Organic electric element comprising compound for organic electric element, and electronic device comprising same

Abstract

The present invention provides an organic electric element and an electronic device comprising same, the organic electric element comprising: a first electrode; a second electrode; and an organic material layer comprising an emission layer formed between the first electrode and the second electrode. The organic material layer comprises a hole transport layer formed between the first electrode and the emission layer and a plurality of auxiliary emission layers formed between the hole transport layer and the emission layer, wherein the plurality of auxiliary emission layers comprise a first auxiliary emission layer adjacent to the hole transport layer and a second auxiliary emission layer adjacent to the emission layer, and an n-type doping material is included in the auxiliary emission layer adjacent to the emission layer among the plurality of auxiliary emission layers between the hole transport layer and the emission layer, thereby lowering the driving voltage of the organic electric element and enhancing the light-emitting efficiency and lifespan thereof.

Description

Organic electric device comprising a compound for organic electric device and electronic device thereof

[0001] The present invention relates to an organic electric device using a compound for an organic electric device 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 with different materials to enhance the efficiency and stability of the device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0003] Typically, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated through recombination.

[0004] However, since the materials used in the hole transport layer must have a low HOMO value, most of them have a low T1 value, which causes excitons generated in the emitting layer to move to the hole transport layer, resulting in charge imbalance within the emitting layer and causing light emission at the hole transport layer interface. To solve this problem of light emission in the hole transport layer, an organic electroluminescent device that forms multiple hole transport layers or forms a light-emitting auxiliary layer between the hole transport layer and the emitting layer has been proposed.

[0005] Korean Patent Publication No. 10-2021-0053209 discloses an organic electroluminescent device comprising a plurality of light-emitting auxiliary layers. This organic electroluminescent device forms a plurality of light-emitting auxiliary layers having a predetermined thickness between a hole transport layer and a light-emitting layer, and appropriately controls the HOMO energy levels of these light-emitting auxiliary layers in consideration of the HOMO energy levels of adjacent organic layers, thereby improving luminous efficiency and lifespan characteristics when forming a plurality of light-emitting auxiliary layers.

[0006] However, although this method can improve luminous efficiency and lifetime characteristics by controlling hole injection characteristics, charge imbalance within the luminescent layer can cause charge accumulation in the luminescent auxiliary layer and the luminescent layer. Accumulated charges that are not resolved through recombination can cause damage due to deterioration of organic materials, resulting in a reduced lifetime of organic electronic devices.

[0007] Therefore, in order to solve the problem of reduced lifespan due to accumulated charges that are not resolved, a material having a LUMO similar to the LUMO of the n-type luminescent material in the luminescent layer is doped into the luminescent auxiliary layer adjacent to the luminescent layer. The electrons accumulated at the interface between the luminescent auxiliary layer and the luminescent layer are transferred to the luminescent auxiliary layer by the doped n-type organic material, and recombine with the holes in the luminescent auxiliary layer to resolve the accumulated charges. This can reduce damage due to deterioration of the interface, thereby improving the lifespan.

[0008] Accordingly, the present invention is intended to supplement the prior art, and an object of the present invention is to provide an organic electric element having an improved lifespan and an electronic device including the same, by forming a plurality of light-emitting auxiliary layers having a predetermined thickness between a hole transport layer and a light-emitting layer, and using an n-type doping material in the light-emitting auxiliary layers adjacent to the light-emitting layer.

[0009] In one aspect, the organic electric device according to the present invention provides an organic electric device including an n-type doping material in a light-emitting auxiliary layer adjacent to the light-emitting layer among a plurality of light-emitting auxiliary layers between a hole transport layer and a light-emitting layer.

[0010] In another aspect, the present invention provides an electronic device including the organic electric element.

[0011] According to the present invention, a plurality of light-emitting auxiliary layers having a predetermined thickness are formed between a hole transport layer and a light-emitting layer, and an n-type material is doped into the light-emitting auxiliary layers adjacent to these light-emitting layers. By using a material having a LUMO energy level similar to that of the n-type material of the light-emitting layer, an organic electric device having improved device stability and enhanced light-emitting efficiency and lifespan, and an electronic device including the same can be provided.

[0012] Figure 1 is an exemplary diagram of an organic light-emitting device according to the present invention.

[0013] 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.

[0014] 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.

[0015] As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

[0016] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0017] The term "alkyl" or "alkyl group" 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, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and a cycloalkyl-substituted alkyl group.

[0018] The term "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise stated, includes, but is not limited to, a straight-chain or branched chain group having a double bond or triple bond of 2 to 60 carbon atoms.

[0019] The term "cycloalkyl" as used in the present invention means, unless otherwise stated, an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0020] The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” as used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise stated, has 1 to 60 carbon atoms, but is not limited thereto.

[0021] 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 stated, has 6 to 60 carbon atoms, but is not limited thereto.

[0022] The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, each have 6 to 60 carbon atoms, but are not limited thereto. 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.

[0023] 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.

[0024] 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.

[0025] The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 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.

[0026] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0027] Additionally, a "heterocyclic group" may also include a ring containing SO2 instead of a ring-forming carbon. For example, a "heterocyclic group" includes the following compounds:

[0028]

[0029] The term "fluorenyl group" or "fluorenylene group" used in the present invention, unless otherwise stated, means a monovalent or divalent functional group in which R, R' and R" in the structure below are all hydrogen, and a "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R' and R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0030]

[0031] 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.

[0032] Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0033] Unless otherwise stated, the term "ring" as used in the present invention refers to a fused ring composed of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, and includes a saturated or unsaturated ring.

[0034] Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds include, but are not limited to, one or more heteroatoms.

[0035] 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 deuterium 20 Aryl group of C8~C 20 Arylalkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group consisting of heterocyclic groups, but is not limited to these substituents.

[0036] 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.

[0037]

[0038] Here, if a is an integer of 0, the substituent R 1 is absent, and if a is an integer of 1, there is one substituent R 1 is bonded to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, in which case R 1 may be the same or different, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0039]

[0040]

[0041] Figure 1 is an exemplary diagram of an organic electric device according to an embodiment of the present invention.

[0042] Referring to FIG. 1, an organic electric element according to one embodiment of the present invention includes a first electrode formed on a substrate (not shown), a second electrode, and an organic layer formed between the first electrode and the second electrode.

[0043] The above first electrode may be an anode, the second electrode may be a cathode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0044] The above organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., and a light-emitting auxiliary layer is formed between the hole transport layer and the light-emitting layer. In addition, a buffer layer may be further formed between the hole transport layer and the light-emitting auxiliary layer.

[0045] Specifically, a hole injection layer, a hole transport layer, a buffer layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer can be sequentially formed on the first electrode.

[0046] Preferably, a light efficiency improvement layer may be formed on one side of the first electrode or the second electrode that is not in contact with the organic layer, and when the light efficiency improvement layer is formed, the light efficiency of the organic electric element may be improved.

[0047] For example, a light efficiency improvement layer can be formed on the second electrode. In the case of a top emission organic light emitting device, the formation of the light efficiency improvement layer can reduce optical energy loss due to SPPs (surface plasmon polaritons) at the second electrode, and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer can serve as a buffer for the second electrode.

[0048] Although not shown in Fig. 1, an electron transport auxiliary layer may be further formed between the light-emitting layer and the electron transport layer.

[0049] An organic material layer according to an embodiment of the present invention includes a plurality of light-emitting auxiliary layers, and represents an organic material layer including two light-emitting auxiliary layers. The plurality of light-emitting auxiliary layers includes a first light-emitting auxiliary layer adjacent to a hole transport layer and a second light-emitting auxiliary layer adjacent to the light-emitting layer. The second light-emitting auxiliary layer adjacent to the light-emitting layer is formed by doping with the first light-emitting auxiliary layer; or a hole transport layer different from the second light-emitting auxiliary layer; or an organic material used in the light-emitting auxiliary layer; or an n-type organic material.

[0050] Preferably, the T1 energy level of the light-emitting auxiliary layer is 2.00 to 3.20 eV.

[0051] Preferably, the LUMO energy level of the n-type doping material doped in the light-emitting auxiliary layer has a difference of 0.01 to 0.5 eV in absolute value from the LUMO energy level of the light-emitting auxiliary layer.

[0052] In this way, the light-emitting auxiliary layer of the present invention is formed only with different compounds, and is formed to a predetermined thickness by doping with a first light-emitting auxiliary layer having an appropriate LUMO energy level for a second light-emitting auxiliary layer adjacent to the light-emitting layer; or a hole transport layer different from the second light-emitting auxiliary layer; or an organic material used in the light-emitting auxiliary layer; or an n-type doping material, thereby improving the lifespan and efficiency of the organic electric device.

[0053] Preferably, the light-emitting layer according to the present invention is a red light-emitting layer or a green light-emitting layer.

[0054] According to another embodiment of the present invention, the organic layer may be formed in a form in which a plurality of stacks including a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, and an electron transport layer are formed.

[0055] Generally, organic light-emitting devices can be divided into single-emitting structure devices (Single OLED) and multilayered light-emitting structure devices (Tandem OLED) depending on the number of light-emitting parts. A multilayered light-emitting structure device (Tandem OLED) is an OLED device composed of two or more light-emitting parts (stack), and it is easy to improve the driving voltage and efficiency compared to the existing single OLED.

[0056] Specifically, an organic electroluminescent device according to one embodiment of the present invention may include a first electrode, a first stack formed on the first electrode, a second stack formed on the first stack, and a second electrode. Here, the stack may correspond to an organic layer, and a light efficiency improvement layer may be further formed on a surface of the first electrode and / or the second electrode that is not in contact with the organic layer.

[0057] The first stack and the second stack are organic layers including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, respectively, and the first stack and the second stack may be formed with the same or different laminated structures.

[0058] At least one of the first stack and the second stack includes a light-emitting auxiliary layer mixing a third compound adjacent to the light-emitting layer according to the present invention. That is, a plurality of light-emitting auxiliary layers according to the present invention are included between the hole transport layer and the light-emitting layer, and these light-emitting auxiliary layers may be included in the first stack and / or the second stack.

[0059] Additionally, a charge generation layer (CGL) may be formed between the first stack and the second stack. The charge generation layer (CGL) may include a first charge generation layer and a second charge generation layer. This charge generation layer (CGL) is formed between the light-emitting layer of the first stack and the light-emitting layer of the second stack, and serves to increase the current efficiency generated in each light-emitting layer and to smoothly distribute charges.

[0060] These organic layer stacks can be formed in two or more layers. For example, when three stacks are formed, a charge generation layer (CGL) and a third stack can be additionally stacked on the second stack.

[0061] In this way, when multiple light-emitting layers are formed by a multi-layer stack structure, it is possible to manufacture an organic light-emitting device that emits white light through the mixing effect of the light emitted from each light-emitting layer, and it is also possible to manufacture an organic light-emitting device that emits light of various colors.

[0062] The organic layer according to the present invention can be manufactured with a smaller number of layers using various polymer materials, rather than a deposition method, through a solution process or a solvent process, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, a screen printing process, or a thermal transfer method. Since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0063] An organic electric device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0064] In addition, the organic electric device according to one embodiment of the present invention may be selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, a device for monochrome lighting, and a device for quantum dot display.

[0065] Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired 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.

[0066] According to the present invention, the plurality of light-emitting auxiliary layers include a first light-emitting auxiliary layer adjacent to the hole transport layer and a second light-emitting auxiliary layer adjacent to the light-emitting layer. The first light-emitting auxiliary layer and the second light-emitting auxiliary layer include a compound represented by the following chemical formula 1 or a compound represented by the following chemical formula 2, and the second light-emitting auxiliary layer is formed by mixing compounds represented by the following chemical formulas 1 to 3.

[0067] At this time, it is preferable that the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are formed of different compounds. That is, even if both the first light-emitting auxiliary layer and the second light-emitting auxiliary layer are formed of a compound represented by the following chemical formula 1 or are formed of a compound represented by the following chemical formula 2, it is preferable that each light-emitting auxiliary layer is formed of a different compound.

[0068] Hereinafter, an organic electric device according to one aspect of the present invention will be described.

[0069] According to one embodiment of the present invention, an organic electric device includes an organic layer including a first electrode, a second electrode, and a light-emitting layer formed between the first electrode and the second electrode, wherein the organic layer includes a hole transport layer formed between the first electrode and the light-emitting layer, and includes a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer, and the plurality of light-emitting auxiliary layers include a first light-emitting auxiliary layer adjacent to the hole transport layer and a second light-emitting auxiliary layer adjacent to the light-emitting layer, and the first light-emitting auxiliary layer is formed of a single material, and the second light-emitting auxiliary layer is formed of a mixture.

[0070] In addition, the present invention provides an organic electric device characterized in that the first light-emitting auxiliary layer includes a first compound, the second light-emitting auxiliary layer includes a mixture of a second compound and a third compound, the first compound, the second compound and the third compound each have different structures, and the first compound and the second compound are compounds represented by one of the following chemical formulas 1 and 2.

[0071] <Chemical Formula 1> <Chemical Formula 2>

[0072]

[0073] In the above chemical formulas 1 and 2, each symbol can be defined as follows.

[0074] Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Cycloalkyl group of; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups;

[0075] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0076] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0077] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0078] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is a cycloalkyl group, preferably C3~C 30 Cycloalkyl group, more preferably C3~C 25 , C3~C 18 , C3~C 12 or C3~C 10 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0079] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 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.

[0080] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0081] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar6 and Ar 7 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0082] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 are independently of each other and are single bonds; C6~C 60 C2~C containing an arylene group; a fluorenylene group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups;

[0083] L 8 Silver C6~C 60 C2~C containing an arylene group; a fluorenylene group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups;

[0084] Above L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 If it is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0085] Above L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L7 and L 8 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0086] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group and cycloalkyl group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Cycloalkyl group of; C7~C 20 Arylalkyl group of; and C8~C 20 It may be further substituted with one or more substituents selected from the group consisting of arylalkenyl groups; and these substituents may also be combined with each other to form a ring, wherein the 'ring' refers to C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0087] In addition, the present invention provides an organic electric device characterized in that the third compound is a compound represented by the chemical formula 1 or chemical formula 2.

[0088]

[0089] In addition, the present invention provides an organic electric device characterized in that the third compound is a compound represented by the following chemical formula 3.

[0090] <Chemical Formula 3>

[0091]

[0092] In the above chemical formula 3, each symbol can be defined as follows.

[0093] L 9 , L 10 and L 11 Silver is the above L 1 is identical to the definition of

[0094] Ar 8 , Ar 9 and Ar 10 are independently cyano groups; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Cycloalkyl group of; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups;

[0095] The above Ar 8 , Ar 9and Ar 10 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0096] The above Ar 8 , Ar 9 and Ar 10 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0097] The above Ar 8 , Ar 9 and Ar 10 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0098] The above Ar 8 , Ar 9 and Ar 10 If it is a cycloalkyl group, preferably C3~C 30 Cycloalkyl group, more preferably C3~C 25 , C3~C 18 , C3~C12 or C3~C 10 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0099] The above Ar 8 , Ar 9 and Ar 10 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.

[0100] The above Ar 8 , Ar 9 and Ar 10 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0101] The above Ar 8 , Ar 9 and Ar 10 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0102]

[0103] In addition, the present invention comprises the Ar 1 Inland Ar 10 At least one of the organic electroluminescent devices is represented by any one of the following chemical formulae Ar-a to Ar-d.

[0104] Chemical formula Ar-a Chemical formula Ar-b

[0105]

[0106] Chemical formula Ar-c Chemical formula Ar-d

[0107]

[0108] In the above chemical formulas Ar-a to Ar-d, each symbol can be defined as follows.

[0109] Y A , Y B and Y C are independently of each other O, S, NR 1A or CR 1B R 1C and,

[0110] R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C are independently of each other, identical or different, and independently of each other, 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 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; or adjacent groups can be combined with each other to form a ring,

[0111] The above R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C If it is an aryl group, preferably C6~C 30Aryl group of, more preferably C6~C 25 , C6~C 18 , C6~C 14 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0112] The above R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 , C2~C 16 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0113] The above R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0114] The above R A , RB , R C , R D , R E , R F , R 1A , R 1B and R 1C 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.

[0115] The above R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0116] The above R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0117] ta and tc are independently integers from 0 to 3, tb and td are independently integers from 0 to 4, te is an integer from 0 to 5, tf is an integer from 0 to 7,

[0118] means the position of joining.}

[0119]

[0120] The above chemical formula Ar-a can be represented by any one of the following chemical formulas Ar-a-1 to Ar-a-4.

[0121] <Chemical formula Ar-a-1> <Chemical formula Ar-a-2>

[0122]

[0123] <Chemical formula Ar-a-3> <Chemical formula Ar-a-4>

[0124]

[0125] {In the above chemical formulas Ar-a-1 to Ar-a-4, R A , R B , Y A , ta, tb and is as defined in the above chemical formula Ar-a.}

[0126]

[0127] The above chemical formula Ar-b can be represented by the following chemical formula Ar-b-1 or chemical formula Ar-b-2.

[0128] <Chemical formula Ar-b-1> <Chemical formula Ar-b-2>

[0129]

[0130] {In the above chemical formula Ar-b-1 and chemical formula Ar-b-2, R C , R D , Y B , Y C , tc, td and is as defined in the above chemical formula Ar-b.}

[0131]

[0132] The above chemical formula Ar-d can be represented by the following chemical formula Ar-d-1 or chemical formula Ar-d-2.

[0133] <Chemical formula Ar-d-1> <Chemical formula Ar-d-2>

[0134]

[0135] {In the above chemical formula Ar-d-1 and chemical formula Ar-d-2, R F , tf and is as defined in the above chemical formula Ar-d.}

[0136] Above L 1 Inland L 11 can be represented by a single bond or any one of the following chemical formulas b-1 to b-13.

[0137] Chemical formula b-1 Chemical formula b-2 Chemical formula b-3 Chemical formula b-4 Chemical formula b-5 Chemical formula b-6

[0138]

[0139] Chemical formula b-7 Chemical formula b-8 Chemical formula b-9 Chemical formula b-10

[0140]

[0141] Chemical formula b-11 Chemical formula b-12 Chemical formula b-13

[0142]

[0143] {In the above chemical formulas b-1 to b-13,

[0144] Z 10 Silver O, S, NR 1D or CR 1E R 1F and,

[0145] a”, c”, d”, e” and i” are each independently an integer from 0 to 4, b” is an integer from 0 to 6, f” and g” are each independently an integer from 0 to 3, h” is an integer from 0 to 2, and j” is an integer of 0 or 1,

[0146] R a1 , R a2 , R a3 , R a4 , R a5 , R a6 , R a7 , R1D , R 1E and R 1F is the above R A is the same as the definition of , or adjacent groups can combine with each other to form a ring,

[0147] Z 49 , Z 50 and Z 51 are independently of each other 1G or N, but Z 49 , Z 50 and Z 51 At least one of them is N,

[0148] R 1G is the above R A is identical to the definition of {

[0149]

[0150] Specifically, the compound of the above chemical formula 1 may be any one of the following compounds P1-1 to P1-97, but is not limited thereto.

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] Specifically, the compound of the above chemical formula 2 may be any one of the following compounds P2-1 to P2-79, but is not limited thereto.

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199] Specifically, the compound of the above chemical formula 3 may be any one of the following compounds P3-1 to P3-48, but is not limited thereto.

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] In addition, the present invention provides an organic electric device in which the first light-emitting auxiliary layer is formed of a first compound represented by the chemical formula 1, and the second light-emitting auxiliary layer is formed by mixing the second compound and the third compound represented by the chemical formula 3.

[0214] In addition, the present invention provides an organic electric device in which the first light-emitting auxiliary layer is made of a compound represented by the chemical formula 2, and the second light-emitting auxiliary layer is a mixture of the second compound and the third compound represented by the chemical formula 3.

[0215] In addition, the present invention provides an organic electronic device in which the difference between the LUMO energy level of the third compound and the LUMO energy level of the host compound of the light-emitting layer is 0.01 to 1.0 eV, preferably 0.01 to 0.7 eV, more preferably 0.01 to 0.6 eV, and even more preferably 0.01 to 0.5 eV. The difference in the LUMO energy levels refers to an absolute value. A reduction in the lifespan may occur due to a deterioration phenomenon at the interface between the light-emitting auxiliary layer and the light-emitting layer due to holes that are not transferred from the light-emitting auxiliary layer to the light-emitting layer and electrons that are not recombined in the light-emitting layer. Therefore, when the above range is satisfied, some of the electrons that are not recombined in the light-emitting layer due to charge imbalance (accumulated at the interface between the light-emitting auxiliary layer and the light-emitting layer) may be transferred to the third compound doped in the light-emitting auxiliary layer. The electrons transferred in this way are resolved through a process of emitting or not emitting light with the holes in the light-emitting auxiliary layer. Therefore, by moving electrons applied to the interface between the light-emitting auxiliary layer and the light-emitting layer to the light-emitting auxiliary layer, deterioration of the light-emitting layer interface is reduced, which is effective in improving the lifespan.

[0216] At this time, light emission occurs in the light-emitting auxiliary layer, not the light-emitting layer, but by controlling the doping concentration to an appropriate level, the efficiency and lifespan characteristics are improved while maintaining a certain level of color purity. In the case of the doping concentration, it is preferable that the mass ratio be 1% to 20%, more preferably 1% to 15%, and even more preferably 1% to 10%, whereby efficiency and lifespan appear to be maximized.

[0217] In addition, the present invention provides an organic electric device in which the T1 energy level of the second compound and the third compound is 2.00 to 3.50 eV.

[0218] The T1 energy level of the second compound and the third compound, which are the second light-emitting auxiliary layers, is preferably 2.0 to 3.40 eV, more preferably 2.00 to 3.30 eV, and even more preferably 2.00 to 3.20 eV, and an appropriate level of the T1 energy level in the light-emitting auxiliary layer adjacent to the light-emitting layer can prevent triplet excitons formed in the light-emitting layer from being transferred to the light-emitting auxiliary layer. This has the effect of maintaining or improving the efficiency characteristics of the organic electronic device.

[0219] At this time, triplet excitons are particles created by combining holes and electrons transferred from the hole-raising layer and electron-transport layer to the light-emitting layer, and electrons refer to excess electrons that are left over after failing to form excitons.

[0220] At this time, if the second compound and the third compound have a lower T1 than the host of the light-emitting layer, triplet excitons may move to the light-emitting auxiliary layer, and the efficiency may decrease rapidly. Therefore, it means that the high T1 can effectively block the movement of triplet excitons to the light-emitting auxiliary layer, and the efficiency increases due to the blocked triplet excitons.

[0221] The present invention may further include a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode, which is opposite to the organic layer.

[0222] In addition, 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 the organic layer may further include a charge generation layer formed between the two or more stacks.

[0223] In another aspect, the present invention provides an electronic device including a display device including the organic electroluminescent element; and a control unit for driving the display device. In this case, the organic electroluminescent element may be at least one of an organic electroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element.

[0224]

[0225] Hereinafter, examples of synthesis of compounds represented by chemical formulas 1 to 3 and examples of manufacturing organic electric devices according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[0226]

[0227] [Synthesis Example 1] Synthesis Example of Chemical Formula 1

[0228] The compound represented by chemical formula 1 according to the present invention (final product 1) can be synthesized according to the reaction path of the following reaction scheme 1, but is not limited thereto.

[0229] <Reaction Scheme 1> (Hal 1 is I, Br or Cl.)

[0230]

[0231] I. Synthesis of Sub 1

[0232] Compounds belonging to Sub 1 of the above reaction scheme 1 may be, but are not limited to, the compounds below, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below.

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252] Compound FD-MS Compound FD-MS Sub 1-1 m / z = 354.08 (C 24 H 15 ClO=354.83)Sub 1-2m / z=238.05(C 16 H 11 Cl=238.71)Sub 1-3m / z=364.10(C 26 H 17 Cl=364.87)Sub 1-4m / z=241.05(C 12D9Br=242.16)Sub 1-5m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-6m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-7m / z=288.07(C 20 H 13 Cl=288.77)Sub 1-8m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-9m / z=354.08(C 24 H 15 ClO=354.83)Sub 1-10m / z=304.10(C 21 H 17 Cl=304.82)Sub 1-11m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-12m / z=402.12(C 29 H 19 Cl=402.92)Sub 1-13m / z=402.12(C 29 H 19 Cl=402.92)Sub 1-14m / z=402.12(C 29 H 19 Cl=402.92)Sub 1-15m / z=354.08(C 24 H 15 ClO=354.83)Sub 1-16m / z=328.07(C 22 H 13 ClO=328.79)Sub 1-17m / z=428.13(C 31 H 21 Cl=428.96)Sub 1-18m / z=353.10(C 24 H 16 ClN=353.85)Sub 1-19m / z=277.07(C 18 H 12 ClN=277.75)Sub 1-20m / z=426.12(C 31 H 19 Cl=426.94)Sub 1-21m / z=353.10(C 24 H 16ClN=353.85)Sub 1-22m / z=353.10(C 24 H 16 ClN=353.85)Sub 1-23m / z=294.03(C 18 H 11 ClS=294.80)Sub 1-24m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-25m / z=458.09(C 31 H 19 ClS=459.00)Sub 1-26m / z=476.13(C 35 H 21 Cl=477.00)Sub 1-27m / z=442.11(C 31 H 19 ClO=442.94)Sub 1-28m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-29m / z=294.03(C 18 H 11 ClS=294.80)Sub 1-30m / z=258.12(C 18 H 14 N2=258.32)Sub 1-31m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-32m / z=410.03(C 25 H 15 BrO=411.30)Sub 1-33m / z=396.05(C 25 H 17 Br=397.31)Sub 1-34m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-35m / z=428.13(C 31 H 21 Cl=428.96)Sub 1-36m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-37m / z=408.16(C 29 H 25 Cl=408.97)Sub 1-38m / z=462.21(C 33 H 31Cl=463.06)Sub 1-39m / z=442.11(C 31 H 19 ClO=442.94)Sub 1-40m / z=441.13(C 31 H 20 ClN=441.96)Sub 1-41m / z=278.09(C 19 H 15 Cl=278.78)Sub 1-42m / z=508.18(C 33 H 33 Br=509.53)Sub 1-43m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-44m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-45m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-46m / z=368.08(C 24 H 17 ClSi=368.94)Sub 1-47m / z=396.05(C 25 H 17 Br=397.31)Sub 1-48m / z=244.05(C 14 H 13 ClSi=244.79)Sub 1-49m / z=302.03(C 16 H 15 BrO=303.20)Sub 1-50m / z=300.05(C 17 H 17 Br=301.23)Sub 1-51m / z=396.05(C 25 H 17 Br=397.31)Sub 1-52m / z=410.07(C 26 H 19 Br=411.34)Sub 1-53m / z=246.12(C 16 H 19 Cl=246.78)Sub 1-54m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-55m / z=242.09(C 16 H 15Cl=242.75)Sub 1-56m / z=428.13(C 31 H 21 Cl=428.96)Sub 1-57m / z=314.09(C 22 H 15 Cl=314.81)Sub 1-58m / z=352.10(C 25 H 17 Cl=352.86)Sub 1-59m / z=428.13(C 31 H 21 Cl=428.96)Sub 1-60m / z=380.13(C 27 H 21 Cl=380.91)Sub 1-61m / z=428.13(C 31 H 21 Cl=428.96)Sub 1-62m / z=428.13(C 31 H 21 Cl=428.96)Sub 1-63m / z=389.19(C 26 H 28 ClN=389.97)Sub 1-64m / z=358.13(C 24 H 11 D5ClN=358.88)Sub 1-65m / z=314.09(C 22 H 15 Cl=314.81)Sub 1-66m / z=320.13(C 22 H 21 Cl=320.86)Sub 1-67m / z=508.18(C 33 H 33 Br=509.53)Sub 1-68m / z=370.15(C 26 H 23 Cl=370.92)Sub 1-69m / z=194.09(C 12 H 15 Cl=194.70)Sub 1-70m / z=394.11(C 27 H 19 ClO=394.90)Sub 1-71m / z=384.04(C 24 H 13 ClOS=384.88)Sub 1-72m / z=443.11(C 30 H 18ClNO=443.93)Sub 1-73m / z=442.12(C 30 H 19 ClN2=442.95)Sub 1-74m / z=442.12(C 30 H 19 ClN2=442.95)Sub 1-75m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-76m / z=283.08(C 18 H6D5ClO=283.77)Sub 1-77m / z=364.10(C 26 H 17 Cl=364.87)Sub 1-78m / z=400.10(C 29 H 17 Cl=400.90)Sub 1-79m / z=402.12(C 29 H 19 Cl=402.92)Sub 1-80m / z=554.18(C 41 H 27 Cl=555.12)Sub 1-81m / z=394.04(C 25 H 15 Br=395.30)Sub 1-82m / z=416.04(C 24 H 19 BrSi=415.40)Sub 1-83m / z=410.03(C 25 H 15 BrO=411.30)Sub 1-84m / z=188.04(C 12 H9Cl=188.65)Sub 1-85m / z=334.11(C 22 H 19 ClO=334.84)Sub 1-86m / z=272.02(C 15 H 13 Br=273.17)Sub 1-87m / z=322.04(C 19 H 15 Br=323.23)Sub 1-88m / z=322.00(C 18 H 11 BrO=323.19)Sub 1-89m / z=322.00(C 18 H 11 BrO=323.19)Sub 1-90m / z=318.08(C21 H 15 ClO=318.80)Sub 1-91m / z=278.05(C 18 H 11 ClO=278.74)Sub 1-92m / z=322.00(C 18 H 11 BrO=323.19)Sub 1-93m / z=327.08(C 22 H 14 ClN=327.81)Sub 1-94m / z=277.07(C 18 H 12 ClN=277.75)

[0253] II. Synthesis of Sub 2 Compounds belonging to Sub 2 of the above reaction scheme 1 may be, but are not limited to, the compounds below, and Table 2 below shows the FD-MS values ​​of the compounds below.

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275] 화합물FD-MS화합물FD-MSSub 2-1m / z=321.15(C 24 H 19 N = 321.42) Sub 2-2m / z = 397.18 (C 30 H 23 N = 397.52) Sub 2-3m / z = 345.15 (C 26 H 19 N = 345.44) Sub 2-4m / z = 371.17 (C 28 H 21 N = 371.48) Sub 2-5m / z = 321.15 (C 24 H 19 N = 321.42) Sub 2-6m / z = 345.15 (C 26 H 19 N = 345.44) Sub 2-7m / z = 371.17 (C 28 H 21 N = 371.48) Sub 2-8m / z = 397.18 (C 30 H 23 N = 397.52) Sub 2-9m / z = 447.20 (C 34 H 25 N = 447.58) Sub 2-10m / z = 295.14 (C 22 H 17 N = 295.38) Sub 2-11m / z = 245.12 (C 18 H 15 N = 245.32) Sub 2-12m / z = 169.09 (C 12 H 11 N = 169.23) Sub 2-13m / z = 395.17 (C 30 H 21N=395.50)Sub 2-14m / z=219.10(C 16 H 13 N=219.29)Sub 2-15m / z=219.10(C 16 H 13 N=219.29)Sub 2-16m / z=219.10(C 16 H 13 N=219.29)Sub 2-17m / z=319.14(C 24 H 17 N=319.41)Sub 2-18m / z=523.23(C 40 H 29 N=523.68)Sub 2-19m / z=369.15(C 28 H 19 N=369.47)Sub 2-20m / z=345.15(C 26 H 19 N=345.44)Sub 2-21m / z=174.12(C 12 H6D5N=174.26)Sub 2-22m / z=339.26(C 24 HD 18 N=339.53)Sub 2-23m / z=351.20(C 26 H 25 N=351.49)Sub 2-24m / z=291.14(C 19 H 21 NSi=291.47)Sub 2-25m / z=361.18(C 27 H 23 N=361.49)Sub 2-26m / z=361.18(C 27 H 23 N=361.49)Sub 2-27m / z=401.21(C 30 H 27 N=401.55)Sub 2-28m / z=401.21(C 30 H 27 N=401.55)Sub 2-29m / z=401.21(C 30 H 27 N=401.55)Sub 2-30m / z=361.18(C 27 H 23 N=361.49)Sub 2-31m / z=401.21(C 30 H 27N=401.55)Sub 2-32m / z=401.21(C 30 H 27 N=401.55)Sub 2-33m / z=401.21(C 30 H 27 N=401.55)Sub 2-34m / z=457.28(C 34 H 35 N=457.66)Sub 2-35m / z=477.25(C 36 H 31 N=477.65)Sub 2-36m / z=319.14(C 24 H 17 N=319.41)Sub 2-37m / z=217.09(C 16 H 11 N=217.27)Sub 2-38m / z=334.15(C 24 H 18 N2=334.42)Sub 2-39m / z=334.15(C 24 H 18 N2=334.42)Sub 2-40m / z=450.21(C 33 H 26 N2=450.59)Sub 2-41m / z=651.27(C 48 H 33 N3=651.81)Sub 2-42m / z=526.24(C 39 H 30 N2=526.68)Sub 2-43m / z=500.19(C 36 H 24 N2O=500.60)Sub 2-44m / z=440.13(C 30 H 20 N2S=440.56)Sub 2-45m / z=451.19(C 33 H 25 NO=451.57)Sub 2-46m / z=451.19(C 33 H 25 NO=451.57)Sub 2-47m / z=451.19(C 33 H 25 NO=451.57)Sub 2-48m / z=451.19(C 33 H 25 NO=451.57)Sub 2-49m / z=501.21(C37 H 27 NO=501.63)Sub 2-50m / z=375.16(C 27 H 21 NO=375.47)Sub 2-51m / z=375.16(C 27 H 21 NO=375.47)Sub 2-52m / z=375.16(C 27 H 21 NO=375.47)Sub 2-53m / z=375.16(C 27 H 21 NO=375.47)Sub 2-54m / z=425.18(C 31 H 23 NO=425.53)Sub 2-55m / z=437.18(C 32 H 23 NO=437.54)Sub 2-56m / z=259.10(C 18 H 13 NO=259.31)Sub 2-57m / z=259.10(C 18 H 13 NO=259.31)Sub 2-58m / z=259.10(C 18 H 13 NO=259.31)Sub 2-59m / z=335.13(C 24 H 17 NO=335.41)Sub 2-60m / z=335.13(C 24 H 17 NO=335.41)Sub 2-61m / z=335.13(C 24 H 17 NO=335.41)Sub 2-62m / z=335.13(C 24 H 17 NO=335.41)Sub 2-63m / z=309.12(C 22 H 15 NO=309.37)Sub 2-64m / z=309.12(C 22 H 15 NO=309.37)Sub 2-65m / z=385.15(C 28 H 19 NO=385.47)Sub 2-66m / z=411.16(C 30 H 21NO=411.50)Sub 2-67m / z=359.13(C 26 H 17 NO=359.43)Sub 2-68m / z=411.16(C 30 H 21 NO=411.50)Sub 2-69m / z=411.16(C 30 H 21 NO=411.50)Sub 2-70m / z=411.16(C 30 H 21 NO=411.50)Sub 2-71m / z=335.13(C 24 H 17 NO=335.41)Sub 2-72m / z=411.16(C 30 H 21 NO=411.50)Sub 2-73m / z=385.15(C 28 H 19 NO=385.47)Sub 2-74m / z=411.16(C 30 H 21 NO=411.50)Sub 2-75m / z=349.11(C 24 H 15 NO2=349.39)Sub 2-76m / z=441.12(C 30 H 19 NOS=441.55)Sub 2-77m / z=529.15(C 37 H 23 NOS=529.66)Sub 2-78m / z=499.19(C 37 H 25 NO=499.61)Sub 2-79m / z=499.19(C 37 H 25 NO=499.61)Sub 2-80m / z=517.15(C 36 H 23 NOS=517.65)Sub 2-81m / z=517.15(C 36 H 23 NOS=517.65)Sub 2-82m / z=275.08(C 18 H 13 NS=275.37)Sub 2-83m / z=351.11(C 24 H 17NS=351.47)Sub 2-84m / z=275.08(C 18 H 13 NS=275.37)Sub 2-85m / z=325.09(C 22 H 15 NS=325.43)Sub 2-86m / z=325.09(C 22 H 15 NS=325.43)Sub 2-87m / z=351.11(C 24 H 17 NS=351.47)Sub 2-88m / z=391.14(C 27 H 21 NS=391.53)Sub 2-89m / z=409.18(C 31 H 23 N=409.53)Sub 2-90m / z=485.21(C 37 H 27 N=485.63)Sub 2-91m / z=485.21(C 37 H 27 N=485.63)Sub 2-92m / z=485.21(C 37 H 27 N=485.63)Sub 2-93m / z=485.21(C 37 H 27 N=485.63)Sub 2-94m / z=485.21(C 37 H 27 N=485.63)Sub 2-95m / z=423.16(C 31 H 21 NO=423.51)Sub 2-96m / z=423.16(C 31 H 21 NO=423.51)Sub 2-97m / z=379.23(C 28 H 29 N=379.55)Sub 2-98m / z=367.23(C 27 H 29 N=367.54)Sub 2-99m / z=367.23(C 27 H 29 N=367.54)Sub 2-100m / z=341.18(C 24 H 23 NO=341.45)Sub 2-101m / z=385.28(C28 H 35 N=385.59)Sub 2-102m / z=345.25(C 25 H 31 N=345.53)Sub 2-103m / z=397.28(C 29 H 35 N=397.61)Sub 2-104m / z=209.12(C 15 H 15 N=209.29)Sub 2-105m / z=411.16(C 30 H 21 NO=411.50)

[0276]

[0277] III. Synthesis example of Final Product 1

[0278] 1. P1-32 Synthesis Example

[0279]

[0280] Sub 1-21 (15 g, 40.6 mmol), Toluene (140 mL), Sub 2-19 (14.4 g, 40.6 mmol), Pd2(dba)3(1.12 g, 1.22 mmol), P(t-Bu)3(0.49 g, 2.44 mmol), NaOt-Bu (7.80 g, 81.2 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with Toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (19.5 g, 70%).

[0281]

[0282] 2. P1-48 Synthesis Example

[0283]

[0284] Sub 1-32 (16 g, 42.6 mmol), Toluene (140 mL), Sub 2-50 (17.5 g, 42.6 mmol), Pd2(dba)3(1.17 g, 1.28 mmol), P(t-Bu)3(0.52 g, 2.56 mmol), NaOt-Bu (8.20 g, 85.2 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with Toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (23.5 g, 78%).

[0285]

[0286] 3. P1-69 Synthesis Example

[0287]

[0288] Sub 1-82 (16 g, 38.5 mmol), toluene (193 mL), Sub 2-87 (13.5 g, 38.5 mmol), Pd2(dba)3 (1.06 g, 1.16 mmol), P(t-Bu)3 (0.47 g, 2.31 mmol), and NaOt-Bu (7.4 g, 77.0 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (19.0 g, 72%).

[0289]

[0290] 4. P1-71 Synthesis Example

[0291]

[0292] Sub 1-53 (15 g, 39.5 mmol), toluene (130 mL), Sub 2-97 (9.75 g, 39.5 mmol), Pd2(dba)3 (1.09 g, 1.19 mmol), P(t-Bu)3 (0.48 g, 2.37 mmol), and NaOt-Bu (7.60 g, 79.0 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (18.9 g, 81%).

[0293]

[0294] 5. P1-95 Synthesis Example

[0295]

[0296] Sub 1-75 (10 g, 47.8 mmol), toluene (160 mL), Sub 2-104 (26.6 g, 100.3 mmol), Pd2(dba)3(2.19 g, 2.39 mmol), P(t-Bu)3(0.97 g, 4.78 mmol), NaOt-Bu (13.8 g, 143.3 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (25.9 g, 78%).

[0297]

[0298] 6. P1-96 Synthesis Example

[0299]

[0300] Sub 1-76 (10 g, 47.8 mmol), toluene (160 mL), Sub 2-104 (27.1 g, 100.3 mmol), Pd2(dba)3(2.19 g, 2.39 mmol), P(t-Bu)3(0.97 g, 4.78 mmol), NaOt-Bu (13.8 g, 143.3 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (25.2 g, 75%).

[0301] The FD-MS values ​​of compounds P1-1 to P1-97 of the present invention manufactured according to the above synthetic examples are as shown in Table 3 below.

[0302] Compound FD-MS Compound FD-MSP1-1 m / z = 473.21 (C 36 H 27 N=473.62)P1-2m / z=471.20(C 36 H 25 N=471.60)P1-3m / z=675.29(C 52 H 37 N=675.88)P1-4m / z=715.29(C 54 H 37 NO=715.90)P1-5m / z=623.26(C 48 H 33 N=623.80)P1-6m / z=649.28(C 50 H 35 N=649.84)P1-7m / z=667.39(C 50 H 17 D 18 N=667.95)P1-8m / z=749.31(C 58 H 39 N=749.96)P1-9m / z=653.24(C 48 H 31 NO2=653.78)P1-10m / z=567.17(C 40 H 25 NOS=567.71)P1-11m / z=531.13(C 36 H21 NO2S=531.63)P1-12m / z=593.18(C 42 H 27 NOS=593.74)P1-13m / z=527.17(C 38 H 25 NS=527.68)P1-14m / z=561.21(C 42 H 27 NO=561.68)P1-15m / z=527.22(C 39 H 29 NO=527.67)P1-16m / z=769.30(C 57 H 39 NO2=769.94)P1-17m / z=643.29(C 48 H 37 NO=643.83)P1-18m / z=719.32(C 54 H 41 NO=719.93)P1-19m / z=767.32(C 58 H 41 NO=767.97)P1-20m / z=651.26(C 49 H 33 NO=651.81)P1-21m / z=717.34(C 55 H 43 N=717.96)P1-22m / z=717.34(C 55 H 43 N=717.96)P1-23m / z=767.36(C 59 H 45 N=768.02)P1-24m / z=767.36(C 59 H 45 N=768.02)P1-25m / z=817.33(C 62 H 43 NO=818.03)P1-26m / z=727.29(C 55 H 37 NO=727.91)P1-27m / z=817.33(C 62 H 43 NO=818.03)P1-28m / z=703.25(C 52 H 33 NO2=703.84)P1-29m / z=869.40(C 67 H 51N=870.15)P1-30m / z=767.36(C 59 H 45 N=768.02)P1-31m / z=562.24(C 42 H 30 N2=562.72)P1-32m / z=686.27(C 52 H 34 N2=686.86)P1-33m / z=586.24(C 44 H 30 N2=586.74)P1-34m / z=602.27(C 45 H 34 N2=602.78)P1-35m / z=602.27(C 45 H 34 N2=602.78)P1-36m / z=649.24(C 49 H 31 NO=649.79)P1-37m / z=673.24(C 51 H 31 NO=673.81)P1-38m / z=711.29(C 55 H 37 N=711.91)P1-39m / z=725.27(C 55 H 35 NO=725.89)P1-40m / z=965.38(C 73 H 47 N3=966.20)P1-41m / z=815.32(C 62 H 41 NO=816.02)P1-42m / z=919.42(C 71 H 53 N=920.21)P1-43m / z=753.30(C 57 H 39 NO=753.94)P1-44m / z=758.24(C 54 H 34 N2OS=758.94)P1-45m / z=717.25(C 53 H 35 NS=717.93)P1-46m / z=891.35(C 68 H 45 NO=892.11)P1-47m / z=759.22(C 54 H 33 NO2S=759.92)P1-48m / z=705.27(C52 H 35 NO2=705.86)P1-49m / z=691.29(C 52 H 37 NO=691.87)P1-50m / z=617.24(C 45 H 31 NO2=617.75)P1-51m / z=849.34(C 66 H 43 N=850.08)P1-52m / z=753.34(C 58 H 43 N=753.99)P1-53m / z=727.29(C 55 H 37 NO=727.91)P1-54m / z=747.35(C 56 H 45 NO=747.98)P1-55m / z=761.37(C 57 H 47 NO=762.01)P1-56m / z=781.30(C 58 H 39 NO2=781.95)P1-57m / z=766.33(C 58 H 42 N2=766.99)P1-58m / z=845.28(C 62 H 39 NOS=846.06)P1-59m / z=727.32(C 56 H 41 N=727.95)P1-60m / z=945.40(C 69 H 55 NOS=946.26)P1-61m / z=643.29(C 48 H 37 NO=643.83)P1-62m / z=682.21(C 48 H 30 N2OS=682.84)P1-63m / z=707.26(C 51 H 37 NOSi=707.95)P1-64m / z=707.26(C 51 H 37 NOSi=707.95)P1-65m / z=679.38(C 50 H 49 NO=679.95)P1-66m / z=801.34(C 62 H43 N=802.03)P1-67m / z=691.32(C 53 H 41 N=691.92)P1-68m / z=705.34(C 54 H 43 N=705.94)P1-69m / z=685.23(C 48 H 35 NSSi=685.96)P1-70m / z=695.36(C 53 H 45 N=695.95)P1-71m / z=589.37(C 44 H 47 N=589.87)P1-72m / z=603.26(C 45 H 33 NO=603.76)P1-73m / z=753.34(C 58 H 43 N=753.99)P1-74m / z=767.32(C 58 H 41 NO=767.97)P1-75m / z=753.34(C 58 H 43 N=753.99)P1-76m / z=705.30(C 53 H 39 NO=705.90)P1-77m / z=829.30(C 62 H 39 NO2=830.00)P1-78m / z=993.36(C 75 H 47 NO2=994.21)P1-79m / z=763.32(C 59 H 41 N=763.98)P1-80m / z=753.34(C 58 H 43 N=753.99)P1-81m / z=639.29(C 49 H 37 N=639.84)P1-82m / z=685.33(C 51 H 43 NO=685.91)P1-83m / z=665.37(C 49 H 47 NO=665.92)P1-84m / z=651.39(C 49 H 49N=651.94)P1-85m / z=750.49(C 55 H 62 N2=751.11)P1-86m / z=577.37(C 43 H 47 N=577.86)P1-87m / z=773.50(C 58 H 63 N=774.15)P1-88m / z=695.36(C 53 H 45 N=695.95)P1-89m / z=533.27(C 39 H 35 NO=533.71)P1-90m / z=719.32(C 54 H 41 NO=719.93)P1-91m / z=709.24(C 51 H 35 NOS=709.91)P1-92m / z=768.31(C 57 H 40 N2O=768.96)P1-93m / z=767.33(C 57 H 41 N3=767.98)P1-94m / z=767.33(C 57 H 41 N3=767.98)P1-95m / z=693.27(C 51 H 35 NO2=693.85)P1-96m / z=703.33(C 51 H 25 D 10 NO2=703.91)P1-97m / z=683.33(C 51 H 33 D5N2=683.91)

[0303] [Synthesis Example 2] Synthesis Example of Chemical Formula 2

[0304] The compound represented by chemical formula 2 according to the present invention (final product 2) can be synthesized according to the reaction path of the following reaction scheme 2, but is not limited thereto.

[0305] <Reaction Scheme 2> (Hal 1 and Hal 2 is I, Br or Cl.)

[0306]

[0307] I. Synthesis of Sub 3

[0308] Compounds belonging to Sub 3 of the above reaction scheme 2 may be, but are not limited to, the compounds below, and Table 4 below shows the FD-MS values ​​of the compounds below.

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] Compound FD-MS Compound FD-MS Sub 3-1 m / z=235.87(C6H4Br2=235.91) Sub 3-2 m / z=235.87(C6H4Br2=235.91) Sub 3-3 m / z=311.90(C 12 H8Br2=312.00)Sub 3-4m / z=311.90(C 12 H8Br2=312.00)Sub 3-5m / z=311.90(C 12 H8Br2=312.00)Sub 3-6m / z=311.90(C 12 H8Br2=312.00)Sub 3-7m / z=343.98(C 18 H 12 BrCl=343.65)Sub 3-8m / z=343.98(C 18 H 12 BrCl=343.65)Sub 3-9m / z=317.96(C 16 H 10 BrCl=317.61)Sub 3-10m / z=341.85(C 12 H6Br2S=342.05)Sub 3-11m / z=297.90(C 12H6BrClS=297.59)Sub 3-12m / z=297.90(C 12 H6BrClS=297.59)Sub 3-13m / z=341.85(C 12 H6Br2S=342.05)Sub 3-14m / z=297.90(C 12 H6BrClS=297.59)Sub 3-15m / z=311.92(C 13 H8BrClS=311.62)Sub 3-16m / z=327.99(C 18 H 10 Cl2S=329.24)Sub 3-17m / z=347.92(C 16 H8BrClS=347.65)Sub 3-18m / z=347.92(C 16 H8BrClS=347.65)Sub 3-19m / z=371.94(C 18 H 10 BrClS=373.69)Sub 3-20m / z=325.88(C 12 H6Br2O=325.99)Sub 3-21m / z=281.93(C 12 H6BrClO=281.53)Sub 3-22m / z=281.93(C 12 H6BrClO=281.53)Sub 3-23m / z=325.88(C 12 H6Br2O=325.99)Sub 3-24m / z=401.91(C 18 H 10 Br2O=402.08)Sub 3-25m / z=357.96(C 18 H 10 BrClO=357.63)Sub 3-26m / z=463.95(C 24 H 12 BrClOS=463.77)Sub 3-27m / z=400.92(C 18 H 11 Br2N=401.10)Sub 3-28m / z=433.01(C 24 H 15 BrClN=432.75)Sub 3-29m / z=387.06(C 24 H 15 Cl2N=388.29)Sub 3-30m / z=437.07(C 28H 17 Cl2N=438.35)Sub 3-31m / z=351.93(C 15 H 12 Br2=352.07)Sub 3-32m / z=338.06(C 21 H 16 Cl2=339.26)Sub 3-33m / z=386.06(C 25 H 16 Cl2=387.30)Sub 3-34m / z=386.06(C 25 H 16 Cl2=387.30)

[0317] II. Synthesis example of Final Product 2

[0318] 1. P2-31 Synthesis Example

[0319]

[0320] Sub 2-28 (25.7 g, 64.1 mmol), toluene (105 mL), Sub 3-3 (10 g, 32.1 mmol), Pd2(dba)3 (1.47 g, 1.60 mmol), P(t-Bu)3 (0.65 g, 3.21 mmol), NaOt-Bu (9.24 g, 96.2 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (25.7 g, 84%).

[0321]

[0322] 2. P2-37 Synthesis Example

[0323]

[0324] Sub 2-12 (16 g, 94.5 mmol), Toluene (160 mL), Sub 3-9 (15 g, 47.2 mmol), Pd2(dba)3(2.16 g, 2.36 mmol), P(t-Bu)3(0.96 g, 4.72 mmol), NaOt-Bu (13.6 g, 141.7 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with Toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (18.1 g, 71%).

[0325]

[0326] 3. P2-42 Synthesis Example

[0327]

[0328] (1) Synthesis of Inter 2-48

[0329] Sub 2-12 (30 g, 177.6 mmol), Toluene (590 mL), Sub 3-21 (50 g, 177.6 mmol), Pd2(dba)3(4.88 g, 2.36 mmol), P(t-Bu)3(2.16 g, 10.6 mmol), NaOt-Bu (34.1 g, 355.2 mmol) were added and stirred at 70°C. Upon completion of the reaction, the mixture was extracted with Toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (48.6 g, 74%).

[0330] (2) Synthesis of P2-42

[0331] Inter 2-48 (18.5 g, 50.0 mmol), Toluene (170 mL), Sub 2-78 (25 g, 50.0 mmol), Pd2(dba)3(1.37 g, 1.50 mmol), P(t-Bu)3(0.61 g, 3.00 mmol), NaOt-Bu (9.62 g, 100.1 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with Toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (27.9 g, 67%).

[0332]

[0333] 4. P2-52 Synthesis Example

[0334]

[0335] (1) Synthesis of Inter 2-52

[0336] Sub 2-12 (15 g, 88.6 mmol), Toluene (300 mL), Sub 3-14 (26.4 g, 88.6 mmol), Pd2(dba)3(2.44 g, 2.66 mmol), P(t-Bu)3(1.08 g, 5.32 mmol), NaOt-Bu (17.0 g, 177.3 mmol) were added and stirred at 70°C. Upon completion of the reaction, the mixture was extracted with Toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (23.6 g, 69%).

[0337] (2) Synthesis of P2-52

[0338] Sub 2-85 (18 g, 55.3 mmol), toluene (180 mL), Inter 2-52 (21.4 g, 55.3 mmol), Pd2(dba)3(1.52 g, 1.66 mmol), P(t-Bu)3(0.67 g, 3.32 mmol), and NaOt-Bu (10.6 g, 110.6 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (27.6 g, 74%).

[0339]

[0340] 5. P2-68 Synthesis Example

[0341]

[0342] (1) Synthesis of Inter 2-68

[0343] Sub 2-12 (10 g, 59.1 mmol), toluene (200 mL), Sub 3-33 (25.5 g, 59.1 mmol), Pd2(dba)3 (1.62 g, 1.77 mmol), P(t-Bu)3 (0.72 g, 3.55 mmol), and NaOt-Bu (11.4 g, 118.2 mmol) were added and stirred at 70°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (20.0 g, 65%).

[0344] (2) Synthesis of P2-68

[0345] Sub 2-105 (15 g, 36.5 mmol), toluene (120 mL), Inter 2-68 (19.0 g, 36.5 mmol), Pd2(dba)3(1.0 g, 1.09 mmol), P(t-Bu)3(0.44 g, 2.19 mmol), and NaOt-Bu (7.01 g, 72.9 mmol) were added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (25.1 g, 77%).

[0346]

[0347] The FD-MS values ​​of compounds P2-1 to P2-81 of the present invention manufactured according to the above synthetic examples are as shown in Table 5 below.

[0348] Compound FD-MS Compound FD-MSP2-1 m / z = 716.32 (C 54 H 40 N2=716.93)P2-2m / z=792.35(C 60 H 44 N2=793.03)P2-3m / z=806.33(C 60 H 42 N2O=807.01)P2-4m / z=822.31(C 60 H 42 N2S=823.07)P2-5m / z=881.38(C 66 H 47 N3=882.12)P2-6m / z=832.38(C 63 H 48 N2=833.09)P2-7m / z=868.38(C 66 H 48 N2=869.12)P2-8m / z=866.37(C 66 H 46 N2=867.11)P2-9m / z=842.37(C 64 H 46 N2=843.09)P2-10m / z=816.35(C 62 H 44 N2=817.05)P2-11m / z=918.40(C70 H 50 N2=919.18)P2-12m / z=931.39(C 70 H 49 N3=932.18)P2-13m / z=790.21(C 54 H 34 N2OS2=791.00)P2-14m / z=912.32(C 66 H 44 N2OS=913.15)P2-15m / z=664.29(C 50 H 36 N2=664.85)P2-16m / z=652.25(C 48 H 32 N2O=652.80)P2-17m / z=550.20(C 40 H 26 N2O=550.66)P2-18m / z=1037.47(C 78 H 59 N3=1038.35)P2-19m / z=756.35(C 57 H 44 N2=756.99)P2-20m / z=698.20(C 48 H 30 N2O2S=698.84)P2-21m / z=894.37(C 66 H 46 N4=895.12)P2-22m / z=885.32(C 64 H 43 N3S=886.13)P2-23m / z=832.32(C 60 H 40 N4O=833.01)P2-24m / z=682.23(C 48 H 30 N2O3=682.78)P2-25m / z=819.32(C 60 H 41 N3O=820.01)P2-26m / z=832.31(C 61 H 40 N2O2=833.00)P2-27m / z=743.29(C 54 H 37 N3O=743.91)P2-28m / z=818.33(C 61 H 42 N2O=819.02)P2-29m / z=791.24(C54 H 37 N3S2=792.03)P2-30m / z=879.36(C 66 H 45 N3=880.11)P2-31m / z=952.48(C 72 H 60 N2=953.29)P2-32m / z=800.23(C 56 H 36 N2S2=801.04)P2-33m / z=780.31(C 58 H 40 N2O=780.97)P2-34m / z=904.38(C 69 H 48 N2=905.16)P2-35m / z=664.29(C 50 H 36 N2=664.85)P2-36m / z=674.19(C 46 H 30 N2S2=674.88)P2-37m / z=538.24(C 40 H 30 N2=538.69)P2-38m / z=674.19(C 46 H 30 N2S2=674.88)P2-39m / z=846.29(C 61 H 38 N2O3=846.99)P2-40m / z=888.32(C 64 H 44 N2OS=889.13)P2-41m / z=830.29(C 61 H 38 N2O2=830.99)P2-42m / z=832.31(C 61 H 40 N2O2=833.00)P2-43m / z=792.39(C 57 H 52 N2Si=793.14)P2-44m / z=896.34(C 66 H 44 N2O2=897.09)P2-45m / z=694.24(C 50 H 34 N2S=694.90)P2-46m / z=608.19(C 42 H 28 N2OS=608.76)P2-47m / z=668.25(C48 H 32 N2O2=668.80)P2-48m / z=791.24(C 54 H 37 N3S2=792.03)P2-49m / z=658.21(C 46 H 30 N2OS=658.82)P2-50m / z=624.17(C 42 H 28 N2S2=624.82)P2-51m / z=700.20(C 48 H 32 N2S2=700.92)P2-52m / z=674.19(C 46 H 30 N2S2=674.88)P2-53m / z=791.24(C 54 H 37 N3S2=792.03)P2-54m / z=638.19(C 43 H 30 N2S2=638.85)P2-55m / z=624.17(C 42 H 28 N2S2=624.82)P2-56m / z=674.19(C 46 H 30 N2S2=674.88)P2-57m / z=684.22(C 48 H 32 N2OS=684.86)P2-58m / z=775.27(C 54 H 37 N3OS=775.97)P2-59m / z=848.29(C 61 H 40 N2OS=849.06)P2-60m / z=800.29(C 57 H 40 N2OS=801.02)P2-61m / z=668.25(C 48 H 32 N2O2=668.80)P2-62m / z=710.28(C 51 H 38 N2S=710.94)P2-63m / z=891.33(C 63 H 45 N3OS=892.13)P2-64m / z=848.29(C 61 H 40N2OS=849.06)P2-65m / z=774.27(C 55 H 38 N2OS=774.98)P2-66m / z=682.23(C 48 H 30 N2O3=682.78)P2-67m / z=758.26(C 54 H 34 N2O3=758.88)P2-68m / z=894.36(C 67 H 46 N2O=895.12)P2-69m / z=1112.43(C 83 H 56 N2O2=1113.37)P2-70m / z=849.30(C 60 H 39 N3O3=849.99)P2-71m / z=834.29(C 60 H 38 N2O3=834.97)P2-72m / z=818.33(C 61 H 42 N2O=819.02)P2-73m / z=744.28(C 54 H 36 N2O2=744.89)P2-74m / z=916.39(C 67 H 52 N2S=917.23)P2-75m / z=837.34(C 61 H 35 D5N2O2=838.03)P2-76m / z=758.26(C 54 H 34 N2O3=758.88)P2-77m / z=758.26(C 54 H 34 N2O3=758.88)P2-78m / z=846.29(C 61 H 38 N2O3=846.99)P2-79m / z=784.31(C 57 H 40 N2O2=784.96)P2-80m / z=922.32(C 67 H 42 N2O3=923.08)P2-81m / z=942.42(C 69 H 54 N2O2=943.20)

[0349]

[0350] [Synthesis Example 3] Synthesis Example of Chemical Formula 3

[0351] The compound represented by chemical formula 3 according to the present invention (final product 3) can be synthesized according to the reaction path of the following reaction scheme 3, but is not limited thereto.

[0352] <Reaction Scheme 3> (Hal 3 is I, Br or Cl.)

[0353]

[0354] I. Synthesis of Sub 4

[0355] Compounds belonging to Sub 4 of the above reaction scheme 3 may be, but are not limited to, the compounds below, and Table 6 below shows the FD-MS values ​​of the compounds below.

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365] Compound FD-MS Compound FD-MS Sub 4-1 m / z = 444.10 (C 28 H 17 BO3S=444.31)Sub 4-2m / z=428.12(C 28 H 17 BO4=428.25)Sub 4-3m / z=444.10(C 28 H 17BO3S=444.31)Sub 4-4m / z=444.10(C 28 H 17 BO3S=444.31)Sub 4-5m / z=428.12(C 28 H 17 BO4=428.25)Sub 4-6m / z=428.12(C 28 H 17 BO4=428.25)Sub 4-7m / z=428.12(C 28 H 17 BO4=428.25)Sub 4-8m / z=428.12(C 28 H 17 BO4=428.25)Sub 4-9m / z=580.18(C 40 H 25 BO4=580.45)Sub 4-10m / z=262.08(C 16 H 11 BO3=262.07)Sub 4-11m / z=262.08(C 16 H 11 BO3=262.07)Sub 4-12m / z=271.14(C 16 H2D9BO3=271.13)Sub 4-13m / z=262.08(C 16 H 11 BO3=262.07)Sub 4-14m / z=338.11(C 22 H 15 BO3=338.17)Sub 4-15m / z=262.08(C 16 H 11 BO3=262.07)Sub 4-16m / z=338.11(C 22 H 15 BO3=338.17)Sub 4-17m / z=378.11(C 24 H 15 BO4=378.19)Sub 4-18m / z=304.07(C 18 H 13 BO2S=304.17)Sub 4-19m / z=304.07(C 18 H 13 BO2S=304.17)Sub 4-20m / z=304.07(C 18 H 13<h2 style=";text-align:left;direction:ltr">BO2S=304.17)Sub 4-21m / z=287.11(C)<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> BNO2=287.12)Sub 4-22m / z=337.13(C)<h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 16 <h2 style=";text-align:left;direction:ltr"> BNO2=337.18)Sub 4-23m / z=285.10(C)<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> BNO2=285.11)Sub 4-24m / z=453.16(C)<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> BN3O2 = 453.31)Sub 4-25m / z = 213.06(C<h2 style=";text-align:left;direction:ltr"> 11 <h2 style=";text-align:left;direction:ltr"> H8BNO3=213.00)Sub 4-26m / z=355.08(C)<h2 style=";text-align:left;direction:ltr"> 21 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> BNO2S=355.22)Sub 4-27m / z=238.09(C)<h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 11 <h2 style=";text-align:left;direction:ltr"> BN2O2 = 238.05)Sub 4-28m / z = 467.13(C<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> BNO4=467.29)Sub 4-29m / z=362.15(C)<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> BO2=362.23)Sub 4-30m / z=348.13(C<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> BO2=348.21)Sub 4-31m / z=324.13(C<h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> BO2=324.19)Sub 4-32m / z=324.13(C<h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> BO2=324.19)Sub 4-33m / z=374.15(C<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> BO2=374.25)Sub 4-34m / z=453.16(C<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> BN3O2 = 453.31)Sub 4-35m / z = 408.16(C<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> N2=408.50)Sub 4-36m / z=333.12(C)<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 15 <h2 style=";text-align:left;direction:ltr"> NO=333.39)Sub 4-37m / z=357.13(C)<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 15N3=357.42)Sub 4-38m / z=332.13(C 24 H 16 N2=332.41)Sub 4-39m / z=323.08(C 22 H 13 NS=323.41)Sub 4-40m / z=399.11(C 28 H 17 NS=399.51)Sub 4-41m / z=484.19(C 36 H 24 N2=484.60)Sub 4-42m / z=333.12(C 24 H 15 NO=333.39)Sub 4-43m / z=273.06(C 18 H 11 NS=273.35)Sub 4-44m / z=373.09(C 26 H 15 NS=373.47)

[0366]

[0367] II. Synthesis of Sub 5

[0368] Compounds belonging to Sub 5 of the above reaction scheme 3 may be, but are not limited to, the compounds below, and Table 7 below shows the FD-MS values ​​of the compounds below.

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376] Compound FD-MS Compound FD-MS Sub 5-1 m / z = 267.06 (C 15 H 10 ClN3=267.72)Sub 5-2m / z=419.12(C27 H 18 ClN3=419.91)Sub 5-3m / z=357.07(C 21 H 12 ClN3O=357.80)Sub 5-4m / z=433.10(C 27 H 16 ClN3O=433.89)Sub 5-5m / z=585.16(C 39 H 24 ClN3O=586.09)Sub 5-6m / z=521.13(C 34 H 20 ClN3O=522.00)Sub 5-7m / z=523.11(C 33 H 18 ClN3O2=523.98)Sub 5-8m / z=449.08(C 27 H 16 ClN3S=449.96)Sub 5-9m / z=530.14(C 33 H 15 D5ClN3S=531.08)Sub 5-10m / z=433.10(C 27 H 16 ClN3O=433.89)Sub 5-11m / z=368.08(C 22 H 13 ClN4=368.82)Sub 5-12m / z=507.15(C 34 H 22 ClN3=508.02)Sub 5-13m / z=433.10(C 27 H 16 ClN3O=433.89)Sub 5-14m / z=433.10(C 27 H 16 ClN3O=433.89)Sub 5-15m / z=382.06(C 22 H 11 ClN4O=382.81)Sub 5-16m / z=343.09(C 21 H 14 ClN3=343.81)Sub 5-17m / z=343.09(C 21 H 14 ClN3=343.81)Sub 5-18m / z=357.07(C 21 H 12ClN3O=357.80)Sub 5-19m / z=317.07(C 19 H 12 ClN3=317.78)Sub 5-20m / z=216.02(C 10 H5ClN4=216.63)Sub 5-21m / z=433.10(C 27 H 16 ClN3O=433.89)Sub 5-22m / z=367.09(C 23 H 14 ClN3=367.84)Sub 5-23m / z=393.10(C 25 H 16 ClN3=393.87)Sub 5-24m / z=373.04(C 21 H 12 ClN3S=373.86)Sub 5-25m / z=493.13(C 33 H 20 ClN3=493.99)Sub 5-26m / z=483.11(C 31 H 18 ClN3O=483.95)Sub 5-27m / z=367.09(C 23 H 14 ClN3=367.84)Sub 5-28m / z=393.10(C 25 H 16 ClN3=393.87)Sub 5-29m / z=384.08(C 22 H 13 ClN4O=384.82)Sub 5-30m / z=482.13(C 31 H 19 ClN4=482.97)Sub 5-31m / z=499.09(C 31 H 18 ClN3S=500.02)

[0377]

[0378] III. Final Product 3의 합성예

[0379] 1. P3-11 합성예

[0380]

[0381] Sub 4-11 (19.8 g, 57.6 mmol), THF (190 mL), Sub 5-4 (25 g, 57.6 mmol), Pd(PPh3)4 (2.0 g, 1.73 mmol) were added, and NaOH (6.91 g, 172.8 mmol) and water (64 mL) were added, and the mixture was stirred at 75°C. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (25.2 g, 71%).

[0382]

[0383] 2. P3-12 Synthesis Example

[0384]

[0385] Sub 4-12 (20.4 g, 57.6 mmol), THF (190 mL), Sub 5-4 (25 g, 57.6 mmol), Pd(PPh3)4 (2.0 g, 1.73 mmol) were added, and NaOH (6.91 g, 172.8 mmol) and water (64 mL) were added, and the mixture was stirred at 75°C. Upon completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (27.4 g, 76%).

[0386]

[0387] 3. P3-32 Synthesis Example

[0388]

[0389] Sub 4-41 (25 g, 51.6 mmol) was portion-wise added to 60% NaH (2.07 g, 86.4 mmol) in DMF (170 mL), followed by addition of Sub 5-16 (22.4 g, 57.6 mmol) and stirring at 50°C. Upon completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The resulting compound was purified by silica gel column chromatography and recrystallization to obtain the product (29.0 g, 71%).

[0390]

[0391] 4. P3-44 Synthesis Example

[0392]

[0393] Sub 4-31 (20 g, 50.8 mmol), THF (170 mL), Sub 5-28 (20.6 g, 50.8 mmol), Pd(PPh3)4 (1.76 g, 1.52 mmol) were added, and NaOH (6.09 g, 152.3 mmol) and water (56 mL) were added, and the mixture was stirred at 75°C. Upon completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The resulting compound was purified by silica gel column chromatography and recrystallized to obtain the product (24.3 g, 75%).

[0394]

[0395] The FD-MS values ​​of compounds P3-1 to P3-48 of the present invention manufactured according to the above synthetic examples are as shown in Table 8 below.

[0396] Compound FD-MS Compound FD-MSP3-1 m / z = 631.17 (C 43 H 25 N3OS=631.75)P3-2m / z=767.26(C 55 H 33 N3O2=767.89)P3-3m / z=721.18(C 49 H 27 N3O2S=721.83)P3-4m / z=721.18(C 49 H 27<h2 style=";text-align:left;direction:ltr">N3O2S=721.83)P3-5m / z=691.23(C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2=691.79)P3-6m / z=781.24(C<h2 style=";text-align:left;direction:ltr"> 55 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> N3O3=781.87)P3-7m / z=615.19(C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> N3O2=615.69)P3-8m / z=691.23(C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2=691.79)P3-9m / z=767.26(C<h2 style=";text-align:left;direction:ltr"> 55 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> N3O2=767.89)P3-10m / z=767.26(C<h2 style=";text-align:left;direction:ltr"> 55 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> N3O2=767.89)P3-11m / z=615.19(C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> N3O2=615.69)P3-12m / z=624.25(C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 16 <h2 style=";text-align:left;direction:ltr"> D9N3O2=624.75)P3-13m / z=779.26(C<h2 style=";text-align:left;direction:ltr"> 56 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 33 <h2 style=";text-align:left;direction:ltr"> N3O2=779.90)P3-14m / z=657.19(C<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3OS=657.79)P3-15m / z=730.24(C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> N4O2=730.83)P3-16m / z=638.21(C<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N4O=638.73)P3-17m / z=707.20(C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS=707.85)P3-18m / z=712.23(C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> D5N3OS=712.88)P3-19m / z=805.27(C<h2 style=";text-align:left;direction:ltr"> 58 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 35 <h2 style=";text-align:left;direction:ltr"> N3O2=805.94)P3-20m / z=654.21(C<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N4O2=654.73)P3-21m / z=657.19(C<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3OS=657.79)P3-22m / z=550.18(C<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> H22 N4O=550.62)P3-23m / z=640.23(C 45 H 28 N4O=640.75)P3-24m / z=744.23(C 52 H 32 N4S=744.92)P3-25m / z=670.18(C 45 H 26 N4OS=670.79)P3-26m / z=805.28(C 57 H 35 N5O=805.94)P3-27m / z=729.25(C 51 H 31 N5O=729.84)P3-28m / z=640.23(C 45 H 28 N4O=640.75)P3-29m / z=640.24(C 44 H 28 N6=640.75)P3-30m / z=664.24(C 46 H 28 N6=664.77)P3-31m / z=606.15(C 40 H 22 N4OS=606.70)P3-32m / z=791.30(C 57 H 37 N5=791.96)P3-33m / z=611.24(C 45 H 29 N3=611.75)P3-34m / z=644.17(C 43 H 24 N4OS=644.75)P3-35m / z=680.20(C 47 H 28 N4S=680.83)P3-36m / z=553.14(C 36 H 19 N5S=553.64)P3-37m / z=566.17(C 38 H 22 N4O2=566.62)P3-38m / z=665.21(C 47 H 27 N3O2=665.75)P3-39m / z=675.27(C 50 H 33 N3=675.83)P3-40m / z=648.14(C 42 H 24N4S2=648.80)P3-41m / z=675.23(C 49 H 29 N3O=675.79)P3-42m / z=727.26(C 53 H 33 N3O=727.87)P3-43m / z=611.24(C 45 H 29 N3=611.75)P3-44m / z=637.25(C 47 H 31 N3=637.79)P3-45m / z=678.24(C 48 H 30 N4O=678.80)P3-46m / z=625.22(C 45 H 27 N3O=625.73)P3-47m / z=657.20(C 44 H 27 N5S=657.79)P3-48m / z=739.27(C 53 H 33 N5=739.88)

[0397] Meanwhile, although the exemplary synthetic examples of the present invention represented by Chemical Formulas 1 to 3 have been described above, they are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and it will be easily understood by those skilled in the art that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic examples is combined.

[0398] Manufacturing and evaluation of organic electronic devices

[0399] [Example 1] Red organic light-emitting diode

[0400] A hole injection layer having a thickness of 70 nm was formed by vacuum-depositing 4,4'4''-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) on a TIO layer (anode) formed on a glass substrate, and then a hole transport layer was formed by vacuum-depositing N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) on the hole injection layer having a thickness of 75 nm.

[0401] A first light-emitting auxiliary layer was formed by vacuum-depositing the compound P1-48 of the present invention to a thickness of 35 nm on the hole transport layer, and then a second light-emitting auxiliary layer was formed by vacuum-depositing the compounds P1-12 and P1-32 of the present invention to a thickness of 5 nm at a weight ratio of 97:3 on the first light-emitting auxiliary layer.

[0402] Next, on the second light-emitting auxiliary layer, the following comparative compounds 1 and 2 were used as host materials, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter, abbreviated as (piq)2Ir(acac)) was used as a dopant material, and the dopant was doped at a weight ratio of 95:5 to form a light-emitting layer having a thickness of 40 nm.

[0403] Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 5 nm on the light-emitting layer to form a hole-blocking layer, and 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (hereinafter abbreviated as BCP) was vacuum-deposited to a thickness of 20 nm on the hole-blocking layer to form an electron transport layer.

[0404] Afterwards, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.

[0405] [Example 2] to [Example 75]

[0406] 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 9 below were used as the first compound, second compound, and third compound materials.

[0407] [Comparative Example 1]

[0408] An organic light-emitting device was manufactured in the same manner as Example 1, except that the first compound, second compound, and third compound materials were used in the configurations described in Table 9 below.

[0409] [Comparative Example 2] to [Comparative Example 6]

[0410] An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds described in Table 9 below were used as the first light-emitting auxiliary layer material and the second light-emitting auxiliary layer material, and the third compound was not used.

[0411] [Comparative Compound 1] [Comparative Compound 2]

[0412]

[0413] The electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch by applying a forward bias DC voltage to the organic electroluminescence devices manufactured by Examples 1 to 75 of the present invention and Comparative Examples 1 to 6, and 2500 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. The measurement results are shown in Table 9 below.

[0414] This measuring device allows the performance of new materials to be evaluated against reference compounds under identical conditions, without being affected by possible daily variations in deposition rate, vacuum quality or other parameters.

[0415] Since, during the evaluation, one batch contains four identically prepared OLEDs including a comparative compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the values ​​of the experimental results obtained in this way exhibit statistical significance.

[0416] Compound 1 Compound 2 Compound 3 Compound Driving voltage (V) Current density (mA / cm) 2)Efficiency (cd / A)T(95)Comparative Example (1)Compound (P1-48)Compound (P1-48)Comparative Compound 1 + Comparative Compound 2 + (piq)2Ir(acac)4.56.4938.5125.5Comparative Example (2) Compound (P1-48) Compound (P1-12)-4.56.1840.490.0Comparative Example (3) Compound (P1-48) Compound (P1-49)-4.26.6337.7139.3Comparative Example (4) Compound (P1-48) Compound (P1-56)-4.46.6937.4143.0Comparative Example (5) Compound (P1-48) Compound (P2-42)-4.26.6337.7129.2Comparative Example (6) Compound (P1-48) Compound (P2-79)-4. 46.5538.1138.4 Example (1) Compound (P1-48) Compound (P1-12) Compound (P3-11) 4.15.7639.3143.8 Example (2) Compound (P1-48) Compound (P1-49) Compound (P3-11) 3.95.8238.5159.7 Example (3) Compound (P1-48) Compound (P1-56) Compound (P3-11) 4.15.8738.1163.9 Example (4) Compound (P1-48) Compound (P2-42) Compound (P3-11) 3.95.7638.5148.0 Example (5) Compound (P1-48) Compound (P2-79) Compound (P3-11) 4.15.5940.4153.3 Example (6) Compound (P1-48) Compound (P1-12) Compound (P3-32) 4.05.8938.5159.7 Example (7) Compound (P1-48) Compound (P1-49) Compound (P3-32) 3.85.9938.1169.2 Example (8) Compound (P1-48) Compound (P1-56) Compound (P3-32) 3.96.0237.7175.5 Example (9) Compound (P1-48) Compound (P2-42) Compound (P3 -32)3.85.9238.5170.2Example (10)Compound (P1-48)Compound (P2-79)Compound (P3-32)4.05.7639.6170.2Example (11)Compound (P1-48)Compound (P1-12)Compound (P3-38)4.15.8637.7169.2Example (12)Compound (P1-48)Compound (P1-49)Compound (P3-38)3.95.9737.0177.6Example (13)Compound (P1-48)Compound (P1-56)Compound (P3-38)4.05.9936.8182.9 Example (14) Compound (P1-48) Compound (P2-42) Compound (P3-38) 3.9 5.87 37.5 17 3.4 Example (15) Compound (P1-48) Compound (P2-79) Compound (P3-38) 4.15 72 38.5 17 0.2 Example (16) Compound (P1-71) Compound (P1-12) Compound (P3-11) 4.2 5.87 42.6 15 8.2 Example (17) Compound (P1-71) Compound (P1-49) Compound (P3-11) 4.0 5.99 41.7 17 5.6 Example (18) Compound (P1-71) Compound (P1-56) Compound (P3-11 )4.26.0541.4180.3 Example (19) Compound (P1-71) Compound (P2-42) Compound (P3-11)4.05.9941.7162.8 Example (20) Compound (P1-71) Compound (P2-79) Compound (P3-11)4.25.7143.8168.6 Real Example (21) Compound (P1-71) Compound (P1-12) Compound (P3-32) 4.15.9941.7175.6 Example (22) Compound (P1-71) Compound (P1-49) Compound (P3-32) 3.96.0541.4186.1 Example (23) Compound (P1-71) Compound (P1-56) Compound (P3-32) 4.06.1041.0193.1 Example (24) Compound (P1-71) Compound (P2-42) Compound (P3-32) 3.95.9941.7187.3 Example (25) Compound (P1-71) Compound (P2-79) Compound (P3-32) 4 .15.8143.0187.3 Example (26) Compound (P1-71) Compound (P1-12) Compound (P3-38) 4.26.1240.9186.1 Example (27) Compound (P1-71) Compound (P1-49) Compound (P3-38) 4.06.2240.2195.4 Example ( 28) Compound (P1-71) Compound (P1-56) Compound (P3-38) 4.16.2639.9201.2 Example (29) Compound (P1-71) Compound (P2-42) Compound (P3-38) 4.06.1540.6190.7 Example (30) Compound (P1-71) Compound (P2 -79) Compound (P3-38) 4.25.9941.7187.3 Example (31) Compound (P2-39) Compound (P1-12) Compound (P3-11) 4.25.9841.8161.1 Example (32) Compound (P2-39) Compound (P1-49) Compound (P3-11) 4.06.1041.0178.8 Example (33) Compound (P2-39) Compound (P1-56) Compound (P3-11) 4.26.1640.6183.6 Example (34) Compound (P2-39) Compound (P2-42) Compound (P3-11) 4.06.1041.0165.8 Example (35) Compound (P2-39) Compound (P2-79) Compound (P3-11) 4.25.8243.0171.7 Example (36) Compound (P2-39) Compound (P1-12) Compound (P3-32) 4.16.1041.0178.8 Example (37) Compound (P2-39) Compound (P1-49) Compound (P3-32) 3.96.1640.6189.5 Example (38) Compound (P2-39) Compound (P1-56) Compound (P3-32) 4.06.2240.2196.6 Example (39) Compound (P2-39) Compound (P2-42) Compound (P3-32) 3.96.1041.0190.7 Example (40) Compound (P2-39) Compound (P2-79) Compound (P3-32) 4.15.9242.2190.7 Example (41) Compound (P2-39) Compound (P1-12) Compound (P3-38) 4.26.2340. 1189.5 Example (42) Compound (P2-39) Compound (P1-49) Compound (P3-38) 4.06.34 39.4 199.0 Example (43) Compound (P2-39) Compound (P1-56) Compound (P3-38) 4.16.38 39.2 20 4.9 Example (44) Compound (P2-39) Compound (P2-42) Compound (P3-38) 4.06.27 39.9 194.2 Example (45) Compound (P2-39) Compound (P2-79) Compound (P3-38) 4.26.10 41.0 190.7 Example (46) Compound (P2-70) Compound (P1 -12) Compound (P3-11) 4.15.69 43.9174.0 Example (47) Compound (P2-70) Compound (P1-49) Compound (P3-11) 3.95.8143.0193.2 Example (48) Compound (P2-70) Compound (P1-56) Compound (P3-11) 4.15.86 42.6198.3 Example (49) Compound (P2-70) Compound (P2-42) Compound (P3-11) 3.95.8143.0179.1 Example (50) Compound (P2-70) Compound (P2-79) Compound (P3-11) 4.15.54 45.1185.5 Example (51) Compound (P2-70) Compound (P1-12) Compound (P3-32) 4.05.8143.0193.2 Example (52) Compound (P2-70) Compound (P1-49) Compound (P3-32) 3.85.8642.6204.7 Example (53) Compound (P2-70) Compound (P1-56) Compound (P3-32) 3.9 5.9 24 2.2 2 12.4 Example (54) Compound (P2-70) Compound (P2-42) Compound (P3-32) 3.8 5.8 14 3.0 2 0 6.0 Example (55) Compound (P2-70) Compound (P2-79) Compound (P3-32 )4.05.6444.3206.0 Example (56) Compound (P2-70) Compound (P1-12) Compound (P3-38)4.15.9342.1204.7 Example (57) Compound (P2-70) Compound (P1-49) Compound (P3-38)3.96.0441.4214.9 Real Example (58) Compound (P2-70) Compound (P1-56) Compound (P3-38) 4.06.0741.2221.3 Example (59) Compound (P2-70) Compound (P2-42) Compound (P3-38) 3.95.9741.9209.8 Example (60) Compound (P2-70) Compound (P2-79) Compound (P3-38) 4.15.8 143.0 206.0 Example (61) Compound (P2-75) Compound (P1-12) Compound (P3-11) 4.0 5.9 242.2 178.8 Example (62) Compound (P2-75) Compound (P1-49) Compound (P3-11) 3 .86.0541.4198.5 Example (63) Compound (P2-75) Compound (P1-56) Compound (P3-11) 4.06.1041.0203.7 Example (64) Compound (P2-75) Compound (P2-42) Compound (P3-11) 3.86.0541.4184.0 Example ( 65) Compound (P2-75) Compound (P2-79) Compound (P3-11) 4.05.7643.4190.6 Example (66) Compound (P2-75) Compound (P1-12) Compound (P3-32) 3.96.0541.4198.5 Example (67) Compound (P2-75) Compound (P1 -49) Compound (P3-32) 3.76.1041.0210.3 Example (68) Compound (P2-75) Compound (P1-56) Compound (P3-32) 3.86.1640.6218.2 Example (69) Compound (P2-75) Compound (P2-42) Compound (P3-32) 3.76.0541.4211.6 Example (70) Compound (P2-75) Compound (P2-79) Compound (P3-32) 3.9 5.87 42.6 211.6 Example (71) Compound (P2-75) Compound (P1-12) Compound (P3-38) 4.06.17 40.5 210.3 Example (72) Compound (P2-75) Compound (P1-49) Compound (P3-38) 3.8 6.28 39.8 220.8 Example (73) Compound (P2-75) Compound (P1-56) Compound (P3-38) 3.9 6.3 239.6 227.4 Example (74) Compound (P2-75) Compound (P2-42) Compound (P3-38) 3.8 6.2 140.3 215.6 Example (75) Compound (P2-75) Compound (P2-79) Compound (P3-38) 4.06.05 41.4 211.6.

[0417] Table 10 below shows the energy levels of the examples measured using the DFT Method (B3LYP / 6-31g(D)) of the Gaussian program.

[0418] Compound P3-11 P3-32 P3-38 Comparative Compound 2 LUMO Energy Level 1.914 1.927 1.967 2.021

[0419] As can be seen from the results in Table 9 above, when a red organic light-emitting device was manufactured by mixing the material for an organic light-emitting device of the present invention into a second light-emitting auxiliary layer, the efficiency and lifespan could be improved compared to a device that was not formed by mixing the host material of the light-emitting layer into the light-emitting auxiliary layer or by mixing a light-emitting auxiliary layer material or a third compound different from the first light-emitting auxiliary layer and the second light-emitting auxiliary layer materials. It can be confirmed that the devices of Examples 1 to 75 of the present invention, in which a plurality of light-emitting auxiliary layers are formed, and a compound similar to the LUMO energy level of the light-emitting layer is formed as the second light-emitting auxiliary layer, have significantly improved driving voltage, efficiency, and lifespan.

[0420] This appears to be because, by forming a compound with a similar LUMO energy level to that of the light-emitting layer in the second light-emitting auxiliary layer, the holes and electrons accumulated at the interface between the light-emitting auxiliary layer and the light-emitting layer due to charge imbalance were resolved, thereby reducing deterioration of the interface and increasing the charge balance within the light-emitting layer.

[0421]

[0422] [Example 76] to [Example 175] Green organic electroluminescent device

[0423] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds in Table 11 were used as the first light-emitting auxiliary layer material and the second light-emitting auxiliary layer material, but the first light-emitting auxiliary layer was formed to a thickness of 30 nm, and the second light-emitting auxiliary layer was formed to a thickness of 5 nm, and 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) was used as the host material, and Tris(2-phenylpyridine)iridium(III) (hereinafter abbreviated as Ir(ppy)3) was used as the dopant material, and the dopant was doped at a weight ratio of 95:5 to form a light-emitting layer having a thickness of 40 nm.

[0424] [Comparative Example 7] to [Comparative Example 11]

[0425] An organic light-emitting device was manufactured in the same manner as Example 76, except that the compounds described in Table 11 below were used as the first light-emitting auxiliary layer material and the second light-emitting auxiliary layer material, and the third compound was not used.

[0426]

[0427] The electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch by applying a forward bias DC voltage to the organic electroluminescence devices manufactured by Examples 76 to 175 of the present invention and Comparative Examples 7 to 11, and the EL characteristics were measured at 5000 cd / m 2The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. The measurement results are shown in Table 11 below.

[0428] This measuring device allows the performance of new materials to be evaluated against reference compounds under identical conditions, without being affected by possible daily variations in deposition rate, vacuum quality or other parameters.

[0429] Since, during the evaluation, one batch contains four identically prepared OLEDs including a comparative compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the values ​​of the experimental results obtained in this way exhibit statistical significance.

[0430] Compound 1 Compound 2 Compound 3 Operating voltage (V) Current density (mA / cm) 2) Efficiency (cd / A) T (95) Comparative Example (7) Compound (P1-48) Compound (P1-12) - 5.2 10.08 49.68 2.6 Comparative Example (8) Compound (P1-48) Compound (P1-49) - 5.1 10.55 47.49 2.6 Comparative Example (9) Compound (P1-48) Compound (P1-56) - 4.9 10.44 47.9 87.3 Comparative Example (10) Compound (P1-48) Compound (P2-76) - 5.3 10.33 48.48 5.9 Comparative Example (11) Compound (P1-48) Compound (P2-79) - 5.0 10.40 48.18 1.7 Example (76) Compound ( P1-48) Compound (P1-12) Compound (P1-65) 5.38.40 59.59 0.9 Example (77) Compound (P1-48) Compound (P1-49) Compound (P1-65) 5.28.79 56.9 101.9 Example (78) Compound (P1-48) Compound (P1-56) Compound (P1-65) 5.08.70 57.59 6.0 Example (79) Compound (P1-48) Compound (P2-76) Compound (P1-65) 5.48.6 158.19 4.5 Example (80) Compound (P1-48) Compound (P2-79) Compound (P1-65) 5.18.66 57.789.9 Example (81) Compound (P1-48) Compound (P1-12) Compound (P1-69) 5.29.3353.6109.0 Example (82) Compound (P1-48) Compound (P1-49) Compound (P1-69) 5.19.7751.2122.2 Example (83) Compound (P1-48) Compound (P1-56) Compound (P1-69) 4.99.6751.7115.2 Example (84) Compound (P1-48) Compound (P2-76) Compound (P1-69) 5.39.5752.3113.4 Example (85) Compound (P1-48) Compound (P 2-79) Compound (P1-69) 5.09.6351.9107.8 Example (86) Compound (P1-48) Compound (P1-12) Compound (P1-95) 5.19.6252.0125.4 Example (87) Compound (P1-48) Compound (P1-49) Compound (P1-95) 5.010.0749.7140.6 Example (88) Compound (P1-48) Compound (P1-56) Compound (P1-95) 4.89.9650.2132.5 Example (89) Compound (P1-48) Compound (P2-76) Compound (P1-95) 5.29.8650.7130.4 Example (90) Compound (P1-48) Compound (P2-79) Compound (P1-95) 4.9 9.9 2 5 0.4 1 2 4.0 Example (91) Compound (P1-48) Compound (P1-12) Compound (P2-59) 5.1 9.9 2 5 0.4 1 0 0.3 Example (92) Compound (P1-48) Compound (P1-49) Compound (P2-59) 5.0 1 0.3 8 4 8.2 1 1 2.5 Example (93) Compound (P1-48) Compound (P1-56) Compound (P2-59) 4.8 1 0.2 7 4 8.7 1 0 6.0 Example (94) Compound (P1-48) Compound (P2-7 6) Compound (P2-59) 5.210.1749.2104.3 Example (95) Compound (P1-48) Compound (P2-79) Compound (P2-59) 4.910.2348.999.2 Example (96) Compound (P1-71) Compound (P1-12) Compound (P1-65) 5.48.0062.590.0 Example (97) Compound (P1-71) Compound (P1-49) Compound (P1-65) 5.38.3759.7100.8 Example (98) Compound (P1-71) Compound (P1-56) Compound (P1-65) 5.18.2860.495.1 Example (99) Compound (P1-71) Compound (P2-76) Compound (P1-65) 5.5 8.20 61.0 93.5 Example (100) Compound (P1-71) Compound (P2-79) Compound (P1-65) 5.28.25 60.68 9.0 Example (101) Compound (P1-71) Compound (P1-12) Compound (P1-69) 5.3 8.89 56.21 07.9 Example (102) Compound (P1-71) Compound (P1-49) Compound (P1-69) 5.29.30 53.81 21.0 Example (103) Compound (P1-71) Compound (P1-56) Compound (P1-69) 5.09.20 54.3 114.1 Example (104) Compound (P1-71) Compound (P2-76) Compound (P1-69) 5.49.1154.9 112.3 Example (105) Compound (P1-71) Compound (P2-79) Compound (P1-69) 5.19.17 54.5 106.8 Example (106) Compound (P1-71) Compound (P1-12) Compound (P1-95) 5.29.16 54.6 124.1 Example (107) Compound (P1-71) Compound (P1-49) Compound (P1-95) 5.19.59 52.1139.2 Example (108) Compound (P1-71) Compound (P1-56) Compound (P1-95) 4.9 9.49 5 2.7 1 3 1.2 Example (109) Compound (P1-71) Compound (P2-76) Compound (P1-95) 5.39 39 5 3.2 1 2 9.1 Example (110) Compound (P1-71) Compound (P2-79) Compound (P1-95) 5.0 9.45 5 2.9 1 2 2.8 Example (111) Compound (P1-71) Compound (P1-12) Compound (P2-59) 5.2 9.45 5 2.9 9.3 Example (112) Compound (P1-71) Compound (P1-4 9) Compound (P2-59) 5.19.89 50.61 11.3 Example (113) Compound (P1-71) Compound (P1-56) Compound (P2-59) 4.9 9.78 51.110 5.0 Example (114) Compound (P1-71) Compound (P2-76) Compound (P2-59) 5.39.68 51.610 3.3 Example (115) Compound (P1-71) Compound (P2-79) Compound (P2-59) 5.0 9.74 51.39 8.2 Example (116) Compound (P2-39) Compound (P1-12) Compound (P1-65) 5.38.32 60.19 9.9 Example (117) Compound (P2-39) Compound (P1-49) Compound (P1-65) 5.18.70 57.41 12.0 Example (118) Compound (P2-39) Compound (P1-56) Compound (P1-65) 4.9 8.6 158.110 5.6 Example (119) Compound (P2-39) Compound (P2-76) Compound (P1-65) 5.4 8.5 258.7 103.9 Example (120) Compound (P2-39) Compound (P2-79) Compound (P1-65) 5.0 8.5 8 58.3 9 8.9 Example (121) Compound (P2-39) Compound (P1-12 ) Compound (P1-69) 5.19.24 54.11 19.9 Example (122) Compound (P2-39) Compound (P1-49) Compound (P1-69) 5.09.67 51.7134.5 Example (123) Compound (P2-39) Compound (P1-56) Compound (P1-69) 4.89.57 52.21 26.8 Example (124) Compound (P2-39) Compound (P2-76) Compound (P1-69) 5.29.47 52.8124.7 Example (125) Compound (P2-39) Compound (P2-79) Compound (P1-69) 4.99.53 52.51 18.6 Example (126) Compound (P2-39) Compound (P1-12) Compound (P1-95) 5.19.5352.5137.9 Example (127) Compound (P2-39) Compound (P1-49) Compound (P1-95) 5.09.9750.2154.6 Example (128) Compound (P 2-39) Compound (P1-56) Compound (P1-95) 4.8 9.8 7 5 0.7 1 4 5.8 Example (129) Compound (P2-39) Compound (P2-76) Compound (P1-95) 5.2 9.7 6 5 1.2 1 4 3.4 Example (130) Compound (P2-39) Compound (P2-79) Compound (P1-95) 4.9 9.8 2 5 0.9 1 3 6.4 Example (131) Compound (P2-39) Compound (P1-12) Compound (P2-59) 5.0 9.8 2 5 0.9 1 1 0.3 Example (132) Compound (P2-39) Compound (P1-49) Compound (P2-59) 4.9 10.2848.6123.7 Example (133) Compound (P2-39) Compound (P1-56) Compound (P2-59) 4.710.1749.2116.6 Example (134) Compound (P2-39) Compound (P2-76) Compound (P2-59) 5.110.0749.7114.7 Example (135) Compound (P2-39) Compound (P2-79) Compound (P2-59) 4.810.1349.4109.1 Example (136) Compound (P2-70) Compound (P1-12) Compound (P1-65) 5.08.5758.3104.5 Example (137) Compound (P2-70) Compound (P1-49) Compound (P1-65) 4.9 8.97 55.7 117.1 Example (138) Compound (P2-70) Compound (P1-56) Compound (P1-65) 4.7 8.88 56.3 110.4 Example (139) Compound (P2-70) Compound (P2-76) Compound (P1-65) 5.1 8.7 8 56.9 108.7 Example (140) Compound (P2-70) Compound (P2-79) Compound (P1-65) 4.8 8.84 56.6 103.4 Example (141) Compound (P2-70) Compound (P1-12) Compound (P1-69) 4 .99.5252.5125.4 Example (142) Compound (P2-70) Compound (P1-49) Compound (P1-69) 4.89.9750.2140.6 Example (143) Compound (P2-70) Compound (P1-56) Compound (P1-69) 4.69.8650.7132.5 Example (144) Compound (P2-70) Compound (P2-76) Compound (P1-69) 5.0 9.76 51.2 13 0.4 Example (145) Compound (P2-70) Compound (P2-79) Compound (P1-69) 4.7 9.8 2 50.9 12 4.0 Example (146) Compound (P 2-70) Compound (P1-12) Compound (P1-95) 4.8 9.8 25 0.9 14 4.2 Example (147) Compound (P2-70) Compound (P1-49) Compound (P1-95) 4.7 10.2 7 48.7 16 1.7 Example (148) Compound (P2-70) Compound (P1-56 ) Compound (P1-95) 4.5 10.17 49.2 152.4 Example (149) Compound (P2-70) Compound (P2-76) Compound (P1-95) 4.9 10.0 6 49.7 150.0 Example (150) Compound (P2-70) Compound (P2-79) Compound (P1-95) 4 .610.1349.4142.6 Example (151) Compound (P2-70) Compound (P1-12) Compound (P2-59) 4.810.1249.4115.4 Example (152) Compound (P2-70) Compound (P1-49) Compound (P2-59) 4.710.5947.212 9.3 Example (153) Compound (P2-70) Compound (P1-56) Compound (P2-59) 4.5 10.48 47.7 121.9 Example (154) Compound (P2-70) Compound (P2-76) Compound (P2-59) 4.9 10.37 48.2 120.0 Example (155) Compound (P2-70) Compound (P2-79) Compound (P2-59) 4.6 10.44 47.9 114.1 Example (156) Compound (P2-75) Compound (P1-12) Compound (P1-65) 5.0 8.49 58.9 100.9 Example (157) Compound (P2-75) Compound (P 1-49) Compound (P1-65) 4.9 8.88 56.3 1 13.1 Example (158) Compound (P2-75) Compound (P1-56) Compound (P1-65) 4.7 8.79 56.9 1 0 6.6 Example (159) Compound (P2-75) Compound (P2-76) Compound (P1-65 )5.18.7057.5104.9Example (160)Compound (P2-75)Compound (P2-79)Compound (P1-65)4.88.7557.199.8Example (161)Compound (P2-75)Compound (P1-12)Compound (P1-69)4.99.4353.0121.0 Example (162) Compound (P2-75) Compound (P1-49) Compound (P1-69) 4.8 9.87 50.7 13 5.7 Example (163) Compound (P2-75) Compound (P1-56) Compound (P1-69) 4.6 9.7 6 5 1.2 12 7.9 Example (164) Compound (P2-75) Compound (P2-76) Compound (P1-69) 5.0 9.6 6 5 1.7 12 5.9 Example (165) Compound (P2-75) Compound (P2-79) Compound (P1-69) 4.7 9.7 25 1.4 1 1 9.7 Example (166) Compound (P2-75) Compound (P1-12) Compound (P1-95) 4.8 9.7 25 1.4 1 3 9.2 Example (167) Compound (P2-75) Compound (P1-49) Compound (P1-95) 4.7 10.1 7 49.2 1 5 6.0 Example (168) Compound (P2-75) Compound (P1-56) Compound (P1-95) 4.6 10.0 6 49.7 1 47.1 Example Example (169) Compound (P2-75) Compound (P2-76) Compound (P1-95) 4.9 9.96 50.2 14 4.7 Example (170) Compound (P2-75) Compound (P2-79) Compound (P1-95) 4.7 10.0 2 4 9.9 1 3 7.7 Example (171) Compound (P2-75) Compound (P1-12) Compound (P2-59) 4.8 10.0 2 4 9.9 1 1 1.3 Example (172) Compound (P2-75) Compound (P1-49) Compound (P2-59) 4.7 10.49 47.7 12 4.8 Example (173) Compound (P2-75) Compound (P1-56) Compound (P2-59) 4.5 10.38 48.2 117.7 Example (174) Compound (P2-75) Compound (P2-76) Compound (P2-59) 4.9 10.27 48.7 115.8 Example (175) Compound (P2-75) Compound (P2-79) Compound (P2-59) 4.6 10.33 48.4 110.1.

[0431] As can be seen from the results in Table 11 above, when a green organic light-emitting device was manufactured by mixing the material for an organic light-emitting device of the present invention into a second light-emitting auxiliary layer, the efficiency and lifespan could be improved compared to a device that was not formed by mixing a light-emitting auxiliary layer material different from the first compound and the second compound material into the light-emitting auxiliary layer. It can be confirmed that the devices of Examples 76 to 175 of the present invention, in which a plurality of light-emitting auxiliary layers were formed by mixing a compound having a similar T1 energy level to that of the second compound into the second light-emitting auxiliary layer, showed a significant improvement in efficiency and a slight improvement in lifespan.

[0432]

[0433] The above description is merely illustrative of the present invention. 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 herein are intended to illustrate, rather than limit, the present invention, and the spirit and scope of the present invention are not limited by these embodiments.

[0434] The scope of protection of the present invention should be interpreted by the claims below, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the rights of the present invention.

[0435]

[0436] 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. In an organic electric device including an organic layer including a first electrode, a second electrode, and a light-emitting layer formed between the first electrode and the second electrode, The organic layer includes a hole transport layer formed between the first electrode and the light-emitting layer, It includes a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer, The above plurality of light-emitting auxiliary layers include a first light-emitting auxiliary layer adjacent to the hole transport layer and a second light-emitting auxiliary layer adjacent to the light-emitting layer, An organic electric device characterized in that the first light-emitting auxiliary layer is made of a single material and the second light-emitting auxiliary layer is made of a mixture material.

2. In the first paragraph, the first light-emitting auxiliary layer includes a first compound, and the second light-emitting auxiliary layer includes a mixture of the second compound and the third compound. The first compound, the second compound and the third compound have different structures, An organic electric device characterized in that the first compound and the second compound are compounds represented by either the following chemical formula 1 or chemical formula 2. <Chemical Formula 1> <Chemical Formula 2> {In the above chemical formula 1 and chemical formula 2, Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Cycloalkyl group of; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 are independently of each other and are single bonds; C6~C 60 C2~C containing an arylene group; a fluorenylene group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups; L 8 Silver C6~C 60 C2~C containing an arylene group; a fluorenylene group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups; Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group and cycloalkyl group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Cycloalkyl group of; C7~C 20 Arylalkyl group of; and C8~C 20 It may be further substituted with one or more substituents selected from the group consisting of arylalkenyl groups; and these substituents may also be combined with each other to form a ring, wherein the 'ring' refers to 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.

3. An organic electric device according to claim 2, wherein the third compound is a compound represented by Chemical Formula 1 or Chemical Formula 2.

4. An organic electric device according to claim 2, characterized in that the third compound is a compound represented by the following chemical formula 3. <Chemical Formula 3> {In the above chemical formula 3, L 9 , L 10 and L 11 L of the above claim 1 1 is identical to the definition of Ar 8 , Ar 9 and Ar 10 are independently cyano groups; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Cycloalkyl group of; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy group; 5. An organic electric device according to claim 2, characterized in that the chemical formula 1 comprises a compound represented by any one of the compounds P1-1 to P1-97 below.

6. An organic electric device according to claim 2, characterized in that the chemical formula 2 comprises a compound represented by any one of the compounds P2-1 to P2-79 below.

7. An organic electric device according to claim 4, characterized in that the chemical formula 3 comprises a compound represented by any one of the compounds P3-1 to P3-48 below.

8. An organic electric device characterized in that in the fourth paragraph, the first light-emitting auxiliary layer is formed of the first compound represented by the chemical formula 1, and the second light-emitting auxiliary layer is formed by mixing the second compound and the third compound represented by the chemical formula 3.

9. An organic electric device characterized in that in paragraph 4, the first light-emitting auxiliary layer is made of a compound represented by the chemical formula 2, and the second light-emitting auxiliary layer is a mixture of the second compound and the third compound represented by the chemical formula 3.

10. An organic electronic device according to claim 2, characterized in that the difference between the LUMO energy level of the third compound and the LUMO energy level of the host compound of the light-emitting layer is 0.01 to 1.0 eV.

11. An organic electric device according to claim 1, 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.

12. An organic electric device according to claim 1, 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.

13. An organic electric device according to claim 12, characterized in that the organic layer further includes a charge generation layer formed between the two or more stacks.

14. An electronic device comprising a display device including the organic electric element of paragraph 1; and a control unit for driving the display device.

15. An electronic device according to claim 14, 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.

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