26)

II. Sub 2 example

Sub 2 of Scheme 1 is the same as Scheme 5 below, but is not limited thereto.

<Scheme 5>

On the other hand, the compound belonging to Sub 2 may be a compound as follows, but is not limited thereto.

Table 2 below shows FD-MS values of compounds belonging to Sub 2.

compound FD-MS compound FD-MS Sub 2-1 m/z=155.96 (C ₆ H ₅ Br=157.01) Sub 2-2 m/z=231.99 (C ₁₂ H ₉ Br=233.11) Sub 2-3 m/z=308.02 (C ₁₈ H ₁₃ Br=309.21) Sub 2-4 m/z=416.13 (C ₃₀ H ₂₁ Cl=416.95) Sub 2-5 m/z=238.05 (C ₁₆ H ₁₁ Cl=238.71) Sub 2-6 m/z=142.08 (C ₁₁ H ₁₀ =142.2) Sub 2-7 m/z=255.99 (C ₁₄ H ₉ Br=257.13) Sub 2-8 m/z=169.97 (C ₇ H ₇ Br=171.04) Sub 2-9 m/z=272.02 (C ₁₅ H ₁₃ Br=273.17) Sub 2-10 m/z=437.08 (C ₂₇ H ₂₀ BrN=438.37) Sub 2-11 m/z=396.05 (C ₂₅ H ₁₇ Br=397.32) Sub 2-12 m/z=446.07 (C ₂₉ H ₁₉ Br=447.38) Sub 2-13 m/z=476.13 (C ₃₅ H ₂₁ Cl=477) Sub 2-14 m/z=444.05 (C ₂₉ H ₁₇ Br=445.36) Sub 2-15 m/z=518.14 (C ₃₇ H ₂₃ ClO=519.04) Sub 2-16 m/z=394.04 (C ₂₅ H ₁₅ Br=395.3) Sub 2-17 m/z=502.15 (C ₃₇ H ₂₃ Cl=503.04) Sub 2-18 m/z=460.05 (C ₂₉ H ₁₇ BrO=461.36) Sub 2-19 m/z=460.05 (C ₂₉ H ₁₇ BrO=461.36) Sub 2-20 m/z=410.03 (C ₂₅ H ₁₅ BrO=411.3) Sub 2-21 m/z=532.12 (C ₃₇ H ₂₁ ClO ₂ =533.02) Sub 2-22 m/z=568.16 (C ₄₁ H ₂₅ ClO=569.1) Sub 2-23 m/z=442.11 (C ₃₁ H ₁₉ ClO=442.94) Sub 2-24 m/z=306 (C ₁₈ H ₁₁ Br=307.19) Sub 2-25 m/z=315.08 (C ₂₁ H ₁₄ ClN=315.8) Sub 2-26 m/z=193.07 (C ₁₂ H ₄ D ₅ Cl=193.68) Sub 2-27 m/z=282.06 (C ₁₈ H ₁₂ ClF=282.74) Sub 2-28 m/z=213.03 (C ₁₃ H ₈ ClN=213.66) Sub 2-29 m/z=245.97 (C ₁₂ H ₇ BrO=247.09) Sub 2-30 m/z=278.05 (C ₁₈ H ₁₁ ClO=278.74) Sub 2-31 m/z=460.07 (C ₃₀ H ₁₇ ClOS=460.98) Sub 2-32 m/z=328.07 (C ₂₂ H ₁₃ ClO=328.8) Sub 2-33 m/z=295.98 (C ₁₆ H ₉ BrO=297.15) Sub 2-34 m/z=420.07 (C ₂₈ H ₁₇ ClS=420.95) Sub 2-35 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub 2-36 m/z=418.08 (C ₂₈ H ₁₅ ClO ₂ =418.88) Sub 2-37 m/z=394.06 (C ₂₆ H ₁₅ ClS=394.92) Sub 2-38 m/z=595.17 (C ₄₂ H ₂₆ ClNO=596.13) Sub 2-39 m/z=609.11 (C ₄₁ H ₂₄ BrN=610.55) Sub 2-40 m/z=411.03 (C ₂₄ H ₁₄ BrNO=412.29) Sub 2-41 m/z=421.05 (C ₂₆ H ₁₆ BrN=422.33) Sub 2-42 m/z=455.12 (C ₂₈ H ₂₆ BrN=456.43) Sub 2-43 m/z=477.02 (C ₂₈ H ₁₆ BrNS=478.41) Sub 2-44 m/z=421.05 (C ₂₆ H ₁₆ BrN=422.33) Sub 2-45 m/z=536.09 (C ₃₄ H ₂₁ BrN ₂ =537.46) Sub 2-46 m/z=575.09 (C ₃₇ H ₂₂ BrNO=576.49) Sub 2-47 m/z=321.02 (C ₁₈ H ₁₂ BrN=322.21) Sub 2-48 m/z=272.02 (C ₁₅ H ₁₃ Br=273.17) Sub 2-49 m/z=314.09 (C ₂₂ H ₁₅ Cl=314.81) Sub 2-50 m/z=189.03 (C ₁₁ H ₈ ClN=189.64) Sub 2-51 m/z=328.07 (C ₂₂ H ₁₃ ClO=328.8) Sub 2-52 m/z=328.07 (C ₂₂ H ₁₃ ClO=328.8) Sub 2-53 m/z=261.95 (C ₁₂ H ₇ BrS=263.15) Sub 2-54 m/z=428.13 (C ₃₁ H ₂₁ Cl=428.96) Sub 2-55 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub 2-56 m/z=410.03 (C ₂₅ H ₁₅ BrO=411.3) Sub 2-57 m/z=575.09 (C ₃₇ H ₂₂ BrNO=576.49) Sub 2-58 m/z=410.03 (C ₂₅ H ₁₅ BrO=411.3) Sub 2-59 m/z=394.04 (C ₂₅ H ₁₅ Br=395.3) Sub 2-60 m/z=570.14 (C ₄₀ H ₂₃ ClO ₂ =571.07) Sub 2-61 m/z=446.09 (C ₃₀ H ₁₉ ClS=446.99) Sub 2-62 m/z=384.04 (C ₂₄ H ₁₃ ClOS=384.88) Sub 2-63 m/z=404.1 (C ₂₈ H ₁₇ ClO=404.89) Sub 2-64 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub 2-65 m/z=494.11 (C ₃₄ H ₁₉ ClO2=494.97) Sub 2-66 m/z=486.07 (C ₃₀ H ₁₉ BrN ₂ =487.4) Sub 2-67 m/z=321.02 (C ₁₈ H ₁₂ BrN=322.21) Sub 2-68 m/z=344.04 (C ₂₂ H ₁₃ ClS=344.86) Sub 2-69 m/z=378.08 (C ₂₆ H ₁₅ ClO=378.86) Sub 2-70 m/z=371.03 (C ₂₂ H ₁₄ BrN=372.27) Sub 2-71 m/z=410.03 (C ₂₅ H ₁₅ BrO=411.3) Sub 2-72 m/z=372.01 (C ₂₂ H ₁₃ BrO=373.25) Sub 2-73 m/z=327.08 (C ₂₂ H ₁₄ ClN=327.81) Sub 2-74 m/z=461.04 (C ₂₈ H ₁₆ BrNO=462.35) Sub 2-75 m/z=522.19 (C ₃₇ H ₁₉ D ₅ ClN=523.09) Sub 2-76 m/z=261.95 (C ₁₂ H ₇ BrS=263.15) Sub 2-77 m/z=505.14 (C ₃₂ H ₂₈ BrN=506.49) Sub 2-78 m/z=229.03 (C ₁₃ H ₈ ClNO=229.66) Sub 2-79 m/z=279.08 (C ₁₈ H ₁₄ ClN=279.77) Sub 2-80 m/z=279.08 (C ₁₈ H ₁₄ ClN=279.77) Sub 2-81 m/z=329.1 (C ₂₂ H ₁₆ ClN=329.83) Sub 2-82 m/z=446.15 (C ₃₀ H ₂₃ ClN ₂ =446.98) Sub 2-83 m/z=385.07 (C ₂₄ H ₁₆ ClNS=385.91) Sub 2-84 m/z=444.14 (C ₃₀ H ₂₁ ClN ₂ =444.96) Sub 2-85 m/z=444.14 (C ₃₀ H ₂₁ ClN ₂ =444.96) Sub 2-86 m/z=419.11 (C ₂₈ H ₁₈ ClNO=419.91) Sub 2-87 m/z=435.08 (C ₂₈ H ₁₈ ClNS=435.97) Sub 2-88 m/z=369.09 (C ₂₄ H ₁₆ ClNO=369.85) Sub 2-89 m/z=369.13 (C ₂₅ H ₂₀ ClN=369.89) Sub 2-90 m/z=561.11 (C ₃₇ H ₂₄ BrN=562.51) Sub 2-91 m/z=431.14 (C ₃₀ H ₂₂ ClN=431.96) Sub 2-92 m/z=405.13 (C ₂₈ H ₂₀ ClN=405.93) Sub 2-93 m/z=329.1 (C ₂₂ H ₁₆ ClN=329.83) Sub 2-94 m/z=419.11 (C ₂₈ H ₁₈ ClNO=419.91) Sub 2-95 m/z=485.1 (C ₃₂ H ₂₀ ClNS=486.03) Sub 2-96 m/z=495.14 (C ₃₄ H ₂₂ ClNO=496.01) Sub 2-97 m/z=525.1 (C ₃₄ H ₂₀ ClNOS=526.05) Sub 2-98 m/z=435.08 (C ₂₈ H ₁₈ ClNS=435.97) Sub 2-99 m/z=537.13 (C ₃₆ H ₂₄ ClNS=538.11) Sub 2-100 m/z=445.12 (C ₃₀ H ₂₀ ClNO=445.95) Sub 2-101 m/z=444.14 (C ₃₀ H ₂₁ ClN ₂ =444.96) Sub 2-102 m/z=444.14 (C ₃₀ H ₂₁ ClN ₂ =444.96) Sub 2-103 m/z=519.14 (C ₃₆ H ₂₂ ClNO=520.03) Sub 2-104 m/z=585.15 (C ₄₀ H ₂₄ ClNO ₂ =586.09) Sub 2-105 m/z=496.17 (C ₃₄ H ₂₅ ClN ₂ =497.04) Sub 2-106 m/z=536.17 (C ₃₆ H ₂₅ ClN ₂ O=537.06) Sub 2-107 m/z=419.11 (C ₂₈ H ₁₈ ClNO=419.91) Sub 2-108 m/z=475.08 (C ₃₀ H ₁₈ ClNOS=475.99) Sub 2-109 m/z=533.15 (C ₃₇ H ₂₄ ClNO=534.06) Sub 2-110 m/z=469.12 (C ₃₂ H ₂₀ ClNO=469.97) Sub 2-111 m/z=607.17 (C ₄₃ H ₂₆ ClNO=608.14) Sub 2-112 m/z=511.12 (C ₃₄ H ₂₂ ClNS=512.07) Sub 2-113 m/z=579.23 (C ₄₀ H ₃₄ ClNO=580.17) Sub 2-114 m/z=420.11 (C ₂₈ H ₂₁ ClSi=421.01) Sub 2-115 m/z=462.1 (C ₂₉ H ₁₉ ClN ₂ S=463) Sub 2-116 m/z=434.05 (C ₂₈ H ₁₅ ClOS=434.94) Sub 2-117 m/z=267.06 (C ₁₅ H ₁₀ ClN ₃ =267.72) Sub 2-118 m/z=317.07 (C ₁₉ H ₁₂ ClN ₃ =317.78) Sub 2-119 m/z=420.11 (C ₂₆ H ₁₇ ClN ₄ =420.9) Sub 2-120 m/z=419.12 (C ₂₇ H ₁₈ ClN ₃ =419.91) Sub 2-121 m/z=367.09 (C ₂₃ H ₁₄ ClN ₃ =367.84) Sub 2-122 m/z=393.1 (C ₂₅ H ₁₆ ClN ₃ =393.87) Sub 2-123 m/z=393.1 (C ₂₅ H ₁₆ ClN ₃ =393.87) Sub 2-124 m/z=499.09 (C ₃₁ H ₁₈ ClN ₃ S=500.02) Sub 2-125 m/z=434.09 (C ₂₆ H ₁₅ ClN ₄ O=434.88) Sub 2-126 m/z=482.13 (C ₃₁ H ₁₉ ClN ₄ =482.97) Sub 2-127 m/z=614.25 (C ₄₄ H ₃₀ N ₄ =614.75) Sub 2-128 m/z=539.09 (C ₃₃ H ₁₈ ClN ₃ OS=540.04) Sub 2-129 m/z=572.14 (C ₃₇ H ₂₁ ClN ₄ O=573.05) Sub 2-130 m/z=504.12 (C ₃₁ H ₁₃ D ₅ ClN ₃ S=505.05) Sub 2-131 m/z=463.05 (C ₂₇ H ₁₄ ClN ₃ OS=463.94) Sub 2-132 m/z=602.11 (C ₃₇ H ₂₃ BrN ₄ =603.52) Sub 2-133 m/z=457.1 (C ₂₉ H ₁₆ ClN ₃ O=457.92) Sub 2-134 m/z=423.06 (C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub 2-135 m/z=497.09 (C ₃₁ H ₁₆ ClN ₃ O ₂ =497.94) Sub 2-136 m/z=407.12 (C ₂₆ H ₁₈ ClN ₃ =407.9) Sub 2-137 m/z=601.17 (C ₃₉ H ₂₈ ClN ₃ Si=602.21) Sub 2-138 m/z=510.16 (C ₃₃ H ₂₃ ClN ₄ =511.03) Sub 2-139 m/z=367.09 (C ₂₃ H ₁₄ ClN ₃ =367.84) Sub 2-140 m/z=344.08 (C ₂₀ H ₁₃ ClN ₄ =344.8) Sub 2-141 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub 2-142 m/z=407.08 (C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub 2-143 m/z=398.13 (C ₂₅ H ₁₁ D ₅ ClN ₃ =398.9) Sub 2-144 m/z=483.11 (C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub 2-145 m/z=539.09 (C ₃₃ H ₁₈ ClN ₃ OS=540.04) Sub 2-146 m/z=407.08 (C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub 2-147 m/z=473.08 (C ₂₉ H ₁₆ ClN ₃ S=473.98) Sub 2-148 m/z=433.1 (C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub 2-149 m/z=483.11 (C ₃₁ H ₁₈ ClN ₃ O=483.96) Sub 2-150 m/z=308.05 (C ₁₆ H ₉ ClN ₄ O=308.73) Sub 2-151 m/z=384.08 (C ₂₂ H ₁₃ ClN ₄ O=384.82) Sub 2-152 m/z=358.06 (C ₂₀ H ₁₁ ClN ₄ O=358.79) Sub 2-153 m/z=539.09 (C ₃₃ H ₁₈ ClN ₃ OS=540.04) Sub 2-154 m/z=521.13 (C ₃₄ H ₂₀ ClN ₃ O=522) Sub 2-155 m/z=510.16 (C ₃₃ H ₂₃ ClN ₄ =511.03) Sub 2-156 m/z=431.12 (C ₂₈ H ₁₈ ClN ₃ =431.92) Sub 2-157 m/z=416.11 (C ₂₈ H ₁₇ ClN ₂ =416.91) Sub 2-158 m/z=580.17 (C ₄₁ H ₂₅ ClN ₂ =581.12) Sub 2-159 m/z=431.12 (C ₂₈ H ₁₈ ClN ₃ =431.92) Sub 2-160 m/z=392.11 (C ₂₆ H ₁₇ ClN ₂ =392.89) Sub 2-161 m/z=392.11 (C ₂₆ H ₁₇ ClN ₂ =392.89) Sub 2-162 m/z=431.12 (C ₂₈ H ₁₈ ClN ₃ =431.92) Sub 2-163 m/z=430.09 (C ₂₈ H ₁₅ ClN ₂ O=430.89) Sub 2-164 m/z=392.11 (C ₂₆ H ₁₇ ClN ₂ =392.89) Sub 2-165 m/z=494.12 (C ₃₃ H ₁₉ ClN ₂ O=494.98) Sub 2-166 m/z=405.1 (C ₂₆ H ₁₆ ClN ₃ =405.89) Sub 2-167 m/z=330.06 (C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 2-168 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ =316.79) Sub 2-169 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ =316.79) Sub 2-170 m/z=423.06 (C ₂₅ H ₁₄ ClN ₃ S=423.92) Sub 2-171 m/z=290.06 (C ₁₈ H ₁₁ ClN ₂ =290.75) Sub 2-172 m/z=390.09 (C ₂₆ H ₁₅ ClN ₂ =390.87) Sub 2-173 m/z=346.05 (C ₂₀ H ₁₁ ClN ₂ O ₂ =346.77) Sub 2-174 m/z=240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub 2-175 m/z=346.03 (C ₂₀ H ₁₁ ClN ₂ S=346.83) Sub 2-176 m/z=416.11 (C ₂₈ H ₁₇ ClN ₂ =416.91) Sub 2-177 m/z=366.09 (C ₂₄ H ₁₅ ClN ₂ =366.85) Sub 2-178 m/z=406.1 (C ₂₅ H ₁₅ ClN ₄ =406.87) Sub 2-179 m/z=461.08 (C ₂₈ H ₁₆ ClN ₃ S=461.97) Sub 2-180 m/z=413.04 (C ₂₃ H ₁₂ ClN ₃ OS=413.88) Sub 2-181 m/z=402.01 (C ₂₂ H ₁₁ ClN ₂ S ₂ =402.91) Sub 2-182 m/z=296.02 (C ₁₆ H ₉ ClN ₂ S=296.77) Sub 2-183 m/z=330.06 (C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub 2-184 m/z=346.03 (C ₂₀ H ₁₁ ClN ₂ S=346.83)

II. Example of final compound synthesis

P-4 Synthesis Example

Sub 1-3 (5.0 g, 20.2 mmol), Sub 2-4 (9.3 g, 22.2 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.6 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.5 ml, 1.2 mmol) and NaOt-Bu (3.0 g, 30.3 mmol) were used for the synthesis of Sub 1-17 to give the product P-4 (8.8 g, yield: 70%).

P-16 Synthesis Example

Sub 1-2 (5.5 g, 23.7 mmol), Sub 2-15 (13.6 g, 26.2 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.7 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.6 ml, 1.4 mmol) and NaOt-Bu (3.4 g, 35.7 mmol) were used for the synthesis of Sub 1-17 to give the product P-16 (9.6 g, yield: 57%).

P-39 Synthesis Example

Sub 1-4 (5.7 g, 23.0 mmol), Sub 2-36 (10.6 g, 25.4 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.6 ml, 1.4 mmol) and NaOt-Bu (3.3 g, 34.6 mmol) were used for the synthesis of Sub 1-17 to give the product P-39 (10.0 g, yield: 69%).

P-54 Synthesis Example

Sub 1-4 (6.0 g, 24.3 mmol), Sub 2-46 (15.4 g, 26.7 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.7 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.6 ml, 1.5 mmol) and NaOt-Bu (3.5 g, 36.4 mmol) were used for the synthesis of Sub 1-17 to give the product P-54 (11.0 g, yield: 61%).

P-59 synthesis example

Sub 1-16 (10.0 g, 15.3 mmol), Sub 2-1 (2.7 g, 16.9 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.5 mmol) obtained by the above synthesis, 50% P(t-Bu) ₃ (0.4 ml, 1.0 mmol) and NaOt-Bu (2.2 g, 23.0 mmol) were used for the synthesis of Sub 1-17 to give the product P-59 (5.5 g, yield: 50%).

P-70 Synthesis Example

Sub 1-1 (4.0 g, 17.3 mmol), Sub 2-103 (9.9 g, 16.9 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol) obtained by the above synthesis, 50% P(t-Bu) ₃ (0.4 ml, 1.0 mmol) and NaOt-Bu (2.5 g, 26.0 mmol) were used for the synthesis of Sub 1-17 to give the product P-70 (8.9 g, yield: 72%).

P-102 Synthesis Example

Sub 1-4 (4.5 g, 18.2 mmol), Sub 2-130 (9.3 g, 20.0 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.4 ml, 1.1 mmol) and NaOt-Bu (2.6 g, 27.3 mmol) were used for the synthesis of Sub 1-17 to give the product P-102 (8.1 g, yield: 66%).

P-103 Synthesis Example

Sub 1-23 (6.0 g, 22.3 mmol), Sub 2-131 (14.8 g, 24.5 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.6 ml, 1.3 mmol) and NaOt-Bu (3.2 g, 33.4 mmol) were used for the synthesis of Sub 1-17 to give the product P-103 (7.7 g, yield: 44%).

P-113 Synthesis Example

Sub 1-1 (4.8 g, 20.8 mmol), Sub 2-164 (11.3 g, 22.8 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.6 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.5 ml, 1.2 mmol) and NaOt-Bu (3.0 g, 31.1 mmol) were used for the synthesis of Sub 1-17 to give the product P-113 (10.6 g, yield: 75%).

P-118 synthesis example

Sub 1-24 (5.3 g, 16.0 mmol), Sub 2-179 (7.3 g, 17.6 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.5 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.4 ml, 1.0 mmol) and NaOt-Bu (2.3 g, 24.0 mmol) were used for the synthesis of Sub 1-17 to give the product P-118 (4.6 g, yield: 41%).

P-148 Synthesis Example

Sub 1-42 (6.1 g, 14.8 mmol), Sub 2-67 (5.3 g, 16.3 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.4 ml, 0.9 mmol) and NaOt-Bu (2.1 g, 22.2 mmol) were used for the synthesis of Sub 1-17 to give the product P-148 (5.5 g, yield: 57%).

P-171 Synthesis Example

Sub 1-68 (7.0 g, 17.2 mmol), Sub 2-116 (8.2 g, 18.9 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.4 ml, 1.0 mmol) and NaOt-Bu (2.5 g, 25.8 mmol) were used for the synthesis of Sub 1-17 to give the product P-171 (4.4 g, yield: 32%).

P-173 synthesis example

Sub 1-53 (6.3 g, 10.3 mmol), Sub 2-76 (3.0 g, 11.3 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.3 ml, 0.6 mmol) and NaOt-Bu (1.5 g, 15.4 mmol) were used for the synthesis of Sub 1-17 to give the product P-173 (4.8 g, yield: 59%).

P-201 synthesis example

Sub 1-62 (6.8 g, 12.5 mmol), Sub 2-173 (3.3 g, 13.7 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.4 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.3 ml, 0.7 mmol) and NaOt-Bu (1.8 g, 18.7 mmol) were used for the synthesis of Sub 1-17 to give the product P-201 (7.3 g, yield: 79%).

P-207 Synthesis Example

Sub 1-36 (7.0 g, 18.5 mmol), Sub 2-152 (13.6 g, 25.1 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), 50% P(t-Bu) obtained by the above synthesis ₃ (0.6 ml, 1.4 mmol) and NaOt-Bu (3.3 g, 34.3 mmol) were used for the synthesis of Sub 1-17 to give the product P-207 (6.6 g, yield: 36%).

Meanwhile, the FD-MS values of the compounds P-1 to P-219 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=307.10 (C ₂₂ H ₁₃ NO=307.35) P-2 m/z=383.13 (C ₂₈ H ₁₇ NO=383.45) P-3 m/z=459.16 (C ₃₄ H ₂₁ NO=459.55) P-4 m/z=627.2 (C ₄₆ H ₂₉ NS=627.81) P-5 m/z=433.15 (C ₃₂ H ₁₉ NO=433.51) P-6 m/z=373.09 (C ₂₆ H ₁₅ NS=373.47) P-7 m/z=407.13 (C ₃₀ H ₁₇ NO=407.47) P-8 m/z=525.16 (C ₃₈ H ₂₃ NS=525.67) P-9 m/z=547.19 (C ₄₁ H ₂₅ NO=547.66) P-10 m/z=423.16 (C ₃₁ H ₂₁ NO=423.52) P-11 m/z=588.22 (C ₄₃ H ₂₈ N ₂ O=588.71) P-12 m/z=563.17 (C ₄₁ H ₂₅ NS=563.72) P-13 m/z=597.21 (C ₄₅ H ₂₇ NO=597.72) P-14 m/z=671.22 (C ₅₁ H ₂₉ NO=671.8) P-15 m/z=611.17 (C ₄₅ H ₂₅ NS=611.76) P-16 m/z=713.24 (C ₅₃ H ₃₁ NO ₂ =713.84) P-17 m/z=561.16 (C ₄₁ H ₂₃ NS=561.7) P-18 m/z=697.24 (C ₅₃ H ₃₁ NO=697.84) P-19 m/z=563.17 (C ₄₁ H ₂₅ NS=563.72) P-20 m/z=611.19 (C ₄₅ H ₂₅ NO ₂ =611.70) P-21 m/z=611.19 (C ₄₅ H ₂₅ NO ₂ =611.70) P-22 m/z=561.17 (C ₄₁ H ₂₃ NO ₂ =561.64) P-23 m/z=743.19 (C ₅₃ H ₂₉ NO ₂ S=743.88) P-24 m/z=763.25 (C ₅₇ H ₃₃ NO ₂ =763.90) P-25 m/z=637.2 (C ₄₇ H ₂₇ NO ₂ =637.74) P-26 m/z=573.16 (C ₄₂ H ₂₃ NS=573.71) P-27 m/z=809.25 (C ₅₇ H ₃₅ N ₃ OS=809.99) P-28 m/z=388.16 (C ₂₈ H ₁₂ D ₅ NO=388.48) P-29 m/z=477.15 (C ₃₄ H ₂₀ FNO=477.54) P-30 m/z=512.13 (C ₃₆ H ₂₀ N ₂ S=512.63) P-31 m/z=497.14 (C ₃₆ H ₁₉ NO ₂ =497.55) P-32 m/z=473.14 (C ₃₄ H ₁₉ NO ₂ =473.53) P-33 m/z=671.14 (C ₄₆ H ₂₅ NOS ₂ =671.83) P-34 m/z=523.16 (C ₃₈ H ₂₁ NO ₂ =523.59) P-35 m/z=447.13 (C ₃₂ H ₁₇ NO ₂ =447.49) P-36 m/z=615.17 (C ₄₄ H ₂₅ NOS=615.75) P-37 m/z=645.12 (C ₄₄ H ₂₃ NOS ₂ =645.79) P-38 m/z=715.2 (C ₅₂ H ₂₉ NOS=715.87) P-39 m/z=629.14 (C ₄₄ H ₂₃ NO ₂ S=629.73) P-40 m/z=589.15 (C ₄₂ H ₂₃ NOS=589.71) P-41 m/z=790.26 (C ₅₈ H ₃₄ N ₂ O ₂ =790.92) P-42 m/z=760.25 (C ₅₇ H ₃₂ N ₂ O=760.9) P-43 m/z=562.17 (C ₄₀ H ₂₂ N ₂ O ₂ =562.63) P-44 m/z=572.19 (C ₄₂ H ₂₄ N ₂ O=572.67) P-45 m/z=622.24 (C ₄₄ H ₃₄ N ₂ S=622.83) P-46 m/z=648.22 (C ₄₈ H ₂₈ N ₂ O=648.77) P-47 m/z=628.16 (C ₄₄ H ₂₄ N ₂ OS=628.75) P-48 m/z=572.19 (C ₄₂ H ₂₄ N ₂ O=572.67) P-49 m/z=703.21 (C ₅₀ H ₂₉ N ₃ S=703.86) P-50 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) P-51 m/z=704.19 (C ₅₀ H ₂₈ N ₂ OS=704.85) P-52 m/z=756.26 (C ₅₅ H ₃₆ N ₂ S=756.97) P-53 m/z=852.26 (C ₆₃ H ₃₆ N ₂ S=853.06) P-54 m/z=742.21 (C ₅₃ H ₃₀ N ₂ OS=742.9) P-55 m/z=490.15 (C ₃₄ H ₂₂ N ₂ S=490.62) P-56 m/z=626.24 (C ₄₆ H ₃₀ N ₂ O=626.76) P-57 m/z=600.22 (C ₄₄ H ₂₈ N ₂ O=600.72) P-58 m/z=540.17 (C ₃₈ H ₂₄ N ₂ S=540.68) P-59 m/z=728.25 (C ₅₃ H ₃₂ N ₂ O ₂ =728.85) P-60 m/z=614.2 (C ₄₄ H ₂₆ N ₂ O ₂ =614.7) P-61 m/z=696.17 (C ₄₈ H ₂₈ N ₂ S ₂ =696.89) P-62 m/z=690.23 (C ₅₀ H ₃₀ N ₂ O ₂ =690.8) P-63 m/z=720.19 (C ₅₀ H ₂₈ N ₂ O ₂ S=720.85) P-64 m/z=630.18 (C ₄₄ H ₂₆ N ₂ OS=630.77) P-65 m/z=748.2 (C ₅₂ H ₃₂ N ₂ S ₂ =748.96) P-66 m/z=640.22 (C ₄₆ H ₂₈ N ₂ O ₂ =640.74) P-67 m/z=639.23 (C ₄₆ H ₂₉ N ₃ O=639.76) P-68 m/z=639.23 (C ₄₆ H ₂₉ N ₃ O=639.76) P-69 m/z=682.24 (C ₄₉ H ₃₄ N ₂ S=682.89) P-70 m/z=714.23 (C ₅₂ H ₃₀ N ₂ O ₂ =714.82) P-71 m/z=796.22 (C ₅₆ H ₃₂ N ₂ O ₂ S=796.94) P-72 m/z=731.29 (C ₅₃ H ₃₇ N ₃ O=731.9) P-73 m/z=691.26 (C ₅₀ H ₃₃ N ₃ O=691.83) P-74 m/z=747.23 (C ₅₂ H ₃₃ N ₃ OS=747.92) P-75 m/z=614.2 (C ₄₄ H ₂₆ N ₂ O ₂ =614.7) P-76 m/z=670.17 (C ₄₆ H ₂₆ N ₂ O ₂ S=670.79) P-77 m/z=706.21 (C ₅₀ H ₃₀ N ₂ OS=706.86) P-78 m/z=728.25 (C ₅₃ H ₃₂ N ₂ O ₂ =728.85) P-79 m/z=664.22 (C ₄₈ H ₂₈ N ₂ O ₂ =664.76) P-80 m/z=854.29 (C ₆₃ H ₃₈ N ₂ O ₂ =855.01) P-81 m/z=802.26 (C ₅₉ H ₃₄ N ₂ O ₂ =802.93) P-82 m/z=706.21 (C ₅₀ H ₃₀ N ₂ OS=706.86) P-83 m/z=790.3 (C ₅₆ H ₄₂ N ₂ OS=791.03) P-84 m/z=665.22 (C ₄₈ H ₃₁ NOSi=665.87) P-85 m/z=673.16 (C ₄₅ H ₂₇ N ₃ S ₂ =673.85) P-86 m/z=478.13 (C ₃₁ H ₁₈ N4S=478.57) P-87 m/z=512.16 (C ₃₅ H ₂₀ N _4O =512.57) P-88 m/z=615.21 (C ₄₂ H ₂₅ N5O=615.7) P-89 m/z=630.19 (C ₄₃ H ₂₆ N ₄ S=630.77) P-90 m/z=562.18 (C ₃₉ H ₂₂ N ₄ O=562.63) P-91 m/z=588.20 (C ₄₁ H ₂₄ N ₄ O=588.67) P-92 m/z=588.20 (C ₄₁ H ₂₄ N ₄ O=588.67) P-93 m/z=694.18 (C ₄₇ H ₂₆ N ₄ OS=694.81) P-94 m/z=679.2 (C ₄₆ H ₂₅ N ₅ O ₂ =679.74) P-95 m/z=677.22 (C ₄₇ H ₂₇ N ₅ O=677.77) P-96 m/z=795.25 (C ₅₅ H ₃₃ N ₅ S=795.96) P-97 m/z=677.22 (C ₄₇ H ₂₇ N ₅ O=677.77) P-98 m/z=775.26 (C ₅₇ H ₃₃ N ₃ O=775.91) P-99 m/z=750.15 (C ₄₉ H ₂₆ N ₄ OS ₂ =750.89) P-100 m/z=767.23 (C ₅₃ H ₂₉ N ₅ O ₂ =767.85) P-101 m/z=699.21 (C ₄₇ H ₂₁ D ₅ N ₄ OS=699.84) P-102 m/z=674.12 (C ₄₃ H ₂₂ N ₄ OS ₂ =674.8) P-103 m/z=791.27 (C ₅₆ H ₃₃ N ₅ O=791.91) P-104 m/z=668.17 (C ₄₅ H ₂₄ N ₄ OS=668.77) P-105 m/z=618.15 (C ₄₁ H ₂₂ N ₄ OS=618.71) P-106 m/z=708.16 (C ₄₇ H ₂₄ N ₄ O ₂ S=708.8) P-107 m/z=626.21 (C ₄₄ H ₂₆ N ₄ O=626.72) P-108 m/z=491.11 (C ₃₂ H ₁₇ N ₃ OS=491.57) P-109 m/z=525.15 (C ₃₆ H ₁₉ N ₃ O ₂ =525.57) P-110 m/z=641.16 (C ₄₄ H ₂₃ N ₃ OS=641.75) P-111 m/z=587.20 (C ₄₂ H ₂₅ N ₃ O=587.68) P-112 m/z=611.20 (C ₄₄ H ₂₅ N ₃ O=611.70) P-113 m/z=689.21 (C ₄₉ H ₂₇ N ₃ O ₂ =689.77) P-114 m/z=616.17 (C ₄₂ H ₂₄ N ₄ S=616.74) P-115 m/z=525.15 (C ₃₆ H ₁₉ N ₃ O ₂ =525.57) P-116 m/z=511.17 (C ₃₆ H ₂₁ N ₃ O=511.58) P-117 m/z=613.07 (C ₃₈ H ₁₉ N ₃ S ₃ =613.77) P-118 m/z=708.16 (C ₄₇ H ₂₄ N ₄ O ₂ S=708.8) P-119 m/z=511.17 (C ₃₆ H ₂₁ N ₃ O=511.58) P-120 m/z=868.28 (C ₆₂ H ₃₆ N ₄ O ₂ =869.00) P-121 m/z=723.14 (C ₄₈ H ₂₅ N ₃ OS ₂ =723.87) P-122 m/z=796.27 (C ₅₅ H ₃₆ N ₄ OSi=797.01) P-123 m/z=654.19 (C ₄₅ H ₂₆ N ₄ S=654.79) P-124 m/z=618.15 (C ₄₁ H ₂₂ N ₄ OS=618.71) P-125 m/z=705.25 (C ₄₉ H ₃₁ N ₅ O=705.82) P-126 m/z=548.23 (C ₄₁ H ₂₈ N ₂ =548.69) P-127 m/z=751.3 (C ₅₆ H ₃₇ N ₃ =751.93) P-128 m/z=624.23 (C ₄₅ H ₂₈ N ₄ =624.75) P-129 m/z=664.2 (C ₄₈ H ₂₈ N ₂ S=664.83) P-130 m/z=688.22 (C ₅₀ H ₂₈ N ₂ O ₂ =688.79) P-131 m/z=648.22 (C ₄₈ H ₂₈ N ₂ O=648.77) P-132 m/z=726.21 (C ₅₃ H ₃₀ N ₂ S=726.9) P-133 m/z=798.3 (C ₆₁ H ₃₈ N ₂ =798.99) P-134 m/z=704.19 (C ₅₀ H ₂₈ N ₂ OS=704.85) P-135 m/z=712.25 (C ₅₃ H ₃₂ N ₂ O=712.85) P-136 m/z=801.28 (C ₅₉ H ₃₅ N ₃ O=801.95) P-137 m/z=803.29 (C ₅₉ H ₃₇ N ₃ O=803.97) P-138 m/z=746.27 (C ₅₇ H ₃₄ N ₂ =746.91) P-139 m/z=787.3 (C ₅ 9H ₃₇ N ₃ =787.97) P-140 m/z=665.28 (C ₄₉ H ₃₅ N ₃ =665.84) P-141 m/z=840.28 (C ₆₂ H ₃₆ N ₂ O ₂ =840.98) P-142 m/z=716.23 (C ₅₂ H ₃₂ N ₂ S=716.9) P-143 m/z=654.18 (C ₄₆ H ₂₆ N ₂ OS=654.79) P-144 m/z=737.25 (C ₅₄ H ₃₁ N ₃ O=737.86) P-145 m/z=704.19 (C ₅₀ H ₂₈ N ₂ OS=704.85) P-146 m/z=764.25 (C ₅₆ H ₃₂ N ₂ O ₂ =764.88) P-147 m/z=712.26 (C ₅₂ H ₃₂ N ₄ =712.86) P-148 m/z=653.19 (C ₄₆ H ₂₇ N ₃ S=653.8) P-149 m/z=690.21 (C ₅₀ H ₃₀ N ₂ S=690.86) P-150 m/z=698.24 (C ₅₂ H ₃₀ N ₂ O=698.83) P-151 m/z=647.24 (C ₄₈ H ₂₉ N ₃ =647.78) P-152 m/z=675.27 (C ₅₀ H ₃₃ N ₃ =675.84) P-153 m/z=597.22 (C ₄₄ H ₂₇ N ₃ =597.72) P-154 m/z=686.24 (C ₅₁ H ₃₀ N ₂ O=686.81) P-155 m/z=598.2 (C ₄₄ H ₂₆ N ₂ O=598.71) P-156 m/z=749.28 (C ₅₆ H ₃₅ N ₃ =749.92) P-157 m/z=687.23 (C ₅₀ H ₂₉ N ₃ O=687.8) P-158 m/z=689.25 (C ₅₀ H ₃₁ N ₃ O=689.82) P-159 m/z=705.22 (C ₅₀ H ₃₁ N ₃ S=705.88) P-160 m/z=804.29 (C ₅₈ H ₃₆ N ₄ O=804.95) P-161 m/z=689.28 (C ₅₁ H ₃₅ N ₃ =689.86) P-162 m/z=716.29 (C ₅₂ H ₃₆ N ₄ =716.89) P-163 m/z=689.25 (C ₅₀ H ₃₁ N ₃ O=689.82) P-164 m/z=787.3 (C ₅₉ H ₃₇ N ₃ =787.97) P-165 m/z=716.29 (C ₅₂ H ₃₆ N ₄ =716.89) P-166 m/z=655.21 (C ₄₆ H ₂₉ N ₃ S=655.82) P-167 m/z=766.31 (C ₅₆ H ₃₈ N ₄ =766.95) P-168 m/z=714.28 (C ₅₂ H ₃₄ N ₄ =714.87) P-169 m/z=714.28 (C ₅₂ H ₃₄ N ₄ =714.87) P-170 m/z=792.33 (C ₅₉ H ₃₂ D ₅ N ₃ =793.00) P-171 m/z=804.22 (C ₅₈ H ₃₂ N ₂ OS=804.97) P-172 m/z=812.28 (C ₆₁ H ₃₆ N ₂ O=812.97) P-173 m/z=795.23 (C ₅₆ H ₃₃ N ₃ OS=795.96) P-174 m/z=781.35 (C ₅₈ H ₄₃ N ₃ =782) P-175 m/z=605.16 (C ₄₁ H ₂₃ N ₃ OS=605.72) P-176 m/z=613.23 (C ₄₃ H ₂₇ N ₅ =613.72) P-177 m/z=637.23 (C ₄₅ H ₂₇ N ₅ =637.75) P-178 m/z=664.24 (C ₄₆ H ₂₈ N ₆ =664.77) P-179 m/z=631.22 (C ₄₃ H ₂₆ FN ₅ =631.71) P-180 m/z=677.22 (C ₄₇ H ₂₇ N ₅ O=677.77) P-181 m/z=727.27 (C ₅₂ H ₃₃ N ₅ =727.87) P-182 m/z=668.27 (C ₄₇ H ₂₄ D ₅ N ₅ =668.81) P-183 m/z=753.25 (C ₅₃ H ₃₁ N ₅ O=753.87) P-184 m/z=777.29 (C ₅₆ H ₃₅ N ₅ =777.93) P-185 m/z=753.25 (C ₅₃ H ₃₁ N ₅ O=753.87) P-186 m/z=753.25 (C ₅₃ H ₃₁ N ₅ O=753.87) P-187 m/z=809.22 (C ₅₅ H ₃₁ N ₅ OS=809.95) P-188 m/z=677.22 (C ₄₇ H ₂₇ N ₅ O=677.77) P-189 m/z=733.19 (C ₄₉ H ₂₇ N ₅ OS=733.85) P-190 m/z=743.21 (C ₅₁ H ₂₉ N ₅ S=743.89) P-191 m/z=767.23 (C ₅₃ H ₂₉ N ₅ O ₂ =767.85) P-192 m/z=654.22 (C ₄₄ H ₂₆ N ₆ O=654.73) P-193 m/z=654.22 (C ₄₄ H ₂₆ N ₆ O=654.73) P-194 m/z=712.26 (C ₅₂ H ₃₂ N ₄ =712.86) P-195 m/z=662.25 (C ₄₈ H ₃₀ N ₄ =662.8) P-196 m/z=807.25 (C ₅₆ H ₃₃ N ₅ S=807.98) P-197 m/z=650.21 (C ₄₆ H ₂₆ N ₄ O=650.74) P-198 m/z=725.26 (C ₅₂ H ₃₁ N ₅ =725.86) P-199 m/z=766.22 (C ₅₄ H ₃₀ N ₄ S=766.92) P-200 m/z=666.21 (C ₄₆ H ₂₆ N ₄ O ₂ =666.74) P-201 m/z=748.26 (C ₅₅ H ₃₂ N ₄ =748.89) P-202 m/z=616.17 (C ₄₂ H ₂₄ N ₄ S=616.74) P-203 m/z=686.25 (C ₅₀ H ₃₀ N ₄ =686.82) P-204 m/z=616.17 (C ₄₂ H ₂₄ N ₄ S=616.74) P-205 m/z=730.22 (C ₅₁ H ₃₀ N ₄ S=730.89) P-206 m/z=686.25 (C ₅₀ H ₃₀ N ₄ =686.82) P-207 m/z=809.22 (C ₅₅ H ₃₁ N ₅ OS=809.95) P-208 m/z=791.27 (C ₅₆ H ₃₃ N ₅ O=791.91) P-209 m/z=727.27 (C ₅₂ H ₃₃ N ₅ =727.87) P-210 m/z=654.22 (C ₄₄ H ₂₆ N ₆ O=654.73) P-211 m/z=780.3 (C ₅₅ H ₃₆ N ₆ =780.94) P-212 m/z=676.24 (C ₄₇ H ₂₈ N ₆ =676.78) P-213 m/z=678.22 (C ₄₆ H ₂₆ N ₆ O=678.76) P-214 m/z=752.26 (C ₅₄ H ₃₂ N ₄ O=752.88) P-215 m/z=701.26 (C ₅₀ H ₃₁ N ₅ =701.83) P-216 m/z=759.17 (C ₅₃ H ₂₉ NOS2=759.94) P-217 m/z=721.17 (C ₅₀ H ₂₇ NO ₃ S=721.83) P-218 m/z=669.15 (C ₄₅ H ₂₃ N ₃ O ₂ S=669.76) P-219 m/z=625.09 (C ₃₉ H ₁₉ N ₃ O ₂ S ₂ =625.72)

Manufacturing evaluation of organic electric devices

(Example 1) Red organic electroluminescent device (emission auxiliary layer)

An organic electroluminescent device was manufactured according to a conventional method by using the compound of the present invention as a material for the light-emitting auxiliary layer.

First, on an ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (hereinafter, abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.

N, N'-Bis(1-naphthalenyl)-N, N'-bis-phenyl-(1, 1'-Biphenyl)-4, 4'-diamine (hereinafter referred to as NPB about Flag) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

On the hole transport layer, the compound (P-3) of the present invention represented by Chemical Formula 1 as a material for the hole hole auxiliary layer was vacuum-deposited to a thickness of 20 nm to form a light emission auxiliary layer.

CBP [4,4'-N,N'-dicarbazole-biphenyl] was used as a host on the light emitting auxiliary layer, and (piq) ₂ Ir (acac) [bis- (1-phenyl isoquinolyl) iridium ( Ⅲ) acetylacetonate] was used, and a light emitting layer with a thickness of 30 nm was deposited by doping at a weight ratio of 95:5.

(1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed.

Tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Then, an organic electroluminescent device was manufactured by depositing an alkali metal halide LiF to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.

(Example 2) to (Example 20)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-3 of the present invention as the material of the light emitting auxiliary layer.

(Comparative Example 1) to (Comparative Example 2)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compounds A to B were used instead of the compound P-3 of the present invention as the light emitting auxiliary layer material.

<Comparative compound A> <Comparative compound B>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 20 and Comparative Examples 1 to 2, the electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, 2500 cd/ The T95 lifetime was measured using a lifetime measuring device manufactured by McScience at m ² standard luminance. Table 4 below shows the manufactured devices and evaluation results.

compound Driving
Voltage (V) current density
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) CIE x y Comparative Example (1) Comparative compound A 5.8 13.6 2500 18.4 88.4 0.63 0.32 Comparative Example (2) Comparative compound B 5.6 12.7 2500 19.7 94.0 0.64 0.31 Example (1) P-3 4.9 9.6 2500 26.1 135.8 0.60 0.32 Example (2) P-4 4.9 9.5 2500 26.3 136.7 0.61 0.31 Example (3) P-22 4.8 10.9 2500 22.8 129.4 0.61 0.35 Example (4) P-35 4.8 10.6 2500 23.5 123.9 0.64 0.32 Example (5) P-44 4.8 10.3 2500 24.3 133.9 0.63 0.34 Example (6) P-51 5.0 10.5 2500 23.9 122.0 0.61 0.31 Example (7) P-56 5.1 9.7 2500 25.8 134.9 0.60 0.34 Example (8) P-59 5.0 10.1 2500 24.8 127.5 0.60 0.35 Example (9) P-67 5.0 10.0 2500 25.0 124.8 0.61 0.31 Example (10) P-76 5.0 10.2 2500 24.6 126.6 0.61 0.31 Example (11) P-134 5.0 10.5 2500 23.7 121.1 0.61 0.31 Example (12) P-140 5.1 9.4 2500 26.5 120.2 0.65 0.35 Example (13) P-143 4.9 11.0 2500 22.6 122.9 0.61 0.32 Example (14) P-151 4.9 10.4 2500 24.1 133.0 0.60 0.35 Example (15) P-152 5.1 9.8 2500 25.6 131.2 0.60 0.31 Example (16) P-159 5.0 9.8 2500 25.4 128.4 0.62 0.34 Example (17) P-162 5.1 9.4 2500 26.7 132.1 0.61 0.34 Example (18) P-168 5.1 9.9 2500 25.2 125.7 0.60 0.34 Example (19) P-174 4.9 10.7 2500 23.3 119.3 0.61 0.34 Example (20) P-216 4.9 10.8 2500 23.1 130.3 0.63 0.35

As can be seen from the results of Table 4, when a red organic electric device is manufactured using the material for an organic electric device of the present invention as a light emitting auxiliary layer material, the light emitting auxiliary layer is not used or Comparative Compounds A to B are used. It can be seen that not only the driving voltage of the organic light emitting diode can be lowered compared to Comparative Examples 1 and 2, but also the luminous efficiency and lifespan are significantly improved.

Comparing Comparative Example 1 and Comparative Example 2, the biggest difference is the difference in elements contained in the core structure. It can be seen that when an oxygen atom is introduced in Comparative Example 2 as compared to carbon in Comparative Example 1, chemical stability is increased, thereby positively affecting device performance.

Comparing the results of Comparative Examples and Examples 1 to 20, it can be seen that a difference in mobility appears significantly depending on the type of element contained in the core core, and this difference in mobility affects the overall device. there is. Since the core element of the Examples has higher chemical stability, a higher refractive index, and a higher Tg value than the carbon element of the Comparative Example, it can be confirmed that the luminous efficiency and thermal stability are improved, thereby increasing the lifespan.

In addition, by using the compound of the present invention as a light emitting auxiliary layer, the HOMO or LUMO energy level of the compound of the present invention has an appropriate value between the hole transport layer and the light emitting layer, so that holes and electrons are in charge balance ), and it can be seen that the efficiency and lifespan are maximized because light is emitted inside the light emitting layer rather than the interface of the hole transport layer.

On the other hand, comparing the results of the embodiments of the present invention, there is a difference in driving voltage and luminous efficiency depending on the presence and substitution position of the element and amino group of the central core, and different lifespan results are obtained depending on the type of element of the core core. know it's coming In the case of a chemical structure with strong resistance to holes and electrons, it was confirmed that overall lifespan increased, and there was a large difference in driving voltage and efficiency according to the HOMO level.

In the case of the light-emitting auxiliary layer, it is necessary to understand the correlation between the hole transport layer and the light-emitting layer (host). It will be very difficult.

Although the device characteristics in which the compound of the present invention is applied to only one layer of the light emitting auxiliary layer has been described in the evaluation result of the above device fabrication, it can be applied even when the hole transport layer or both the hole transport layer and the light emission auxiliary layer are formed with the compound of the present invention. will be.

(Example 21) Red organic electroluminescent device (phosphorescent host)

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a red host material of the light emitting layer.

First, on an ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (hereinafter, abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.

On the hole injection layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) as a hole transport compound was vacuum deposited to a thickness of 60 nm to form a hole transport layer. formed.

Compound P-1 of the present invention represented by Formula 1 was used as a host on the hole transport layer, and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] was used as a dopant Thus, a light emitting layer with a thickness of 30 nm was deposited by doping at a 95:5 weight ratio.

(1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed.

Tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Then, an organic electroluminescent device was manufactured by depositing an alkali metal halide LiF to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.

(Example 21) to (Example 37)

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

(Comparative Example 3) to (Comparative Example 4)

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that the following comparative compounds C to D were used instead of the compound P-1 of the present invention as the host material of the light emitting layer.

<Comparative compound C> <Comparative compound D>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 21 to 37 and Comparative Examples 3 to 4, the electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and 2500 cd / The T95 lifetime was measured using a lifetime measuring device manufactured by McScience at m ² standard luminance. Table 5 below shows the manufactured devices and evaluation results.

compound Driving
Voltage (V) current density
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) CIE x y Comparative Example (3) Comparative compound C 5.6 12.9 2500 19.4 87.4 0.64 0.32 Comparative Example (4) Comparative compound D 5.4 12.3 2500 20.3 101.1 0.60 0.33 Example (21) P-1 5.0 10.0 2500 25.0 118.0 0.64 0.34 Example (22) P-8 5.0 10.1 2500 24.7 116.9 0.62 0.32 Example (23) P-20 4.9 10.3 2500 24.4 113.5 0.63 0.34 Example (24) P-86 4.8 9.1 2500 27.5 128.0 0.62 0.30 Example (25) P-91 4.8 9.3 2500 26.9 125.8 0.65 0.31 Example (26) P-93 4.7 8.8 2500 28.4 119.1 0.62 0.34 Example (27) P-98 4.9 9.6 2500 26.1 122.4 0.61 0.31 Example (28) P-154 4.9 10.4 2500 24.1 112.4 0.62 0.31 Example (29) P-178 4.7 8.9 2500 28.1 126.9 0.64 0.33 Example (30) P-179 4.8 9.2 2500 27.2 111.3 0.61 0.31 Example (31) P-197 4.8 9.8 2500 25.5 114.6 0.64 0.30 Example (32) P-198 4.9 9.7 2500 25.8 115.7 0.60 0.31 Example (33) P-200 4.9 9.5 2500 26.4 123.5 0.61 0.30 Example (34) P-202 4.8 9.4 2500 26.7 121.3 0.62 0.30 Example (35) P-208 4.7 9.0 2500 27.8 124.6 0.65 0.31 Example (36) P-212 4.6 9.9 2500 25.2 110.2 0.63 0.31 Example (37) P-218 4.7 8.7 2500 28.7 120.2 0.65 0.33

As can be seen from the results of Table 5, when the compound of the present invention is used as a material for the light emitting layer, it can be seen that the driving voltage is lowered and the efficiency and lifespan are significantly improved compared to the case where Comparative Compounds C to D are used.

That is, the characteristic of the present invention is that there is a big difference in performance depending on the difference between the elements contained in the core and the substitution position of the heteroaryl group. Among the heteroaryl groups, triazine showed the best performance, and this effect is due to the strong electrical properties of triazine. In addition, there were differences in driving voltage, efficiency, and lifespan depending on the type of secondary substituent connected to the heteroaryl group. In the case of secondary substituents with increased planarity, the driving voltage was lowered, and secondary substituents containing carbon atoms In this case, it had a bad result on the lifespan.

The compound of the present invention contains S, O, or N elements in the structure of Formula 1, thereby exhibiting a higher refractive index and a higher Tg value than the comparative compound, and has a LUMO level at which the energy transfer effect is maximized, resulting in light emission. It can be seen that the efficiency is greatly improved, and the lifespan is also remarkably improved due to the high thermal stability.

Through comparison with the comparative compound, it was confirmed that the device results were improved depending on the substitution position, and the core of the present invention also showed significantly different device results depending on the position of the heterocyclic group.

These results show that the energy level or thin film characteristics of the compound are significantly different depending on the type of heteroelement or specific substituent as well as the physical aspect, and such a difference is an important factor (for example, energy balance, stability, etc.), suggesting that such unpredictable device results can be derived.

(Example 38) Red organic electroluminescent device (phosphorescent host)

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a red host material of the light emitting layer.

First, on an ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (hereinafter, abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.

4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) as a hole transport compound on the hole injection layer was vacuum deposited to a thickness of 60 nm to form a hole transport layer. formed.

Compound P-86 of the present invention represented by Formula 1 was used as a host on the hole transport layer, and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] was used as a dopant Thus, a light emitting layer with a thickness of 30 nm was deposited by doping at a 95:5 weight ratio.

(1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed.

Tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

(Example 39) to (Example 41)

An organic electroluminescent device was manufactured in the same manner as in Example 38, except that the compound of the present invention shown in Table 6 was used instead of the compound P-86 of the present invention as the host material of the light emitting layer.

(Example 42) to (Example 45)

As the host material of the light emitting layer, a mixture of compound P-1 to compound P-86 (weight ratio 5:5) and the compound of the present invention described in Table 6 were used instead of compound P-86 of the present invention. An organic electroluminescent device was manufactured in the same manner as in Example 38.

(Example 46) to (Example 49)

An organic electroluminescent device was manufactured in the same manner as in Example 42, except that the compound D-21 of the present invention was used as a dopant material for the emission layer.

(Comparative Example 5)

An organic electroluminescent device was manufactured in the same manner as in Example 38, except that a mixture of Comparative Compound C and Comparative Compound D (weight ratio 5:5) was used as the host material of the light emitting layer.

<Comparative compound C> <Comparative compound D>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 38 to 49 and Comparative Example 5, the electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, 2500cd/m ² The T95 lifetime was measured using a lifetime measuring device manufactured by McScience at the reference luminance. Table 6 below shows the manufactured devices and evaluation results.

dopant first compound second compound Driving
Voltage
(V) electric current
density
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) CIE x y comparative example
(5) (piq) ₂ Ir
(acac) comparison
compound C comparison
compound D 5.3 11.8 2500.0 21.1 103.4 0.61 0.34 Example
(38) (piq) ₂ Ir
(acac) - P-86 4.7 8.8 2500.0 28.3 127.4 0.62 0.31 Example
(39) (piq) ₂ Ir
(acac) - P-90 4.6 9.1 2500.0 27.4 124.7 0.63 0.34 Example
(40) (piq) ₂ Ir
(acac) - P-191 4.5 9.2 2500.0 27.1 119.7 0.61 0.33 Example
(41) (piq) ₂ Ir
(acac) - P-185 4.6 8.9 2500.0 28.1 121.4 0.61 0.33 Example
(42) (piq) ₂ Ir
(acac) P-1 P-86 4.6 8.6 2500.0 29.0 130.4 0.62 0.33 Example
(43) (piq) ₂ Ir
(acac) P-35 P-90 4.5 9.0 2500.0 27.8 128.1 0.61 0.33 Example
(44) (piq) ₂ Ir
(acac) P-73 P-191 4.4 9.0 2500.0 27.7 123.7 0.60 0.33 Example
(45) (piq) ₂ Ir
(acac) P-163 P-185 4.5 8.7 2500.0 28.6 126.3 0.65 0.30 Example
(46) D-21 P-1 P-86 4.6 8.4 2500.0 29.8 132.4 0.62 0.35 Example
(47) D-21 P-35 P-90 4.5 8.8 2500.0 28.4 130.8 0.65 0.34 Example
(48) D-21 P-73 P-191 4.4 8.9 2500.0 28.2 125.5 0.62 0.31 Example
(49) D-21 P-163 P-185 4.5 8.5 2500.0 29.5 128.6 0.64 0.32

As can be seen from the results of Table 6, when the compound of the present invention is used as a material for the light emitting layer, it can be seen that the driving voltage is lowered and the efficiency and lifespan are significantly improved compared to the case of Comparative Example 5.

In the case of using the mixed light emitting layer material in the example compounds, the performance was better than that of using a single material, and this effect was also shown in the mixture of the compounds of the comparative example. However, the performance increased according to the type of mixture, and a material with high performance as a single material showed good performance even in the mixture.

In Examples 46 to 49, the type of dopant was changed under the conditions of the same mixture. In the case of the dopant, the driving voltage decreased, the efficiency increased, and the lifetime was increased. Through this, it was found that the type of a specific dopant has a positive effect on device performance. This result is considered to have a positive effect on overall device performance as electron and hole injection becomes smooth due to a decrease in the difference in energy level generated between the dopant and the mixture.

The above description is merely illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains may include other compounds within a range that does not depart from the essential characteristics of the present invention, such as a method for improving performance, etc. transformation will be possible.

Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to limit the present invention, and the scope of the spirit of the present invention is not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

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

Claims (20)

A compound represented by the following formula (1):
<Formula 1>

In Formula 1,
1) X and Y are each independently O, S or -NL ₁ -Ar ₃ ,
2) a is an integer from 0 to 5; b is an integer from 0 to 3,
3) L ₁ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; or a combination thereof,
4) Ar ₃ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or C ₃ ~ C ₆₀ An aliphatic ring and C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; amine group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or a combination thereof,
5) R ¹ and R ² are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,
6) the R ¹ to R ² , Ar ₃ , L ₁ and the rings formed by bonding adjacent groups to each other are deuterium; halogen; C ₁ ~ C ₃₀ Alkyl group or C ₆ ~ C ₃₀ A silane group unsubstituted or substituted with an aryl group; siloxane group; boron group; germanium group; cyano group; amino group; nitro group; C ₁ ~ C ₃₀ Alkylthio group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Arylalkoxy group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ Aryl group substituted with deuterium; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₃₀ A heterocyclic group; C ₃ ~ C ₃₀ of an aliphatic ring; C ₇ ~ C ₃₀ Arylalkyl group; C ₈ ~ C ₃₀ Aryl alkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof, and adjacent substituents may form a ring. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-10:
(Formula 1-1) (Formula 1-2) (Formula 1-3) (Formula 1-4)

(Formula 1-5) (Formula 1-6) (Formula 1-7) (Formula 1-8)

(Formula 1-9) (Formula 1-10)

In Formulas 1-1 to 1-10,
1) The R ¹ to R ² , Ar ₃ , L ₁ and a to b are the same as defined in Formula 1 of claim 1,
2) Ar ₄ is the same as the definition of Ar ₃ in Formula 1 of claim 1. The compound according to claim 1, wherein R ¹ , R ² and Ar ₃ of Formula 1 are each independently represented by Formula 2-1 or Formula 2-2:
(Formula 2-1) (Formula 2-2)

In Formulas 2-1 to 2-2,
1) The L ₁ is the same as defined in Formula 1 of claim 1,
2) Z ¹ to Z ⁵ are each independently C(R ₁ ) or N; At least one of Z ¹ to Z ⁵ is N,
3) Z ⁶ ~Z ⁸ are each independently C(R ₁ ) or N; At least one of Z ⁶ to Z ⁸ is N,
4) R ₁ is hydrogen; heavy hydrogen; halogen; C ₁ ~ C ₂₀ Alkyl group or C ₆ ~ C ₂₀ A silane group unsubstituted or substituted with an aryl group; cyano group; nitro group; C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy 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; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic ring group; C ₇ ~ C ₂₀ Arylalkyl group; And C ₈ ~ C ₂₀ It is selected from the group consisting of an aryl alkenyl group; Or it may combine with a neighboring group to form a ring,
5) C ring is a C ₆ ~ C ₃₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₃₀ A heterocyclic group; C ₃ ~ C ₃₀ of an aliphatic ring; C ₇ ~ C ₃₀ Arylalkyl group; C ₈ ~ C ₃₀ Aryl alkenyl group; or a combination thereof; Alternatively, it may combine with a neighboring group to form a ring. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-3 to 2-8:
(Formula 2-3) (Formula 2-4) (Formula 2-5)

(Formula 2-6) (Formula 2-7) (Formula 2-8)

In Formula 2-3 to Formula 2-8,
1) The R ¹ to R ² , L ₁ , Ar ₃ and a to b are the same as defined in Formula 1 of claim 1,
2) Ar ₁ to Ar ₂ are the same as the definition of Ar ₃ in Formula 1 of claim 1,
3) X ₁ to X ₃ are each independently N or CH; At least one of X ₁ to X ₃ is N. The compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-11 or Chemical Formula 1-12:
(Formula 1-11) (Formula 1-12)

In Formulas 1-11 to 1-12,
1) R ¹ to R ² , X, Y and a to b are the same as defined in Formula 1 of claim 1,
2) L ₂ ~ L ₄ is the same as the definition of L ₁ in Formula 1 of claim 1,
3) Ar ₄ to Ar ₅ are the same as the definition of Ar ₃ in Formula 1 of claim 1. The compound according to claim 1, wherein Formula 1 is represented by Formula 1-13 or Formula 1-14:
(Formula 1-13) (Formula 1-14)

In Formulas 1-13 to 1-14,
1) R ¹ to R ² , X, Y and a to b are the same as defined in Formula 1 of claim 1,
2) L ₂ ~ L ₄ is the same as the definition of L ₁ in Formula 1 of claim 1,
3) Ar ₅ is the same as the definition of Ar ₃ in Formula 1 of claim 1,
4) Z is substituted or unsubstituted C, O, S or N. The compound according to claim 1, wherein the compound represented by Formula 1 is one of the following P-1 to P-219:

a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound represented by the formula (1) of claim 1 alone or in combination. a first electrode; a second electrode; an organic material layer formed between the first electrode and the second electrode; And in the organic electric device comprising a capping layer,
The capping layer is formed on one surface of both surfaces of the first electrode and the second electrode that is not in contact with the organic material layer,
The organic material layer or the capping layer is an organic electric device comprising the compound represented by Formula 1 of claim 1 alone or in combination. [10] The organic electric device according to claim 8 or 9, wherein the organic material layer further comprises a compound of formula (3) as a dopant material:
(Formula 3)

In Formula 3,
1) M is a metal with an atomic weight of 40 or more,
2) L is an auxiliary ligand,
3) m is the oxidation number of M,
4) n is greater than or equal to 1,
5) R ⁷ and R ⁸ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,
6) c and d are each independently an integer of 0-4. The organic electric device according to claim 10, wherein Chemical Formula 3 is represented by any one of the following Chemical Formulas 3-1 to 3-6:
(Formula 3-1) (Formula 3-2) (Formula 3-3)

(Formula 3-4) (Formula 3-5) (Formula 3-6)

In Formulas 3-1 to 3-6,
1) M, L, m, n, d, R ⁷ and R ⁸ are as defined in Formula 3 of claim 8,
2) In Formulas 3-1 to 3-3, c is an integer of 0 to 6,
3) In Formulas 3-4 to 3-6, c is an integer of 0 to 8. 11. The organic electric device according to claim 10, wherein Chemical Formula 3 is represented by the following Chemical Formula 3-7:
(Formula 3-7)

In Formula 3-7,
1) R ⁷ and R ⁸ are as defined in Formula 3 of claim 8,
2) c is an integer from 0 to 8; d is an integer from 0 to 4,
3) Ar ₆ to Ar ₈ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; Alternatively, adjacent groups may be bonded to each other to form a ring. 11. The method of claim 10,
An organic electric device, characterized in that L is selected from a ligand represented by the following formula (3A) to a ligand represented by the following formula (3D):
(Formula 3A) (Formula 3B)

(Formula 3C) (Formula 3D)

In Formulas 3A to 3D,
1) Y ₁₁ ~ Y ₁₆ are each independently C or N,
2) CY ₃ ~CY ₄ are each independently a C ₂ ~ C ₂₀ alkynyl group; C ₆ ~ C ₂₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic ring group; C ₇ ~ C ₂₀ Arylalkyl group; And C ₈ ~ C ₂₀ It is selected from the group consisting of an aryl alkenyl group; Or it may combine with a neighboring group to form a ring,
3) C1~C2 are each independently an integer of 0~6,
4) X ₁₁ to X14 are each independently N, O, NR ₄₀ or PR ₄₁ R ₄₂ ,
5) Z ₂₁ , Z ₂₂ and R ₃₃ to R ₄₂ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,
6) * and *1 represent bonding positions. The organic electric device according to claim 10, wherein the compound represented by Formula 3 is one of the following D-1 to D-28:

10. The method according to claim 8 or 9,
The organic material layer is an organic electric device comprising at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. 16. The method of claim 15,
The organic material layer comprises at least one of the hole transport layer, the light emitting auxiliary layer and the light emitting layer. 10. The method according to claim 8 or 9,
The organic material layer comprises at least two stacks including a hole transport layer, a light emitting layer, and a light emitting auxiliary layer sequentially formed on the anode. 18. The method of claim 17,
The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 8 or 9; and a controller for driving the display device. 20. The method of claim 19,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, an electronic device, characterized in that selected from the group consisting of a single color lighting device and a quantum dot display device.

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