Compound for organic electric element, organic electric element using same, and electronic device having same

Abstract

The present invention provides: a novel compound that can improve the luminous efficiency, stability, and lifespan of an element; an organic electric element using same; and an electronic device having same.

Description

Compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof

[0001] The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

[0002] Generally, organic light emitting diodes (OLEDs) are devices that convert electrical energy into light energy using organic materials. Organic electronic devices utilizing the organic light emitting diode (OLED) phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. These organic layers are often multilayered, composed of different materials, to enhance the efficiency and stability of the device. For example, these layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic layers in organic electronic devices can be classified into light-emitting materials and charge-transporting materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions. In addition, the light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on their luminescence mechanism. In addition, light-emitting materials can be classified into blue, green, and red light-emitting materials depending on their luminescence color, and yellow and orange light-emitting materials required to realize better natural colors.

[0004] Meanwhile, when only one substance is used as a light-emitting material, the maximum light-emitting wavelength shifts to a longer wavelength due to intermolecular interactions, resulting in a decrease in color purity or a decrease in device efficiency due to light-emitting attenuation. Therefore, a host / dopant system can be used as a light-emitting material to increase color purity and light-emitting efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, resulting in high-efficiency light emission. At this time, the wavelength of the host shifts to the wavelength of the dopant, so light of a desired wavelength can be obtained depending on the type of dopant used.

[0005] The current portable display market is trending toward larger displays, which are increasing in size and demanding greater power consumption than traditional portable displays. Therefore, power consumption has become a crucial factor for portable displays, which rely on batteries as their limited power source. Efficiency and longevity also need to be addressed.

[0006] Efficiency, lifespan, and operating voltage are all interrelated. As efficiency increases, the operating voltage relatively decreases. As the operating voltage decreases, the crystallization of organic materials due to Joule heating generated during operation decreases, which tends to result in a longer lifespan. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved simultaneously when the energy level and T1 value between each organic layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.

[0007] Therefore, it is necessary to delay the penetration and diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of shortened lifespan of organic electronic devices, into the organic layer, and to have stable characteristics against Joule heating generated when the device is operated. In addition, OLED devices are mainly formed by a deposition method, so there is a need to develop materials that can withstand the deposition process for a long time, i.e., materials with strong heat resistance.

[0008] In other words, in order to fully demonstrate the excellent characteristics of organic electronic devices, the materials that make up the organic layers within the devices, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must first be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic electronic devices has not yet been sufficiently accomplished. Therefore, the development of new materials continues to be required, and among them, the development of host materials for the light-emitting layer is particularly urgent.

[0009] In order to solve the problems of the above-described background technology, the present invention has discovered a compound having a novel structure, and has also discovered that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be greatly improved.

[0010] Accordingly, the present invention aims to provide a novel compound, an organic electric element using the same, and an electronic device thereof.

[0011] The present invention provides a compound represented by the following chemical formula 1.

[0012] <Chemical Formula 1>

[0013]

[0014] In another aspect, the present invention provides a composition for an organic electric device comprising a mixture of a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula 5 or chemical formula 6.

[0015]

[0016] * Chemical Formula 5 Chemical Formula 6

[0017]

[0018] In another aspect, the present invention provides an organic electric device and an electronic device thereof comprising a compound represented by the above chemical formula 1 or a composition for an organic electric device.

[0019] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved.

[0020] Figures 1 to 3 are exemplary diagrams of an organic light-emitting device according to the present invention.

[0021] Figure 4 shows a chemical formula according to one aspect of the present invention.

[0022] 100, 200, 300: Organic electric element 110: First electrode

[0023] 120: hole injection layer 130: hole transport layer

[0024] 140: Emitting layer 150: Electron transport layer

[0025] 160: Electron injection layer 170: Second electrode

[0026] 180: Light efficiency improvement layer 210: Buffer layer

[0027] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0028] 330: First hole transport layer 340: First light-emitting layer

[0029] 350: First electron transport layer 360: First charge generation layer

[0030] 361: Second charge generation layer 420: Second hole injection layer

[0031] 430: Second hole transport layer 440: Second light-emitting layer

[0032] 450: Second electron transport layer CGL: Charge generation layer

[0033] ST1: 1st stack ST2: 2nd stack

[0034] Hereinafter, the present invention will be described in detail with reference to embodiments. In describing the present invention, if a detailed description of a related known configuration or function is judged to obscure the gist of the present invention, such detailed description will be omitted.

[0035] Additionally, terms such as first, second, A, B, (a), (b), etc. may be used to describe components of the present invention. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

[0036] As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

[0037] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0038] The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, 1 to 12 carbon atoms or 1 to 10 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group or a cycloalkyl-substituted alkyl group.

[0039] The term "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise stated, includes, but is not limited to, a straight-chain or branched chain group having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, 2 to 12 carbon atoms or 2 to 10 double bonds or triple bonds, respectively.

[0040] The term "cycloalkyl" as used in the present invention means, unless otherwise stated, an alkyl forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms or 3 to 10 carbon atoms, but is not limited thereto.

[0041] The term "alkoxyl group", "alkoxy group", or "alkyloxy group" used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise stated, has, but is not limited to, 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, 1 to 12 carbon atoms, or 1 to 10 carbon atoms.

[0042] The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms.

[0043] The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, have, but are not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms, respectively. In the present invention, the aryl group or arylene group means a single ring or multi-ring aromatic group, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0044] The prefix "aryl" or "ar" refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the aryl-substituted radical has the number of carbon atoms described herein.

[0045] Also, when prefixes are named consecutively, it means that the substituents are listed in the order they were first written. For example, in the case of arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0046] The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, 2 to 16 carbon atoms or 2 to 12 carbon atoms, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by bonding adjacent functional groups.

[0047] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0048] Additionally, a "heterocyclic group" may also include a ring containing SO2 instead of a ring-forming carbon. For example, a "heterocyclic group" includes the following compounds:

[0049]

[0050] The term "fluorenyl group" or "fluorenylene group" used in the present invention, unless otherwise stated, means a monovalent or divalent functional group in which R, R' and R" in the structure below are all hydrogen, and a "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R' and R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0051]

[0052] The term "spiro compound" used in the present invention has a "spiro union," and a spiro union means a connection formed by two rings sharing only one atom. In this case, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are called "monospiro-," "dicepiro-," and "trispiro-" compounds, respectively.

[0053] Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60, 1 to 30, 1 to 25, 1 to 18, 1 to 12, or 1 to 10 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60, 3 to 30, 3 to 25, 3 to 18, 3 to 12, or 3 to 10 carbon atoms.

[0054] Unless otherwise stated, the term "ring" as used herein refers to a fused ring composed of an aliphatic ring having 3 to 60, 3 to 60, 3 to 30, 3 to 25, 3 to 18, 3 to 12 or 3 to 10 carbon atoms, an aromatic ring having 6 to 60, 6 to 30, 6 to 25, 6 to 18, 6 to 14, 6 to 12 or 6 to 10 carbon atoms, or a heterocyclic ring having 2 to 60, 2 to 30, 2 to 25, 2 to 18, 2 to 14, 2 to 12 or 2 to 10 carbon atoms, or a combination thereof, including a saturated or unsaturated ring.

[0055] Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds include, but are not limited to, one or more heteroatoms.

[0056] Also, unless explicitly stated otherwise, the term "substituted" in the term "substituted or unsubstituted" used in the present invention means deuterium, halogen, amino group, nitrile group, nitro group, C1~C 20 Alkyl group of C1~C 20 Alkoxyl group, C1~C 20 Alkylamine group of C1~C 20 Alkylthiophene group, C6~C 20 Arylthiophene group, C2~C 20 Alkenyl group, C2~C 20 Alkyne group, C3~C 20Cycloalkyl group of C6~C 20 Aryl group of C6~C substituted with deuterium 20 Aryl group of C8~C 20 Arylalkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group consisting of heterocyclic groups, but is not limited to these substituents.

[0057] Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

[0058]

[0059] Here, if a is an integer of 0, the substituent R 1 is absent, and if a is an integer of 1, there is one substituent R 1 is bonded to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, in which case R 1 may be the same or different, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0060]

[0061] The term "composition" as used herein is intended to be broadly interpreted to include not only compounds but also solutions, dispersions, liquids, and solid mixtures (mixtures, admixtures). The composition of the present invention may contain the compound of the present invention alone, or may contain two or more different compounds in combination, or may contain the compound in combination with two or more other compounds. In other words, the composition may contain the compound corresponding to Chemical Formula 1 alone, may contain a mixture of two or more compounds of Chemical Formula 1, or may contain a mixture of the compound of Chemical Formula 1 and a compound not corresponding to the present invention. Here, the compound not corresponding to the present invention may be a single compound, or may be two or more compounds. In this case, when the compound is contained in a combination of two or more other compounds, the other compounds may be already known compounds of each organic layer, or may be compounds to be developed in the future. In this case, the compounds contained in the organic layer may be composed solely of compounds of the same type, but may also be a mixture of two or more heterogeneous compounds represented by Chemical Formula 1.

[0062]

[0063] Hereinafter, a compound according to one aspect of the present invention, a composition for a phosphorescent light-emitting layer of an organic electric device, and an organic electric device including the same will be described.

[0064] The present invention provides a compound represented by the following chemical formula 1.

[0065] <Chemical Formula 1>

[0066]

[0067] In the above chemical formula 1, each symbol can be defined as follows.

[0068] Ar 1 and Ar 2 are independently C6~C 60 Aryl group of; preferably C6~C 30Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 , C6~C 12 or C6~C 10 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0069] X is O or S,

[0070] R 1 , R 2 , R 3 and R 4 are each the same or different and independently hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxy group of; and C6~C 30 aryloxy group of; selected from the group consisting of, or a plurality of R 2 They can combine with each other to form rings,

[0071] The above R 1 , R 2 , R 3 and R 4 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 , C6~C 12 or C6~C 10 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0072] The above R 1 , R 2 , R 3 and R 4 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.

[0073] The above R 1 , R 2 , R 3 and R 4 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0074] The above R 1 , R 2 , R 3 and R 4 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0075] The above R 1 , R 2 , R 3 and R 4If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0076] The above R 1 , R 2 , R 3 and R 4 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0077] a is an integer from 0 to 6, b and d are independently integers from 0 to 4, c is an integer from 0 to 3,

[0078] Here, the aryl group, heterocyclic group, fluorenyl group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each independently selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Cycloalkyl group of; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0079]

[0080] In addition, the present invention provides a compound represented by any one of the following chemical formulas 2 to 4, wherein the chemical formula 1 is:

[0081] <Chemical Formula 2> <Chemical Formula 3>

[0082]

[0083] <Chemical Formula 4>

[0084]

[0085] {In the above chemical formulas 2 to 4, X, Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d are as defined in the above chemical formula 1.

[0086]

[0087] In addition, the present invention comprises the Ar 1 and Ar 2 At least one of the compounds is represented by any one of the following chemical formulas a-1 to a-8.

[0088] <Chemical Formula A-1> <Chemical Formula A-2> <Chemical Formula A-3> <Chemical Formula A-4>

[0089]

[0090] <Chemical Formula A-5> <Chemical Formula A-6> <Chemical Formula A-7> <Chemical Formula A-8>

[0091]

[0092] {In the above chemical formulas a-1 to a-8,

[0093] R 5are each the same or different, and independently of each other, hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Cycloalkyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxyl group of; selected from the group consisting of, or a plurality of adjacent R 5 They can combine with each other to form rings,

[0094] e is an integer from 0 to 5, f is an integer from 0 to 7, g is an integer from 0 to 9,

[0095] * indicates the position where it is combined.}

[0096]

[0097] Specifically, the compound represented by the above chemical formula 1 may be any one of the following compounds P-1 to P-104, but is not limited thereto.

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] In another aspect, the present invention provides a composition for an organic electric device comprising a mixture of a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula 5 or chemical formula 6.

[0126] Chemical Formula 5 Chemical Formula 6

[0127]

[0128] In the above chemical formulas 5 and 6, each symbol can be defined as follows.

[0129] L 12 , L13 , L 14 and L 15 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0130] Above L 12 , L 13 , L 14 and L 15 If it is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 , C6~C 14 , C6~C 12 or C6~C 10 The arylene group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0131] Above L 12 , L 13 , L 14 and L 15 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.

[0132] Above L 12 , L13 , L 14 and L 15 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0133] Ar 12 , Ar 13 and Ar 14 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Aliphatic ring group; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups;

[0134] The above Ar 12 , Ar 13 and Ar 14 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 , C6~C 12 or C6~C 10 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0135] The above Ar 12 , Ar 13 and Ar 14 If it is a heterocyclic group, preferably C2~C 30A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.

[0136] The above Ar 12 , Ar 13 and Ar 14 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0137] The above Ar 12 , Ar 13 and Ar 14 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0138] The above Ar 12 , Ar 13 and Ar 14 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0139] The above Ar 12 , Ar13 and Ar 14 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0140] Ar 15 is C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and -L'-NR'R"; is selected from the group consisting of,

[0141] The above Ar 15 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 , C6~C 12 or C6~C 10 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0142] The above Ar 15 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.

[0143] The above Ar 15If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0144] Y 10 Silver O, S, CR 51 R 52 or NR 53 And,

[0145] Ring B is C6~C 20 is an aryl group,

[0146] L' is a single bond; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 is selected from the group consisting of aliphatic rings;

[0147] If the above L' is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0148] If the above L' is a heterocyclic group, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0149] If the above L' is an aliphatic ring group, preferably C3~C 30 Aliphatic ring group, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be an aliphatic ring.

[0150] R 51 , R 52 , R 53 , R' and R" are the above Ar 12 is identical to the definition of , or R 51 and R 52 can combine with each other to form spy rings,

[0151] R 31 and R 32 are identical or different from each other, and independently of each other, hydrogen; deuterium; halogen; cyano group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 An aryloxy group of R is selected from the group consisting of, or a plurality of adjacent R 31 R's or multiple R's32 They can combine with each other to form rings,

[0152] The above R 31 and R 32 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0153] The above R 31 and R 32 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0154] The above R 31 and R 32 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0155] The above R 31 and R 32 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0156] The above R 31 and R 32 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0157] The above R 31 and R 32 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0158] ba and bb are integers from 0 to 4, independently of each other,

[0159] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Cycloalkyl group of; C7~C 20 Arylalkyl group of; C8~C 20Aryl alkenyl group of; and -L'-NR'R"; may be further substituted with one or more substituents selected from the group consisting of, and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a group consisting of C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0160] Preferably, the composition for the organic electric element may be a host for the light-emitting layer.

[0161] The above chemical formula 5 can be represented by any one of the following chemical formulas 5-1 to 5-3.

[0162] <Chemical Formula 5-1> <Chemical Formula 5-2>

[0163]

[0164] <Chemical Formula 5-3>

[0165]

[0166] {In the above chemical formulas 5-1 to 5-3,

[0167] Ar 13 , Ar 14 , L 12 , L 13 and L 14 is the same as defined in the above chemical formula 5,

[0168] X 11 , X 12 and X 13 Y of the above chemical formula 6 10 is identical to the definition of

[0169] R 33 , R 34 , R 35 , R 36 , R 37 and R 38are the same or different from each other, and independently represent hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Cycloalkyl group of; C7~C 20 Arylalkyl group of; and C8~C 20 is selected from the group consisting of arylalkenyl groups; or adjacent multiple R 33 R's or multiple R's 34 R's or multiple R's 35 R's or multiple R's 36 R's or multiple R's 37 R's or multiple R's 38 They can combine with each other to form rings,

[0170] bc, be, and bg are independently integers from 0 to 4, and bd, bf, and bh are independently integers from 0 to 3.

[0171]

[0172] The above chemical formula 6 can be represented by any one of the following chemical formulas 6-1 to 6-6.

[0173] <Chemical Formula 6-1> <Chemical Formula 6-2>

[0174]

[0175] <Chemical Formula 6-3> <Chemical Formula 6-4>

[0176]

[0177] <Chemical Formula 6-5> <Chemical Formula 6-6>

[0178]

[0179] {In the above chemical formulas 6-1 to 6-6,

[0180] Y 10 , Ar 15 , L 15 , R 31 , R 32 , ba and bb are the same as defined in the above chemical formula 6,

[0181] R 39 is the above R 31 Same as the definition of , or adjacent multiple R 39 They can combine with each other to form rings,

[0182] bi is an integer from 0 to 2.}

[0183]

[0184] The above chemical formula 6 can be represented by any one of the following chemical formulas 6-7 to 6-9.

[0185] <Chemical Formula 6-7> <Chemical Formula 6-8>

[0186]

[0187] <Chemical Formula 6-9>

[0188]

[0189] {In the above chemical formulas 6-7 to 6-9,

[0190] Y 10 , B ring, Ar 15 , L 15 , R 32 and bb are the same as defined in the above chemical formula 6,

[0191] R 40 Silver is the above R 31 Same as the definition of , or adjacent multiple R 40 They can combine with each other to form rings,

[0192] bj is an integer from 0 to 6.}

[0193]

[0194] The above chemical formula 6 can be represented by any one of the following chemical formulas 6-10 to 6-12.

[0195] <Chemical Formula 6-10> <Chemical Formula 6-11>

[0196]

[0197] <Chemical Formula 6-12>

[0198]

[0199] {In the above chemical formulas 6-10 to 6-12,

[0200] Y 10 , B ring, Ar 15 , L 15 , R 31 and ba are the same as defined in the above chemical formula 6,

[0201] R 41 Silver is the above R 31 Same as the definition of , or adjacent multiple R 41 They can combine with each other to form rings,

[0202] bk is an integer from 0 to 6.}

[0203]

[0204] The above chemical formula 6 can be represented by any one of the following chemical formulas 6-13 to 6-18.

[0205] <Chemical Formula 6-13> <Chemical Formula 6-14>

[0206]

[0207] <Chemical Formula 6-15> <Chemical Formula 6-16>

[0208]

[0209] <Chemical Formula 6-17> <Chemical Formula 6-18>

[0210]

[0211] {In the above chemical formulas 6-13 to 6-18,

[0212] Y 10 , Ar 15 , L 15 , R 31 , R 32 , ba and bb are the same as defined in the above chemical formula 6,

[0213] R 39 , R 40 and R 41 Silver is the above R 31 Same as the definition of , or adjacent multiple R 39 R's or multiple R's 40 R's or multiple R's 41 They can combine with each other to form rings,

[0214] bi is an integer from 0 to 2, and bj and bk are integers from 0 to 6, independently of each other.

[0215]

[0216] The above chemical formula 6 can be represented by the following chemical formula 6-19.

[0217] <Chemical Formula 6-19>

[0218]

[0219] {In the above chemical formula 6-19,

[0220] Ar 15 , L 15 , R 53 , R 32 and bb are the same as defined in the above chemical formula 6,

[0221] R 39 and R 40 Silver is the above R 31 Same as the definition of , or adjacent multiple R 39 R's or multiple R's 40 They can combine with each other to form rings,

[0222] bi is an integer from 0 to 2, and bj is an integer from 0 to 6.

[0223]

[0224] Specifically, the compound represented by the above chemical formula 5 may be a compound represented by any one of the following compounds H-1 to H-124, but is not limited thereto.

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] Specifically, the compound represented by the above chemical formula 6 may be represented by any one of the following compounds S-1 to S-116, but is not limited thereto.

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288] In addition, in another aspect, the present invention provides an organic electric device comprising a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by the chemical formula 1 or a composition for an organic electric device.

[0289]

[0290] In addition, in another aspect, the present invention provides a method for reusing a compound represented by the above chemical formula 1, including the steps of: depositing an organic light-emitting material including a compound represented by the above chemical formula 1 in a process for manufacturing an organic light-emitting device; removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; recovering the removed impurities; and purifying the recovered impurities to a purity of 99.9% or higher.

[0291] The step of removing impurities from the crude organic light-emitting material recovered from the above deposition device may preferably include performing a preliminary purification process to obtain a purity of 98% or higher by recrystallization under a recrystallization solvent.

[0292] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0293]

[0294] *The above recrystallization solvent can be used by mixing a polar solvent having a polarity value of 5.5 to 7.2 and a non-polar solvent having a polarity value of 2.0 to 4.7.

[0295] When the above recrystallization solvent is used by mixing a polar solvent and a non-polar solvent, the non-polar solvent may be used in a ratio of 15% (v / v) or less compared to the polar solvent.

[0296] The above recrystallization solvent is preferably a single solvent of methylpyrrolidone (N-Methylpyrrolidone; NMP); or a mixed polar solvent in which any one selected from the group consisting of methylpyrrolidone, dimethyl imidazolidinone (1,3-Dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-Dimethyl formamide), dimethylacetamide, and dimethyl sulfoxide is mixed; or a single solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone; or a mixed nonpolar solvent; Alternatively, a mixture of polar solvent and non-polar solvent can be used.

[0297] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C and then cooling to 0°C to 5°C to precipitate crystals.

[0298] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C to precipitate a crystal.

[0299] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

[0300] The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

[0301] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing an adsorption separation process to adsorb and remove the impurities by adsorbing them on an adsorbent.

[0302] The above adsorbent may be activated carbon, silica gel, alumina or a known material for adsorption purposes.

[0303] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0304]

[0305] Referring to FIG. 1, an organic electric device (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer comprising a single compound represented by Chemical Formula 1 or two or more compounds between the first electrode (110) and the second electrode (170). At this time, the first electrode (110) may be an anode or positive electrode, the second electrode (170) may be a cathode or negative electrode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0306] The organic layer may sequentially 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) on the first electrode (110). At this time, the remaining layers except for the light-emitting layer (140) may not be formed. A hole-blocking layer, an electron-blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc. may be further included, and the electron transport layer (150), etc. may also function as a hole-blocking layer. (See FIG. 2)

[0307] In addition, the organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). This light efficiency improvement layer may be formed on a surface of both sides of the first electrode that is not in contact with the organic layer or on a surface of both sides of the second electrode that is not in contact with the organic layer. The compound or material for an organic electric device according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (120), a hole transport layer (130), a light emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a light emitting layer (140), or a material for a light efficiency improvement layer. Preferably, for example, a composition for an organic electric device comprising a compound according to Chemical Formula 1 of the present invention, or a mixture of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 5 or Chemical Formula 6, may be used as a host material for the light emitting layer.

[0308] The organic 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, and may further include a charge generation layer formed between the two or more stacks. (See Fig. 3)

[0309] Meanwhile, even if the core is the same, the band gap, electrical properties, and interface properties can vary depending on which substituent is bonded at which position, so the selection of the core and the combination of sub-substituents bonded to it are also very important, and in particular, when the energy level and T1 value between each organic layer, and the inherent properties of the material (mobility, interface properties, etc.) are optimally combined, both a long lifespan and high efficiency can be achieved.

[0310] An organic light emitting device according to one embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and an organic layer including 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) is formed thereon, and then a material that can be used as a cathode is deposited thereon.

[0311] In addition, in the present invention, the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and an organic electric device is provided, characterized in that the organic layer includes the compound or the composition for an organic electric device as an electron transport material.

[0312] As another specific example, the present invention provides an organic electric device characterized in that the organic layer includes a mixture of the same or different compounds of the compound represented by the chemical formula 1. Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer may include a composition for an organic electric device including a compound represented by the chemical formula 1 or a mixture of a compound represented by the chemical formula 1 and a compound represented by the chemical formula 5 or 6.

[0313] In addition, the present invention provides a composition for an organic electric device comprising a compound represented by the chemical formula 1 or a mixture of a compound represented by the chemical formula 1 and a compound represented by the chemical formula 5 or 6, and provides an organic electric device comprising the composition.

[0314] In addition, the present invention provides an electronic device including a display device including the organic electric element; and a control unit for driving the display device.

[0315] In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as cell phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

[0316]

[0317] Hereinafter, examples of synthesis of compounds represented by the chemical formulas 1, 5 and 6 of the present invention and examples of manufacturing organic electric devices of the present invention will be described in detail by way of examples, but the present invention is not limited to the following examples.

[0318] [Synthesis example]

[0319] The compound (final product) represented by chemical formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as in the following reaction scheme 1, but is not limited thereto.

[0320] <Reaction Scheme 1>

[0321]

[0322] I. Synthesis of Sub1

[0323] Sub1 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

[0324] <Reaction Formula 2>

[0325]

[0326] 1. Sub1-3 Synthesis Example

[0327]

[0328] Sub1a-1 (20 g, 67.99 mmol) was dissolved in THF (Tetrahydrofuran) (230 mL) in a round-bottomed flask, and then Sub1b-3 (24.65 g, 81.59 mmol), NaOH (5.4 g, 135.98 mmol), Pd(PPh3)4 (2.36 g, 2.04 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 23.9 g of the product (yield 81%).

[0329] 2. Sub1-9 Synthesis Example

[0330]

[0331] Sub1a-1 (20 g, 67.99 mmol) was dissolved in THF (Tetrahydrofuran) (230 mL) in a round-bottomed flask, and then Sub1b-9 (22.53 g, 81.59 mmol), NaOH (5.4 g, 135.98 mmol), Pd(PPh3)4 (2.36 g, 2.04 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 20.8 g of the product (yield: 75%).

[0332] 3. Sub1-52 Synthesis Example

[0333]

[0334] Sub1a-2 (20 g, 64.47 mmol) was dissolved in THF (Tetrahydrofuran) (210 mL) in a round-bottomed flask, and then Sub1b-24 (31.12 g, 77.36 mmol), NaOH (5.2 g, 128.94 mmol), Pd(PPh3)4 (2.24 g, 1.93 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 24.5 g of the product (yield 69%).

[0335] 4. Sub1-57 Synthesis Example

[0336]

[0337] Sub1a-3 (20 g, 66.4 mmol) was dissolved in THF (Tetrahydrofuran) (220 mL) in a round-bottomed flask, and then Sub1b-29 (18.41 g, 79.68 mmol), NaOH (5.3 g, 132.8 mmol), Pd(PPh3)4 (2.3 g, 1.99 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 20.4 g of the product (yield 83%).

[0338] 5. Sub1-68 synthesis example

[0339]

[0340] Sub1a-11 (20 g, 40.29 mmol) was dissolved in THF (Tetrahydrofuran) (130 mL) in a round-bottomed flask, and then Sub1b-8 (13.35 g, 48.35 mmol), NaOH (3.2 g, 80.58 mmol), Pd(PPh3)4 (1.4 g, 1.21 mmol), and water (40 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 19.17 g of the product (yield 78%).

[0341]

[0342] Compounds belonging to Sub1 may be, but are not limited to, the compounds below, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub1.

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363] Compound FD-MS Compound FD-MS Sub1-1 m / z = 357.07 (C 21 H 12 ClN3O = 357.8) Sub1-2 m / z = 433.1 (C 27 H 16 ClN3O = 433.9) Sub1-3 m / z = 433.1 (C 27 H 16 ClN3O = 433.9) Sub1-4 m / z = 433.1 (C 27 H 16 ClN3O = 433.9) Sub1-5 m / z = 509.13 (C 33 H 20 ClN3O = 509.99) Sub1-6 m / z = 509.13 (C 33 H 20 ClN3O = 509.99) Sub1-7 m / z = 509.13 (C 33 H 20 ClN3O = 509.99) Sub1-8 m / z = 407.08 (C 25 H 14 ClN3O = 407.86) Sub1-9 m / z = 407.08 (C 25 H 14 ClN3O = 407.86) Sub1-10 m / z = 483.11 (C 31 H 18 ClN3O = 483.96) Sub1-11 m / z = 483.11 (C 31 H 18 ClN3O = 483.96) Sub1-12 m / z = 483.11 (C 31 H 18ClN3O=483.96)Sub1-13m / z=483.11(C 31 H 18 ClN3O=483.96)Sub1-14m / z=483.11(C 31 H 18 ClN3O=483.96)Sub1-15m / z=483.11(C 31 H 18 ClN3O=483.96)Sub1-16m / z=559.15(C 37 H 22 ClN3O=560.05)Sub1-17m / z=585.16(C 39 H 24 ClN3O=586.09)Sub1-18m / z=559.15(C 37 H 22 ClN3O=560.05)Sub1-19m / z=559.15(C 37 H 22 ClN3O=560.05)Sub1-20m / z=609.16(C 41 H 24 ClN3O=610.11)Sub1-21m / z=457.1(C 29 H 16 ClN3O=457.92)Sub1-22m / z=457.1(C 29 H 16 ClN3O=457.92)Sub1-23m / z=457.1(C 29 H 16 ClN3O=457.92)Sub1-24m / z=533.13(C 35 H 20 ClN3O=534.02)Sub1-25m / z=583.15(C 39 H 22 ClN3O=584.08)Sub1-26m / z=533.13(C 35 H 20 ClN3O=534.02)Sub1-27m / z=583.15(C 39 H 22 ClN3O=584.08)Sub1-28m / z=533.13(C 35 H 20 ClN3O=534.02)Sub1-29m / z=373.04(C 21 H 12ClN3S=373.86)Sub1-30m / z=449.08(C 27 H 16 ClN3S=449.96)Sub1-31m / z=449.08(C 27 H 16 ClN3S=449.96)Sub1-32m / z=449.08(C 27 H 16 ClN3S=449.96)Sub1-33m / z=525.11(C 33 H 20 ClN3S=526.05)Sub1-34m / z=525.11(C 33 H 20 ClN3S=526.05)Sub1-35m / z=525.11(C 33 H 20 ClN3S=526.05)Sub1-36m / z=423.06(C 25 H 14 ClN3S=423.92)Sub1-37m / z=423.06(C 25 H 14 ClN3S=423.92)Sub1-38m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-39m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-40m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-41m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-42m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-43m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-44m / z=575.12(C 37 H 22 ClN3S=576.11)Sub1-45m / z=601.14(C 39 H 24 ClN3S=602.15)Sub1-46m / z=575.12(C 37 H 22ClN3S=576.11)Sub1-47m / z=575.12(C 37 H 22 ClN3S=576.11)Sub1-48m / z=625.14(C 41 H 24 ClN3S=626.17)Sub1-49m / z=473.08(C 29 H 16 ClN3S=473.98)Sub1-50m / z=473.08(C 29 H 16 ClN3S=473.98)Sub1-51m / z=473.08(C 29 H 16 ClN3S=473.98)Sub1-52m / z=549.11(C 35 H 20 ClN3S=550.08)Sub1-53m / z=599.12(C 39 H 22 ClN3S=600.14)Sub1-54m / z=549.11(C 35 H 20 ClN3S=550.08)Sub1-55m / z=599.12(C 39 H 22 ClN3S=600.14)Sub1-56m / z=549.11(C 35 H 20 ClN3S=550.08)Sub1-57m / z=369.14(C 21 D 12 ClN3O=369.87)Sub1-58m / z=437.15(C 25 D 14 ClN3S=438)Sub1-59m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-60m / z=566.19(C 37 H 15 D7ClN3O=567.1)Sub1-61m / z=433.1(C 27 H 16 ClN3O=433.9)Sub1-62m / z=575.12(C 37 H 22 ClN3S=576.11)Sub1-63m / z=514.16(C 33 H 15D5ClN3O=515.02)Sub1-64m / z=609.16(C 41 H 24 ClN3O=610.11)Sub1-65m / z=661.19(C 45 H 28 ClN3O=662.19)Sub1-66m / z=727.18(C 49 H 30 ClN3S=728.31)Sub1-67m / z=585.16(C 39 H 24 ClN3O=586.09)Sub1-68m / z=609.16(C 41 H 24 ClN3O=610.11)Sub1-69m / z=549.11(C 35 H 20 ClN3S=550.08)Sub1-70m / z=635.18(C 43 H 26 ClN3O=636.15)Sub1-71m / z=640.21(C 43 H 21 D5ClN3O=641.18)Sub1-72m / z=735.21(C 51 H 30 ClN3O=736.27)Sub1-73m / z=651.15(C 43 H 26 ClN3S=652.21)Sub1-74m / z=651.15(C 43 H 26 ClN3S=652.21)Sub1-75m / z=685.19(C 47 H 28 ClN3O=686.21)Sub1-76m / z=640.21(C 43 H 21 D5ClN3O=641.18)Sub1-77m / z=672.26(C 45 H 17 D 11 ClN3O=673.26)Sub1-78m / z=662.22(C 43 H 15 D 11 ClN3S=663.28)Sub1-79m / z=727.18(C 49 H 30ClN3S=728.31)Sub1-80m / z=785.22(C 55 H 32 ClN3O=786.33)

[0364] II. Synthesis of Sub2

[0365] Sub2 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 3, but is not limited thereto.

[0366] <Reaction Formula 3>

[0367]

[0368] 1. Sub2-1 Synthesis Example

[0369]

[0370] Sub2a-1 (20 g, 70.63 mmol) was dissolved in THF (Tetrahydrofuran) (230 mL) in a round-bottomed flask, and then Sub2b-1 (27.97 g, 84.75 mmol), NaOH (5.7 g, 141.26 mmol), Pd(PPh3)4 (2.45 g, 2.12 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 25.83 g of the product (yield 90%).

[0371] 2. Sub2-5 Synthesis Example

[0372]

[0373] Sub2a-2 (20 g, 67.97 mmol) was dissolved in THF (Tetrahydrofuran) (230 mL) in a round-bottomed flask, and then Sub2b-5 (27.25 g, 81.57 mmol), NaOH (5.4 g, 135.94 mmol), Pd(PPh3)4 (2.36 g, 2.04 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 21.67 g of the product (yield: 76%).

[0374] 3. Sub2-16 Synthesis Example

[0375]

[0376] Sub2a-10 (20 g, 52.18 mmol) was dissolved in THF (Tetrahydrofuran) (170 mL) in a round-bottomed flask, and then Sub2b-7 (23.8 g, 62.62 mmol), NaOH (4.2 g, 104.36 mmol), Pd(PPh3)4 (1.81 g, 1.57 mmol), and water (50 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 19.75 g of the product (yield 68%).

[0377] 4. Sub2-20 Synthesis Example

[0378]

[0379] Sub2a-1 (20 g, 70.63 mmol) was dissolved in THF (Tetrahydrofuran) (230 mL) in a round-bottomed flask, and then Sub2b-12 (45.11 g, 84.75 mmol), NaOH (5.7 g, 141.26 mmol), Pd(PPh3)4 (2.45 g, 2.12 mmol), and water (70 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 39.55 g of the product (yield: 92%).

[0380] 5. Sub2-23 Synthesis Example

[0381]

[0382] Sub2a-14 (20 g, 48.15 mmol) was dissolved in THF (Tetrahydrofuran) (160 mL) in a round-bottomed flask, and then Sub2b-1 (19.07 g, 57.78 mmol), NaOH (3.9 g, 96.3 mmol), Pd(PPh3)4 (1.67 g, 1.45 mmol), and water (50 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 17.37 g of the product (yield 67%).

[0383]

[0384] Compounds belonging to Sub2 may include, but are not limited to, the compounds below, and Table 2 below shows the FD-MS values ​​of compounds belonging to Sub2.

[0385]

[0386]

[0387]

[0388] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0389] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0390] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0391] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0392] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0393] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0394] <h2 style=";text-align:left;direction:ltr"> 화합물FD-MS화합물FD-MSSub2-1m / z=406.21(C)<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2=406.33)Sub2-2m / z=406.21(C<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2=406.33)Sub2-3m / z=420.3(C<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> BO2=420.42)Sub2-4m / z=406.21(C<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2=406.33)Sub2-5m / z=419.29(C<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> BO2=419.41)Sub2-6m / z=512.29(C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 37 <h2 style=";text-align:left;direction:ltr"> BO2=512.5)Sub2-7m / z=456.23(C<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> BO2=456.39)Sub2-8m / z=456.23(C<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> BO2=456.39)Sub2-9m / z=506.24(C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=506.45)Sub2-10m / z=506.24(C)<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=506.45)Sub2-11m / z=456.23(C<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> BO2=456.39)Sub2-12m / z=532.26(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> BO2=532.49)Sub2-13m / z=448.26(C<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33<h2 style=";text-align:left;direction:ltr">BO2=448.41)Sub2-14m / z=532.26(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> BO2=532.49)Sub2-15m / z=415.27(C<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> D9BO2=415.39)Sub2-16m / z=556.26(C)<h2 style=";text-align:left;direction:ltr"> 40 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> BO2=556.51)Sub2-17m / z=532.26(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> BO2=532.49)Sub2-18m / z=482.24(C)<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=482.43)Sub2-19m / z=482.24(C<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=482.43)Sub2-20m / z=608.29(C<h2 style=";text-align:left;direction:ltr"> 44 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 37 <h2 style=";text-align:left;direction:ltr"> BO2=608.59)Sub2-21m / z=582.27(C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 35 <h2 style=";text-align:left;direction:ltr"> BO2=582.55)Sub2-22m / z=532.26(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> BO2=532.49)Sub2-23m / z=538.3(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 39 <h2 style=";text-align:left;direction:ltr"> BO2=538.54)Sub2-24m / z=456.23(C<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> BO2=456.39)Sub2-25m / z=506.24(C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=506.45)Sub2-26m / z=532.26(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> BO2=532.49)Sub2-27m / z=482.24(C<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=482.43)Sub2-28m / z=482.24(C<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=482.43)Sub2-29m / z=482.24(C<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=482.43)Sub2-30m / z=482.24(C<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> BO2=482.43)Sub2-31m / z=482.24(C34 H 31 BO2=482.43)Sub2-32m / z=532.26(C 38 H 33 BO2=532.49)Sub2-33m / z=532.26(C 38 H 33 BO2=532.49)Sub2-34m / z=482.24(C 34 H 31 BO2=482.43)

[0395] III. Final Product Synthesis

[0396] 1. P-1 synthesis example

[0397]

[0398] Sub1-1 (15 g, 41.92 mmol) was dissolved in THF (Tetrahydrofuran) (140 mL) in a round-bottomed flask, and then Sub2-1 (20.44 g, 50.31 mmol), NaOH (3.4 g, 83.84 mmol), Pd(PPh3)4 (1.45 g, 1.26 mmol), and water (40 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 19.93 g of the product (yield 79%).

[0399] 2. P-9 synthetic example

[0400]

[0401] After dissolving Sub1-9 (15 g, 36.78 mmol) in THF (120 mL) in a round-bottom flask, Sub2-1 (17.93 g, 44.13 mmol), NaOH (2.9 g, 73.56 mmol), Pd(PPh3)4 (1.28 g, 1.10 mmol), and water (40 mL) were added, and 19.66 g of the product (yield 82%) was obtained using the synthesis method of P-1.

[0402] 3. P-47 synthetic example

[0403]

[0404] After dissolving Sub1-47 (15 g, 26.04 mmol) in THF (90 mL) in a round-bottom flask, Sub2-1 (12.70 g, 31.25 mmol), NaOH (2.1 g, 52.08 mmol), Pd(PPh3)4 (0.9 g, 0.78 mmol), and water (30 mL) were added, and 13.45 g of the product (yield 63%) was obtained using the synthesis method of P-1.

[0405] 4. P-57 synthetic example

[0406]

[0407] After dissolving Sub1-57 (15 g, 40.55 mmol) in THF (140 mL) in a round-bottom flask, Sub2-3 (20.46 g, 48.67 mmol), NaOH (3.2 g, 81.1 mmol), Pd(PPh3)4 (1.41 g, 1.22 mmol), and water (40 mL) were added, and 18.08 g of the product (yield 71%) was obtained using the synthesis method of P-1.

[0408] 5. P-61 synthetic example

[0409]

[0410] After dissolving Sub1-5 (15 g, 29.41 mmol) in THF (100 mL) in a round-bottom flask, Sub2-4 (14.34 g, 35.29 mmol), NaOH (2.4 g, 58.82 mmol), Pd(PPh3)4 (1.02 g, 0.88 mmol), and water (30 mL) were added, and 20.18 g of the product (yield 91%) was obtained using the synthesis method of P-1.

[0411] 6. P-65 synthetic example

[0412]

[0413] After dissolving Sub1-9 (15 g, 36.78 mmol) in THF (120 mL) in a round-bottom flask, Sub2-6 (22.62 g, 44.13 mmol), NaOH (2.9 g, 73.56 mmol), Pd(PPh3)4 (1.28 g, 1.10 mmol), and water (40 mL) were added, and 21.74 g of the product (yield 78%) was obtained using the synthesis method of P-1.

[0414] 7. P-78 synthetic example

[0415]

[0416] After dissolving Sub1-50 (15 g, 31.65 mmol) in THF (105 mL) in a round-bottom flask, Sub2-3 (15.97 g, 37.98 mmol), NaOH (2.5 g, 63.3 mmol), Pd(PPh3)4 (1.10 g, 0.95 mmol), and water (30 mL) were added, and 16.7 g of the product (yield 72%) was obtained using the synthesis method of P-1.

[0417] 8. P-87 synthetic example

[0418]

[0419] After dissolving Sub1-63 (15 g, 29.13 mmol) in THF (100 mL) in a round-bottom flask, Sub2-22 (18.61 g, 34.95 mmol), NaOH (2.3 g, 58.26 mmol), Pd(PPh3)4 (1.01 g, 0.87 mmol), and water (30 mL) were added, and 23.72 g of the product (yield 92%) was obtained using the synthesis method of P-1.

[0420] 9. P-95 synthetic example

[0421]

[0422] After dissolving Sub1-71 (15 g, 23.39 mmol) in THF (80 mL) in a round-bottom flask, Sub2-1 (11.41 g, 28.07 mmol), NaOH (1.9 g, 46.78 mmol), Pd(PPh3)4 (1.45 g, 1.26 mmol), and water (20 mL) were added, and 15.94 g of the product (yield 77%) was obtained using the synthesis method of P-1.

[0423] 10. P-101 Synthetic Example

[0424]

[0425] After dissolving Sub1-77 (15 g, 22.28 mmol) in THF (80 mL) in a round-bottom flask, Sub2-1 (10.86 g, 26.74 mmol), NaOH (1.8 g, 44.56 mmol), Pd(PPh3)4 (0.77 g, 0.67 mmol), and water (20 mL) were added, and 17.17 g of the product (yield 84%) was obtained using the synthesis method of P-1.

[0426]

[0427] Meanwhile, the FD-MS values ​​of the compounds P-1 to P-104 of the present invention are as shown in Table 3 below.

[0428] Compound FD-MS Compound FD-MSP-1 m / z = 601.22 (C 43 H 27 N3O=601.71)P-2m / z=677.25(C 49 H 31 N3O=677.81)P-3m / z=677.25(C 49 H 31 N3O=677.81)P-4m / z=677.25(C 49 H 31 N3O=677.81)P-5m / z=753.28(C 55 H 35 N3O=753.91)P-6m / z=753.28(C 55 H 35 N3O=753.91)P-7m / z=753.28(C55 H 35 N3O=753.91)P-8m / z=651.23(C 47 H 29 N3O=651.77)P-9m / z=651.23(C 47 H 29 N3O=651.77)P-10m / z=727.26(C 53 H 33 N3O=727.87)P-11m / z=727.26(C 53 H 33 N3O=727.87)P-12m / z=727.26(C 53 H 33 N3O=727.87)P-13m / z=727.26(C 53 H 33 N3O=727.87)P-14m / z=727.26(C 53 H 33 N3O=727.87)P-15m / z=727.26(C 53 H 33 N3O=727.87)P-16m / z=803.29(C 59 H 37 N3O=803.97)P-17m / z=829.31(C 61 H 39 N3O=830)P-18m / z=803.29(C 59 H 37 N3O=803.97)P-19m / z=803.29(C 59 H 37 N3O=803.97)P-20m / z=853.31(C 63 H 39 N3O=854.03)P-21m / z=701.25(C 51 H 31 N3O=701.83)P-22m / z=701.25(C 51 H 31 N3O=701.83)P-23m / z=701.25(C 51 H 31 N3O=701.83)P-24m / z=777.28(C 57 H 35 N3O=777.93)P-25m / z=827.29(C 61 H 37N3O=827.99)P-26m / z=777.28(C 57 H 35 N3O=777.93)P-27m / z=827.29(C 61 H 37 N3O=827.99)P-28m / z=777.28(C 57 H 35 N3O=777.93)P-29m / z=617.19(C 43 H 27 N3S=617.77)P-30m / z=693.22(C 49 H 31 N3S=693.87)P-31m / z=693.22(C 49 H 31 N3S=693.87)P-32m / z=693.22(C 49 H 31 N3S=693.87)P-33m / z=769.26(C 55 H 35 N3S=769.97)P-34m / z=769.26(C 55 H 35 N3S=769.97)P-35m / z=769.26(C 55 H 35 N3S=769.97)P-36m / z=667.21(C 47 H 29 N3S=667.83)P-37m / z=667.21(C 47 H 29 N3S=667.83)P-38m / z=743.24(C 53 H 33 N3S=743.93)P-39m / z=743.24(C 53 H 33 N3S=743.93)P-40m / z=743.24(C 53 H 33 N3S=743.93)P-41m / z=743.24(C 53 H 33 N3S=743.93)P-42m / z=743.24(C 53 H 33 N3S=743.93)P-43m / z=743.24(C 53 H 33 N3S=743.93)P-44m / z=819.27(C59 H 37 N3S=820.03)P-45m / z=845.29(C 61 H 39 N3S=846.06)P-46m / z=819.27(C 59 H 37 N3S=820.03)P-47m / z=819.27(C 59 H 37 N3S=820.03)P-48m / z=869.29(C 63 H 39 N3S=870.09)P-49m / z=717.22(C 51 H 31 N3S=717.89)P-50m / z=717.22(C 51 H 31 N3S=717.89)P-51m / z=717.22(C 51 H 31 N3S=717.89)P-52m / z=793.26(C 57 H 35 N3S=793.99)P-53m / z=843.27(C 61 H 37 N3S=844.05)P-54m / z=793.26(C 57 H 35 N3S=793.99)P-55m / z=843.27(C 61 H 37 N3S=844.05)P-56m / z=793.26(C 57 H 35 N3S=793.99)P-57m / z=627.38(C 43 HD 26 N3O=627.87)P-58m / z=677.25(C 49 H 31 N3O=677.81)P-59m / z=677.25(C 49 H 31 N3O=677.81)P-60m / z=677.25(C 49 H 31 N3O=677.81)P-61m / z=753.28(C 55 H 35 N3O=753.91)P-62m / z=753.28(C 55 H 35N3O=753.91)P-63m / z=753.28(C 55 H 35 N3O=753.91)P-64m / z=694.38(C 47 H2D 27 N3S=694.99)P-65m / z=757.31(C 55 H 39 N3O=757.94)P-66m / z=777.28(C 57 H 35 N3O=777.93)P-67m / z=793.26(C 57 H 35 N3S=793.99)P-68m / z=843.27(C 61 H 37 N3S=844.05)P-69m / z=827.29(C 61 H 37 N3O=827.99)P-70m / z=793.26(C 57 H 35 N3S=793.99)P-71m / z=853.31(C 63 H 39 N3O=854.03)P-72m / z=808.33(C 59 H 32 D5N3O=809)P-73m / z=887.33(C 64 H 45 N3S=888.15)P-74m / z=945.32(C 69 H 43 N3S=946.18)P-75m / z=819.39(C 59 H 21 D 16 N3O=820.06)P-76m / z=1003.36(C 75 H 45 N3O=1004.21)P-77m / z=827.29(C 61 H 37 N3O=827.99)P-78m / z=732.32(C 51 H 16 D 15 N3S=732.98)P-79m / z=717.22(C 51 H 31 N3S=717.89)P-80m / z=777.28(C 57 H 35N3O=777.93)P-81m / z=903.32(C 67 H 41 N3O=904.09)P-82m / z=869.29(C 63 H 39 N3S=870.09)P-83m / z=1029.37(C 77 H 47 N3O=1030.24)P-84m / z=953.34(C 71 H 43 N3O=954.15)P-85m / z=677.25(C 49 H 31 N3O=677.81)P-86m / z=819.27(C 59 H 37 N3S=820.03)P-87m / z=884.36(C 65 H 36 D5N3O=885.09)P-88m / z=985.4(C 73 H 51 N3O=986.23)P-89m / z=955.36(C 71 H 45 N3O=956.16)P-90m / z=1071.36(C 79 H 49 N3S=1072.34)P-91m / z=955.36(C 71 H 45 N3O=956.16)P-92m / z=903.32(C 67 H 41 N3O=904.09)P-93m / z=869.29(C 63 H 39 N3S=870.09)P-94m / z=955.36(C 71 H 45 N3O=956.16)P-95m / z=884.36(C 65 H 36 D5N3O=885.09)P-96m / z=1055.39(C 79 H 49 N3O=1056.28)P-97m / z=971.33(C 71 H 45 N3S=972.22)P-98m / z=971.33(C 71 H 45N3S=972.22)P-99m / z=1055.39(C 79 H 49 N3O=1056.28)P-100m / z=1010.4(C 75 H 42 D5N3O=1011.25)P-101m / z=916.41(C 67 H 32 D11N3O=917.17)P-102m / z=906.37(C 65 H 30 D 11 N3S=907.19)P-103m / z=1047.36(C 77 H 49 N3S=1048.32)P-104m / z=1029.37(C 77 H 47 N3O=1030.24)

[0429] [Synthesis Example 2]

[0430] The compound represented by the above chemical formula 5 or the above chemical formula 6 can be manufactured by a known synthetic method (named reaction) or by referring to published patent publications, such as Korean Patent Registration No. 10-2395819 and U.S. Patent Publication No. 2023-0129535, but is not limited thereto.

[0431]

[0432] Meanwhile, the FD-MS values ​​of compounds H-1 to H-124 and S-1 to S-116 of the present invention are as shown in Tables 4 and 5 below.

[0433] Compound FD-MS Compound FD-MSH-1 m / z = 487.19 (C 36 H 25 NO=487.60)H-2m / z=553.19(C 40 H 27 NS=553.72)H-3m / z=563.26(C 43 H 33 N=563.74)H-4m / z=602.27(C 45 H 34 N2=602.78)H-5m / z=517.15(C 36 H 23NOS=517.65)H-6m / z=603.20(C 44 H 29 NS=603.78)H-7m / z=735.29(C 57 H 37 N=735.93)H-8m / z=562.24(C 42 H 30 N2=562.72)H-9m / z=565.17(C 40 H 23 NO3=565.63)H-10m / z=581.14(C 40 H 23 NO2S=581.69)H-11m / z=823.24(C 59 H 37 NS2=824.07)H-12m / z=727.30(C 54 H 37 N3=727.91)H-13m / z=627.22(C 46 H 29 NO2=627.74)H-14m / z=633.16(C 44 H 27 NS2=633.83)H-15m / z=675.29(C 52 H 37 N=675.88)H-16m / z=678.30(C 51 H 38 N2=678.88)H-17m / z=669.21(C 48 H 31 NOS=669.84)H-18m / z=785.22(C 56 H 35 NS2=786.02)H-19m / z=617.18(C 44 H 27 NOS=617.77)H-20m / z=601.20(C 44 H 27 NO2=601.71)H-21m / z=779.32(C 59 H 41 NO=779.98)H-22m / z=583.23(C 42 H 33 NS=583.79)H-23m / z=679.32(C 52 H 41 N=679.91)H-24m / z=726.27(C 54 H34 N2O=726.88)H-25m / z=593.18(C 42 H 27 NOS=593.74)H-26m / z=774.22(C 54 H 34 N2S2=775.00)H-27m / z=557.24(C 40 H 31 NO2=557.69)H-28m / z=652.25(C 48 H 32 N2O=652.80)H-29m / z=619.29(C 46 H 37 NO=619.81)H-30m / z=603.20(C 44 H 29 NS=603.78)H-31m / z=813.30(C 62 H 39 NO=814.00)H-32m / z=784.29(C 57 H 40 N2S=785.02)H-33m / z=577.20(C 42 H 27 NO2=577.68)H-34m / z=607.14(C 42 H 25 NS2=607.79)H-35m / z=801.34(C 62 H 43 N=802.03)H-36m / z=575.24(C 42 H 29 N3=575.72)H-37m / z=577.20(C 42 H 27 NO2=577.68)H-38m / z=607.14(C 42 H 25 NS2=607.79)H-39m / z=801.34(C 62 H 43 N=802.03)H-40m / z=575.24(C 42 H 29 N3=575.72)H-41m / z=601.20(C 44 H 27 NO2=601.71)H-42m / z=471.11(C 31 H 21NS2=471.64)H-43m / z=675.29(C 52 H 37 N=675.88)H-44m / z=727.30(C 54 H 37 N3=727.91)H-45m / z=603.20(C 44 H 29 NS=603.78)H-46m / z=561.16(C 38 H 27 NS2=561.76)H-47m / z=799.32(C 62 H 41 N=800.02)H-48m / z=702.27(C 52 H 34 N2O=702.86)H-49m / z=729.27(C 54 H 35 NO2=729.88)H-50m / z=785.22(C 56 H 35 NS2=786.02)H-51m / z=812.32(C 62 H 40 N2=813.02)H-52m / z=681.22(C 48 H 31 N3S=681.86)H-53m / z=615.18(C 44 H 25 NO3=615.69)H-54m / z=763.15(C 52 H 29 NS3=763.99)H-55m / z=593.31(C 45 H 39 N=593.81)H-56m / z=840.33(C 62 H 40 N4=841.03)H-57m / z=657.18(C 46 H 27 NO2S=657.79)H-58m / z=824.23(C 58 H 36 N2S2=825.06)H-59m / z=1195.42(C 91 H 57 NS=1196.52)H-60m / z=656.19(C 46 H 28 N2OS=656.80)H-61m / z=607.16(C42 H 25 NO2S=607.73)H-62m / z=773.20(C 54 H 31 NO3S=773.91)H-63m / z=1013.4(C 79 H 51 N=1014.28)H-64m / z=758.24(C 54 H 34 N2OS=758.94)H-65m / z=623.14(C 42 H 25 NOS2=623.79)H-66m / z=763.16(C 52 H 29 NO2S2=763.93)H-67m / z=799.20(C 56 H 33 NOS2=800.01)H-68m / z=743.23(C 54 H 33 NOS=743.92)H-69m / z=872.25(C 62 H 36 N2O2S=873.04)H-70m / z=772.22(C 54 H 32 N2O2S=772.92)H-71m / z=830.28(C 61 H 38 N2S=831.05)H-72m / z=808.25(C 58 H 33 FN2O2=808.91)H-73m / z=929.21(C 64 H 35 NO3S2=930.11)H-74m / z=963.27(C 68 H 41 N3S2=964.22)H-75m / z=809.24(C 58 H 35 NO2S=809.98)H-76m / z=893.29(C 66 H 39 NO3=894.04)H-77m / z=794.28(C 58 H 38 N2S=795.02)H-78m / z=900.26(C 64 H 40 N2S2=901.16)H-79m / z=758.28(C 55 H38 N2S=758.98)H-80m / z=1082.37(C 81 H 50 N2S=1083.37)H-81m / z=573.25(C 44 H 31 N=573.74)H-82m / z=649.28(C 50 H 35 N=649.84)H-83m / z=699.29(C 54 H 37 N=699.90)H-84m / z=699.29(C 54 H 37 N=699.90)H-85m / z=673.28(C 52 H 35 N=673.86)H-86m / z=649.28(C 50 H 35 N=649.84)H-87m / z=625.28(C 48 H 35 N=625.82)H-88m / z=673.28(C 52 H 35 N=673.86)H-89m / z=773.31(C 60 H 39 N=773.98)H-90m / z=749.31(C 58 H 39 N=749.96)H-91m / z=699.29(C 54 H 37 N=699.90)H-92m / z=599.26(C 46 H 33 N=599.78)H-93m / z=639.26(C 48 H 33 NO=639.8)H-94m / z=765.25(C 57 H 35 NS=765.97)H-95m / z=677.31(C 52 H 39 N=677.89)H-96m / z=727.30(C 54 H 37 N3=727.91)H-97m / z=552.18(C 39 H 24 N2O2=552.63)H-98m / z=628.22(C 45 H28 N2O2=628.73)H-99m / z=614.24(C 45 H 30 N2O=614.75)H-100m / z=614.24(C 45 H 30 N2O=614.75)H-101m / z=691.21(C 50 H 29 NO3=691.79)H-102m / z=739.29(C 56 H 37 NO=739.92)H-103m / z=673.15(C 46 H 27 NOS2=673.85)H-104m / z=726.27(C 54 H 34 N2O=726.88)H-105m / z=617.18(C 44 H 27 NOS=617.77)H-106m / z=611.22(C 46 H 29 NO=611.74)H-107m / z=769.24(C 56 H 35 NOS=769.96)H-108m / z=701.28(C 52 H 35 N3=701.87)H-109m / z=527.22(C 39 H 29 NO=527.67)H-110m / z=643.20(C 46 H 29 NOS=643.80)H-111m / z=593.18(C 42 H 27 NOS=593.74)H-112m / z=726.27(C 54 H 34 N2O=726.88)H-113m / z=726.27(C 54 H 34 N2O=726.88)H-114m / z=558.14(C 37 H 22 N2O2S=558.65)H-115m / z=620.19(C 43 H 28 N2OS=620.77)H-116m / z=686.27(C 52 H 34N2=686.86)H-117m / z=718.24(C 52 H 34 N2S=718.92)H-118m / z=728.28(C 54 H 36 N2O=728.89)H-119m / z=592.20(C 42 H 28 N2S=592.76)H-120m / z=756.22(C 54 H 32 N2OS=756.92)H-121m / z=547.70(C 42 H 29 N=547.70)H-122m / z=672.28(C 49 H 24 D7NO2=672.83)H-123m / z=626.28(C 48 H 26 D5N=558.75)H-124m / z=558.22(C 40 H 22 D5NS=558.75)

[0434] 화합물FD-MS화합물FD-MSS-1m / z=408.16(C 30 H 20 N2=408.50)S-2m / z=534.21(C 40 H 26 N2=534.66)S-3m / z=560.23(C 42 H 28 N2=560.70)S-4m / z=584.23(C 44 H 28 N2=584.72)S-5m / z=560.23(C 42 H 28 N2=560.70)S-6m / z=634.24(C 48 H 30 N2=634.78)S-7m / z=610.24(C 46 H 30 N2=610.76)S-8m / z=498.17(C 36 H 22 N2O=498.59)S-9m / z=574.20(C 42 H 26 N2O=574.68)S-10m / z=660.26(C 50 H32 N2=660.82)S-11m / z=686.27(C 52 H 34 N2=686.86)S-12m / z=620.14(C 42 H 24 N2S2=620.79)S-13m / z=640.20(C 46 H 28 N2S=640.80)S-14m / z=560.23(C 42 H 28 N2=560.70)S-15m / z=558.21(C 42 H 26 N2=558.68)S-16m / z=548.19(C 40 H 24 N2O=548.65)S-17m / z=573.22(C 42 H 27 N3=573.70)S-18m / z=564.17(C 40 H 24 N2S=564.71)S-19m / z=574.20(C 42 H 26 N2O=574.68)S-20m / z=564.17(C 40 H 24 N2S=564.71)S-21m / z=564.17(C 40 H 24 N2S=564.71)S-22m / z=813.31(C 61 H 39 N3=814.00)S-23m / z=696.26(C 53 H 32 N2=696.85)S-24m / z=691.23(C 49 H 29 N3O2=691.79)S-25m / z=710.27(C 54 H 34 N2=710.88)S-26m / z=610.24(C 46 H 30 N2=610.76)S-27m / z=670.15(C 46 H 26 N2S2=670.85)S-28m / z=640.29(C 48 H 36N2=640.83)S-29m / z=598.20(C 44 H 26 N2O=598.71)S-30m / z=623.24(C 46 H 29 N3=623.76)S-31m / z=458.18(C 34 H 22 N2=458.56)S-32m / z=548.19(C 40 H 24 N2O=548.65)S-33m / z=508.19(C 38 H 24 N2=508.62)S-34m / z=508.19(C 38 H 24 N2=508.62)S-35m / z=623.24(C 46 H 29 N3=623.76)S-36m / z=564.17(C 40 H 24 N2S=564.71)S-37m / z=627.20(C 46 H 29 NS=627.81)S-38m / z=505.10(C 34 H 19 NS2=505.65)S-39m / z=514.15(C 36 H 22 N2S=514.65)S-40m / z=575.17(C 42 H 25 NS=575.73)S-41m / z=642.21(C 46 H 30 N2S=642.82)S-42m / z=575.17(C 42 H 25 NS=575.73)S-43m / z=606.18(C 42 H 26 N2OS=606.74)S-44m / z=575.17(C 42 H 25 NS=575.73)S-45m / z=551.17(C 40 H 25 NS=551.71)S-46m / z=607.14(C 42 H 25 NS2=607.79)S-47m / z=525.16(C 38H 23 NS=525.67)S-48m / z=642.21(C 46 H 30 N2S=642.82)S-49m / z=548.19(C 40 H 24 N2O=548.65)S-50m / z=473.14(C 34 H 19 NO2=473.53)S-51m / z=566.15(C 39 H 22 N2OS=566.68)S-52m / z=459.16(C 34 H 21 NO=459.55)S-53m / z=473.14(C 34 H 19 NO2=473.53)S-54m / z=523.16(C 38 H 21 NO2=523.59)S-55m / z=539.13(C 38 H 21 NOS=539.65)S-56m / z=548.19(C 40 H 24 N2O=548.65)S-57m / z=489.12(C 34 H 19 NOS=489.59)S-58m / z=545.09(C 36 H 19 NOS2=545.67)S-59m / z=549.17(C 40 H 23 NO2=549.63)S-60m / z=565.15(C 40 H 23 NOS=565.69)S-61m / z=523.16(C 38 H 21 NO2=523.59)S-62m / z=598.2(C 44 H 26 N2O=598.71)S-63m / z=539.13(C 38 H 21 NOS=539.65)S-64m / z=589.15(C 42 H 23 NOS=589.71)S-65m / z=498.17(C 36 H 22N2O=498.59)S-66m / z=509.18(C 38 H 23 NO=509.61)S-67m / z=548.19(C 40 H 24 N2O=548.65)S-68m / z=549.17(C 40 H 23 NO2=549.63)S-69m / z=449.12(C 32 H 19 NS=449.57)S-70m / z=439.1(C 30 H 17 NOS=439.53)S-71m / z=647.22(C 49 H 29 NO=647.78)S-72m / z=717.28(C 52 H 35 N3O=717.87)S-73m / z=459.16(C 34 H 21 NO=459.55)S-74m / z=533.18(C 40 H 23 NO=533.63)S-75m / z=525.16(C 38 H 23 NS=525.67)S-76m / z=564.17(C 40 H 24 N2S=564.71)S-77m / z=575.19(C 42 H 25 NO2=575.67)S-78m / z=663.22(C 49 H 29 NO2=663.78)S-79m / z=647.22(C 49 H 29 NO=647.78)S-80m / z=496.16(C 36 H 20 N2O=496.57)S-81m / z=565.15(C 40 H 23 NOS=565.69)S-82m / z=505.1(C 34 H 19 NS2=505.65)S-83m / z=765.25(C 56 H 35 NOSi=765.99)S-84m / z=615.17(C44 H 25 NOS=615.75)S-85m / z=603.17(C 43 H 25 NOS=603.74)S-86m / z=772.29(C 59 H 36 N2=772.95)S-87m / z=802.33(C 61 H 42 N2=803.02)S-88m / z=607.23(C 47 H 29 N=607.76)S-89m / z=524.23(C 39 H 28 N2=524.67)S-90m / z=665.22(C 49 H 31 NS=665.85)S-91m / z=633.25(C 49 H 31 N=633.79)S-92m / z=775.29(C 59 H 37 NO=775.95)S-93m / z=535.23(C 41 H 29 N=535.69)S-94m / z=623.22(C 47 H 29 NO=623.76)S-95m / z=687.20(C 51 H 29 NS=687.86)S-96m / z=735.29(C 57 H 37 N=735.93)S-97m / z=611.26(C 47 H 33 N=611.79)S-98m / z=679.23(C 50 H 33 NS=679.88)S-99m / z=787.32(C 61 H 41 N=788.01)S-100m / z=743.33(C 55 H 41 N3=743.95)S-101m / z=485.21(C 37 H 27 N=485.63)S-102m / z=471.20(C 36 H 25N=471.60)S-103m / z=571.19(C 43 H 25 NO=571.68)S-104m / z=584.23(C 44 H 28 N2=584.72)S-105m / z=539.24(C 40 H 21 D5N2=539.69)S-106m / z=453.15(C 32 H 15 NS=471.6)S-107m / z=563.26(C 43 H 26 D4NO=563.74)S-108m / z=589.26(C 44 H 23 D5N2=584.72)S-109m / z=589.26(C 44 H 23 D5N2=589.75)S-110m / z=562.23(C 42 H 22 D4N2=562.71)S-111m / z=660.26(C 50 H 32 N2=660.82)S-112m / z=553.22(C 40 H 19 D5N2O=553.68)S-113m / z=634.24(C 48 H 30 N2=634.78)S-114m / z=589.26(C 44 H 23 D5N2=589.75)S-115m / z=588.25(C 44 H 24 D4N2=588.75)S-116m / z=513.23(C 38 H 19 D5N2=513.65)

[0435] Although the exemplary synthetic examples of the present invention represented by Chemical Formula 1, Chemical Formula 5 and Chemical Formula 6 have been described above, these are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504) and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and it will be easily understood by those skilled in the art that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic examples is combined in Chemical Formula 1, Chemical Formula 5 or Chemical Formula 6.

[0436]

[0437] [Example 1] Red organic electroluminescent device (phosphorescent host)

[0438] Compound A and Compound B were used on an ITO layer (anode) formed on a glass substrate, and Compound B was doped at a weight ratio of 98:2 to form a hole injection layer with a thickness of 10 nm. Then, Compound A was vacuum-deposited on the hole injection layer with a thickness of 110 nm to form a hole transport layer.

[0439] Next, a compound CR was vacuum-deposited on the hole transport layer to a thickness of 10 nm to form a light-emitting auxiliary layer. Thereafter, the host material of the light-emitting layer used compound P-1, a compound of the present invention, as a first host, and compound H-17, a compound of the present invention, as a second host, a mixture of the first host and the second host at a weight ratio of 5:5, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as '(piq)2Ir(acac)') as a dopant material, and the dopant was doped so that the weight ratio of the host and the dopant was 95:5, thereby forming a light-emitting layer with a thickness of 30 nm.

[0440] Next, compound E was vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and a mixture of compound F and compound G at a weight ratio of 5:5 was used to form an electron-transporting layer with a thickness of 30 nm on the hole-blocking layer. Thereafter, compound G was deposited on the electron-transporting layer to form an electron-injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0441]

[0442] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0443] Compound B: 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0444] Compound CR:N 7 -(dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7-triphenyldibenzo[b,d]thiophene-2,7-diamine

[0445] Compound E: 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0446] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0447] Compound G: (8-quinolinolato)lithium

[0448]

[0449] [Example 2] to [Example 28]

[0450] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 6 below were used instead of the compounds P-1 and H-17 of the present invention as host materials.

[0451]

[0452] [Comparative Example 1] to [Comparative Example 3]

[0453] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound A or Comparative Compound C was used instead of Compound P-1 of the present invention as a host material.

[0454] Comparative Compound A Comparative Compound B Comparative Compound C

[0455]

[0456]

[0457] The organic electroluminescence devices manufactured in this way were subjected to a direct current bias voltage and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch. The measured result was 2500 cd / m 2The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. Table 6 below shows the results of the device fabrication and evaluation.

[0458] This measuring device allows the performance of new materials to be evaluated against reference compounds under identical conditions, without being affected by possible daily variations in deposition rate, vacuum quality or other parameters.

[0459] Since, during the evaluation, one batch contains four identically prepared OLEDs including a comparative compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the values ​​of the experimental results obtained in this way exhibit statistical significance.

[0460] Compound 1 Compound 2 Driving voltage current (mA / cm) 2) Efficiency (cd / A) T (95) Comparative Example 1 Comparative Compound A Compound (H-17) 5.1 10.6 2 3.5 10 3.2 Comparative Example 2 Comparative Compound B Compound (H-17) 5.0 1 1.0 2 2.8 9 8.6 Comparative Example 3 Comparative Compound C Compound (H-17) 4.9 9.8 2 5.4 9 0.3 Example 1 Compound (P-1) Compound (H-17) 4.5 6.4 3 8.8 1 2 8.5 Example 2 Compound (P-9) Compound (H-17) 4.5 6.4 3 9.3 1 3 0.6 Example 3 Compound (P-29) Compound (H-17) 4.4 6.4 3 9.3 1 2 4.3 Example 4 Compound (P-57) Compound (H-17) 4.5 6.4 3 8.9 1 3 3.4 Example 5 Compound (P-58) Compound (H-17) 4.6 6.6 3 8.1 1 3 1.3 Example 6 Compound (P-61) Compound (H-17) 4.76.936.5124.1 Example 7 Compound (P-85) Compound (H-17) 4.56.339.6131.5 Example 8 Compound (P-1) Compound (H-100) 4.56.439.2132.7 Example 9 Compound (P-9) Compound (H-100) 4.56.339.7134.8 Example 10 Compound (P-29) Compound (H-100) 4.46.339.7128.3 Example 11 Compound (P-57) Compound (H-100) 4.56.439.3137.7 Example 12 Compound (P-58) Compound (H-100) 4.56.538.5135.5 Example 13 Compound (P-61) Compound (H-100) 4.76.836.9128.1 Example 14 Compound (P-85) Compound (H-100) 4.56.240.0135.7 Example 15 Compound (P-1) Compound (S-8) 4.66.737.2135.1 Example 16 Compound (P-9) Compound (S-8) 4.66.637.7137.3 Example 17 Compound (P-29) Compound (S-8) 4.56.637.7130.7 Example Example 18 Compound (P-57) Compound (S-8) 4.66.7 37.4 140.2 Example 19 Compound (P-58) Compound (S-8) 4.76.8 36.6 138.0 Example 20 Compound (P-61) Compound (S-8) 4.87.1 35.0 130.4 Example 21 Compound (P-85) Compound (S-8) 4.66.6 38.0 138.2 Example 22 Compound (P-1) Compound (S-108) 4.66.5 38.5 136.6 Example 23 Compound (P-9) Compound (S-108) 4.56.4 39.1138.8 Example 24 Compound (P-29) Compound (S-108) 4.5 6.4 39.1 132.2 Example 25 Compound (P-57) Compound (S-108) 4.66.5 38.7 141.8 Example 26 Compound (P-58) Compound (S-108) 4.66.6 37.9 139.5 Example 27 Compound (P-61) Compound (S-108) 4.7 6.9 36.3 131.9 Example 28 Compound (P-85) Compound (S-108) 4.66.3 39.4 139.8.

[0461] As can be seen in Table 6 above, when a red organic electroluminescent device is manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, the compound of the present invention exhibits remarkable characteristics in device performance, and particularly, excellent characteristics in terms of efficiency, compared to the case where comparative compounds A to C were used. As can be seen above, when a plurality of compounds are mixed to form a host for the light-emitting layer, it can be confirmed that a significant difference in characteristics appears depending on the type of the first compound and the second compound. Similarly, differences are shown in driving voltage, efficiency, and lifespan depending on the type of the second compound.

[0462] Comparing the comparative compound A with the compound of the present invention, the substituent of the compound of the present invention is different from the comparative compound A in that it has a substituent having a -phenyl-naphthyl-aryl structure, and comparing the comparative compound B with the compound of the present invention, there is a difference in the substitution position of dibenzofuran or dibenzothiophene. These structural differences may affect the properties of the compounds, and can be confirmed through Table 7 below. Table 7 below shows the LUMO energy levels of the comparative compound A, the comparative compound B, and the compound P-9 of the present invention measured using the DFT Method (B3LYP / 6-31g(D)) of the Gaussian program.

[0463] Comparative Compound A Comparative Compound BP-9 LUMO (eV) -1.83-1.85-1.94

[0464] According to Table 7 above, the LUMO of compound P-9 of the present invention is lower than that of comparative compounds A and B. This indicates that electrons injected from the electron transport layer or hole blocking layer can be injected more easily, and in particular, electron transfer to the dopant can be facilitated due to the lower LUMO. It appears that this significantly increases the efficiency of the device.

[0465] Table 8 below shows the HOMO energy levels of comparative compound C and compound P-9 of the present invention measured using the DFT Method (B3LYP / 6-31g(D)) of the Gaussian program.

[0466] Comparative compound CP-9HOMO (eV)-5.50-5.65

[0467] According to Table 8 above, it can be seen that the compound P-9 of the present invention has a lower HOMO compared to the comparative compound C, which means that holes are blocked better. In the case of the host of the present invention, since the HOMO is lower, hole injection is not good, and therefore, it seems that the compound can minimize damage caused by holes. Therefore, it seems that the compound of the present invention significantly increases the lifespan of the device. The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains can make various modifications within a range that does not depart from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present specification are not intended to limit the present invention but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all techniques within a range equivalent thereto should be interpreted as being included in the scope of the present invention.

[0468]

[0469]

[0470]

[0471] According to the present invention, an organic device having excellent device characteristics such as high brightness, high luminescence, and long lifespan can be manufactured, and thus has industrial applicability.

Claims

1. A compound represented by the following chemical formula 1 <Chemical Formula 1> {In the above chemical formula 1, Ar 1 and Ar 2 are independent of each other C 6 ~C 60 is the aryl group of; X is O or S, R 1 , R 2 , R 3 and R 4 are each the same or different from each other, and independently of each other, hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 Fused ring group of aromatic ring; C 1 ~C 50 Alkyl group of ; C 2 ~C 20 Alkenyl group of ; C 2 ~C 20 Alkyne group of ; C 1 ~C 30 Alkoxy group of; and C 6 ~C 30 aryloxy group of; selected from the group consisting of, or a plurality of R 2 They can combine with each other to form rings, a is an integer from 0 to 6, b and d are independently integers from 0 to 4, c is an integer from 0 to 3, Here, the aryl group, heterocyclic group, fluorenyl group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each independently selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C 1 ~C 20 Alkylthio group of; C 1 ~C 20 Alkoxyl group of; C 1 ~C 20 Alkyl group of ; C 2 ~C 20 Alkenyl group of ; C 2 ~C 20 Alkyne group of ; C 6 ~C 20 Aryl group of ; C substituted with deuterium 6 ~C 20 Aryl group of; Fluorenyl group; C 2 ~C 20 Heterocyclic group of ; C 3 ~C 20 Cycloalkyl group of; C 7 ~C 20 Arylalkyl group of; C 8 ~C 20 Aryl alkenyl group of ; and C 7 ~C 20 may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C 3 ~C 60 Aliphatic ring or C 6 ~C 60 Aromatic ring of or C 2 ~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

2. In the first paragraph, the chemical formula 1 is a compound characterized by being represented by any one of the following chemical formulas 2 to 4. <Chemical Formula 2> <Chemical Formula 3> <Chemical Formula 4> {In the chemical formulas 2 to 4 above, X, Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d are as defined in claim 1.} 3. In paragraph 1, the Ar 1 and Ar 2 A compound characterized in that at least one of the following chemical formulas a-1 to a-8 is represented by <Chemical formula a-1> <Chemical formula a-2> <Chemical formula a-3> <Chemical formula a-4> <Chemical formula a-5> <Chemical formula a-6> <Chemical formula a-7> <Chemical formula a-8> {In the chemical formulas a-1 to a-8 above, R 5 are each the same or different, and independently of each other, hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ~C 20 Aryl group of ; C substituted with deuterium 6 ~C 20 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 20 Heterocyclic group of ; C 3 ~C 20 Cycloalkyl group of; C 1 ~C 20 Alkyl group of ; C 2 ~C 20 Alkenyl group of ; C 2 ~C 20 Alkyne group of ; C 1 ~C 20 Alkoxyl group of R is selected from the group consisting of; or a plurality of adjacent R 5 They can combine with each other to form rings, e is an integer from 0 to 5, f is an integer from 0 to 7, g is an integer from 0 to 9, * indicates the position where it is combined.} 4. Composition for organic electric device comprising the compound of paragraph 1 and a compound represented by the following chemical formula 5 or chemical formula 6 Chemical Formula 5 Chemical Formula 6 {In the above chemical formulas 5 and 6, L 12 , L 13 , L 14 and L 15 are single bonds independently of each other; C 6 ~C 60 Arylene group of; Fluorenylene group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; and C 3 ~C 60 Aliphatic ring and C 6 ~C 60 is selected from the group consisting of a fused ring group of an aromatic ring; Ar 12 , Ar 13 and Ar 14 are independent of each other C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 Fused ring group of aromatic ring; C 3 ~C 60 Aliphatic ring of; C 1 ~C 50 Alkyl group of ; C 2 ~C 20 Alkenyl group of ; C 2 ~C 20 Alkyne group of ; C 1 ~C 30 Alkoxyl group of ; and C 6 ~C 30 is selected from the group consisting of aryloxy group; Ar 15 is C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 A fused ring group of an aromatic ring; and -L'-NR'R"; is selected from the group consisting of, Y 10 Silver O, S, CR 51 R 52 or NR 53 And, B ring is C 6 ~C 20 is the aryl group of L' is a single bond; C 6 ~C 60 Arylene group of; Fluorenylene group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; and C 3 ~C 60 is selected from the group consisting of aliphatic ring groups; R 51 , R 52 , R 53 , R' and R" are the above Ar 12 is identical to the definition of , or R 51 and R 52 can combine with each other to form a spy ring, R 31 and R 32 are each identical or different from each other and independently represent hydrogen; deuterium; halogen; cyano group; C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 Fused ring group of aromatic ring; C 1 ~C 50 Alkyl group of ; C 2 ~C 20 Alkenyl group of ; C 2 ~C 20 Alkyne group of ; C 1 ~C 30 Alkoxyl group of ; and C 6 ~C 30 aryloxy group of; selected from the group consisting of, or adjacent multiple R 31 R's or multiple R's 32 They can combine with each other to form rings, ba and bb are integers from 0 to 4, independently of each other. Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each independently selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C 1 ~C 20 Alkylthio group of; C 1 ~C 20 Alkoxyl group of; C 1 ~C 20 Alkyl group of ; C 2 ~C 20 Alkenyl group of ; C 2 ~C 20 Alkyne group of ; C 6 ~C 20 Aryl group of ; C substituted with deuterium 6 ~C 20 Aryl group of; Fluorenyl group; C 2 ~C 20 Heterocyclic group of ; C 3 ~C 20 Cycloalkyl group of; C 7 ~C 20 Arylalkyl group of; C 8 ~C 20 Aryl alkenyl group of; and -L'-NR'R"; may be further substituted with one or more substituents selected from the group consisting of, and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C 3 ~C 60 Aliphatic ring or C 6 ~C 60 Aromatic ring of or C 2 ~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

5. In the fourth paragraph, the composition for an organic electric device is characterized in that it is a host for a light-emitting layer.

6. In an organic electric device comprising a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, An organic electric device characterized in that the organic layer comprises a compound represented by the chemical formula 1 of claim 1 or a composition for an organic electric device of claim 4.

7. A step of depositing an organic light-emitting material including a compound represented by the chemical formula 1 of claim 1 in a manufacturing process of an organic light-emitting device; A step of removing impurities from an unrefined organic light-emitting material recovered from a deposition device; A step of recovering the removed impurities; and A method for reusing a compound represented by chemical formula 1 according to claim 1, comprising a step of purifying the recovered impurities to a purity of 99.9% or higher.

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