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

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 thereof.

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 an organic electric element and an electronic device thereof comprising a compound represented by the above chemical formula 1.

[0015] 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.

[0016] Figures 1 to 3 are exemplary diagrams of an organic light-emitting device according to the present invention.

[0017] Figure 4 shows a chemical formula according to one aspect of the present invention.

[0018] 100, 200, 300: Organic electric element 110: First electrode

[0019] 120: hole injection layer 130: hole transport layer

[0020] 140: Emitting layer 150: Electron transport layer

[0021] 160: Electron injection layer 170: Second electrode

[0022] 180: Light efficiency improvement layer 210: Buffer layer

[0023] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0024] 330: First hole transport layer 340: First light-emitting layer

[0025] 350: First electron transport layer 360: First charge generation layer

[0026] 361: Second charge generation layer 420: Second hole injection layer

[0027] 430: Second hole transport layer 440: Second light-emitting layer

[0028] 450: Second electron transport layer CGL: Charge generation layer

[0029] ST1: 1st stack ST2: 2nd stack

[0030] 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.

[0031] 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.

[0032] As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

[0033] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0034] 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, or 1 to 12 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.

[0035] The term "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise stated, includes a straight-chain or branched chain group having a double bond or triple bond of 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms or 2 to 12 carbon atoms, but is not limited thereto.

[0036] The term "cycloalkyl" or "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 or 3 to 12 carbon atoms, but is not limited thereto.

[0037] 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 specified, 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, or 1 to 12 carbon atoms.

[0038] 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, or 6 to 12 carbon atoms.

[0039] 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, or 6 to 12 carbon atoms, respectively. In the present invention, the aryl group or arylene group refers to 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.

[0040] 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.

[0041] 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.

[0042] 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, 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.

[0043] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0044] Additionally, the term "heterocyclic group" refers to a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc. containing a heteroatom. In addition, compounds containing a heteroatom group such as SO2, P=O, etc. instead of carbon forming a ring, such as the compounds below, may also be included in the heterocyclic group. For example, the term "heterocyclic group" includes the following compounds.

[0045]

[0046] The term "aliphatic ring" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, means a ring having 3 to 60 carbon atoms, a ring having 3 to 30 carbon atoms, a ring having 3 to 25 carbon atoms, a ring having 3 to 18 carbon atoms, or a ring having 3 to 12 carbon atoms, but is not limited thereto. For example, even when an aromatic ring, benzene, and a non-aromatic ring, cyclohexane, are fused, it is considered an aliphatic ring.

[0047] The term "fluorenyl group", "fluorenylene group" or "fluorenetriyl group" used in the present invention, unless otherwise stated, means a monovalent, divalent or trivalent functional group in which R, R' and R" in the structure below are all hydrogen, and a "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl 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. In the present specification, regardless of valence, a fluorenyl group, a fluorenylene group and a fluorenetriyl group may all be referred to as a fluorene group.

[0048]

[0049] 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.

[0050] Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms or 1 to 12 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms or 3 to 12 carbon atoms.

[0051] Unless otherwise stated, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heterocycle having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms; or a fused ring composed of a combination thereof, including a saturated or unsaturated ring.

[0052] Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds include, but are not limited to, one or more heteroatoms.

[0053] 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 20 Cycloalkyl group of C6~C 20 Aryl group of C6~C substituted with deuterium20 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.

[0054] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', but may also be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, but it may also be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent. In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing the compound name or substituent name. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine can be written as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene can be written as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0055] 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.

[0056]

[0057] 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 1is 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.

[0058]

[0059] In addition, unless explicitly stated otherwise, the terms "ortho", "meta", and "para" used in the present invention mean the substitution positions of all substituents, and the ortho position refers to a compound in which the positions of the substituents are immediately adjacent, for example, in the case of benzene, it refers to the 1st and 2nd positions, the meta position refers to the substitution position next to the immediately adjacent substitution position, and refers to the 1st and 3rd positions in the case of benzene as an example, and the para position refers to the substitution position next to the meta position, and refers to the 1st and 4th positions in the case of benzene as an example. A more detailed description of examples of substitution positions is as follows, and it can be confirmed that the ortho- and meta- positions are substituted in a non-linear type, and the para- position is substituted in a linear type.

[0060] [Example of ortho-position]

[0061]

[0062] [Example of meta-position]

[0063]

[0064] [Example of para-location]

[0065]

[0066]

[0067] Hereinafter, a compound according to one aspect of the present invention and an organic electric device including the same will be described.

[0068] The present invention provides a compound represented by the following chemical formula 1.

[0069] <Chemical Formula 1>

[0070]

[0071] In the above chemical formula 1, each symbol can be defined as follows.

[0072] R 1 , R 2 and R 3 are each independently the same or different from each other, and are independently hydrogen; or deuterium;

[0073] Ar 1 and Ar 2 are independently C6~C excluding fluorenyl group 60 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.

[0074] Ar 3 Silver C6~C 60 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group; and

[0075] The above Ar 3 In this case, it is 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.

[0076] The above Ar 3 In this case, it is preferably C2~C 30A 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, naphthobenzofuran, naphthobenzothiophene, etc.

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

[0078] Here, the aryl group and heterocyclic group are deuterium; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 aryl group of; or C2~C 20 may be further substituted with a heterocyclic group;

[0079]

[0080] In addition, the present invention provides a compound represented by the chemical formula 1 as any one of the following chemical formulas 1-1 to 1-4.

[0081] <Chemical Formula 1-1> <Chemical Formula 1-2>

[0082]

[0083] <Chemical Formula 1-3> <Chemical Formula 1-4>

[0084]

[0085] {In the above chemical formulas 1-1 to 1-4, R 1 , R 2 , R 3 , Ar 1 , Ar 2 , Ar 3 , a, b and c are the same as defined in claim 1 above.}

[0086]

[0087] In addition, the present invention comprises the Ar 1 , Ar 2 and Ar 3 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 4 are each identical or different and independently of each other deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 aryl group of;

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

[0095] refers to a part that binds to the aryl group or triazine of the above chemical formula 1.

[0096]

[0097] In addition, the present invention comprises the Ar 3 A compound represented by any one of the following chemical formulas b-1 to b-4 is provided.

[0098] <Chemical Formula B-1> <Chemical Formula B-2> <Chemical Formula B-3> <Chemical Formula B-4>

[0099]

[0100] {In the above chemical formulas b-1 to b-4,

[0101] X is NR 6 , O or S,

[0102] R 5 are each identical or different and independently of one another deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 is the aryl group of;

[0103] R 6 are each identical or different, and are independently C6~C 20 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 20 is a heterocyclic group; and

[0104] g is an integer from 0 to 7,

[0105] refers to a part that binds to the triazine of the above chemical formula 1.

[0106]

[0107] Specifically, the compound represented by the above chemical formula 1 may be any one of the following compounds P-1 to P-152, but is not limited thereto.

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] In addition, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer, and includes a first host compound represented by the chemical formula 1 of claim 1 and a second host compound represented by the following chemical formula 3 or chemical formula 4.

[0148] <Chemical Formula 3> <Chemical Formula 4>

[0149]

[0150] In the above chemical formulas 3 and 4, each symbol can be defined as follows.

[0151] L 4 , L 5 , L 6 and L 7 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C 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;

[0152] Above L 4 , L 5 , L 6 and L 7 In the case of this arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, etc.

[0153] Above L 4 , L 5 , L 6 and L 7 In this case, it is 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0154] Above L 4 , L 5 , L 6 and L 7 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0155] Ar 3 , Ar 4 and Ar 5 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; 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;

[0156] The above Ar 3 , Ar 4 and Ar 5 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.

[0157] The above Ar 3 , Ar 4 and Ar 5 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0158] The above Ar 3 , Ar 4 and Ar 5 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 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0159] Ar 6 Silver 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~C60 Aliphatic ring and C6~C 60 A fused ring group of the aromatic ring; and -L'-N(R b )(R c ); is selected from the group consisting of,

[0160] The above Ar 6 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.

[0161] The above Ar 6 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0162] The above Ar 6 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 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0163] Ring A is C6~C 20 is an aryl group,

[0164] Z is O, S, CR'R" or NR a and,

[0165] R 8 and R 9 are independently the same or different from each other, 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 60 Alkyl group of; C2~C 60 Alkenyl group of; C2~C 60 Alkynyl group of; C1~C 60 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups; or adjacent multiple R 8 R's or multiple R's 9 They can combine with each other to form rings,

[0166] The above R 8 and R 9 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.

[0167] The above R 8 and R 9 If it is a heterocyclic group, 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0168] The above R 8 and R 9 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 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0169] The above R 8 and R 9 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.

[0170] The above R 8 and R 9 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0171] The above R 8 and R 9 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0172] The above L' is a single bond; C6~C 60 Arylene group; Fluorenylene group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 A heterocyclic group of R; and a combination thereof, wherein R is selected from the group consisting of b and R c are independently C6~C 60 Aryl group of; Fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 A heterocyclic group; and a combination thereof, selected from the group consisting of

[0173] When 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, etc.

[0174] If the above L' is an aliphatic ring group, preferably C3~C 30 aliphatic ring, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be an aliphatic ring group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0175] If the above L' is a heterocyclic group, 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0176] The above R b and R c 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.

[0177] The above R b and R c If it is an aliphatic ring, preferably C3~C 30 aliphatic ring, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be an aliphatic ring group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0178] The above R b and R c If it is a heterocyclic group, 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0179] The above R' and R" are independently hydrogen; deuterium; 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 is selected from the group consisting of aryloxy groups; or R' and R" can be combined with each other to form a spiro ring,

[0180] When the above R' and R" are aryl groups, 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.

[0181] When the above R' and R" are heterocyclic groups, 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0182] When the above R' and R" are fused ring groups, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0183] When the above R' and R" are alkyl groups, 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.

[0184] When the above R' and R" are alkoxyl groups, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0185] When the above R' and R" are aryloxy groups, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0186] The above R a is C6~C 60 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60is a heterocyclic group; and

[0187] The above R a 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.

[0188] The above R a 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0189] n and o are integers from 0 to 4, independently of each other,

[0190] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; C6~C 20 Silane group substituted with aryl 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 deuterium20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of C7~C 20 alkylaryl group of; and -L'-N(R b )(R c ); 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 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.

[0191]

[0192] The above chemical formula 3 can be represented by any one of the following chemical formulas 3-1 to 3-3.

[0193] <Chemical Formula 3-1> <Chemical Formula 3-2>

[0194]

[0195] <Chemical Formula 3-3>

[0196]

[0197] {In the above chemical formulas 3-1 to 3-3,

[0198] Ar 4 , Ar 5 , L 4 , L 5 , L 6 is the same as defined in the above chemical formula 3,

[0199] X 1 , X 2 and X 3 is identical to the definition of Z above,

[0200] R 10 , R 11 , R 12 , R 13 , R 14 and R 15 is the above R 8 Same as the definition of , or adjacent multiple R 10 R's or multiple R's 11 R's or multiple R's 12 R's or multiple R's 13 R's or multiple R's 14 R's or multiple R's 15 They can combine with each other to form rings,

[0201] p, r and t are independently integers from 0 to 4, and q, s and u are independently integers from 0 to 3.

[0202]

[0203] The above chemical formula 4 can be represented by any one of the following chemical formulas 4-1 to 4-6.

[0204] <Chemical Formula 4-1> <Chemical Formula 4-2>

[0205]

[0206] <Chemical Formula 4-3> <Chemical Formula 4-4>

[0207]

[0208] <Chemical Formula 4-5> <Chemical Formula 4-6>

[0209]

[0210] {In the above chemical formulas 4-1 to 4-6,

[0211] Z, R 8 , R 9 , Ar 6 , L 7 , n and o are the same as defined in the above chemical formula 4,

[0212] R 16 Silver is the above R 8Same as the definition of , or adjacent multiple R 16 They can combine with each other to form rings,

[0213] v is an integer from 0 to 2.}

[0214]

[0215] The above chemical formula 4 can be represented by any one of the following chemical formulas 4-7 to 4-9.

[0216] <Chemical Formula 4-7> <Chemical Formula 4-8>

[0217]

[0218] <Chemical Formula 4-9>

[0219]

[0220] {In the above chemical formulas 4-7 to 4-9,

[0221] Z, A ring, R 9 , Ar 6 , L 7 and o are the same as defined in the above chemical formula 4,

[0222] R 17 Silver is the above R 8 Same as the definition of , or adjacent multiple R 17 They can combine with each other to form rings,

[0223] w is an integer from 0 to 6.}

[0224]

[0225] The above chemical formula 4 can be represented by any one of the following chemical formulas 4-10 to 4-12.

[0226] <Chemical Formula 4-10> <Chemical Formula 4-11>

[0227]

[0228] <Chemical Formula 4-12>

[0229]

[0230] {In the above chemical formulas 4-10 to 4-12,

[0231] Z, A ring, R 8 , Ar 6 , L 7 and n are the same as defined in the above chemical formula 4,

[0232] R 18 Silver is the above R 8 Same as the definition of , or adjacent multiple R 18 They can combine with each other to form rings,

[0233] x is an integer from 0 to 6.}

[0234]

[0235] The above chemical formula 4 can be represented by any one of the following chemical formulas 4-13 to 4-18.

[0236] <Chemical Formula 4-13> <Chemical Formula 4-14>

[0237]

[0238] <Chemical Formula 4-15> <Chemical Formula 4-16>

[0239]

[0240] <Chemical Formula 4-17> <Chemical Formula 4-18>

[0241]

[0242] {In the above chemical formulas 4-13 to 4-18,

[0243] Z, Ar 6 , L 7 , R 8 , R 9 , n and o are the same as defined in the above chemical formula 4,

[0244] R 16 , R 17 and R 18 Silver is the above R 8 Same as the definition of , or adjacent multiple R 16 R's or multiple R's 17R's or multiple R's 18 They can combine with each other to form rings,

[0245] v is an integer from 0 to 2, and w and x are integers from 0 to 6, independently of each other.

[0246]

[0247] The above chemical formula 4 can be represented by the following chemical formula 4-19.

[0248] <Chemical Formula 4-19>

[0249]

[0250] {In the above chemical formula 4-19,

[0251] Ar 6 , L 7 , R a , R 9 and o are the same as defined in the above chemical formula 4,

[0252] R 16 and R 17 Silver is the above R 8 Same as the definition of , or adjacent multiple R 16 R's or multiple R's 17 They can combine with each other to form rings,

[0253] v is an integer from 0 to 2, and w is an integer from 0 to 6.

[0254]

[0255] Specifically, the compound represented by the above chemical formula 3 may be any one of the following compounds N-1 to N-96, but is not limited thereto.

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281] Specifically, the compound represented by the above chemical formula 4 may be any one of the following compounds S-1 to S-108, but is not limited thereto.

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310] In addition, in another aspect, the present invention provides a method for reusing a compound represented by the above chemical formula 1, comprising: a step 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; a step of removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; a step of recovering the removed impurities; and a step of purifying the recovered impurities to a purity of 99.9% or higher.

[0311] 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.

[0312] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0313] The above recrystallization solvent may preferably 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.

[0314] 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.

[0315] 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.

[0316] 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 it to 0°C to 5°C to precipitate crystals.

[0317] 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.

[0318] 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.

[0319] 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.

[0320] 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.

[0321] The above adsorbent may be activated carbon, silica gel, alumina or a material known for adsorption purposes.

[0322] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0323]

[0324] 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.

[0325] 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)

[0326] 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 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 of a light efficiency improvement layer. Preferably, for example, the compound according to Chemical Formula 1 of the present invention may be used as a host material of the light emitting layer.

[0327] 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)

[0328] 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.

[0329] 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.

[0330] 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 as an electron transport material.

[0331] As another specific example, the present invention provides an organic electric device characterized in that a compound of the same or different types represented by the chemical formula 1 is mixed and used in the organic layer.

[0332] In addition, the present invention provides a light-emitting layer composition comprising a compound represented by the above chemical formula 1, and provides an organic electric device comprising the light-emitting layer.

[0333] In addition, the present invention provides an electronic device including a display device including the above-described organic electric element; and a control unit for driving the display device.

[0334] 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.

[0335]

[0336] Hereinafter, examples of the synthesis of the compound represented by the chemical formula 1 of the present invention and examples of the manufacture of the organic electric device of the present invention will be described in detail by way of examples, but the present invention is not limited to the following examples.

[0337] [Synthesis example]

[0338] The compound (final product) represented by chemical formula 1 according to the present invention is synthesized by reacting Sub1 and Sub2 as shown in the following reaction scheme 1, but is not limited thereto.

[0339] <Reaction Scheme 1>

[0340]

[0341] I. Synthesis of Sub1

[0342] Sub1 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

[0343] <Reaction Formula 2>

[0344]

[0345] 1. Sub1-1 Synthesis Example

[0346]

[0347] Sub1a-1 (30.0 g, 105.94 mmol) was dissolved in THF (Tetrahydrofuran) (350 mL) in a round-bottomed flask, and then Sub1b-1 (34.97 g, 105.94 mmol), NaOH (8.48 g, 211.89 mmol), Pd(PPh3)4 (3.67 g, 3.18 mmol), and water (110 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 31.4 g of the product (yield 73%).

[0348]

[0349] 2. Sub1-8 synthesis example

[0350]

[0351] Sub1a-2 (24 g, 72.02 mmol) was dissolved in THF (Tetrahydrofuran) (240 mL) in a round-bottomed flask, and then Sub1b-2 (23.77 g, 72.02 mmol), NaOH (5.76 g, 144.04 mmol), Pd(PPh3)4 (2.5 g, 2.16 mmol), and water (80 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 23.3 g of the product (yield 71%).

[0352]

[0353] 3. Sub1-18 Synthesis Example

[0354]

[0355] Sub1a-3 (35 g, 119.36 mmol) was dissolved in THF (Tetrahydrofuran) (397 mL) in a round-bottomed flask, and then Sub1b-3 (39.87 g, 119.36 mmol), NaOH (9.55 g, 238.72 mmol), Pd(PPh3)4 (4.14 g, 3.58 mmol), and water (132 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 33.62 g of the product (yield 67%).

[0356]

[0357] 4. Sub1-20 Synthesis Example

[0358]

[0359] Sub1a-3 (28 g, 95.49 mmol) was dissolved in THF (Tetrahydrofuran) (318 mL) in a round-bottomed flask, and then Sub1b-4 (31.90 g, 95.49 mmol), NaOH (7.64 g, 190.98 mmol), Pd(PPh3)4 (3.31 g, 2.86 mmol), and water (106 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 26.09 g of the product (yield: 65%).

[0360]

[0361] 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.

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368] 화합물FD-MS화합물FD-MSSub1-1m / z=406.21(C 28 H 27 BO2=406.33)Sub1-2m / z=442.21(C 31 H 27 BO2=442.36)Sub1-3m / z=456.23(C 32 H 29 BO2=456.39)Sub1-4m / z=506.24(C 36 H 31 BO2=506.45)Sub1-5m / z=506.24(C 36 H 31 BO2=506.45)Sub1-6m / z=406.21(C 28 H 27 BO2=406.33)Sub1-7m / z=506.24(C 36 H 31 BO2=506.45)Sub1-8m / z=456.23(C 32 H 29 BO2=456.39)Sub1-9m / z=456.23(C 32 H 29 BO2=456.39)Sub1-10m / z=506.24(C 36 H 31 BO2=506.45)Sub1-11m / z=482.24(C 34 H 31 BO2=482.43)Sub1-12m / z=482.24(C 34 H 31 BO2=482.43)Sub1-13m / z=482.24(C 34 H 31 BO2=482.43)Sub1-14m / z=482.24(C 34 H 31BO2=482.43)Sub1-15m / z=406.21(C 28 H 27 BO2=406.33)Sub1-16m / z=456.23(C 32 H 29 BO2=456.39)Sub1-17m / z=482.24(C 34 H 31 BO2=482.43)Sub1-18m / z=420.3(C 28 H 13 D 14 BO2=420.42)Sub1-19m / z=420.3(C 28 H 13 D 14 BO2=420.42)Sub1-20m / z=420.3(C 28 H 13 D 14 BO2=420.42)Sub1-21m / z=482.24(C 34 H 31 BO2=482.43)

[0369] II. Synthesis of Sub2

[0370] Sub2 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 3, but is not limited thereto.

[0371] <Reaction Formula 3>

[0372]

[0373] 1. Sub2-1 Synthesis Example

[0374]

[0375] Sub2b-1 (17.8 g, 78.73 mmol) was dissolved in THF (Tetrahydrofuran) (260 mL) in a round-bottomed flask, and then Sub2a-1 (26.0 g, 78.73 mmol), NaOH (6.3 g, 157.47 mmol), Pd(PPh3)4 (2.73 g, 2.36 mmol), and water (190 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 19.8 g of the product (yield 64%).

[0376]

[0377] 2. Sub2-9 Synthesis Example

[0378]

[0379] (1) Sub2b-9 synthesis example

[0380] Sub2c-2 (19.43 g, 105.38 mmol) was dissolved in THF (350 mL) in a round-bottom flask, and then Sub2a-2 (31 g, 105.38 mmol), NaOH (8.43 g, 210.77 mmol), Pd(PPh3)4 (3.65 g, 3.16 mmol), and water (117 mL) were added, and 21.9 g of the product (yield 66%) was obtained using the synthesis method of Sub2-1 above.

[0381] (2) Sub2-9 Synthesis Example

[0382] Sub2b-9 (21.9 g, 69.27 mmol) was dissolved in THF (230 mL) in a round-bottom flask, and then Sub2a-1 (22.8 g, 69.27 mmol), NaOH (5.54 g, 138.55 mmol), Pd(PPh3)4 (2.4 g, 2.08 mmol), and water (76 mL) were added, and 33.5 g of the product (yield 62%) was obtained using the synthesis method of Sub2-1 above.

[0383]

[0384] 3. Sub2-42 Synthesis Example

[0385]

[0386] After dissolving Sub2b-1 (18 g, 79.62 mmol) in THF (265 mL) in a round-bottom flask, Sub2a-3 (30.84 g, 79.62 mmol), NaOH (6.37 g, 159.25 mmol), Pd(PPh3)4 (2.76 g, 2.39 mmol), and water (88 mL) were added, and 24.4 g of the product (yield 68%) was obtained using the synthesis method of Sub2-1 above.

[0387]

[0388] 4. Sub2-66 synthesis example

[0389]

[0390] After dissolving Sub2b-3 (23 g, 99.53 mmol) in THF (330 mL) in a round-bottom flask, Sub2a-4 (38.55 g, 99.53 mmol), NaOH (7.96 g, 199.06 mmol), Pd(PPh3)4 (3.45 g, 2.99 mmol), and water (110 mL) were added, and 29.5 g of the product (yield 65%) was obtained using the synthesis method of Sub2-1 above.

[0391]

[0392] 5. Sub2-71 Synthesis Example

[0393]

[0394] (1) Sub2b-71 synthesis example

[0395] Sub2c-2 (19 g, 103.04 mmol) was dissolved in THF (343 mL) in a round-bottom flask, and then Sub2a-5 (29.80 g, 103.04 mmol), NaOH (8.24 g, 206.07 mmol), Pd(PPh3)4 (3.57 g, 3.09 mmol), and water (114 mL) were added, and 19.5 g of the product (yield 61%) was obtained using the synthesis method of Sub2-1.

[0396] (2) Sub2-71 Synthesis Example

[0397] After dissolving Sub2b-71 (19.5 g, 105.75 mmol) in THF (352 mL) in a round-bottom flask, Sub2a-6 (36.09 g, 105.75 mmol), NaOH (8.46 g, 211.5 mmol), Pd(PPh3)4 (3.67 g, 3.17 mmol), and water (117 mL) were added, and 32.1 g of the product (yield 62%) was obtained using the synthesis method of Sub2-1 above.

[0398]

[0399] Compounds belonging to Sub2 may include, but are not limited to, the compounds below, and Table 2 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub2.

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418] 화합물FD-MS화합물FD-MSSub2-1m / z=393.1(C 25 H 16 ClN3=393.87)Sub2-2m / z=443.12(C 29 H 18 ClN3=443.93)Sub2-3m / z=449.16(C 29 H 12 D6ClN3=449.97)Sub2-4m / z=443.12(C 29 H 18 ClN3=443.93)Sub2-5m / z=443.12(C 29 H 18 ClN3=443.93)Sub2-6m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-7m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-8m / z=543.15(C 37 H 22 ClN3=544.05)Sub2-9m / z=483.11(C 31 H 18 ClN3O=483.95)Sub2-10m / z=533.13(C 35 H 20ClN3O=534.01)Sub2-11m / z=533.13(C 35 H 20 ClN3O=534.01)Sub2-12m / z=483.11(C 31 H 18 ClN3O=483.95)Sub2-13m / z=499.09(C 31 H 18 ClN3S=500.02)Sub2-14m / z=499.09(C 31 H 18 ClN3S=500.02)Sub2-15m / z=558.16(C 37 H 23 ClN4=559.07)Sub2-16m / z=558.16(C 37 H 23 ClN4=559.07)Sub2-17m / z=398.13(C 25 H 11 D5ClN3=398.9)Sub2-18m / z=398.13(C 25 H 11 D5ClN3=398.9)Sub2-19m / z=450.16(C 29 H 11 D7ClN3=450.98)Sub2-20m / z=488.15(C 31 H 13 D5ClN3O=488.99)Sub2-21m / z=490.16(C 31 H 11 D7ClN3O=491)Sub2-22m / z=540.17(C 35 H 13 D7ClN3O=541.06)Sub2-23m / z=393.1(C 25 H 16 ClN3=393.87)Sub2-24m / z=443.12(C 29 H 18 ClN3=443.93)Sub2-25m / z=443.12(C 29 H 18 ClN3=443.93)Sub2-26m / z=449.16(C 29 H 12 D6ClN3=449.97)Sub2-27m / z=493.13(C 33 H 20ClN3=493.99)Sub2-28m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-29m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-30m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-31m / z=543.15(C 37 H 22 ClN3=544.05)Sub2-32m / z=483.11(C 31 H 18 ClN3O=483.95)Sub2-33m / z=533.13(C 35 H 20 ClN3O=534.01)Sub2-34m / z=533.13(C 35 H 20 ClN3O=534.01)Sub2-35m / z=483.11(C 31 H 18 ClN3O=483.95)Sub2-36m / z=499.09(C 31 H 18 ClN3S=500.02)Sub2-37m / z=499.09(C 31 H 18 ClN3S=500.02)Sub2-38m / z=558.16(C 37 H 23 ClN4=559.07)Sub2-39m / z=558.16(C 37 H 23 ClN4=559.07)Sub2-40m / z=398.13(C 25 H 11 D5ClN3=398.9)Sub2-41m / z=398.13(C 25 H 11 D5ClN3=398.9)Sub2-42m / z=450.16(C 29 H 11 D7ClN3=450.98)Sub2-43m / z=488.15(C 31 H 13 D5ClN3O=488.99)Sub2-44m / z=540.17(C 35 H 13D7ClN3O=541.06)Sub2-45m / z=490.16(C 31 H 11 D7ClN3O=491)Sub2-46m / z=469.13(C 31 H 20 ClN3=469.97)Sub2-47m / z=469.13(C 31 H 20 ClN3=469.97)Sub2-48m / z=469.13(C 31 H 20 ClN3=469.97)Sub2-49m / z=469.13(C 31 H 20 ClN3=469.97)Sub2-50m / z=469.13(C 31 H 20 ClN3=469.97)Sub2-51m / z=545.17(C 37 H 24 ClN3=546.07)Sub2-52m / z=559.15(C 37 H 22 ClN3O=560.05)Sub2-53m / z=559.15(C 37 H 22 ClN3O=560.05)Sub2-54m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-55m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-56m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-57m / z=493.13(C 33 H 20 ClN3=493.99)Sub2-58m / z=499.17(C 33 H 14 D6ClN3=500.03)Sub2-59m / z=543.15(C 37 H 22 ClN3=544.05)Sub2-60m / z=634.19(C 43 H 27 ClN4=635.17)Sub2-61m / z=409.2(C 25 D 16ClN3=409.97)Sub2-62m / z=461.23(C 29 D 18 ClN3=462.04)Sub2-63m / z=449.16(C 29 H 12 D6ClN3=449.97)Sub2-64m / z=455.19(C 29 H6D 12 ClN3=456.01)Sub2-65m / z=399.14(C 25 H 10 D6ClN3=399.91)Sub2-66m / z=455.19(C 29 H6D 12 ClN3=456.01)Sub2-67m / z=501.23(C 31 D 18 ClN3O=502.06)Sub2-68m / z=489.15(C 31 H 12 D6ClN3O=489.99)Sub2-69m / z=547.22(C 35 H6D 14 ClN3O=548.1)Sub2-70m / z=504.2(C 33 H9D 11 ClN3=505.06)Sub2-71m / z=489.26(C 31 D 20 ClN3=490.09)

[0419] III. Final Product synthesis

[0420] 1. P-1 synthesis

[0421]

[0422] Sub2-1 (13.41 g, 33.01 mmol) was dissolved in THF (Tetrahydrofuran) (110 mL) in a round-bottomed flask, and then Sub1-1 (13 g, 33.01 mmol), NaOH (2.64 g, 66.01 mmol), Pd(PPh3)4 (1.14 g, 0.99 mmol), and water (36 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 13.26 g of the product (yield 63%).

[0423]

[0424] 2. P-13 Synthetic Example

[0425]

[0426] Sub2-9 (16.4 g, 33.89 mmol) was dissolved in THF (Tetrahydrofuran) (112 mL) in a round-bottomed flask, and Sub1-1 (13.77 g, 33.89 mmol), NaOH (2.71 g, 67.78 mmol), Pd(PPh3)4 (1.18 g, 1.02 mmol), and water (37 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 17.51 ​​g of the product (yield 71%).

[0427]

[0428] 3. P-30 synthetic example

[0429]

[0430] Sub2-24 (15 g, 33.79 mmol) was dissolved in THF (Tetrahydrofuran) (110 mL) in a round-bottomed flask, and Sub1-1 (13.73 g, 33.79 mmol), NaOH (2.7 g, 67.58 mmol), Pd(PPh3)4 (1.17 g, 1.01 mmol), and water (37 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 15.8 g of the product (yield 68%).

[0431]

[0432] 4. P-54 synthetic example

[0433]

[0434] Sub2-43 (23.2 g, 47.44 mmol) was dissolved in THF (Tetrahydrofuran) (158 mL) in a round-bottomed flask, and Sub1-1 (19.28 g, 47.44 mmol), NaOH (3.8 g, 94.89 mmol), Pd(PPh3)4 (1.65 g, 1.42 mmol), and water (52 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 25.38 g of the product (yield 73%).

[0435]

[0436] 5. P-69 synthetic example

[0437]

[0438] In a round-bottomed flask, Sub2-9 (12.4 g, 25.62 mmol) was dissolved in THF (Tetrahydrofuran) (85 mL), and Sub1-6 (10.41 g, 25.62 mmol), NaOH (2.05 g, 51.24 mmol), Pd(PPh3)4 (0.89 g, 0.77 mmol), and water (28 mL) were added, and the mixture was 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 then recrystallized through a silica gel column to obtain 13.98 g of the product (yield: 75%).

[0439]

[0440] 6. P-81 synthetic example

[0441]

[0442] Sub2-19 (11 g, 24.39 mmol) was dissolved in THF (Tetrahydrofuran) (81 mL) in a round-bottomed flask, and Sub1-6 (9.9 g, 24.39 mmol), NaOH (1.95 g, 48.78 mmol), Pd(PPh3)4 (0.85 g, 0.73 mmol), and water (27 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 11.0 g of the product (yield: 65%).

[0443]

[0444] 7. P-88 synthetic example

[0445]

[0446] Sub2-26 (11.7 g, 26 mmol) was dissolved in THF (Tetrahydrofuran) (86 mL) in a round-bottomed flask, and then Sub1-6 (10.57 g, 26 mmol), NaOH (2.08 g, 52 mmol), Pd(PPh3)4 (0.90 g, 0.78 mmol), and water (28 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 10.46 g of the product (yield 58%).

[0447]

[0448] 8. P-102 Synthetic Example

[0449]

[0450] In a round-bottomed flask, Sub2-35 (28 g, 57.86 mmol) was dissolved in THF (Tetrahydrofuran) (192 mL), and Sub1-9 (26.41 g, 57.86 mmol), NaOH (4.63 g, 115.71 mmol), Pd(PPh3)4 (2.01 g, 1.74 mmol), and water (64 mL) were added, and the mixture was 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 27.4 g of the product (yield 62%).

[0451]

[0452] 9. P-106 Synthetic Example

[0453]

[0454] Sub2-39 (12 g, 21.46 mmol) was dissolved in THF (Tetrahydrofuran) (71 mL) in a round-bottomed flask, and then Sub1-6 (8.72 g, 21.46 mmol), NaOH (1.72 g, 42.93 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol), and water (24 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 11.9 g of the product (yield 69%).

[0455]

[0456] 10. P-118 Synthetic Example

[0457]

[0458] Sub2-49 (14 g, 29.79 mmol) was dissolved in THF (Tetrahydrofuran) (99 mL) in a round-bottomed flask, and Sub1-1 (12.1 g, 29.79 mmol), NaOH (2.38 g, 59.58 mmol), Pd(PPh3)4 (1.03 g, 0.89 mmol), and water (33 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 11.05 g of the product (yield 52%).

[0459]

[0460] 11. P-138 Synthetic Example

[0461]

[0462] Sub2-62 (19.3 g, 41.77 mmol) was dissolved in THF (Tetrahydrofuran) (139 mL) in a round-bottomed flask, and Sub1-1 (16.97 g, 41.77 mmol), NaOH (3.34 g, 83.54 mmol), Pd(PPh3)4 (1.45 g, 1.25 mmol), and water (46 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 16.80 g of the product (yield 57%).

[0463]

[0464] 12. P-149 Synthetic Example

[0465]

[0466] Sub2-61 (21 g, 51.22 mmol) was dissolved in THF (Tetrahydrofuran) (170 mL) in a round-bottomed flask, and then Sub1-20 (21.54 g, 51.22 mmol), NaOH (4.1 g, 102.45 mmol), Pd(PPh3)4 (1.78 g, 1.54 mmol), and water (56 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 19.8 g of the product (yield 58%).

[0467]

[0468] Meanwhile, the FD-MS values ​​of compounds P-1 to P-152 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 3 below.

[0469] Compound FD-MS Compound FD-MSP-1 m / z = 637.25 (C 47 H31N3=637.79)P-2m / z=687.27(C 51 H 33N3=687.85)P-3m / z=693.31(C 51 H 27 D6N3=693.88)P-4m / z=687.27(C 51 H 33 N3=687.85)P-5m / z=687.27(C 51 H 33 N3=687.85)P-6m / z=687.27(C 51 H 33 N3=687.85)P-7m / z=737.28(C 55 H 35 N3=737.91)P-8m / z=737.28(C 55 H 35 N3=737.91)P-9m / z=687.27(C 51 H 33 N3=687.85)P-10m / z=737.28(C 55 H 35 N3=737.91)P-11m / z=737.28(C 55 H 35 N3=737.91)P-12m / z=787.3(C 59 H 37 N3=787.97)P-13m / z=727.26(C 53 H 33 N3O=727.87)P-14m / z=777.28(C 57 H 35 N3O=777.93)P-15m / z=777.28(C 57 H 35 N3O=777.93)P-16m / z=777.28(C 57 H 35 N3O=777.93)P-17m / z=727.26(C 53 H 33 N3O=727.87)P-18m / z=777.28(C 57 H 35 N3O=777.93)P-19m / z=743.24(C 53 H 33 N3S=743.93)P-20m / z=743.24(C 53 H 33 N3S=743.93)P-21m / z=802.31(C 59 H38 N4=802.98)P-22m / z=802.31(C 59 H 38 N4=802.98)P-23m / z=642.28(C 47 H 26 D5N3=642.82)P-24m / z=642.28(C 47 H 26 D5N3=642.82)P-25m / z=694.31(C 51 H 26 D7N3=694.89)P-26m / z=732.29(C 53 H 28 D5N3O=732.9)P-27m / z=734.31(C 53 H 26 D7N3O=734.91)P-28m / z=784.32(C 57 H 28 D7N3O=784.97)P-29m / z=637.25(C 47 H 31 N3=637.79)P-30m / z=687.27(C 51 H 33 N3=687.85)P-31m / z=687.27(C 51 H 33 N3=687.85)P-32m / z=693.31(C 51 H 27 D6N3=693.88)P-33m / z=687.27(C 51 H 33 N3=687.85)P-34m / z=687.27(C 51 H 33 N3=687.85)P-35m / z=737.28(C 55 H 35 N3=737.91)P-36m / z=687.27(C 51 H 33 N3=687.85)P-37m / z=687.27(C 51 H 33 N3=687.85)P-38m / z=737.28(C 55 H 35 N3=737.91)P-39m / z=737.28(C 55 H 35N3=737.91)P-40m / z=787.3(C 59 H 37 N3=787.97)P-41m / z=727.26(C 53 H 33 N3O=727.87)P-42m / z=777.28(C 57 H 35 N3O=777.93)P-43m / z=777.28(C 57 H 35 N3O=777.93)P-44m / z=777.28(C 57 H 35 N3O=777.93)P-45m / z=727.26(C 53 H 33 N3O=727.87)P-46m / z=777.28(C 57 H 35 N3O=777.93)P-47m / z=743.24(C 53 H 33 N3S=743.93)P-48m / z=743.24(C 53 H 33 N3S=743.93)P-49m / z=802.31(C 59 H 38 N4=802.98)P-50m / z=802.31(C 59 H 38 N4=802.98)P-51m / z=642.28(C 47 H 26 D5N3=642.82)P-52m / z=642.28(C47H 26 D5N3=642.82)P-53m / z=694.31(C 51 H 26 D7N3=694.89)P-54m / z=732.29(C 53 H 28 D5N3O=732.9)P-55m / z=734.31(C 53 H 26 D7N3O=734.91)P-56m / z=784.32(C 57 H 28 D7N3O=784.97)P-57m / z=637.25(C 47 H 31 N3=637.79)P-58m / z=687.27(C 51H 33 N3=687.85)P-59m / z=693.31(C 51 H 27 D6N3=693.88)P-60m / z=687.27(C 51 H 33 N3=687.85)P-61m / z=687.27(C 51 H 33 N3=687.85)P-62m / z=687.27(C 51 H 33 N3=687.85)P-63m / z=737.28(C 55 H 35 N3=737.91)P-64m / z=737.28(C 55 H 35 N3=737.91)P-65m / z=687.27(C 51 H 33 N3=687.85)P-66m / z=737.28(C 55 H 35 N3=737.91)P-67m / z=737.28(C 55 H 35 N3=737.91)P-68m / z=787.3(C 59 H37N3=787.97)P-69m / z=727.26(C 53 H 33 N3O=727.87)P-70m / z=777.28(C 57 H 35 N3O=777.93)P-71m / z=777.28(C 57 H 35 N3O=777.93)P-72m / z=777.28(C 57 H 35 N3O=777.93)P-73m / z=727.26(C 53 H 33 N3O=727.87)P-74m / z=777.28(C 57 H 35 N3O=777.93)P-75m / z=743.24(C 53 H 33 N3S=743.93)P-76m / z=743.24(C 53 H 33 N3S=743.93)P-77m / z=802.31(C59 H 38 N4=802.98)P-78m / z=802.31(C 59 H 38 N4=802.98)P-79m / z=642.28(C 47 H 26 D5N3=642.82)P-80m / z=642.28(C 47 H 26 D5N3=642.82)P-81m / z=694.31(C 51 H 26 D7N3=694.89)P-82m / z=732.29(C 53 H 28 D5N3O=732.9)P-83m / z=734.31(C 53 H 26 D7N3O=734.91)P-84m / z=784.32(C 57 H 28 D7N3O=784.97)P-85m / z=637.25(C 47 H 31 N3=637.79)P-86m / z=687.27(C 51 H 33 N3=687.85)P-87m / z=687.27(C 51 H 33 N3=687.85)P-88m / z=693.31(C 51 H 27 D6N3=693.88)P-89m / z=687.27(C 51 H 33 N3=687.85)P-90m / z=687.27(C 51 H 33 N3=687.85)P-91m / z=737.28(C 55 H 35 N3=737.91)P-92m / z=687.27(C 51 H 33 N3=687.85)P-93m / z=687.27(C 51 H 33 N3=687.85)P-94m / z=737.28(C 55 H 35 N3=737.91)P-95m / z=737.28(C 55 H 35N3=737.91)P-96m / z=787.3(C 59 H 37 N3=787.97)P-97m / z=727.26(C 53 H 33 N3O=727.87)P-98m / z=777.28(C 57 H 35 N3O=777.93)P-99m / z=777.28(C 57 H 35 N3O=777.93)P-100m / z=777.28(C 57 H 35 N3O=777.93)P-101m / z=727.26(C 53 H 33 N3O=727.87)P-102m / z=777.28(C 57 H 35 N3O=777.93)P-103m / z=777.28(C 57 H 35 N3O=777.93)P-104m / z=743.24(C 53 H 33 N3S=743.93)P-105m / z=802.31(C 59 H 38 N4=802.98)P-106m / z=802.31(C 59 H 38 N4=802.98)P-107m / z=642.28(C 47 H 26 D5N3=642.82)P-108m / z=642.28(C 47 H 26 D5N3=642.82)P-109m / z=694.31(C 51 H 26 D7N3=694.89)P-110m / z=732.29(C 53 H 28 D5N3O=732.9)P-111m / z=734.31(C 53 H 26 D7N3O=734.91)P-112m / z=784.32(C 57 H 28 D7N3O=784.97)P-113m / z=713.28(C 53 H 35N3=713.88)P-114m / z=713.28(C 53 H 35 N3=713.88)P-115m / z=713.28(C 53 H 35 N3=713.88)P-116m / z=713.28(C 53 H 35 N3=713.88)P-117m / z=713.28(C 53 H 35 N3=713.88)P-118m / z=713.28(C 53 H 35 N3=713.88)P-119m / z=713.28(C 53 H 35 N3=713.88)P-120m / z=789.31(C 59 H 39 N3=789.98)P-121m / z=803.29(C 59 H 37 N3O=803.97)P-122m / z=803.29(C 59 H 37 N3O=803.97)P-123m / z=819.27(C 59 H 37 N3S=820.03)P-124m / z=878.34(C 65 H 42 N4=879.08)P-125m / z=737.28(C 55 H 35 N3=737.91)P-126m / z=737.28(C 55 H 35 N3=737.91)P-127m / z=737.28(C 55 H 35 N3=737.91)P-128m / z=737.28(C 55 H 35 N3=737.91)P-129m / z=737.28(C 55 H 35 N3=737.91)P-130m / z=737.28(C 55 H 35 N3=737.91)P-131m / z=743.32(C 55 H 29D6N3=743.94)P-132m / z=787.3(C 59 H 37 N3=787.97)P-133m / z=637.25(C 47 H 31 N3=637.79)P-134m / z=727.26(C 53 H 33 N3O=727.87)P-135m / z=843.27(C 61 H 37 N3S=844.05)P-136m / z=954.37(C 71 H 46 N4=955.18)P-137m / z=667.44(C 47 HD 30 N3=667.97)P-138m / z=705.38(C 51 H 15 D 18 N3=705.96)P-139m / z=707.39(C 51 H 13 D 20 N3=707.97)P-140m / z=699.34(C 51 H 21 D 12 N3=699.92)P-141m / z=667.44(C 47 HD 30 N3=667.97)P-142m / z=705.38(C 51 H 15 D 18 N3=705.96)P-143m / z=657.38(C 47 H 11 D 20 N3=657.91)P-144m / z=699.34(C 51 H 21 D 12 N3=699.92)P-145m / z=759.46(C 53 HD 32 N3O=760.06)P-146m / z=745.38(C 53 H 15 D 18 N3O=745.98)P-147m / z=747.39(C 53 H 13 D 20N3O=747.99)P-148m / z=791.37(C 57 H 21 D 14 N3O=792.01)P-149m / z=667.44(C 47 HD 30 N3=667.97)P-150m / z=745.38(C 53 H 15 D 18 N3O=745.98)P-151m / z=748.35(C 55 H 24 D 11 N3=748.97)P-152m / z=809.44(C 59 H 19 D 20 N3=810.1)

[0470] [Synthesis Example 2]

[0471] 1. N-12 synthesis example

[0472]

[0473] N-12a (30 g, 0.08 mol), N-12b (34.8 g, 0.08 mol), Pd2(dba)3(2.3 g, 0.003 mol), NaOt-Bu (24.5 g, 0.25 mol), P(t-Bu)3(2.1 g, 0.005 mol), and toluene (170 mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 53 g (85.8%) of product N-12 was obtained using the isolation method of P-1 described above.

[0474]

[0475] 2. N-19 synthetic example

[0476]

[0477] N-19a (50 g, 0.13 mol), N-19b (35 g, 0.13 mol), Pd2(dba)3(3.6 g, 0.004 mol), NaOt-Bu (37.6 g, 0.40 mol), P(t-Bu)3(3.2 g, 0.008 mol), and toluene (260 mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 67 g (83.4%) of product N-19 was obtained using the isolation method of P-1 described above.

[0478]

[0479] 3. S-32 synthetic example

[0480]

[0481] S-32a (10 g, 0.04 mol), S-32b (15.6 g, 0.04 mol), Pd2(dba)3(1.1 g, 0.001 mol), NaOt-Bu (11.7 g, 0.12 mol), P(t-Bu)3(1.0 g, 0.002 mol), and toluene (80 mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 18 g (80.8%) of product S-32 was obtained using the isolation method of P-1 described above.

[0482]

[0483] 4. S-74 synthetic example

[0484]

[0485] S-74a (15 g, 0.06 mol), S-74b (20.9 g, 0.06 mol), Pd2(dba)3(1.6 g, 0.002 mol), NaOt-Bu (16.9 g, 0.18 mol), P(t-Bu)3(1.4 g, 0.004 mol), and toluene (120 mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 27 g (86.4%) of product S-74 was obtained using the isolation method of P-1 described above.

[0486]

[0487] 5. S-104 Synthetic Example

[0488]

[0489] S-104a (30 g, 0.13 mol), S-104b (48.2.9 g, 0.13 mol), Pd2(dba)3(3.5 g, 0.004 mol), NaOt-Bu (36.4 g, 0.38 mol), P(t-Bu)3(3.1 g, 0.008 mol), and toluene (250 mL) were added and reacted at 135°C for 6 hours. When the reaction was completed, 60 g (81.5%) of product S-104 was obtained using the isolation method of P-1 described above.

[0490]

[0491] Meanwhile, the FD-MS values ​​of compounds N-1 to N-96 and S-1 to S-108 of the present invention manufactured according to the above-described synthetic examples are as shown in Tables 4 and 5 below.

[0492] Compound FD-MS Compound FD-MSN-1 m / z = 487.19 (C 36 H 25 NO=487.6)N-2m / z=553.19(C 40 H 27 NS=553.72)N-3m / z=563.26(C 43 H 33 N=563.74)N-4m / z=602.27(C 45 H 34 N2=602.78)N-5m / z=517.15(C 36 H 23 NOS=517.65)N-6m / z=603.2(C 44 H 29 NS=603.78)N-7m / z=735.29(C 57 H 37 N=735.93)N-8m / z=562.24(C 42 H 30 N2=562.72)N-9m / z=565.17(C 40 H 23 NO3=565.63)N-10m / z=581.14(C40 H 23 NO2S=581.69)N-11m / z=823.24(C 59 H 37 NS2=824.07)N-12m / z=727.3(C 54 H 37 N3=727.91)N-13m / z=627.22(C 46 H 29 NO2=627.74)N-14m / z=633.16(C 44 H 27 NS2=633.83)N-15m / z=675.29(C 52 H 37 N=675.88)N-16m / z=678.3(C 51 H 38 N2=678.88)N-17m / z=669.21(C 48 H 31 NOS=669.84)N-18m / z=785.22(C 56 H 35 NS2=786.02)N-19m / z=617.18(C 44 H 27 NOS=617.77)N-20m / z=601.2(C 44 H 27 NO2=601.71)N-21m / z=779.32(C 59 H 41 NO=779.98)N-22m / z=583.23(C 42 H 33 NS=583.79)N-23m / z=679.32(C 52 H 41 N=679.91)N-24m / z=726.27(C 54 H 34 N2O=726.88)N-25m / z=593.18(C 42 H 27 NOS=593.74)N-26m / z=774.22(C 54 H 34 N2S2=775)N-27m / z=557.24(C 40 H 31 NO2=557.69)N-28m / z=652.25(C 48 H 32N2O=652.8)N-29m / z=619.29(C 46 H 37 NO=619.81)N-30m / z=603.2(C 44 H 29 NS=603.78)N-31m / z=813.3(C 62 H 39 NO=814)N-32m / z=784.29(C 57 H 40 N2S=785.02)N-33m / z=577.2(C 42 H 27 NO2=577.68)N-34m / z=607.14(C 42 H 25 NS2=607.79)N-35m / z=801.34(C 62 H 43 N=802.03)N-36m / z=575.24(C 42 H 29 N3=575.72)N-37m / z=577.2(C 42 H 27 NO2=577.68)N-38m / z=607.14(C 42 H 25 NS2=607.79)N-39m / z=801.34(C 62 H 43 N=802.03)N-40m / z=575.24(C 42 H 29 N3=575.72)N-41m / z=601.2(C 44 H 27 NO2=601.71)N-42m / z=471.11(C 31 H 21 NS2=471.64)N-43m / z=675.29(C 52 H 37 N=675.88)N-44m / z=727.3(C 54 H 37 N3=727.91)N-45m / z=603.2(C 44 H 29 NS=603.78)N-46m / z=561.16(C 38 H 27 NS2=561.76)N-47m / z=799.32(C 62 H 41N=800.02)N-48m / z=702.27(C 52 H 34 N2O=702.86)N-49m / z=729.27(C 54 H 35 NO2=729.88)N-50m / z=785.22(C 56 H 35 NS2=786.02)N-51m / z=812.32(C 62 H 40 N2=813.02)N-52m / z=681.22(C 48 H 31 N3S=681.86)N-53m / z=615.18(C 44 H 25 NO3=615.69)N-54m / z=763.15(C 52 H 29 NS3=763.99)N-55m / z=593.31(C 45 H 39 N=593.81)N-56m / z=840.33(C 62 H 40 N4=841.03)N-57m / z=657.18(C 46 H 27 NO2S=657.79)N-58m / z=824.23(C 58 H 36 N2S2=825.06)N-59m / z=1195.42(C 91 H 57 NS=1196.52)N-60m / z=656.19(C 46 H 28 N2OS=656.8)N-61m / z=607.16(C 42 H 25 NO2S=607.73)N-62m / z=773.2(C 54 H 31 NO3S=773.91)N-63m / z=1013.4(C 79 H 51 N=1014.28)N-64m / z=758.24(C 54 H 34 N2OS=758.94)N-65m / z=623.14(C 42 H 25 NOS2=623.79)N-66m / z=763.16(C52 H 29 NO2S2=763.93)N-67m / z=799.2(C 56 H 33 NOS2=800.01)N-68m / z=743.23(C 54 H 33 NOS=743.92)N-69m / z=872.25(C 62 H 36 N2O2S=873.04)N-70m / z=772.22(C 54 H 32 N2O2S=772.92)N-71m / z=830.28(C 61 H 38 N2S=831.05)N-72m / z=808.25(C 58 H 33 FN2O2=808.91)N-73m / z=929.21(C 64 H 35 NO3S2=930.11)N-74m / z=963.27(C 68 H 41 N3S2=964.22)N-75m / z=809.24(C 58 H 35 NO2S=809.98)N-76m / z=893.29(C 66 H 39 NO3=894.04)N-77m / z=794.28(C 58 H 38 N2S=795.02)N-78m / z=900.26(C 64 H 40 N2S2=901.16)N-79m / z=758.28(C 55 H 38 N2S=758.98)N-80m / z=1082.37(C 81 H 50 N2S=1083.37)N-81m / z=573.25(C 44 H 31 N=573.74)N-82m / z=649.28(C 50 H 35 N=649.84)N-83m / z=699.29(C 54 H 37 N=699.9)N-84m / z=699.29(C 54 H37 N=699.9)N-85m / z=673.28(C 52 H 35 N=673.86)N-86m / z=649.28(C 50 H 35 N=649.84)N-87m / z=625.28(C 48 H 35 N=625.82)N-88m / z=673.28(C 52 H 35 N=673.86)N-89m / z=773.31(C 60 H 39 N=773.98)N-90m / z=749.31(C 58 H 39 N=749.96)N-91m / z=699.29(C 54 H 37 N=699.9)N-92m / z=599.26(C 46 H 33 N=599.78)N-93m / z=639.26(C 48 H 33 NO=639.8)N-94m / z=765.25(C 57 H 35 NS=765.97)N-95m / z=677.31(C 52 H 39 N=677.89)N-96m / z=727.3(C 54 H 37 N3=727.91)

[0493] 화합물FD-MS화합물FD-MSS-1m / z=408.16(C 30 H 20 N2=408.5)S-2m / z=534.21(C 40 H 26 N2=534.66)S-3m / z=560.23(C 42 H 28 N2=560.7)S-4m / z=584.23(C 44 H 28 N2=584.72)S-5m / z=560.23(C 42 H 28 N2=560.7)S-6m / z=634.24(C 48 H 30N2=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=574.2(C 42 H 26 N2O=574.68)S-10m / z=660.26(C 50 H 32 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=640.2(C 46 H 28 N2S=640.8)S-14m / z=560.23(C 42 H 28 N2=560.7)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=573.7)S-18m / z=564.17(C 40 H 24 N2S=564.71)S-19m / z=574.2(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)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 H34 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 36 N2=640.83)S-29m / z=598.2(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=627.2(C 46 H 29 NS=627.81)S-38m / z=505.1(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(C42 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 38 H 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 26N2O=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 22 N2O=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(C40 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(C 44 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=687.2(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 41N=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=471.2(C 36 H 25 N=471.6)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)

[0494] Meanwhile, although the exemplary synthetic examples of the present invention represented by Chemical Formula 1, Chemical Formula 3 and Chemical Formula 4 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 other substituents defined in Chemical Formula 1, Chemical Formula 3 and Chemical Formula 4 are combined in addition to the substituents specified in the specific synthetic examples.

[0495]

[0496] Manufacturing and evaluation of organic electronic devices

[0497] [Example 1] Red organic light-emitting device (phosphorescent host)

[0498] An organic electroluminescent device was fabricated using the compound obtained through synthesis as a light-emitting host material of the light-emitting layer according to a conventional method. First, a N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter, 2-TNATA) film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 60 nm thick hole injection layer. Then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, -NPD) was vacuum-deposited to a 50 nm thickness as a hole transport compound on the hole injection layer to form a hole transport layer. On the upper part of the hole transport layer, tris(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter, TCTA) was vacuum-deposited to a 10 nm thickness as a light-emitting auxiliary layer material to form a light-emitting auxiliary layer. After forming the light-emitting auxiliary layer, the present invention compound P-1 represented by the chemical formula 1 and the present invention compound N-12 represented by the chemical formula 3 were used as hosts at a weight ratio of (5:5) on the upper portion of the light-emitting auxiliary layer, and (piq)2Ir(acac) was doped as a dopant material at a weight ratio of 95:5 to deposit a light-emitting layer with a thickness of 30 nm. Subsequently, (1,1 '-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter, BAlq) was vacuum-deposited with a thickness of 10 nm as a hole-blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, BeBq2) was deposited with a thickness of 45 nm as an electron transport layer. Afterwards, LiF, a halogenated alkali metal, was deposited as an electron injection layer with a thickness of 0.2 nm, and Al was then deposited with a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light emitting device.

[0499]

[0500] [Example 2] to [Example 36]

[0501] An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds of the present invention described in Table 6 below were used instead of the compounds P-1 and N-12 of the present invention as phosphorescent host materials.

[0502]

[0503] [Comparative Example 1] to [Comparative Example 3]

[0504] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compounds A to C were used as phosphorescent host materials.

[0505] [Comparative Compound A] [Comparative Compound B] [Comparative Compound C]

[0506]

[0507] 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 2 The 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.

[0508] This measuring device can evaluate the performance of new materials compared to reference compounds under identical conditions, regardless of possible daily variations in deposition rate, vacuum quality, or other parameters. Since each batch contains four identically prepared OLEDs containing the reference compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this manner demonstrate statistical significance.

[0509] Compound 1 Compound 2 Driving voltage (V) Current (mA / cm) 2) Efficiency (cd / A) T (95) Comparative Example 1 Comparative Compound A Compound (N-12) 5.2 8.0 3 1.1 10 1.9 Comparative Example 2 Comparative Compound B Compound (N-12) 5.4 9.9 2 5.2 9 9.1 Comparative Example 3 Comparative Compound C Compound (N-12) 5.4 10.1 2 4.7 9 8.5 Example 1 Compound (P-1) Compound (N-12) 4.9 7.3 3 4.1 1 2 4.4 Example 2 Compound (P-4) Compound (N-12) 4.9 7.5 3 3.4 1 2 7.2 Example 3 Compound (P-6) Compound (N-12) 4.9 7.5 3 3.5 1 2 7.3 Example 4 Compound (P-13) Compound (N-12)4.87.433.7127.3 Example 5 Compound (P-21) Compound (N-12)4.87.633.0127.8 Example 6 Compound (P-23) Compound (N-12)4.97.334.2127.0 Example 7 Compound (P-29) Compound (N-12)4.97.135.4119.3 Example 8 Compound (P-37) Compound (N-12)5.07.234.6121.9 Example 9 Compound (P-54) Compound (N-12)4.97.135.0124.6 Example 10 Compound (P-57) Compound (N-12)5.07.234.8121.6Example 11 Compound (P-59) Compound (N-12)5.07.135.1124.7Example 12 Compound (P-61) Compound (N-12)5.07.334.2124.4Example 13 Compound (P-65) Compound (N-12)5.07.334.0124.3Example 14 Compound (P-77) Compound (N-12)4.97.433.6124.9Example 15 Compound (P-85) Compound (N-12)5.06.936.1116.6Example 16 Compound (P-91) Compound (N-12)5.17.334.4111.9 Example 17 Compound (P-93) Compound (N-12)5.17.135.3119.2 Example 18 Compound (P-101) Compound (N-12)5.07.035.6119.3 Example 19 Compound (P-109) Compound (N-12)5.17.135.4121.7 Example 20 Compound (P-115) Compound (N-12)5.07.234.9122.3 Example 21 Compound (P-125) Compound (N-12)4.97.135.2123.1 Example 22 Compound (P-133) Compound (N-12)4.97.732.4116.1 Example 23 Compound (P-137) Compound (N-12) 4.9 7.2 34.7 129.0 Example 24 Compound (P-141) Compound (N-12) 5.0 7.1 35.3 126.1 Example 25 Compound (P-1) Compound (N-17) 4.7 7.0 35.8 131.9 Example 26 Compound (P-29) Compound (N-17) 4.7 6.7 37.1 126.5 Example 27 Compound (P-57) Compound (N-17) 4.8 6.8 36.5 128.9 Example 28 Compound (P-133) Compound (N-17) 4.6 7.3 34.1 123.0 Example 29 Compound (P-1) Compound (S-32) 4.87.0 35.5 136.9 Example 30 Compound (P-29) Compound (S-32) 4.96.8 36.8 131.2 Example 31 Compound (P-57) Compound (S-32) 4.96.9 36.2 133.8 Example 32 Compound (P-133) Compound (S-32) 4.87.4 33.7 127.7 Example 33 Compound (P-1) Compound (S-108) 4.76.8 36.8 140.6 Example 34 Compound (P-29) Compound (S-108) 4.86.5 38.2 134.8 Example 35 Compound (P-57) Compound (S-108)4.86.737.6137.5Example 36 Compound (P-133) Compound (S-108)4.77.135.0131.2.

[0510] As can be seen from the results 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, it can be confirmed that the performance is significantly improved compared to when comparative compounds A to C are used.

[0511] As can be seen above, when a host for a light-emitting layer is formed by mixing multiple compounds, the characteristics differ depending on the type of the first and second compounds. In addition, when the same compound is applied to the second compound, it can be confirmed that there is a significant difference in characteristics depending on the type of the first compound. Similarly, differences are shown in driving voltage, efficiency, and lifespan depending on the type of the second compound.

[0512] Comparing Compounds A to C with the compound of the present invention, it can be seen that the compound of the present invention has improved performance in the device overall, as can be seen in Table 6. Comparing Compound A with the compound of the present invention, Comparative Compound A has a structure in which -phenyl-naphthyl is substituted on triazine, whereas the compound of the present invention has a structure in which -phenyl-naphthyl-aryl is substituted on triazine, which is a structure in which an aryl group is further substituted compared to Comparative Compound A. In addition, Comparative Compound B has a structure similar to the compound of the present invention but in which a fluorene is further substituted, and Comparative Compound C has a structure in which a cyano group is further substituted compared to the compound of the present invention. Additionally, in Comparative Compounds B and C, unlike the compound of the present invention, the remaining substituents of the triazine are all phenyl, whereas in the case of the compound of the present invention, -naphthyl-aryl must also be substituted on triazine, so there is a difference.

[0513] As a result, it can be confirmed that the device results of Examples 1 to 36 produced with the compound of the present invention represented by Chemical Formula 1, characterized in that a -naphthyl-aryl substituent and a -phenyl-naphthyl-aryl substituent are simultaneously substituted as substituents of triazine, show remarkably superior results, and it can be confirmed that the device performance is superior to that of other comparative compounds not described in the present specification.

[0514] Table 7 below shows the results of measuring the Tg values ​​of comparative compound A and compound P-1 of the present invention.

[0515] Tg (℃) Comparative compound A102.85P-1120.12

[0516] As can be seen in Table 7 above, the Tg value of the compound P-1 of the present invention is higher than that of the comparative compound A. This can be said to indicate that the thermal stability of the compound of the present invention is superior, which appears to have influenced the device results. Table 8 below shows the data for measuring the T1 values ​​of the comparative compound B, comparative compound C, and the compound P-1 of the present invention using the DFT Method (B3LYP / 6-31(D)) of the Gaussian program.

[0517] G.T1 (eV)Comparative compound B2.504Comparative compound C2.468P-12.408

[0518] As can be seen in Table 8 above, the T1 of Comparative Compound B and Comparative Compound C is higher than that of Compound P-1 of the present invention. In the case of Comparative Compound B and Comparative Compound C, the gap between the T1 of the host and the T1 of the dopant is widened, so that the Dexter energy transfer does not occur smoothly. In other words, the time that energy remains in the triplet increases, so the probability of Triplet-triplet annihilation (TTA) occurring increases. In other words, when TTA occurs frequently, the efficiency and lifespan of the entire device are reduced due to energy loss and structural stress. In other words, in the case of Compound P-1 of the present invention, since the T1 is lower, the Dexter energy transfer occurs well compared to Comparative Compound B and Comparative Compound C, and thus the efficiency and lifespan appear to increase.

[0519] From another perspective, as can be seen in Examples 25 to 36, the characteristics of the first compound and the second compound differ depending on the type of the multiple host compounds, and it is judged that the performance of the device is ultimately determined by the injection characteristics of holes and electrons into the dopant.

[0520] That is, it is judged that the effect is maximized as a synergistic effect when a naphthyl-aryl substituent and a specific phenyl-naphthyl-aryl substituent are simultaneously substituted as substituents of triazine, as in the present invention.

[0521] The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are intended to illustrate, not limit, the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all techniques within a scope equivalent thereto should be interpreted as being included within the scope of the present invention.

[0522] 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, R 1 , R 2 and R 3 are each independently the same or different from each other, and are independently hydrogen; or deuterium; Ar 1 and Ar 2 are independently C6~C excluding fluorenyl group 60 is an aryl group, Ar 3 Silver C6~C 60 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group; and a and c are independently integers from 0 to 6, b is an integer from 0 to 4, Here, the aryl group and heterocyclic group are deuterium; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 aryl group of; or C2~C 20 may be further substituted with a heterocyclic group; 2. A compound characterized in that, in paragraph 1, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4. <Chemical Formula 1-1> <Chemical Formula 1-2> <Chemical Formula 1-3> <Chemical Formula 1-4> {In the above chemical formulas 1-1 to 1-4, R 1 , R 2 , R 3 , Ar 1 , Ar 2 , Ar 3 , a, b and c are the same as defined in claim 1 above.} 3. In the first paragraph, the Ar 1 , Ar 2 and Ar 3 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 above chemical formulas a-1 to a-8, R 4 are each identical or different and independently of each other deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 aryl group of; d is an integer from 0 to 5, e is an integer from 0 to 7, f is an integer from 0 to 9, refers to a part that binds to the aryl group or triazine of the above chemical formula 1.

4. In the first paragraph, the Ar 3 A compound characterized by being represented by any one of the following chemical formulas b-1 to b-4 <Chemical Formula B-1> <Chemical Formula B-2> <Chemical Formula B-3> <Chemical Formula B-4> {In the above chemical formulas b-1 to b-4, X is NR 6 , O or S, R 5 are each identical or different and independently of one another deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 is the aryl group of; R 6 are each identical or different, and are independently C6~C 20 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 20 is a heterocyclic group; and g is an integer from 0 to 7, refers to a part that binds to the triazine of the above chemical formula 1.

5. A compound characterized in that the compound represented by the above chemical formula 1 is any one of the compounds P-1 to P-152 below.

6. An organic electric device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer is a phosphorescent light-emitting layer, characterized in that it comprises a first host compound represented by the chemical formula 1 of claim 1 and a second host compound represented by the chemical formula 3 or 4 below. <Chemical Formula 3> <Chemical Formula 4> {In the above chemical formulas 3 and 4, L 4 , L 5 , L 6 and L 7 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; Ar 3 , Ar 4 and Ar 5 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; 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; Ar 6 Silver 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 the aromatic ring; and -L'-N(R b )(R c ) is selected from the group consisting of, Ring A is C6~C 20 is an aryl group, Z is O, S, CR'R" or NR a and, R 8 and R 9 are independently the same or different from each other, 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 60 Alkyl group of; C2~C 60 Alkenyl group of; C2~C 60 Alkynyl group of; C1~C 60 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups; or adjacent multiple R 8 R's or multiple R's 9 They can combine with each other to form rings, The above L' is a single bond; C6~C 60 Arylene group; Fluorenylene group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 A heterocyclic group of R; and a combination thereof, wherein R is selected from the group consisting of b and R c are independently C6~C 60 Aryl group of; Fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 A heterocyclic group; and a combination thereof, selected from the group consisting of The above R' and R" are independently hydrogen; deuterium; 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 is selected from the group consisting of aryloxy groups; or R' and R" can be combined with each other to form a spiro ring, The above R a is C6~C 60 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group; and n and o are integers from 0 to 4, independently of each other, Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; C6~C 20 Silane group substituted with aryl 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 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of C7~C 20 alkylaryl group of; and -L'-N(R b )(R c ); 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 C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

7. In the 6th paragraph, a compound characterized in that the compound represented by the chemical formula 3 is any one of the following compounds N-1 to N-96 8. In the 6th paragraph, a compound characterized in that the compound represented by the chemical formula 4 is any one of the following compounds S-1 to S-108 9. An organic electric device according to claim 6, further comprising a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic layer.

10. An organic electric device according to claim 6, characterized in that the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.

11. An organic electric device according to claim 10, characterized in that the organic layer further includes a charge generation layer formed between the two or more stacks.

12. An electronic device comprising a display device including an organic electric element of clause 6; and a control unit for driving the display device.

13. An electronic device according to claim 12, wherein 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.

14. 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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