Compound for organic electronic device, organic electronic device using same, and electronic device therefor

Abstract

The present invention provides a compound represented by chemical formula 1, a method for recovering same, an organic electronic device material containing chemical formula 1 and chemical formula I, and an organic electronic device comprising a first electrode, a second electrode and an organic material layer between the first electrode and the second electrode. The organic material layer includes a compound of chemical formula 1 or a mixture of the compounds represented by chemical formula 1 and chemical formula I, and thus the driving voltage of the organic electronic device can be lowered and the luminous efficiency and lifespan thereof can be improved.

Description

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

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

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

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

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

[0005] The current portable display market is trending toward larger displays, increasing in size. This demand for greater power consumption exceeds that of existing portable displays. Therefore, power consumption has become a crucial factor for portable displays, which rely on batteries as a limited power source. Efficiency and longevity also need to be addressed.

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

[0007] Therefore, there is a need for the development of light-emitting materials that have high thermal stability and can efficiently achieve charge balance within the light-emitting layer. In other words, in order to fully demonstrate the excellent characteristics of organic electronic devices, the materials that make up the organic layers within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must first be supported by stable and efficient materials, and among these, development of host materials for the light-emitting layer is particularly necessary.

[0008] The purpose of the present invention is to provide a compound for an organic electric device that can lower the driving voltage of the device and improve the luminous efficiency and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

[0009] In one aspect, the present invention provides a compound represented by the following chemical formula 1.

[0010] <Chemical Formula 1> <Chemical Formula A> <Chemical Formula 1-1>

[0011]

[0012] (A is chemical formula A, and Q is chemical formula 1-1)

[0013] In another aspect, the present invention provides a material for an organic electric device containing a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula I.

[0014] <Chemical Formula I>

[0015]

[0016] In another aspect, the present invention provides an organic electric device and an electronic device thereof, including a material for an organic electric device comprising a compound of the above chemical formula 1 or containing compounds of the above chemical formula 1 and chemical formula I.

[0017] In another aspect, the present invention provides a method for recovering a compound represented by the above chemical formula 1.

[0018] By using the compound according to an embodiment of the present invention as a material for an organic electric device, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan can be improved.

[0019] Figures 1 to 3 are exemplary diagrams of organic light-emitting devices according to embodiments of the present invention.

[0020] [Explanation of symbols]

[0021] 100, 200, 300: Organic electroluminescent element 110: First electrode

[0022] 120: Hole injection layer 130: Hole transport layer

[0023] 140: Emitting layer 150: Electron transport layer

[0024] 160: Electron injection layer 170: Second electrode

[0025] 180: Light efficiency improvement layer 210: Buffer layer

[0026] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0027] 330: First hole transport layer 340: First light-emitting layer

[0028] 350: First electron transport layer 360: First charge generation layer

[0029] 361: Second charge generation layer 420: Second hole injection layer

[0030] 430: Second hole transport layer 440: Second light-emitting layer

[0031] 450: Second electron transport layer CGL: Charge generation layer

[0032] ST1: First stack ST2: Second stack

[0033] The terms "aryl group," "arylene group," and "aromatic ring" used herein mean a hydrocarbon aromatic ring group, each having 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto. In the present invention, the aryl group or arylene group includes a monocyclic ring, a polycyclic ring, a condensed ring, and the like.

[0034] As used herein, the term "fluorenyl group" means a substituted or unsubstituted fluorenyl group, and "fluorenylene group" means a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' bonding to each other in the structure below, and also includes a compound in which adjacent R" bonds to each other to form a ring. The "substituted fluorenyl group" and the "substituted fluorenylene group" mean that at least one of R, R', and R" in the structure below is a substituent other than hydrogen, and the number of R" in the chemical formula below may be 1 to 8. In the present specification, regardless of the valence, a fluorenyl group, a fluorenylene group, etc. may be described as a fluorene group or fluorene.

[0035]

[0036] The term "spiro compound" as used herein has a "spiro linkage," which means a linkage formed by two rings sharing only one atom. 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.

[0037] The term "heterocyclic group" used herein includes not only aromatic heterocycles such as "heteroaryl group" or "heteroarylene group" but also non-aromatic heterocycles, and unless otherwise stated means, but is not limited to, a ring having 2 to 60 carbon atoms each containing one or more heteroatoms. The term "heteroatom" used herein, unless otherwise stated, represents an element other than carbon, such as N, O, S, P, or Si, and may include a heteroatom group such as SO2, P=O, etc. instead of carbon forming the ring, as in the following compounds.

[0038]

[0039] In addition, a heterocyclic group includes a monocyclic ring, polycyclic ring, or condensed ring containing a heteroatom, and in the case of a condensed ring, if at least one of the condensed rings is a ring containing a heteroatom, it is defined as a heterocyclic ring. For example, a condensed ring in which a heterocyclic ring such as furan, dihydrofuran, thiophene, pyrrole, pyridine, etc. and an aromatic ring such as benzene, naphthalene, phenanthrene, etc. are condensed, or an aliphatic ring such as cyclopentane, cyclohexane, etc. are condensed is also considered a heterocyclic ring, and a spiro compound in which at least one ring contains a heteroatom is also considered a heterocyclic ring.

[0040] The term "aliphatic ring" used in this specification refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, including a monocyclic ring, a polycyclic ring, a condensed ring, a spiro compound, etc., and unless otherwise stated, refers to a ring having 3 to 60 carbon atoms, but is not limited thereto. In particular, an aliphatic ring (group) in this specification is defined as a hydrocarbon ring that does not contain any aromatic rings. Therefore, not only a saturated hydrocarbon ring such as a cycloalkyl group, but also a ring having one or more double bonds in the ring is considered to be an aliphatic ring as long as it is not an aromatic hydrocarbon.

[0041] The term "fused ring(group)" or "condensed ring(group)" used herein, unless otherwise stated, means a ring in which an aliphatic ring and an aromatic hydrocarbon (aromatic ring group or aryl ring) are condensed with each other, and unless otherwise stated, means a ring in which an aliphatic ring having 3 to 60 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms are condensed with each other.

[0042] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', or may be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, or it may be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent.

[0043] In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0044] 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.

[0045]

[0046] Here, if a is an integer of 0, the substituent R 1 means that it is absent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R 1It binds to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can bind as follows, for example, and when a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different.

[0047]

[0048] In addition, unless otherwise stated herein, a ring refers to an aryl ring, a heteroaryl ring, a fluorene ring, an aliphatic ring, a fused ring, etc., and a number-ring refers to a condensed ring, and a number-atom ring refers to a ring shape. For example, naphthalene corresponds to a two-ring condensed ring, anthracene corresponds to a three-ring condensed ring, thiophene and furan correspond to a five-membered heterocycle, and benzene and pyridine correspond to a six-membered aromatic ring.

[0049] In addition, unless otherwise stated in this specification, the rings formed by bonding adjacent groups to each other are C6~C 60 Aromatic ring group; 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 group; and C3~C 60 Aliphatic ring and C6~C 60 The aromatic ring may be selected from the group consisting of a fused ring group. Here, the aromatic ring group may be an aryl ring, and the heterocyclic group may include a heteroaryl ring.

[0050] Unless otherwise stated herein, 'neighboring groups' includes, for example, R1 and R2, R2 and R3, R3 and R4, R5 and R6, as well as R7 and R8 sharing a carbon, and may also include substituents bonded to non-adjacent ring elements (carbon, nitrogen, etc.), such as R1 and R7, R1 and R8, or R4 and R5. That is, when there is a substituent on a ring element such as a carbon or nitrogen that is immediately adjacent, they can be neighboring groups, but when no substituent is bonded to the ring element at the immediately adjacent position, the substituent bonded to the next ring element can be a neighboring group, and substituents bonded to the same ring carbon can also be neighboring groups. In the following chemical formula, when substituents bonded to the same carbon, such as R7 and R8, bond to each other to form a ring, a compound including a spiro moiety can be formed.

[0051]

[0052] Additionally, in this specification, the expression 'adjacent groups can combine with each other to form a ring' is used with the same meaning as 'adjacent groups combine with each other to selectively form a ring', and means a case where at least one pair of adjacent groups combine with each other to form a ring.

[0053] In addition, unless otherwise stated herein, substituents such as aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, etc., rings formed by bonding adjacent groups to each other, etc., are each deuterium; halogen; cyano group; nitro group; siloxane group; C6-C 30Aryl group of; Fluorenyl group; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 Heterocyclic group of; C3-C 30 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C1-C 20 Alkoxy group of; C6-C 20 Aryloxy group of; C1-C 20 Alkylthio group of; C6-C 20 Arylthio group of; C1-C 20 Alkyl group or C6-C 20 A silane group substituted or unsubstituted with an aryl group; and C1-C 20 Alkyl group or C6-C 20 It may be substituted with one or more substituents selected from the group consisting of phosphine oxide groups substituted or unsubstituted with an aryl group.

[0054] Unless otherwise stated in this specification, the symbols "*" or " " represents the joining part.

[0055] Hereinafter, the laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.

[0056] When assigning reference numerals to components in each drawing, it should be noted that identical components are assigned the same numerals whenever possible, even if they appear on different drawings. Furthermore, when describing the present invention, if a detailed description of a related known configuration or function is deemed likely to obscure the gist of the present invention, such detailed description will be omitted.

[0057] When describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. 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.

[0058] Furthermore, when a component such as a layer, membrane, region, or plate is said to be "on" or "over" another component, it should be understood that this includes not only the case where it is "directly on" the other component, but also the case where there are other components in between. Conversely, when a component is said to be "directly on" another part, it should be understood that there are no other components in between.

[0059] Figures 1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.

[0060] Referring to FIG. 1, an organic electric element (100) according to one embodiment of the present invention includes a first electrode (110), a second electrode (170), and an organic layer formed between the first electrode (110) and the second electrode (170) formed on a substrate (not shown), and an inorganic layer may be included between the first electrode (110) and the second electrode (120).

[0061] For example, the first electrode (110) may be an anode, the second electrode (170) 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.

[0062] The above organic layer refers to a layer containing at least one organic material. For example, the organic layer may include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160). However, the electron injection layer (160) may be an inorganic layer that does not contain an organic material.

[0063] Specifically, a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) can be sequentially formed on a first electrode (110).

[0064] Preferably, a light efficiency improvement layer (180) may be formed on one side of the first electrode (110) or the second electrode (170) that is not in contact with the organic layer or the inorganic layer, and when the light efficiency improvement layer (180) is formed, the light efficiency of the organic electric element may be improved.

[0065] For example, a light efficiency improvement layer (180) can be formed on the second electrode (170). In the case of a top emission organic light emitting device, the formation of the light efficiency improvement layer (180) can reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode (170), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer (180) can serve as a buffer for the second electrode (170).

[0066] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will be described with reference to FIG. 2.

[0067] Referring to FIG. 2, an organic electric device (200) according to another embodiment of the present invention may include a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) sequentially formed on a first electrode (110), and a light efficiency improvement layer (180) may be formed on the second electrode.

[0068] Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light-emitting layer (140) and the electron transport layer (150).

[0069] Additionally, 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 transport layer, a light-emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

[0070] Referring to FIG. 3, an organic electric element (300) according to another embodiment of the present invention may have two or more sets of stacks (ST1, ST2) of organic layers formed of multiple layers formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stacks of organic layers.

[0071] Specifically, an organic electric device according to one embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL: Charge Generation Layer), a second stack (ST2), a second electrode (170), and a light efficiency improvement layer (180).

[0072] The first stack (ST1) is an organic layer formed on the first electrode (110), which may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450). In this way, the first stack and the second stack may be organic layers having the same stacked structure, but may also be organic layers having different stacked structures.

[0073] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). This charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to smoothly distribute charges.

[0074] The first light-emitting layer (340) may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer (440) may include a material doped with a greenish yellow dopant and a red dopant in a green host, but the materials of the first light-emitting layer (340) and the second light-emitting layer (440) according to the embodiment of the present invention are not limited thereto.

[0075] In FIG. 3, n can be an integer from 1 to 5, and when n is 2, a charge generation layer (CGL) and a third stack can be additionally stacked on the second stack (ST2).

[0076] When a plurality of light-emitting layers are formed by a multi-layer stack structure as shown in Fig. 3, not only can an organic light-emitting device that emits white light be manufactured by the mixing effect of the light emitted from each light-emitting layer, but an organic light-emitting device that emits light of various colors can also be manufactured.

[0077] The compound represented by the chemical formula 1 of the present invention or a mixture of the compound of the chemical formula 1 and the compound of the chemical formula I may be included in an organic layer. For example, the compound represented by the chemical formula 1 of the present invention or a mixture of the compound of the chemical formula 1 and the compound of the chemical formula I may be used as a material for a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light-emitting auxiliary layer (220), an electron transport layer (150, 350, 450), a light-emitting layer (140, 340, 440), or a light efficiency improvement layer (180), but may preferably be used as a host for the light-emitting layer (140, 340, 440).

[0078] Even if the core is identical or similar, the band gap, electrical properties, and interface properties can vary depending on which substituent is bonded at which position. Therefore, research on the selection of the core and the combination of sub-substituents bonded to it is necessary. In particular, when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

[0079] Therefore, in the present invention, by using a compound represented by chemical formula 1 or a mixture of a compound of chemical formula 1 and a compound of chemical formula I as a host of a light-emitting layer (140, 340, 440), the energy level and T1 value between each organic layer, and the inherent properties of the material (mobility, interface properties, etc.) can be optimized, thereby simultaneously improving the lifespan and efficiency of the organic electric device.

[0080] An organic light emitting diode according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD. For example, it may be manufactured by forming an anode (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) thereon, and then depositing a material that can be used as a cathode (170) thereon. In addition, an emission auxiliary layer (220) may be further formed between the hole transport layer (130) and the light emitting layer (140), and an electron transport auxiliary layer (not shown) may be further formed between the emission layer (140) and the electron transport layer (150), or may be formed in a stack structure as described above.

[0081] In addition, the organic layer can be manufactured with a smaller number of layers by using various polymer materials and a solution process or solvent process other than a deposition method, 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.

[0082] 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.

[0083] 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.

[0084] 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, navigation systems, game consoles, various TVs, and various computers.

[0085] Hereinafter, a compound according to one aspect of the present invention will be described.

[0086] A compound according to one aspect of the present invention is represented by the following chemical formula 1.

[0087] <Chemical Formula 1> <Chemical Formula A> <Chemical Formula 1-1>

[0088]

[0089] In the above chemical formula 1, each symbol is defined as follows.

[0090] A is chemical formula A, Q is chemical formula 1-1, X is O or S, and Z is O, S, or N(R 3 )am.

[0091] B ring is C 10 ~C 60 is a condensed aryl ring, and ring B is one or more identical or different R 4 can be replaced by . For example, ring B is C 10 ~C 60 , C 10 ~C 30 , C 10 ~C 20 , C 10 ~C 18 , C 10 ~C 14 , C 10 ~C 12 It may be a condensed aryl ring, and specifically, it may be naphthyl, phenanthryl, anthracenyl, benzanthracenyl, benzophenanthryl, etc.

[0092] Ar 1 and Ar 2 are independently C6~C60 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 group; C6~C 60 Aromatic ring and C3~C 60 A fused ring group in which an aliphatic ring is fused; and C1~C 20 is selected from the group consisting of alkyl groups.

[0093] L 1 Inland L 3 , L a are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; and C6~C 60 Aromatic ring and C3~C 60 It is selected from the group consisting of fused ring groups in which the aliphatic rings are fused.

[0094] R 1 Inland R 4 are independently hydrogen; deuterium; halogen; cyano group; nitro group; silane group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 Fused ring group of aliphatic ring; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups, and adjacent groups can be combined with each other to form a ring, and R 3 or R 4Go L a is combined into

[0095] a and b are integers from 0 to 3, and if they are integers greater than or equal to 2, multiple R 1 Each, multiple R 2 Each is either the same or different from the other.

[0096] Neighboring units, for example, neighboring R 1 Kiri, neighboring R 2 When they combine with each other to form a ring, the ring is C6~C 60 Aromatic ring group; Fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 It can be selected from the group consisting of fused ring groups of aromatic rings.

[0097] Ar 1 , Ar 2 , R 1 Inland R 4 At least one of them is an aryl group, or L 1 Inland L 3 If at least one of them is an arylene group, the aryl group or arylene group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12, C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aryl group or an arylene group, and specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, benzophenanthrene, triphenylene, chrysene, etc.

[0098] Ar 1 , Ar 2 , R 1 Inland R 4 , L 1 Inland L 3 If at least one of them is a heterocyclic group, the heterocyclic group is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 It may be a heterocyclic group such as, and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, phenanthrobenzofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, phenantrobenzothiophene, carbazole, phenyl-carbazole, Benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothiopyridine, benzofuropyridine, benzothiopyrimidine, benzofuropyrimidine, benzothiopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzosilole, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, thianthrene, oxazole, benzoxazole, naphthooxazole, phenanthrooxazole, dibenzothiobenzoxazole, dibenzofurobenzoxazole, It may be 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthrene], etc.

[0099] R 1 Inland R 4 If at least one of them is an alkyl group, the alkyl group is, for example, C1~C 20 , C1~C 10, C1~C4, C1, C2, C3, C4, etc., and may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, etc.

[0100] The above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, silane group, alkoxy group, aryloxy group, and the ring formed by bonding adjacent groups to each other are each deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It may be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and adjacent substituents may be combined with each other to form a ring, and hydrogen of the substituents may be replaced with deuterium.

[0101] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, silane group, alkoxy group, aryloxy group, and ring formed by bonding adjacent groups to each other is substituted with an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It can be an aryl group such as .

[0102] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, silane group, alkoxy group, aryloxy group, and rings formed by bonding adjacent groups to each other is substituted with a heterocyclic group, the heterocyclic group is, for example, C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14, C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 It may be a heterocyclic group such as the following.

[0103] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, silane group, alkoxy group, aryloxy group, and ring formed by bonding adjacent groups to each other is substituted with an alkyl group, the alkyl group is, for example, C1~C 20 , C1~C 10 , C1~C4, C1, C2, C3, C4, etc., and may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, etc.

[0104] The above Ar 1 and Ar 2 At least one of the compounds may be selected from the group consisting of the following chemical formulae Ar-1 to Ar-12, but is not limited thereto.

[0105] <Chemical Formula Ar-1> <Chemical Formula Ar-2> <Chemical Formula Ar-3> <Chemical Formula Ar-4>

[0106]

[0107] <Chemical formula Ar-5> <Chemical formula Ar-6> <Chemical formula Ar-7> <Chemical formula Ar-8>

[0108]

[0109] <Chemical formula Ar-9> <Chemical formula Ar-10> <Chemical formula Ar-11> <Chemical formula Ar-12>

[0110]

[0111] In the above chemical formulas Ar-1 to Ar-12, each symbol is defined as follows.

[0112] V is O, S, C(R1)(R2) or N(R3), provided that V is L 1 or L 2 When combined, V is C(R1) or N.

[0113] R 5 Inland R 11 , R1 to R3 are each independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It is selected from the group consisting of heterocyclic groups, and adjacent groups can combine with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

[0114] c and g are each integers from 0 to 5, d is an integer from 0 to 7, e is an integer from 0 to 9, f, h and i are each integers from 0 to 4, and if they are integers greater than or equal to 2, multiple R 5 Each or multiple R 11 Each is either the same or different from the other.

[0115] The above chemical formula 1-1 may be represented by one of the following chemical formulas Q-1 to Q-13, but is not limited thereto.

[0116] <Chemical Formula Q-1> <Chemical Formula Q-2> <Chemical Formula Q-3> <Chemical Formula Q-4>

[0117]

[0118] <Chemical Formula Q-5> <Chemical Formula Q-6> <Chemical Formula Q-7> <Chemical Formula Q-8>

[0119]

[0120] <Chemical Formula Q-9> <Chemical Formula Q-10> <Chemical Formula Q-11> <Chemical Formula Q-12>

[0121]

[0122] <Chemical Formula Q-13>

[0123]

[0124] In the above chemical formulas Q-1 to Q-13, Z is as defined in chemical formula 1, and R 12 Inland R 16 is hydrogen or deuterium, j, l and m are each integers from 0 to 2, and k and n are each integers from 0 to 4.

[0125] The above chemical formula A may be selected from the group consisting of the following chemical formulas C-1 to C-9, but is not limited thereto.

[0126] <Chemical Formula C-1> <Chemical Formula C-2> <Chemical Formula C-3> <Chemical Formula C-4>

[0127]

[0128] <Chemical Formula C-5> <Chemical Formula C-6> <Chemical Formula C-7> <Chemical Formula C-8>

[0129]

[0130] <Chemical Formula C-9>

[0131]

[0132] In the above chemical formulas C-1 to C-9, X, L a, Q, R 1 , R 2 , a, b are as defined in chemical formula 1.

[0133] L 1 , L 2 , L 3 and L a At least one of the compounds may be selected from a group consisting of a single bond or formulae L-1 to L-20, but is not limited thereto.

[0134] <Chemical Formula L-1> <Chemical Formula L-2> <Chemical Formula L-3> <Chemical Formula L-4>

[0135]

[0136] <Chemical Formula L-5> <Chemical Formula L-6> <Chemical Formula L-7> <Chemical Formula L-8>

[0137]

[0138] <Chemical Formula L-9> <Chemical Formula L-10> <Chemical Formula L-11> <Chemical Formula L-12>

[0139]

[0140] <Chemical Formula L-13> <Chemical Formula L-14> <Chemical Formula L-15> <Chemical Formula L-16>

[0141]

[0142] <Chemical Formula L-17> <Chemical Formula L-18> <Chemical Formula L-19> <Chemical Formula L-20>

[0143]

[0144] In the above chemical formulas L-1 to L-20, each symbol is defined as follows.

[0145] W is O, S, C(R 11 )(R 12 ) or N(R 13 ) and, however, when combined through W, W is C(R 11 ) or N.

[0146] R 17 Inland R 22 , R 11 Inland R 13 are independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30It is selected from the group consisting of heterocyclic groups, and adjacent groups can combine with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

[0147] o, q, r, s and t are each integers from 0 to 4, p is an integer from 0 to 6, and if they are integers greater than or equal to 2, multiple R 17 Each or multiple R 22 Each is either the same or different from the other.

[0148] Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.

[0149]

[0150]

[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]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] .

[0189] In another aspect, the present invention provides a material for an organic electric device containing a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula I below. Preferably, the material for an organic electric device is a host material for a light-emitting layer. That is, a mixture of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula I can be used as a host for an organic material layer.

[0190] Hereinafter, the following chemical formula I will be described in detail.

[0191] <Chemical Formula I>

[0192]

[0193] In the above chemical formula I, each symbol can be defined as follows.

[0194] X A Inland X C is N or C(R'), at least one of which is N. For example, X A Inland X C The ring containing may be pyridine, pyrimidine or triazine.

[0195] Ar A Inland Ar C 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 group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and C1~C 30 is selected from the group consisting of alkyl groups.

[0196] L A Inland L C are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60Aliphatic ring group; and C3~C 60 Aliphatic ring and C6~C 60 It is selected from the group consisting of fused ring groups of aromatic rings.

[0197] The above R' is hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 Fused ring group of aliphatic ring; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups.

[0198] The above Ar A Inland Ar C , at least one of R' is an aryl group, or L A Inland L C If at least one of them is an arylene group, the aryl group or arylene group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11, C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aryl group or an arylene group, and specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

[0199] The above Ar A Inland Ar C , R', L A Inland L C If at least one of them is a heterocyclic group, the heterocyclic group is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 It may be a heterocyclic group such as, and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, Naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothiopyridine, benzofuropyridine, benzothiopyrimidine, benzofuropyrimidine, benzothiopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilole, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, thianthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthrene], etc.

[0200] The above Ar A Inland Ar C , at least one of R' is a fluorenyl group, or L A Inland L CWhen at least one of them is a fluorenylene group, the fluorenyl group or fluorenylene group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0201] The above Ar A Inland Ar C , R', L A Inland L C If at least one of them is an aliphatic ring group, the aliphatic ring group is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring group such as a cyclohexanyl group, an adamantyl group, etc., specifically, it may be a cyclohexanyl group, an adamantyl group, etc.

[0202] The above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group are each deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It may be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and adjacent substituents may be combined with each other to form a ring, and hydrogen of the substituents may be replaced with deuterium.

[0203] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and ring formed by bonding adjacent groups to each other is substituted with an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It can be an aryl group such as .

[0204] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and rings formed by bonding adjacent groups to each other is substituted with a heterocyclic group, the heterocyclic group is, for example, C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C17 , C 18 , C 19 , C 20 It may be a heterocyclic group such as the following.

[0205] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and rings formed by bonding adjacent groups to each other is substituted with an aliphatic ring group, the aliphatic ring group is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring such as the back.

[0206] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and ring formed by bonding adjacent groups to each other is substituted with a fluorenyl group, the fluorenyl group may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0207] The above Ar A Inland Ar C At least one of the compounds may be selected from the group consisting of the following chemical formulae Ar-a to Ar-d, but is not limited thereto.

[0208] <Chemical formula Ar-a> <Chemical formula Ar-b>

[0209]

[0210] <Chemical formula Ar-c> <Chemical formula Ar-d>

[0211]

[0212] In the above chemical formulas Ar-a to Ar-d, each symbol is defined as follows.

[0213] Y A Inland Y C are independently O, S, C(R5)(R6) or N(Ar2).

[0214] R A Inland R F , R5 and R6 are independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It is selected from the group consisting of heterocyclic groups, and adjacent groups can combine with each other to form a ring.

[0215] Neighboring R A R in the neighborhood F When at least one pair of them combines with each other to form a ring, the ring is C6~C 60 Aryl ring; fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 It can be selected from the group consisting of fused ring groups of aromatic rings.

[0216] When adjacent R5 and R6 combine to form a ring, a spiro compound can be formed.

[0217] Ar2 is C1-C 20 alkyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 is selected from the group consisting of heterocyclic groups.

[0218] ta and tc are integers from 0 to 3, tb and td are integers from 0 to 4, te is integer from 0 to 5, tf is integer from 0 to 7, and if these are integers greater than or equal to 2, multiple R A Each or multiple R F Each is either the same or different from the other.

[0219] The above R A Inland R F , R5 and R6 are each deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It may be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and the hydrogen of the substituents may be replaced with deuterium.

[0220] The above chemical formula Ar-a may be selected from the group consisting of the following chemical formulas Ar-a-1 to Ar-a-4, the above chemical formula Ar-b may be represented by the following chemical formula Ar-b-1 or chemical formula Ar-b-2, and the above chemical formula Ar-d may be represented by the following chemical formula Ar-d-1 or chemical formula Ar-d-2.

[0221] <Chemical formula Ar-a-1> <Chemical formula Ar-a-2>

[0222]

[0223] <Chemical formula Ar-a-3> <Chemical formula Ar-a-4>

[0224]

[0225] <Chemical formula Ar-b-1> <Chemical formula Ar-b-2>

[0226]

[0227] <Chemical formula Ar-d-1> <Chemical formula Ar-d-2>

[0228]

[0229] In the above chemical formulas Ar-a-1 to Ar-a-4, Y A , R A , R B , ta, tb are as defined in the chemical formula Ar-a, and in the chemical formula Ar-b-1 and chemical formula Ar-b-2, Y B , Y C , R D , tc, td are as defined in the chemical formula Ar-b, and in the chemical formula Ar-d-1 and chemical formula Ar-d- 2, R F , tf is as defined in the chemical formula Ar-d.

[0230] L A Inland L C At least one of which is a single bond; and may be selected from the group consisting of the following chemical formulas b-1 to b-13, but is not limited thereto.

[0231] <Chemical Formula B-1> <Chemical Formula B-2> <Chemical Formula B-3>

[0232]

[0233] <Chemical Formula B-4> <Chemical Formula B-5> <Chemical Formula B-6>

[0234]

[0235] <Chemical Formula B-7> <Chemical Formula B-8> <Chemical Formula B-9> <Chemical Formula B-10>

[0236]

[0237] <Chemical Formula B-11> <Chemical Formula B-12> <Chemical Formula B-13>

[0238]

[0239] In the above chemical formulas b-1 to b-13, each symbol can be defined as follows.

[0240] Z 10 Silver O, S, N(Ar 12 ) or C(R 11 )(R 12 )am.

[0241] Z 49 , Z 50 , Z 51 are independently N or C(R 13 ), and at least one of them is N.

[0242] R a1 Inland R a7 , R 11 , R 12 , R 13 are independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It is selected from the group consisting of heterocyclic groups, and adjacent groups can combine with each other to form a ring.

[0243] Neighboring R a1 R in the neighborhood a7 When at least one pair of them combines with each other to form a ring, the ring is C6~C 60 Aryl ring; fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 It can be selected from the group consisting of fused ring groups of aromatic rings, and adjacent R 11 and R 12 When they combine with each other to form rings, spiro compounds can be formed.

[0244] Ar 12 is C1-C 20 alkyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30is selected from the group consisting of heterocyclic groups.

[0245] a", c", d", e" are each integers from 0 to 4, b" is an integer from 0 to 6, f" and g" are each integers from 0 to 3, h" is an integer from 0 to 2, i" is an integer of 0 or 1, and if these are integers greater than or equal to 2, a plurality of R a1 Each to R a7 Each is either the same or different from the other.

[0246] The above R a1 Inland R a7 , R 11 , R 12 , R 13 , Ar 12 are respectively deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It may be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and the hydrogen of the substituents may be replaced with deuterium.

[0247] Specifically, the compound represented by the above chemical formula I may be one of the following compounds, but is not limited thereto.

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317] In another aspect, the present invention provides an electronic device including a display device including an organic electric element and a control unit for driving the display device, wherein the organic electric element includes a compound represented by the above chemical formula 1 or contains compounds represented by the above chemical formula 1 and chemical formula I. Preferably, these compounds are included in a light-emitting layer, and more preferably, they are used as a host for the light-emitting layer.

[0318] The rearrangement energy of the compound used as a material of the light-emitting layer can affect the performance of the organic light-emitting device, and the rearrangement energy is explained below.

[0319] Reorganization energy (RE) refers to the energy lost due to changes in molecular structure during charge transfer (electrons and holes). It depends on molecular geometry and has the characteristic of decreasing as the difference between the neutral PES (Potential Energy Surface) and the charged PES decreases. The RE value can be calculated using the following formula.

[0320]

[0321] NONE: Neutral geometry of the molecule (= NO opt.)

[0322] NOAE: Anion geometry of neutral molecules

[0323] NOCE: Cation geometry of a neutral molecule

[0324] AONE: Neutral geometry of anion molecules

[0325] AOAE: Anion geometry of anion molecules (= AO opt.)

[0326] CONE: Neutral geometry of cation molecules

[0327] COCE: Cation geometry of the cation molecule (= CO opt.)

[0328] The rearrangement energy value and the mobility of charges are inversely proportional, and under the condition that they have the same r and T values, the RE value of each material directly affects the mobility.

[0329] The relationship between RE value and mobility is expressed as follows and is described by the charge transfer matrix element.

[0330]

[0331] (λ: Reorganization energy, μ: mobility, r: dimer displacement, t: intermolecular charge transfer matrix element)

[0332] According to the above equation, it can be seen that the smaller the RE value, the faster the mobility of charges.

[0333] To obtain rearrangement energy values, a simulation tool capable of calculating potential energy based on molecular structure is required. For example, Gaussian09 (G09) and Schrödinger Materials Science's Jaguar (JG) modules can be used. Both G09 and JG analyze molecular properties through quantum mechanical (QM) calculations and offer the ability to optimize molecular structures or calculate single-point energy for a given molecular structure.

[0334] Performing QM calculations on molecular structures requires significant computational resources. For example, two cluster servers could be used for these calculations. Each cluster server consists of four node workstations and one master workstation, with each node using CPUs with 36 or more cores, enabling molecular QM calculations through parallel computing via symmetric multiprocessing (SMP).

[0335] Using G09, we calculate the molecular structures optimized for neutral / charge states and their potential energies (NONE / COCE) required for rearrangement energy. By changing only the charges of the two optimized structures, we calculate the charge-state potential energy (NOCE) of the structure optimized for the neutral state and the neutral-state potential energy (CONE) of the structure optimized for the charge state. Then, we calculate the rearrangement energy according to the following equation.

[0336]

[0337] Since Schrödinger provides a function to automatically perform this calculation process, the JG module can sequentially calculate the potential energy for each state and calculate the RE value simply by providing the molecular structure (NO) of the basic state.

[0338] The RE value of chemical formula 1 calculated in this manner may preferably be 0.100 to 0.200, and more preferably 0.120 to 0.170.

[0339] In another aspect, the present invention provides a compound represented by the chemical formula 1 obtained by recovering and purifying the material of an organic layer from a deposition device after depositing the organic layer in a manufacturing process of an organic electric device. The purity of the compound obtained by recovery and purification is 99.9% or higher.

[0340] In another aspect, the present invention provides a method for recovering a compound, comprising the steps of depositing an organic layer material including a compound represented by Chemical Formula 1, recovering the organic layer material attached to a deposition device, and purifying the recovered organic layer material to obtain a compound represented by Chemical Formula 1 having a purity of 99.9% or higher.

[0341] The above purification step may include a step of recrystallizing the recovered organic layer material using a recrystallization solvent, a step of adsorption separation using an adsorbent, and a step of sublimation purification.

[0342] The above recrystallization step may include a preliminary purification process for obtaining a compound represented by the above chemical formula 1 with a purity of 98% using a recrystallization solvent.

[0343] A polar solvent having a polarity index (PI) of 5.5 to 7.2 is preferably used as the recrystallization solvent, or a mixture of a polar solvent having a polarity index of 5.5 to 7.2 and a non-polar solvent having a polarity index of 2.0 to 4.7 may be used.

[0344] When using a mixture of a polar solvent and a non-polar solvent as a recrystallization solvent, the non-polar solvent may be used in a ratio of 15% (v / v) or less compared to the polar solvent.

[0345] In addition, as a recrystallization solvent, a single solvent of methylpyrrolidone (N-methylpyrrolidone: NMP) is preferably used; or a mixed polar solvent in which any one selected from the group consisting of methylpyrrolidone, dimethyl imidazolidinone (1,3-dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-dimethyl formamide), dimethyl acetamide, and dimethyl sulfoxide is mixed; or a single or mixed nonpolar solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone, or a mixture of polar solvents and nonpolar solvents can be used.

[0346] The above preliminary purification process may include a step of dissolving the unrefined organic light-emitting material recovered from the deposition equipment in a polar solvent at 90°C to 120°C and then cooling it to 0°C to 5°C to precipitate crystals.

[0347] The above preliminary purification process may include a step of dissolving an unrefined organic light-emitting material recovered from a deposition device in a polar solvent at 90°C to 120°C, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C to precipitate a crystal.

[0348] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition equipment in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

[0349] The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

[0350] In the adsorption separation step using the above adsorbent, activated carbon, silica gel, alumina or a known material for adsorption purposes can be used as the adsorbent.

[0351] Hereinafter, examples of the synthesis of the compound represented by chemical formula 1 and chemical formula 15 according to the present invention and examples of the manufacture of organic electric devices will be described in detail by way of examples, but the present invention is not limited thereto.

[0352] [Synthesis example]

[0353] Synthesis example of a compound represented by chemical formula 1

[0354] The compound (final product) represented by chemical formula 1 according to the present invention can be synthesized by reacting Sub 1 and Sub 2 as in the following reaction scheme 1, but is not limited thereto.

[0355] <Reaction Scheme 1>

[0356]

[0357] Examples of compounds in Sub 1

[0358] Compounds belonging to Sub 1 may include, but are not limited to, the compounds below, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below are as shown in Table 1.

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371] 화합물FD-MS화합물FD-MSSub1-1m / z=259.10(C 18 H 13 NO=259.31)Sub1-2m / z=259.10(C 18 H 13 NO=259.31)Sub1-3m / z=259.10(C 18 H 13 NO=259.31)Sub1-4m / z=275.08(C 18 H 13 NS=275.37)Sub1-5m / z=275.08(C 18 H 13 NS=275.37)Sub1-6m / z=275.08(C 18 H 13 NS=275.37)Sub1-7m / z=282.12(C 18 H6D7NS=282.41)Sub1-8m / z=264.13(C 18 H8D5NO=264.34)Sub1-9m / z=325.09(C 22 H 15 NS=325.43)Sub1-10m / z=309.12(C 22 H 15 NO=309.37)Sub1-11m / z=309.12(C 22 H 15 NO=309.37)Sub1-12m / z=385.15(C 28 H 19 NO=385.47)Sub1-13m / z=335.13(C 24 H 17 NO=335.41)Sub1-14m / z=309.12(C 22 H 15 NO=309.37)Sub1-15m / z=385.15(C 28 H 19NO=385.47)Sub1-16m / z=335.13(C 24 H 17 NO=335.41)Sub1-17m / z=461.18(C 34 H 23 NO=461.56)Sub1-18m / z=475.16(C 34 H 21 NO2=475.16)Sub1-19m / z=617.18(C 44 H 27 NOS=617.77)Sub1-20m / z=516.22(C 37 H 28 N2O=516.64)Sub1-21m / z=401.12(C 28 H 19 NS=401.53)Sub1-22m / z=515.15(C 35 H 21 N3S=515.63)Sub1-23m / z=435.16(C 32 H 21 NO=435.53)Sub1-24m / z=284.09(C 19 H 12 N2O=284.32)Sub1-25m / z=277.09(C 18 H 12 FNO=277.30)Sub1-26m / z=284.09(C 19 H 12 N2O=284.32)Sub1-27m / z=353.13(C 24 H 17 NO=335.41)Sub1-28m / z=335.13(C 24 H 17 NO=335.41)Sub1-29m / z=435.16(C 32 H 21 NO=435.53)Sub1-30m / z=359.13(C 26 H 17 NO=359.43)Sub1-31m / z=359.13(C 26 H 17 NO=359.43)Sub1-32m / z=485.18(C 36 H 23 NO=485.59)Sub1-33m / z=424.16(C 30H 20 N2O=424.50)Sub1-34m / z=359.13(C 26 H 17 NO=359.43)Sub1-35m / z=390.17(C 27 H 22 N2O=390.49)Sub1-36m / z=284.09(C 19 H 12 N2O=284.32)Sub1-37m / z=335.13(C 24 H 17 NO=335.41)Sub1-38m / z=315.16(C 22 H 21 NO=315.42)Sub1-39m / z=277.09(C 18 H 12 FNO=277.30)Sub1-40m / z=461.18(C 34 H 23 NO=461.56)Sub1-41m / z=335.13(C 24 H 17 NO=335.41)Sub1-42m / z=169.09(C 12 H 11 N=169.23)Sub1-43m / z=319.14(C 24 H 17 N=319.41)Sub1-44m / z=319.14(C 24 H 17 N=319.41)Sub1-45m / z=219.10(C 16 H 13 N=219.29)Sub1-46m / z=369.15(C 28 H 19 N=369.47)Sub1-47m / z=219.10(C 16 H 13 N=219.29)Sub1-48m / z=295.14(C 22 H 17 N=295.39)Sub1-49m / z=371.17(C 28 H 21 N=371.48)Sub1-50m / z=371.17(C 28 H 21 N=371.48)Sub1-51m / z=371.17(C 28H 21 N=371.48)Sub1-52m / z=371.17(C 28 H 21 N=371.48)Sub1-53m / z=521.21(C 40 H 27 N=521.66)Sub1-54m / z=371.17(C 28 H 21 N=371.48)Sub1-55m / z=295.14(C 22 H 17 N=295.39)Sub1-56m / z=245.12(C 18 H 15 N=245.33)Sub1-57m / z=321.15(C 24 H 19 N=321.42)Sub1-58m / z=445.18(C 34 H 23 N=445.57)Sub1-59m / z=421.18(C 32 H 23 N=421.54)Sub1-60m / z=410.18(C 30 H 22 N2=410.52)Sub1-61m / z=351.20(C 26 H 25 N=351.49)Sub1-62m / z=471.20(C 36 H 25 N=471.60)Sub1-63m / z=392.10(C 25 H 16 N2OS=392.48)Sub1-64m / z=478.19(C 31 H 22 N6=478.56)

[0372] Examples of compounds in Sub 2

[0373] Compounds belonging to Sub 2 may include, but are not limited to, the compounds below, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below are as shown in Table 2.

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398] Compound FD-MS Compound FD-MS Sub2-1 m / z = 445.09 (C 29 H 16 ClNO2=445.90)Sub2-2m / z=445.09(C29 H 16 ClNO2=445.90)Sub2-3m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-4m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-5m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-6m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-7m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-8m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-9m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-10m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-11m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-12m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-13m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-14m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-15m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-16m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-17m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-18m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-19m / z=451.12(C29 H 10 D6ClNO2=451.94)Sub2-20m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-21m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-22m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-23m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-24m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-25m / z=450.12(C 29 H 11 D5ClNO2=450.93)Sub2-26m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-27m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-28m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-29m / z=445.09(C 29 H 16 ClNO2=445.90)Sub3-30m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-31m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-32m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-33m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-34m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-35m / z=461.06(C 29 H 16ClNOS=461.96)Sub2-36m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-37m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-38m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-39m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-40m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-41m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-42m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-43m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-44m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-45m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-46m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-47m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-48m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-49m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-50m / z=451.12(C 29 H 10 D6ClNO2=451.94)Sub2-51m / z=466.10(C 29 H 11 D5ClNOS=466.99)Sub2-52m / z=461.06(C29 H 16 ClNOS=461.96)Sub2-53m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-54m / z=466.10(C 29 H 11 D5ClNOS=466.99)Sub2-55m / z=450.12(C 29 H 11 D5ClNO2=450.93)Sub2-56m / z=450.12(C 29 H 11 D5ClNO2=450.93)Sub2-57m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-58m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-59m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-60m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-61m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-62m / z=467.10(C 29 H 10 D6ClNOS=468.00)Sub2-63m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-64m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-65m / z=445.09(C 29 H 16 ClNO2=445.90)Sub2-66m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-67m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-68m / z=461.06(C 29 H 16ClNOS=461.96)Sub2-69m / z=449.11(C 29 H 12 D4ClNO2=449.93)Sub2-70m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-71m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-72m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-73m / z=511.08(C 33 H 18 ClNOS=512.02)Sub2-74m / z=511.08(C 33 H 18 ClNOS=512.02)Sub2-75m / z=511.08(C 33 H 18 ClNOS=512.02)Sub2-76m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-77m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-78m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-79m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-80m / z=561.10(C 37 H 20 ClNOS=562.08)Sub2-81m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-82m / z=537.10(C 35 H 20 ClNOS=538.06)Sub2-83m / z=517.13(C 33 H 24 ClNOS=518.07)Sub2-84m / z=587.11(C 39 H 22 ClNOS=588.12)Sub2-85m / z=637.13(C 43 H24 ClNOS=638.18)Sub2-86m / z=513.10(C 33 H 20 ClNOS=514.04)Sub2-87m / z=561.10(C 37 H 20 ClNOS=562.08)Sub2-88m / z=511.08(C 33 H 18 ClNOS=512.02)Sub2-89m / z=561.10(C 37 H 20 ClNOS=562.08)Sub2-90m / z=567.14(C 37 H 26 ClNOS=568.13)Sub2-91m / z=537.10(C 35 H 20 ClNOS=538.06)Sub2-92m / z=461.06(C 29 H 16 ClNOS=461.96)Sub2-93m / z=613.13(C 41 H 24 ClNOS=614.16)Sub2-94m / z=537.10(C 35 H 20 ClNOS=538.06)Sub2-95m / z=643.08(C 41 H 22 ClNO2=644.20)Sub2-96m / z=628.10(C 40 H 21 ClN-2O2S=629.13)Sub2-97m / z=627.11(C 41 H 22 ClNO2S=628.14)Sub2-98m / z=587.11(C 39 H 22 ClNOS=588.12)Sub2-99m / z=517.13(C 33 H 24 ClNOS=518.07)Sub2-100m / z=593.16(C 39 H 28 ClNOS=594.17)Sub2-101m / z=517.13(C 33 H 24 ClNOS=518.07)Sub2-102m / z=766.18(C52 H 31 ClN2OS=767.34)Sub2-103m / z=534.11(C 35 H 19 ClN2O2=535.00)Sub2-104m / z=396.06(C 23 H 12 ClNO2=369.80)Sub2-105m / z=537.10(C 35 H 20 ClNOS=538.06)Sub2-106m / z=521.12(C 35 H 20 ClNO2=522.00)Sub2-107m / z=587.11(C 39 H 22 ClNOS=588.12)Sub2-108m / z=587.11(C 39 H 22 ClNOS=588.12)Sub2-109m / z=593.15(C 39 H 16 D6ClNOS=594.16)Sub2-110m / z=587.11(C 39 H 22 ClNOS=588.12)Sub2-111m / z=592.14(C 39 H 17 D5ClNOS=593.15)Sub2-112m / z=619.16(C 41 H 18 D6ClNOS=620.20)Sub2-113m / z=663.14(C 45 H 26 ClNOS=664.22)Sub2-114m / z=627.11(C 41 H 22 ClNO2S=628.14)Sub2-115m / z=769.13(C 51 H 28 ClNOS2=770.36)Sub2-116m / z=778.18(C 53 H 31 ClN2OS=779.35)

[0399] final compound compound

[0400] 1. P-1 synthesis

[0401]

[0402] 1) Synthesis of Sub 2-1b

[0403] In a round-bottomed flask, Sub 2-1a (100.0 g, 308.5 mmol), Bis(pinacolato)diboron (117.5 g, 462.7 mmol), KOAc (60.55 g, 98.14 mmol), and Pd(dppf)Cl2 (6.8 g, 9.3 mmol) were added, dissolved in toluene (1028 ml), and stirred at 100 °C for 2 hours. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 57.3 g of the product (yield: 50.0%).

[0404] 2) Synthesis of Sub 2-1

[0405] Sub 2-1c (35.0 g, 124.3 mmol) was dissolved in toluene (389 ml), and then Sub 2-1b (55.4 g, 149.2 mmol), Pd(PPh3)4 (4.3 g, 3.7 mmol), K2CO3 (34.4 g, 248.6 mmol), ethanol (13 ml), and water (129 ml) were added and the reaction was carried out at 80°C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 37.4 g of the product. (Yield: 67.5%)

[0406] 3) Synthesis of P-1

[0407] Sub 1-1 (35.0 g, 78.5 mmol) was dissolved in toluene (261 mL), and then Sub 2-1 (20.4 g, 78.49 mmol), Pd2(dba)3 (2.2 g, 2.4 mmol), P(t-Bu)3 (1.0 g, 4.7 mmol), and NaOt-Bu (15.1 g, 157.0 mmol) were added and stirred at 120 °C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated on a silica gel column and recrystallized to obtain 43.0 g of the product. (Yield: 82.0%)

[0408] 2. P-33 synthetic example

[0409]

[0410] 1) Synthesis of Sub 2-29

[0411] After dissolving Sub 2-1c (35.0 g, 124.3 mmol) in toluene (389 ml), Sub 2-17a (55.4 g, 149.2 mmol), Pd(PPh3)4 (4.3 g, 3.7 mmol), K2CO3 (34.4 g, 248.6 mmol), ethanol (13 ml), and water (129 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 37.7 g of the product. (Yield: 68.0%)

[0412] 2) Synthesis of P-33

[0413] After dissolving Sub 1-2 (35.0 g, 78.5 mmol) in toluene (261 mL), Sub 2-29 (20.4 g, 78.49 mmol), Pd2(dba)3 (2.2 g, 2.4 mmol), P(t-Bu)3 (1.0 g, 4.7 mmol), and NaOt-Bu (15.1 g, 157.0 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 33.9 g of the product. (Yield: 64.6%)

[0414] 3. P-37 synthetic example

[0415]

[0416] 1) Synthesis of Sub 2-32

[0417] Sub 2-1c (40.0 g, 142.1 mmol) was placed in a round-bottom flask and dissolved in toluene (444 ml), then Sub 2-18a (63.3 g, 170.50 mmol), Pd(PPh3)4 (4.9 g, 4.3 mmol), K2CO3 (39.3 g, 284.16 mmol), ethanol (15 ml), and water (148 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 43.1 g of the product. (Yield: 68.0%)

[0418] 2) Synthesis of P-37

[0419] After dissolving Sub 1-1 (33.0 g, 71.4 mmol) in toluene (238 mL) in a round-bottomed flask, Sub 2-32 (18.5 g, 71.4 mmol), Pd2(dba)3 (2.0 g, 2.1 mmol), P(t-Bu)3 (0.9 g, 4.3 mmol), and NaOt-Bu (13.7 g, 142.9 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 33.5 g of the product. (Yield: 67.6%)

[0420] 4. P-52 synthetic example

[0421]

[0422] 1) Synthesis of Sub 2-42

[0423] Sub 2-42b (100.0 g, 336.0 mmol) was placed in a round-bottom flask and dissolved in toluene (1050 ml), then Sub 2-17a (149.7 g, 403.2 mmol), Pd(PPh3)4 (11.7 g, 10.1 mmol), K2CO3 (92.9 g, 672.1 mmol), ethanol (35 ml), and water (350 ml) were added, and the mixture was stirred as in the synthesis example of Sub 2-1 to obtain 96.4 g of the product. (Yield: 62.1%)

[0424] 2) Synthesis of P-52

[0425] After dissolving Sub 1-5 (53.7 g, 194.8 mmol) in toluene (649 mL) in a round-bottomed flask, Sub 2-42 (90 g, 194.8 mmol), Pd2(dba)3 (5.4 g, 5.8 mmol), P(t-Bu)3 (2.4 g, 11.7 mmol), and NaOt-Bu (37.5 g, 389.6 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 93.5 g of the product. (Yield: 68.5%)

[0426] 5. P-55 synthetic example

[0427]

[0428] 1) Synthesis of Sub 2-44

[0429] Sub 2-44b (80.0 g, 263.5 mmol) was placed in a round-bottom flask and dissolved in toluene (823 ml), then Sub 2-18a (117.4 g, 316.2 mmol), Pd(PPh3)4 (9.1 g, 7.9 mmol), K2CO3 (72.8 g, 527.0 mmol), ethanol (27 ml), and water (274 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 85.2 g of the product. (Yield: 69.1%)

[0430] 2) Synthesis of P-55

[0431] Sub 1-1 (80.0 g, 173.2 mmol) was dissolved in toluene (577 mL) in a round-bottomed flask, and then Sub 2-44 (44.9 g, 173.2 mmol), Pd2(dba)3 (4.8 g, 5.2 mmol), P(t-Bu)3 (2.1 g, 10.4 mmol), and NaOt-Bu (33.3 g, 346.4 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 87.8 g of the product. (Yield: 73.4%)

[0432] 6. P-63 synthetic example

[0433]

[0434] 1) Synthesis of Sub 2-52

[0435] Sub 2-52b (60.0 g, 201.6 mmol) was placed in a round-bottom flask and dissolved in toluene (630 ml), then Sub 2-29a (89.8 g, 241.9 mmol), Pd(PPh3)4 (7.0 g, 6.1 mmol), K2CO3 (55.7 g, 403.2 mmol), ethanol (21 ml), and water (210 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 60.5 g of the product. (Yield: 64.9%)

[0436] 2) Synthesis of P-63

[0437] Sub 1-2 (33.7 g, 129.9 mmol) was dissolved in toluene (432 mL) in a round-bottomed flask, and then Sub 2-52 (60.0 g, 129.9 mmol), Pd2(dba)3 (3.6 g, 3.9 mmol), P(t-Bu)3 (1.6 g, 7.8 mmol), and NaOt-Bu (25.0 g, 259.8 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 63.9 g of the product. (Yield: 71.8%)

[0438] 7. P-65 synthetic example

[0439]

[0440] 1) Synthesis of Sub 2-54

[0441] Sub 2-54b (80.0 g, 268.8 mmol) was placed in a round-bottom flask and dissolved in toluene (840 ml), then Sub 2-66a (121.4 g, 322.6 mmol), Pd(PPh3)4 (9.3 g, 8.1 mmol), K2CO3 (74.3 g, 537.7 mmol), ethanol (28 ml), and water (280 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above, to obtain 77.3 g of the product. (Yield: 61.6%)

[0442] 2) Synthesis of P-65

[0443] Sub 1-8 (39.6 g, 149.9 mmol) was dissolved in toluene (499 mL) in a round-bottomed flask, and then Sub 2-54 (70.0 g, 149.9 mmol), Pd2(dba)3 (4.1 g, 4.5 mmol), P(t-Bu)3 (1.8 g, 9.0 mmol), and NaOt-Bu (28.8 g, 299.8 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 71.7 g of the product. (Yield: 68.8%)

[0444] 8. P-69 synthetic example

[0445]

[0446] 1) Synthesis of Sub 2-57

[0447] Sub 2-52b (80.0 g, 268.8 mmol) was placed in a round-bottom flask and dissolved in toluene (840 ml), then Sub 2-31a (121.4 g, 322.6 mmol), Pd(PPh3)4 (9.3 g, 8.1 mmol), K2CO3 (74.3 g, 537.7 mmol), ethanol (28 ml), and water (280 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above, to obtain 75.6 g of the product. (Yield: 60.9%)

[0448] 2) Synthesis of P-69

[0449] Sub 1-1 (39.3 g, 151.5 mmol) was dissolved in toluene (505 mL) in a round-bottomed flask, and then Sub 2-57 (70.0 g, 151.5 mmol), Pd2(dba)3 (4.2 g, 4.6 mmol), P(t-Bu)3 (1.8 g, 9.1 mmol), and NaOt-Bu (29.1 g, 303.1 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 76.2 g of the product. (Yield: 73.4%)

[0450] 9. P-71 synthetic example

[0451]

[0452] 1) Synthesis of Sub 2-59

[0453] Sub 2-59b (80.0 g, 268.8 mmol) was placed in a round-bottom flask and dissolved in toluene (840 ml), then Sub 2-33a (119.8 g, 322.6 mmol), Pd(PPh3)4 (9.3 g, 8.1 mmol), K2CO3 (74.3 g, 537.7 mmol), ethanol (28 ml), and water (280 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above, to obtain 79.1 g of the product. (Yield: 63.7%)

[0454] 2) Synthesis of P-71

[0455] Sub 1-11 (46.9 g, 151.5 mmol) was dissolved in toluene (505 mL) in a round-bottomed flask, and then Sub 2-59 (70.0 g, 151.5 mmol), Pd2(dba)3 (4.2 g, 4.6 mmol), P(t-Bu)3 (1.8 g, 9.1 mmol), and NaOt-Bu (29.1 g, 303.1 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 77.4 g of the product. (Yield: 69.5%)

[0456] 10. P-75 synthetic example

[0457]

[0458] 1) Synthesis of Sub 2-61

[0459] Sub 2-61b (50.0 g, 168.0 mmol) was placed in a round-bottom flask and dissolved in toluene (525 ml), then Sub 2-34a (74.9 g, 201.6 mmol), Pd(PPh3)4 (5.8 g, 5.0 mmol), K2CO3 (46.4 g, 336.0 mmol), ethanol (17 ml), and water (175 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 48.3 g of the product. (Yield: 62.2%)

[0460] 2) Synthesis of P-75

[0461] After dissolving Sub 1-15 (37.6 g, 97.4 mmol) in toluene (324 mL) in a round-bottomed flask, Sub 2-61 (45.0 g, 97.4 mmol), Pd2(dba)3 (2.7 g, 2.9 mmol), P(t-Bu)3 (1.2 g, 5.8 mmol), and NaOt-Bu (18.7 g, 194.8 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 53.8 g of the product. (Yield: 68.1%)

[0462] 11. P-76 synthetic example

[0463]

[0464] 1) Synthesis of Sub 2-62

[0465] Sub 2-62b (50.0 g, 168.0 mmol) was placed in a round-bottom flask and dissolved in toluene (525 ml), then Sub 2-17a (74.9 g, 201.6 mmol), Pd(PPh3)4 (5.8 g, 5.0 mmol), K2CO3 (46.4 g, 336.0 mmol), ethanol (17 ml), and water (175 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 48.3 g of the product. (Yield: 71.3%)

[0466] 2) Synthesis of P-76

[0467] Sub 1-15 (37.6 g, 97.4 mmol) was dissolved in toluene (324 mL) in a round-bottomed flask, and then Sub 2-62 (45.0 g, 97.4 mmol), Pd2(dba)3 (2.7 g, 2.9 mmol), P(t-Bu)3 (1.2 g, 5.8 mmol), and NaOt-Bu (18.7 g, 194.8 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 53.8 g of the product. (Yield: 68.1%)

[0468] 12. P-83 Synthetic Example

[0469]

[0470] 1) Synthesis of Sub 2-68

[0471] Sub 2-52b (100.0 g, 336.0 mmol) was placed in a round-bottom flask and dissolved in toluene (1050 ml), then Sub 2-31a (149.7 g, 403.2 mmol), Pd(PPh3)4 (11.7 g, 10.1 mmol), K2CO3 (92.9 g, 672.1 mmol), ethanol (35 ml), and water (350 ml) were added, and the mixture was stirred as in the synthesis example of Sub 2-1 to obtain 107.3 g of the product. (Yield: 69.1%)

[0472] 2) Synthesis of Sub 1-18c

[0473] Sub 1-18a (100.0 g, 355.2 mmol) was added to a round-bottom flask and dissolved in toluene (1110 ml), then Sub 1-18b (90.4 g, 426.2 mmol), Pd(PPh3)4 (12.3 g, 10.7 mmol), K2CO3 (98.2 g, 710.4 mmol), ethanol (37 ml), and water (370 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 84.1 g of the product. (Yield: 64.2%)

[0474] 3) Synthesis of Sub 1-18

[0475] Sub 1-18d (34.9 g, 244.0 mmol) was dissolved in toluene (813 mL) in a round-bottomed flask, and then Sub 1-18c (90.0 g, 244.0 mmol), Pd2(dba)3 (6.7 g, 7.3 mmol), P(t-Bu)3 (3.0 g, 14.6 mmol), and NaOt-Bu (46.9 g, 488.0 mmol) were added and stirred at 120°C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 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 83.7 g of the product. (Yield: 72.1%)

[0476] 4) Synthesis of P-83

[0477] Sub 1-18 (75.0 g, 162.4 mmol) was dissolved in toluene (541 mL) in a round-bottom flask, and then Sub 2-68 (77.2 g, 162.4 mmol), Pd2(dba)3 (4.5 g, 4.9 mmol), P(t-Bu)3 (2.0 g, 9.7 mmol), and NaOt-Bu (31.2 g, 324.7 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 99.8 g of the product. (Yield: 68.2%)

[0478] 13. P-99 synthetic example

[0479]

[0480] 1) Synthesis of Sub 2-78

[0481] Sub 2-78b (50.0 g, 168.0 mmol) was placed in a round-bottom flask and dissolved in toluene (525 ml), then Sub 2-17a (74.9 g, 201.6 mmol), Pd(PPh3)4 (5.8 g, 5.0 mmol), K2CO3 (46.4 g, 336.0 mmol), ethanol (17 ml), and water (175 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above, to obtain 58.3 g of the product. (Yield: 75.1%)

[0482] 2) Synthesis of P-99

[0483] Sub 1-33 (45.95 g, 108.2 mmol) was dissolved in toluene (360 mL) in a round-bottomed flask, and then Sub 2-78 (50.0 g, 108.2 mmol), Pd2(dba)3 (3.0 g, 3.3 mmol), P(t-Bu)3 (1.3 g, 6.5 mmol), and NaOt-Bu (20.8 g, 216.5 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 57.2 g of the product. (Yield: 65.6%)

[0484] 14. P-105 Synthetic Example

[0485]

[0486] 1) Synthesis of Sub 2-75

[0487] Sub 2-52b (60.0 g, 201.6 mmol) was placed in a round-bottom flask and dissolved in toluene (630 ml), then Sub 2-65a (101.9 g, 241.9 mmol), Pd(PPh3)4 (7.0 g, 6.1 mmol), K2CO3 (55.7 g, 403.2 mmol), ethanol (21 ml), and water (210 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above, to obtain 76.3 g of the product. (Yield: 73.9%)

[0488] 2) Synthesis of P-105

[0489] Sub 1-38 (43.1 g, 136.7 mmol) was dissolved in toluene (455 mL) in a round-bottomed flask, and then Sub 2-75 (70.0 g, 136.7 mmol), Pd2(dba)3 (3.8 g, 4.1 mmol), P(t-Bu)3 (1.7 g, 8.2 mmol), and NaOt-Bu (26.3 g, 273.4 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 70.4 g of the product. (Yield: 65.1%)

[0490] 15. P-139 Synthetic Example

[0491]

[0492] 1) Synthesis of Sub 2-98c

[0493] Sub 2-98a (100.0 g, 236.1 mmol) was added to a round-bottom flask and dissolved in toluene (738 ml), then Sub 2-98b (48.7 g, 283.4 mmol), Pd(PPh3)4 (8.2 g, 7.1 mmol), K2CO3 (65.3 g, 472.3 mmol), ethanol (24 ml), and water (245 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 38.9 g of the product. (Yield: 35.0%)

[0494] 2) Synthesis of Sub 2-98

[0495] Sub 2-98c (35.0 g, 74.4 mmol) was placed in a round-bottom flask and dissolved in toluene (232 ml), then Sub 2-98d (33.1 g, 89.2 mmol), Pd(PPh3)4 (2.6 g, 2.2 mmol), K2CO3 (20.6 g, 148.7 mmol), ethanol (7 ml), and water (77 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 21.5 g of the product. (Yield: 49.2%)

[0496] 3) Synthesis of P-139

[0497] Sub 1-57 (10.9 g, 34.0 mmol) was dissolved in toluene (113 mL) in a round-bottomed flask, and then Sub 2-98 (20.0 g, 34.0 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), P(t-Bu)3 (0.4 g, 2.0 mmol), and NaOt-Bu (6.5 g, 68.0 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 22.8 g of the product. (Yield: 76.8%)

[0498] 16. P-140 synthetic example

[0499]

[0500] 1) Synthesis of Sub 1-58

[0501] Sub 1-58b (29.0 g, 150.1 mmol) was dissolved in toluene (500 mL), and then Sub 1-58a (50.0 g, 150.1 mmol), Pd2(dba)3 (4.1 g, 4.5 mmol), P(t-Bu)3 (1.8 g, 9.0 mmol), and NaOt-Bu (28.8 g, 300.1 mmol) were added and stirred at 120 °C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated on a silica gel column and recrystallized to obtain 40.9 g of the product. (Yield: 61.2%)

[0502] 2) Synthesis of Sub 2-91c

[0503] Sub 2-91a (100.0 g, 236.1 mmol) was placed in a round-bottom flask and dissolved in toluene (787 ml). Sub 2-91b (43.2 g, 354.2 mmol), Pd(PPh3)4 (8.2 g, 7.1 mmol), K2CO3 (65.3 g, 472.3 mmol), ethanol (26 ml), and water (262 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 34.7 g of the product. (Yield: 35.0%)

[0504] 3) Synthesis of Sub 2-91

[0505] Sub 2-91c (34.0 g, 80.8 mmol) was placed in a round-bottom flask and dissolved in toluene (269 ml), then Sub 2-98d (45.0 g, 121.2 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), K2CO3 (22.3 g, 161.6 mmol), ethanol (9 ml), and water (89 ml) were added, and the reaction was carried out as in the synthesis example of Sub 2-1 above to obtain 64.0 g of the product. (Yield: 50.0%)

[0506] 4) Synthesis of P-140

[0507] Sub 1-58 (29.0 g, 65.1 mmol) was dissolved in toluene (216 mL) in a round-bottomed flask, and then Sub 2-91 (35.0 g, 65.1 mmol), Pd2(dba)3 (1.8 g, 2.0 mmol), P(t-Bu)3 (0.8 g, 3.9 mmol), and NaOt-Bu (12.5 g, 130.1 mmol) were added, and the reaction was carried out as in the synthesis example of P-1, obtaining 39.4 g of the product. (Yield: 63.9%)

[0508] The FD-MS values ​​of compounds P-1 to P-158 of the present invention manufactured according to the above synthetic examples are as shown in Table 3 below.

[0509] Compound FD-MS Compound FD-MSP-1 m / z = 668.21 (C 47 H 28 N2O3=668.75)P-2m / z=668.21(C 47 H 28 N2O3=668.75)P-3m / z=668.21(C 47 H 28 N2O3=668.75)P-4m / z=668.21(C 47 H 28 N2O3=668.75)P-5m / z=684.19(C 47 H 28 N2O2S=684.81)P-6m / z=684.19(C 47 H 28 N2O2S=684.81)P-7m / z=684.19(C 47 H 28 N2O2S=684.81)P-8m / z=684.19(C 47 H 28 N2O2S=684.81)P-9m / z=684.19(C 47 H 28 N2O2S=684.81)P-10m / z=684.19(C 47 H 28 N2O2S=684.81)P-11m / z=684.19(C 47 H 28 N2O2S=684.81)P-12m / z=684.19(C 47 H28 N2O2S=684.81)P-13m / z=684.19(C 47 H 28 N2O2S=684.81)P-14m / z=684.19(C 47 H 28 N2O2S=684.81)P-15m / z=684.19(C 47 H 28 N2O2S=684.81)P-16m / z=700.16(C 47 H 28 N2OS2=700.87)P-17m / z=700.16(C 47 H 28 N2OS2=700.87)P-18m / z=700.16(C 47 H 28 N2OS2=700.87)P-19m / z=700.16(C 47 H 28 N2OS2=700.87)P-20m / z=700.16(C 47 H 28 N2OS2=700.87)P-21m / z=700.16(C 47 H 28 N2OS2=700.87)P-22m / z=674.25(C 47 H 22 D6N2O3=674.79)P-23m / z=674.25(C 47 H 22 D6N2O3=674.79)P-24m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-25m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-26m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-27m / z=706.20(C 47 H 22 D6N2OS2=706.91)P-28m / z=706.20(C 47 H 22 D6N2OS2=706.91)P-29m / z=696.26(C 47 H 16 D 12N2O2S=696.89)P-30m / z=668.21(C 47 H 28 N2O3=668.75)P-31m / z=668.21(C 47 H 28 N2O3=668.75)P-32m / z=668.21(C 47 H 28 N2O3=668.75)P-33m / z=668.21(C 47 H 28 N2O3=668.75)P-34m / z=760.22(C 53 H 32 N2O2S=760.91)P-35m / z=668.21(C 47 H 28 N2O3=668.75)P-36m / z=668.21(C 47 H 28 N2O3=668.75)P-37m / z=684.81(C 47 H 28 N2O2S=684.81)P-38m / z=684.81(C 47 H 28 N2O2S=684.81)P-39m / z=684.81(C 47 H 28 N2O2S=684.81)P-40m / z=684.81(C 47 H 28 N2O2S=684.81)P-41m / z=684.81(C 47 H 28 N2O2S=684.81)P-42m / z=684.81(C 47 H 28 N2O2S=684.81)P-43m / z=684.81(C 47 H 28 N2O2S=684.81)P-44m / z=684.81(C 47 H 28 N2O2S=684.81)P-45m / z=684.81(C 47 H 28 N2O2S=684.81)P-46m / z=684.81(C 47 H 28 N2O2S=684.81)P-47m / z=684.81(C 47 H 28N2O2S=684.81)P-48m / z=684.81(C 47 H 28 N2O2S=684.81)P-49m / z=684.81(C 47 H 28 N2O2S=684.81)P-50m / z=700.16(C 47 H 28 N2OS2=700.87)P-51m / z=700.16(C 47 H 28 N2OS2=700.87)P-52m / z=700.16(C 47 H 28 N2OS2=700.87)P-53m / z=700.16(C 47 H 28 N2OS2=700.87)P-54m / z=674.25(C 47 H 22 D6N2O3=674.79)P-55m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-56m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-57m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-58m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-59m / z=690.22(C 47 H 22 D6N2O2S=690.85)P-60m / z=706.20(C 47 H 22 D6N2OS2=706.91)P-61m / z=696.26(C 47 H 16 D 12 N2O2S=696.89)P-62m / z=712.24(C 47 H 16 D 12 N2OS2=712.95)P-63m / z=684.19(C 47 H 28 N2O2S=684.81)P-64m / z=690.22(C 47 H 22D6N2O2S=690.85)P-65m / z=694.25(C 47 H 18 D 10 N2O2S=694.87)P-66m / z=696.26(C 47 H 16 D 12 N2O2S=696.89)P-67m / z=739.23(C 51 H 25 D5N2O2S=739.90)P-68m / z=734.20(C 51 H 30 N2O2S=734.87)P-69m / z=684.19(C 47 H 28 N2O2S=684.81)P-70m / z=684.19(C 47 H 28 N2O2S=684.81)P-71m / z=734.20(C 51 H 30 N2O2S=734.87)P-72m / z=872.29(C 63 H 40 N2OS=873.09)P-73m / z=760.22(C 53 H 32 N2O2S=760.91)P-74m / z=734.20(C 51 H 30 N2O2S=734.87)P-75m / z=810.23(C 57 H 34 N2O2S=810.97)P-76m / z=740.24(C 51 H 24 D6N2O2S=740.91)P-77m / z=810.23(C 57 H 34 N2O2S=810.97)P-78m / z=734.20(C 51 H 30 N2O2S=734.87)P-79m / z=734.20(C 51 H 30 N2O2S=734.87)P-80m / z=739.23(C 51 H 25 D5N2O2S=739.90)P-81m / z=760.22(C 53 H 32N2O2S=760.91)P-82m / z=886.27(C 63 H 38 N2O2S=887.07)P-83m / z=900.24(C 63 H 36 N2O3S=901.05)P-84m / z=1042.27(C 73 H 42 N2O2S2=1043.27)P-85m / z=941.31(C 66 H 43 N3O2S=942.15)P-86m / z=814.26(C 57 H 30 D4N2O2S=815.00)P-87m / z=940.23(C 64 H 36 N4OS2=941.14)P-88m / z=860.25(C 61 H 36 N2O2S=861.03)P-89m / z=709.18(C 48 H 27 N3O2S=709.82)P-90m / z=702.18(C 47 H 27 FN2O2S=702.80)P-91m / z=709.18(C 48 H 27 N3O2S=709.82)P-92m / z=760.22(C 53 H 32 N2O2S=760.91)P-93m / z=760.22(C 53 H 32 N2O2S=760.91)P-94m / z=760.22(C 53 H 32 N2O2S=760.91)P-95m / z=860.25(C 61 H 36 N2O2S=861.03)P-96m / z=784.22(C 55 H 32 N2O2S=784.93)P-97m / z=784.22(C 55 H 32 N2O2S=784.93)P-98m / z=910.27(C 65 H 38 N2O2S=911.09)P-99m / z=849.24(C 59 H35 N3O2S=850.01)P-100m / z=784.22(C 55 H 32 N2O2S=784.93)P-101m / z=815.26(C 56 H 37 N3O2S=815.99)P-102m / z=709.18(C 48 H 27 N3O2S=709.82)P-103m / z=734.20(C 51 H 30 N2O2S=734.87)P-104m / z=810.23(C 57 H 34 N2O2S=810.97)P-105m / z=790.27(C 55 H 38 N2O2S=790.98)P-106m / z=702.18(C 47 H 27 FN2O2S=702.80)P-107m / z=684.19(C 47 H 28 N2O2S=684.81)P-108m / z=684.19(C 47 H 28 N2O2S=684.81)P-109m / z=684.19(C 47 H 28 N2O2S=684.81)P-110m / z=886.27(C 63 H 38 N2O2S=887.07)P-111m / z=684.19(C 47 H 28 N2O2S=684.81)P-112m / z=684.19(C 47 H 28 N2O2S=684.81)P-113m / z=815.27(C 57 H 19 D5N2O2S=816.00)P-114m / z=784.22(C 55 H 32 N2O2S=784.93)P-115m / z=760.22(C 53 H 32 N2O2S=760.91)P-116m / z=734.20(C 51 H 30N2O2S=734.87)P-117m / z=810.23(C 57 H 34 N2O2S=810.97)P-118m / z=816.28(C 57 H 40 N2O2S=817.02)P-119m / z=810.23(C 57 H 34 N2O2S=810.97)P-120m / z=876.23(C 61 H 36 N2OS2=877.09)P-121m / z=594.18(C 41 H 26 N2OS=594.73)P-122m / z=744.22(C 53 H 32 N2OS=744.91)P-123m / z=744.22(C 53 H 32 N2OS=744.91)P-124m / z=644.19(C 45 H 28 N2OS=644.79)P-125m / z=646.21(C 45 H 30 N2OS=646.81)P-126m / z=694.21(C 49 H 30 N2OS=694.85)P-127m / z=644.19(C 45 H 28 N2OS=644.79)P-128m / z=794.24(C 57 H 34 N2OS=794.97)P-129m / z=744.22(C 53 H 32 N2OS=744.91)P-130m / z=826.30(C 59 H 42 N2OS=827.06)P-131m / z=796.25(C 57 H 36 N2OS=796.99)P-132m / z=872.29(C 63 H 40 N2OS=873.09)P-133m / z=796.25(C 57 H 36 N2OS=796.99)P-134m / z=948.32(C 69 H44 N2OS=949.18)P-135m / z=1022.33(C 75 H 46 N2OS=1023.27)P-136m / z=978.27(C 69 H 42 N2OS2=979.23)P-137m / z=887.26(C 62 H 37 N3O2S=888.06)P-138m / z=836.25(C 59 H 36 N2O2S=837.01)P-139m / z=872.29(C 63 H 40 N2OS=873.09)P-140m / z=946.30(C 69 H 42 N2OS=947.17)P-141m / z=902.33(C 65 H 46 N2OS=903.16)P-142m / z=967.36(C 69 H 49 N3OS=968.23)P-143m / z=832.35(C 59 H 48 N2OS=833.11)P-144m / z=1201.41(C 88 H 55 N3OS=1202.49)P-145m / z=890.24(C 60 H 34 N4O3S=891.02)P-146m / z=811.27(C 54 H 33 N7O2=811.91)P-147m / z=836.25(C 59 H 36 N2O2S=837.01)P-148m / z=744.24(C 53 H 32 N2O3=744.85)P-149m / z=810.23(C 57 H 34 N2O2S=810.97)P-150m / z=826.21(C 57 H 34 N2OS2=827.03)P-151m / z=816.27(C 57 H 28D6N2O2S=817.01)P-152m / z=810.23(C 57 H 34 N2O2S=810.97)P-153m / z=820.30(C 57 H 24 D 10 N2O2S=821.03)P-154m / z=892.30(C 63 H 32 D6N2O2S=893.11)P-155m / z=942.33(C 57 H 46 N2O2S=943.18)P-156m / z=1015.29(C 71 H 41 N3O3S=1016.19)P-157m / z=1054.31(C 75 H 46 N2OS2=1055.33)P-158m / z=1187.39(C 87 H 53 N3OS=1188.46)

[0510] Synthesis example of chemical formula I

[0511] The compound represented by Chemical Formula I can be prepared by a known synthetic method (named reaction) or by referring to published patent publications, such as Korean Patent Publication Nos. 2020-0129334, 2022-0055392, and 2023-000502, but is not limited thereto.

[0512] The FD-MS values ​​of compounds N-1 to N-276 represented by chemical formula I are as shown in Table 4 below.

[0513] Compound FD-MS Compound FD-MSN-1 m / z = 399.14 (C 27 H 17 N3O=399.45)N-2m / z=415.11(C 27 H 17 N3S=415.51)N-3m / z=474.18(C 33 H 22 N4=474.57)N-4m / z=449.15(C 31 H 19 N3O=449.51)N-5m / z=449.15(C31 H 19 N3O=449.51)N-6m / z=515.15(C 35 H 21 N3S=515.63)N-7m / z=600.23(C 43 H 28 N4=600.73)N-8m / z=499.17(C 35 H 21 N3O=499.57)N-9m / z=551.20(C 39 H 25 N3O=551.65)N-10m / z=567.18(C 39 H 25 N3S=567.71)N-11m / z=702.28(C 51 H 34 N4=702.86)N-12m / z=657.22(C 46 H 31 N3S=657.84)N-13m / z=551.20(C 39 H 25 N3O=551.65)N-14m / z=541.16(C 37 H 23 N3S=541.67)N-15m / z=700.26(C 51 H 32 N4=700.85)N-16m / z=703.21(C 50 H 29 N3S=703.86)N-17m / z=525.18(C 37 H 23 N3O=525.61)N-18m / z=591.18(C 41 H 25 N3S=591.73)N-19m / z=627.24(C 44 H 29 N5=627.75)N-20m / z=524.20(C 37 H 24 N4=524.63)N-21m / z=551.20(C 39 H 25 N3O=551.65)N-22m / z=567.18(C 39 H 25 N3S=567.71)N-23m / z=702.28(C 51 H 34N4=702.86)N-24m / z=474.18(C 33 H 22 N4=474.57)N-25m / z=779.29(C 57 H 37 N3O=779.94)N-26m / z=731.24(C 52 H 33 N3S=731.92)N-27m / z=601.23(C 42 H 27 N5=601.71)N-28m / z=475.17(C 33 H 21 N3O=475.55)N-29m / z=641.21(C 45 H 27 N3O2=641.73)N-30m / z=746.21(C 51 H 30 N4OS=746.89)N-31m / z=716.26(C 51 H 32 N4O=716.84)N-32m / z=681.19(C 47 H 27 N3OS=681.81)N-33m / z=475.17(C 33 H 21 N3O=475.55)N-34m / z=491.15(C 33 H 21 N3S=491.61)N-35m / z=550.22(C 39 H 26 N4=550.67)N-36m / z=525.18(C 37 H 23 N3O=525.61)N-37m / z=475.17(C 33 H 21 N3O=475.55)N-38m / z=491.15(C 33 H 21 N3S=491.61)N-39m / z=704.27(C 49 H 32 N6=704.84)N-40m / z=541.16(C 37 H 23 N3S=541.67)N-41m / z=551.20(C 39 H 25 N3O=551.65)N-42m / z=541.16(C37 H 23 N3S=541.67)N-43m / z=626.25(C 45 H 30 N4=626.76)N-44m / z=676.26(C 49 H 32 N4=676.82)N-45m / z=551.2(C 39 H 25 N3O=551.65)N-46m / z=567.18(C 39 H 25 N3S=567.71)N-47m / z=614.25(C 44 H 30 N4=614.75)N-48m / z=575.17(C 39 H 21 N5O=575.63)N-49m / z=525.18(C 37 H 23 N3O=525.61)N-50m / z=541.16(C 37 H 23 N3S=541.67)N-51m / z=600.23(C 43 H 28 N4=600.73)N-52m / z=625.22(C 45 H 27 N3O=625.73)N-53m / z=525.18(C 37 H 23 N3O=525.61)N-54m / z=591.18(C 41 H 25 N3S=591.73)N-55m / z=600.23(C 43 H 28 N4=600.73)N-56m / z=693.22(C 49 H 31 N3S=693.87)N-57m / z=505.12(C 33 H 19 N3OS=505.60)N-58m / z=641.21(C 45 H 27 N3O2=641.73)N-59m / z=571.12(C 37 H 21 N3S2=571.72)N-60m / z=564.20(C 39 H 24N4O=564.65)N-61m / z=581.16(C 39 H 23 N3OS=581.69)N-62m / z=521.10(C 33 H 19 N3S2=521.66)N-63m / z=489.15(C 33 H 19 N3O2=489.53)N-64m / z=640.23(C 45 H 28 N4O=640.75)N-65m / z=489.15(C 33 H 19 N3O2=489.53)N-66m / z=505.12(C 33 H 19 N3OS=505.60)N-67m / z=580.17(C 39 H 24 N4S=580.71)N-68m / z=564.20(C 39 H 24 N4O=564.65)N-69m / z=489.15(C 33 H 19 N3O2=489.53)N-70m / z=505.12(C 33 H 19 N3OS=505.60)N-71m / z=505.12(C 33 H 19 N3OS=505.60)N-72m / z=639.24(C 45 H 29 N5=639.76)N-73m / z=607.21(C 42 H 29 N3S=607.78)N-74m / z=715.26(C 52 H 33 N3O=715.86)N-75m / z=640.23(C 45 H 28 N4O=640.75)N-76m / z=707.20(C 49 H 29 N3OS=707.85)N-77m / z=591.23(C 42 H 29 N3O=591.71)N-78m / z=617.28(C 45 H 35N3=617.80)N-79m / z=653.25(C 47 H 31 N3O=653.79)N-80m / z=733.22(C 51 H 31 N3OS=733.89)N-81m / z=615.19(C 43 H 25 N3O2=615.69)N-82m / z=681.19(C 47 H 27 N3OS=681.81)N-83m / z=716.29(C 52 H 36 N4=716.89)N-84m / z=690.24(C 49 H 30 N4O=690.81)N-85m / z=641.25(C 46 H 31 N3O=641.77)N-86m / z=693.22(C 49 H 31 N3S=693.87)N-87m / z=690.24(C 49 H 30 N4O=690.81)N-88m / z=631.17(C 43 H 25 N3OS=631.75)N-89m / z=595.14(C 39 H 21 N3O2S=595.68)N-90m / z=659.24(C 45 H 21 D5N4O2=659.76)N-91m / z=637.16(C 42 H 27 N3S2=637.82)N-92m / z=729.25(C 51 H 31 N5O=729.84)N-93m / z=578.17(C 39 H 22 N4O2=578.63)N-94m / z=746.21(C 51 H 30 N4OS=746.89)N-95m / z=681.24(C 48 H 31 N3O2=681.80)N-96m / z=762.19(C 51 H 30N4S2=762.95)N-97m / z=436.17(C 30 H 20 N4=436.52)N-98m / z=437.16(C 29 H 19 N5=437.51)N-99m / z=513.20(C 35 H 23 N5=513.60)N-100m / z=589.23(C 41 H 27 N5=589.70)N-101m / z=486.18(C 34 H 22 N4=486.58)N-102m / z=527.17(C 35 H 21 N5O=527.59)N-103m / z=589.23(C 41 H 27 N5=589.70)N-104m / z=502.18(C 34 H 22 N4O=502.58)N-105m / z=511.20(C 37 H 25 N3=511.63)N-106m / z=563.21(C 39 H 25 N5=563.66)N-107m / z=511.20(C 37 H 25 N3=511.63)N-108m / z=589.23(C 41 H 27 N5=589.70)N-109m / z=513.20(C 35 H 23 N5=513.60)N-110m / z=462.16(C 30 H 18 N6=462.52)N-111m / z=612.21(C 42 H 24 N6=612.70)N-112m / z=499.20(C 36 H 25 N3=499.62)N-113m / z=569.17(C 37 H 23 N5S=569.69)N-114m / z=629.22(C 43 H 27N5O=629.72)N-115m / z=629.22(C 43 H 27 N5O=629.72)N-116m / z=563.21(C 39 H 25 N5=563.66)N-117m / z=565.2(C 37 H 23 N7=565.64)N-118m / z=630.22(C 42 H 26 N6O=630.71)N-119m / z=611.24(C 45 H 29 N3=611.75)N-120m / z=803.29(C 59 H 37 N3O=803.97)N-121m / z=563.20(C 40 H 25 N3O=563.66)N-122m / z=549.22(C 40 H 27 N3=549.68)N-123m / z=449.15(C 31 H 19 N3O=449.51)N-124m / z=579.18(C 40 H 25 N3S=579.72)N-125m / z=435.17(C 31 H 21 N3=435.53)N-126m / z=435.17(C 31 H 21 N3=435.53)N-127m / z=435.17(C 31 H 21 N3=435.53)N-128m / z=435.17(C 31 H 21 N3=435.53)N-129m / z=435.17(C 31 H 21 N3=435.53)N-130m / z=435.17(C 31 H 21 N3=435.53)N-131m / z=435.17(C 31 H 21 N3=435.53)N-132m / z=434.18(C 32 H 22N2=434.54)N-133m / z=511.20(C 37 H 25 N3=511.63)N-134m / z=611.24(C 45 H 29 N3=611.75)N-135m / z=485.19(C 35 H 23 N3=485.59)N-136m / z=511.2(C 37 H 25 N3=511.63)N-137m / z=511.20(C 37 H 25 N3=511.63)N-138m / z=485.19(C 35 H 23 N3=485.59)N-139m / z=434.18(C 32 H 22 N2=434.54)N-140m / z=434.18(C 32 H 22 N2=434.54)N-141m / z=511.20(C 37 H 25 N3=511.63)N-142m / z=561.22(C 41 H 27 N3=561.69)N-143m / z=587.24(C 43 H 29 N3=587.73)N-144m / z=511.20(C 37 H 25 N3=511.63)N-145m / z=511.20(C 37 H 25 N3=511.63)N-146m / z=511.20(C 37 H 25 N3=511.63)N-147m / z=511.20(C 37 H 25 N3=511.63)N-148m / z=587.24(C 43 H 29 N3=587.73)N-149m / z=435.17(C 31 H 21 N3=435.53)N-150m / z=435.17(C 31 H 21 N3=435.53)N-151m / z=435.17(C31 H 21 N3=435.53)N-152m / z=435.17(C 31 H 21 N3=435.53)N-153m / z=435.17(C 31 H 21 N3=435.53)N-154m / z=435.17(C 31 H 21 N3=435.53)N-155m / z=435.17(C 31 H 21 N3=435.53)N-156m / z=434.18(C 32 H 22 N2=434.54)N-157m / z=485.19(C 35 H 23 N3=485.59)N-158m / z=511.2(C 37 H 25 N3=511.63)N-159m / z=511.20(C 37 H 25 N3=511.63)N-160m / z=511.20(C 37 H 25 N3=511.63)N-161m / z=485.19(C 35 H 23 N3=485.59)N-162m / z=511.20(C 37 H 25 N3=511.63)N-163m / z=485.19(C 35 H 23 N3=485.59)N-164m / z=611.24(C 45 H 29 N3=611.75)N-165m / z=511.20(C 37 H 25 N3=511.63)N-166m / z=511.20(C 37 H 25 N3=511.63)N-167m / z=587.24(C 43 H 29 N3=587.73)N-168m / z=587.24(C 43 H 29 N3=587.73)N-169m / z=587.24(C 43 H 29N3=587.73)N-170m / z=561.22(C 41 H 27 N3=561.69)N-171m / z=511.20(C 37 H 25 N3=511.63)N-172m / z=587.24(C 43 H 29 N3=587.73)N-173m / z=485.19(C 35 H 23 N3=485.59)N-174m / z=485.19(C 35 H 23 N3=485.59)N-175m / z=485.19(C 35 H 23 N3=485.59)N-176m / z=485.19(C 35 H 23 N3=485.59)N-177m / z=485.19(C 35 H 23 N3=485.59)N-178m / z=535.20(C 39 H 25 N3=535.65)N-179m / z=485.19(C 35 H 23 N3=485.59)N-180m / z=485.19(C 35 H 23 N3=485.59)N-181m / z=561.22(C 41 H 27 N3=561.69)N-182m / z=561.22(C 41 H 27 N3=561.69)N-183m / z=561.22(C 41 H 27 N3=561.69)N-184m / z=637.25(C 47 H 31 N3=637.79)N-185m / z=561.22(C 41 H 27 N3=561.69)N-186m / z=561.22(C 41 H 27 N3=561.69)N-187m / z=637.25(C 47 H 31 N3=637.79)N-188m / z=637.25(C47 H 31 N3=637.79)N-189m / z=637.25(C 47 H 31 N3=637.79)N-190m / z=485.19(C 35 H 23 N3=485.59)N-191m / z=485.19(C 35 H 23 N3=485.59)N-192m / z=611.24(C 45 H 29 N3=611.75)N-193m / z=485.19(C 35 H 23 N3=485.59)N-194m / z=485.19(C 35 H 23 N3=485.59)N-195m / z=611.24(C 45 H 29 N3=611.75)N-196m / z=485.19(C 35 H 23 N3=485.59)N-197m / z=485.19(C 35 H 23 N3=485.59)N-198m / z=561.22(C 41 H 27 N3=561.69)N-199m / z=485.19(C 35 H 23 N3=485.59)N-200m / z=485.19(C 35 H 23 N3=485.59)N-201m / z=611.24(C 45 H 29 N3=611.75)N-202m / z=611.24(C 45 H 29 N3=611.75)N-203m / z=485.19(C 35 H 23 N3=485.59)N-204m / z=485.19(C 35 H 23 N3=485.59)N-205m / z=485.19(C 35 H 23 N3=485.59)N-206m / z=485.19(C 35 H 23N3=485.59)N-207m / z=535.20(C 39 H 25 N3=535.65)N-208m / z=535.2(C 39 H 25 N3=535.65)N-209m / z=585.22(C 43 H 27 N3=585.71)N-210m / z=535.2(C 39 H 25 N3=535.65)N-211m / z=585.22(C 43 H 27 N3=585.71)N-212m / z=585.22(C 43 H 27 N3=585.71)N-213m / z=611.24(C 45 H 29 N3=611.75)N-214m / z=611.24(C 45 H 29 N3=611.75)N-215m / z=585.22(C 43 H 27 N3=585.71)N-216m / z=611.24(C 45 H 29 N3=611.75)N-217m / z=687.27(C 51 H 33 N3=687.85)N-218m / z=611.24(C 45 H 29 N3=611.75)N-219m / z=511.20(C 37 H 25 N3=511.63)N-220m / z=611.24(C 45 H 29 N3=611.75)N-221m / z=561.22(C 41 H 27 N3=561.69)N-222m / z=587.24(C 43 H 29 N3=587.73)N-223m / z=663.27(C 49 H 33 N3=663.82)N-224m / z=713.28(C 53 H 35 N3=713.88)N-225m / z=575.20(C41 H 25 N3O=575.67)N-226m / z=601.22(C 43 H 27 N3O=601.71)N-227m / z=700.26(C 51 H 32 N4=700.85)N-228m / z=701.25(C 51 H 31 N3O=701.83)N-229m / z=667.21(C 47 H 29 N3S=667.83)N-230m / z=541.16(C 37 H 23 N3S=541.67)N-231m / z=612.23(C 44 H 28 N4=612.74)N-232m / z=562.22(C 40 H 26 N4=562.68)N-233m / z=689.26(C 49 H 31 N5=689.82)N-234m / z=639.24(C 45 H 29 N5=639.76)N-235m / z=701.25(C 51 H 31 N3O=701.83)N-236m / z=631.17(C 43 H 25 N3OS=631.75)N-237m / z=625.22(C 45 H 27 N3O=625.73)N-238m / z=591.18(C 41 H 25 N3S=591.73)N-239m / z=687.27(C 51 H 33 N3=687.85)N-240m / z=701.25(C 51 H 31 N3O=701.83)N-241m / z=619.30(C 45 H 37 N3=619.81)N-242m / z=601.25(C 44 H 31 N3=601.75)N-243m / z=667.23(C 47 H29 N3O2=667.77)N-244m / z=540.24(C 39 H 20 D5N3=540.68)N-245m / z=521.17(C 35 H 21 F2N3=521.57)N-246m / z=510.18(C 36 H 22 N4=510.60)N-247m / z=652.23(C 46 H 28 N4O=652.76)N-248m / z=527.24(C 38 H 29 N3=527.67)N-249m / z=535.20(C 39 H 25 N3=535.65)N-250m / z=535.20(C 39 H 25 N3=535.65)N-251m / z=535.20(C 39 H 25 N3=535.65)N-252m / z=535.20(C 39 H 25 N3=535.65)N-253m / z=587.24(C 43 H 29 N3=587.73)N-254m / z=612.23(C 44 H 28 N4=612.74)N-255m / z=561.22(C 41 H 27 N3=561.69)N-256m / z=687.27(C 51 H 33 N3=687.85)N-257m / z=663.27(C 49 H 33 N3=663.82)N-258m / z=601.22(C 43 H 27 N3O=601.71)N-259m / z=617.19(C 43 H 27 N3S=617.77)N-260m / z=752.29(C 55 H 36 N4=752.92)N-261m / z=651.23(C 47 H 29N3O=651.77)N-262m / z=677.25(C 49 H 31 N3O=677.81)N-263m / z=541.16(C 37 H 23 N3S=541.67)N-264m / z=750.28(C 55 H 34 N4=750.91)N-265m / z=707.24(C 50 H 33 N3S=707.90)N-266m / z=651.23(C 47 H 29 N3O=651.77)N-267m / z=617.19(C 43 H 27 N3S=617.77)N-268m / z=667.21(C 47 H 29 N3S=667.83)N-269m / z=631.17(C 43 H 25 N3OS=631.75)N-270m / z=767.26(C 55 H 33 N3O2=767.89)N-271m / z=647.15(C 43 H 25 N3S2=647.81)N-272m / z=690.24(C 49 H 30 N4O=690.81)N-273m / z=575.2(C 41 H 25 N3O=575.67)N-274m / z=614.21(C 43 H 26 N4O=614.71)N-275m / z=575.2(C 41 H 25 N3O=575.67)N-276m / z=549.18(C 39 H 23 N3O=549.63)

[0514] Although the above has been described with respect to synthetic examples of compounds represented by Chemical Formula 1 and Chemical Formula I, these are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and those skilled in the art will easily understand that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic example is combined in Chemical Formula 1 or Chemical Formula I.

[0515] Manufacturing and evaluation of organic electronic devices

[0516] [Example 1] Red organic light-emitting device (phosphorescent host)

[0517] N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (hereinafter referred to as compound A) and 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile) (hereinafter referred to as compound B) are vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm. At this time, compound B is doped so that the weight ratio of compound A and compound B is 98:2.

[0518] Afterwards, compound A is vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 110 nm.

[0519] Afterwards, N is added to the hole transport layer 7 -(dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7 -Triphenyldibenzo[b,d]thiophene-2,7-diamine is vacuum-deposited to form a 10 nm thick light-emitting auxiliary layer.

[0520] Thereafter, a mixture host of the compound P-1 (first host) and the compound N-8 (second host) of the present invention in a weight ratio of 5:5 and a dopant bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as '(piq)2Ir(acac)') are vacuum-deposited on the light-emitting auxiliary layer to form a light-emitting layer having a thickness of 30 nm. At this time, the dopant is doped so that the weight ratio of the host and the dopant becomes 95:5.

[0521] Afterwards, 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine is vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm.

[0522] Afterwards, a mixture of 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene and (8-quinolinolato)lithium in a weight ratio of 5:5 is vacuum-deposited on the hole-blocking layer to form an electron transport layer with a thickness of 30 nm.

[0523] Afterwards, a compound (8-quinolinolato)lithium is vacuum-deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al is deposited to form a cathode with a thickness of 150 nm.

[0524] [Example 2] to [Example 33]

[0525] An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds described in Table 5 below were used as the first host and second host of the light-emitting layer.

[0526] [Comparative Example 1] and [Comparative Example 2]

[0527] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound A or Comparative Compound B was used as the first host of the light-emitting layer.

[0528] Comparative Compound A <Comparative Compound B>

[0529]

[0530] The organic electroluminescence devices manufactured by Examples 1 to 33 of the present invention and Comparative Examples 1 and 2 were subjected to a forward bias DC voltage, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch, and 2500 cd / m 2 T95 was measured using a life-span measuring device manufactured by Maxscience at a reference luminance. The measurement results are shown in Table 5 below.

[0531] These measuring devices are unaffected by daily variations in deposition rate, vacuum quality, or other parameters, and can evaluate new performance compared to reference compounds under identical conditions. Since each batch contains four identically prepared OLEDs containing the reference compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this manner are statistically significant.

[0532] 1st host 2nd host driving voltage (V) current (mA / cm) 2 ) Luminance (cd / m 2) Efficiency (cd / A) T(95) Comparative Example 1 Comparative Compound AH-175.110.52500.023.797.6 Comparative Example 2 Comparative Compound BH-175.512.82500.019.690.2Example 1P-1H-174.26.32500.040.0129.9Example 2P-5H-174.16.32500.039.7127.3Example 3P-19H-174.35.92500.042.2132.6Example 4P-26H-174.36.32500.039.9131.8Example 5P-32H-174.16.12500.041.3127.2Example 6P-34H-174.25.72500.044.2131.3Example 7P-35H-17 4.35.82500.043.2132.2Embodiment 8P-38H-174.36.32500.039.7127.3Embodiment 9P-67H-174.26.22500.040.4125.6Embodiment 10P-71H-174.35.92500.042.6129.5Embodiment 11P-72H-174.15.72500.043.8125.8Embodiment 12P-83H-174.26.12500.041.2126.7Embodiment 13P-94H-174.45.82500.043.0130.6Embodiment 14P-104H- 174.15.62500.044.6127.2Embodiment 15P-105H-174.36.32500.039.4128.2Embodiment 16P-118H-174.46.22500.040.2131.4Embodiment 17P-131H-174.26.32500.039.7127.0Embodiment 18P-138H-174.36.22500.040.5129.6Embodiment 19P-145H-174.67.12500.035.0125.1Embodiment 20P-146H-174.77.32500.034.2124.4Embodiment Example 21P-1N-1764.26.72500.037.5141.8Embodiment 22P-38N-1764.36.92500.036.3144.7Embodiment 23P-67N-1764.36.72500.037.4143.9Embodiment 24P-72N-1764.26.82500.036.5142.5Embodiment 25P-104N-1764.37.02500.035.8142.6Embodiment 26P-118N-1764.26.72500.037.5143.3Embodiment 27P-131N-1764.17.02500.035.5140.6Embodiment 28P-19N-2584.45.82500.043.0137.4Embodiment 29P-26N-2584.26.02500.041.7139.0Embodiment 30P-34N-2584.26.32500.039.4135.7Embodiment 31P-83N-2584.16.12500.041.3139.5Embodiment 32P-105N-2584.36.12500.041.0133.7Embodiment 33P-138N-2584.26.12500.041.2136.2.

[0533] As can be seen from the results in Table 5 above, when the material for an organic electroluminescent device of the present invention is used as a host material of a light-emitting layer, the driving voltage, luminous efficiency and lifespan of the organic electroluminescent device are significantly improved compared to when Comparative Compound A or Comparative Compound B, which have a similar basic skeleton to the compound of the present invention, are used. Comparative Compound A and Comparative Compound B are similar to the compound of the present invention in that an oxazole derivative is substituted on a 3-condensed ring, but in that they are benzoxazoles in which a benzene ring is condensed on an oxazole, the B ring (C 10 The above condensed aryl ring is different from the compound of the present invention.

[0534] First, in order to determine the difference in energy levels of compounds according to structural differences between these compounds, the energy levels of comparative compound A and similar compound P-146 of the present invention were measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program. The measurement results are shown in Table 6 below.

[0535] Example P-145 Comparative compound AHOMO(eV)-5.1421-5.1745 LUMO(eV)-1.4993-1.5173 Eg(eV)3.64283.6572 T1(eV)2.53352.508 S1(eV)3.12473.1798 ㅿST(eV)0.59120.6718

[0536] From the above Table 6, it can be seen that the energy levels of the compound P-145 of the present invention and the comparative compound A are formed differently. In particular, it can be seen that the HOMO energy level of the compound of the present invention is formed larger (shallow) than that of the comparative compound A. Therefore, when the compound of the present invention is used as a host, hole injection from the hole transport band to the light-emitting layer is facilitated, and as a result, the light-emitting layer becomes rich in holes, so that exciton formation increases, and the charge balance of the device is improved, and thus the driving voltage and efficiency appear to be improved.

[0537] In addition, since the compound P-145 of the present invention has a smaller ㅿST value than the comparative compound A, energy transfer from the host to the dopant is facilitated, and thus the energy of the unstable excited state can be well transferred, so the lifespan improvement effect appears to be maximized when used as a host.

[0538] Next, the Reorganization Energy (hereinafter abbreviated as RE) of Comparative Compound B and similar Compound P-146 of the present invention was measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program. The measurement results are as shown in Table 7 below, where RE is RE hole Indicates a value.

[0539] Compound Reorganization Energy (RE)P-1460.3048Comparative Compound A0.4952

[0540] From the above Table 7, it can be seen that the RE values ​​of Comparative Compound B and Compound P-146 of the present invention are significantly different. Therefore, when the compound of the present invention with a low RE value is used as a host, it has higher hole mobility and faster HOD (Hole On Device) than Comparative Compound B, so that hole transport and hole injection are excellent, and the driving voltage of the device is reduced, and since the light-emitting layer becomes rich in holes, hole injection into the dopant increases, which seems to improve efficiency and lifespan. From the above Tables 5 to 7, it can be confirmed that the compound of the present invention, which satisfies all complex factors such as the type of substituent and the substitution position of the substituent, exhibits a remarkable effect compared to other comparative compounds in organic electric devices, even though it is a compound with a similar structure, and through this, it can be seen that the compound of the present invention exhibits a remarkable effect in organic electric devices compared to simple structural isomers or other compounds with similar structures not described herein.

[0541] These results suggest that even if the molecular components are similar, the properties of the compound, such as hole characteristics, light efficiency characteristics, energy levels, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance, can differ significantly to an extent that is difficult to predict depending on the type and position of the substituted substituent, and that the performance of the device can vary not only due to a single component but also due to complex factors, rather than affecting the results of the entire device.

[0542] 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. The scope of protection of the present invention should be construed in accordance with the claims below, and all techniques within the scope equivalent thereto should be construed as being included within the scope of the present invention.

Claims

1. A compound represented by the following chemical formula 1: <Chemical Formula 1> <Chemical Formula A> <Chemical Formula 1-1> In the above chemical formula 1, A is chemical formula A, Q is chemical formula 1-1, X is O or S, and Z is O, S, or N(R 3 ) and B ring is C 10 ~C 60 A condensed aryl ring, and the B ring is one or more identical or different R 4 can be replaced with, R 3 or R 4 Go L a is combined with, Ar 1 and Ar 2 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 group; C6~C 60 Aromatic ring and C3~C 60 A fused ring group in which an aliphatic ring is fused; and C1~C 20 is selected from the group consisting of alkyl groups, L 1 Inland L 3 , L a are independently a single bond; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of ; C3~C 60 Aliphatic ring group of; and C6~C 60 Aromatic ring and C3~C 60 is selected from the group consisting of fused ring groups in which an aliphatic ring is fused, R 1 Inland R 4 are independently hydrogen; deuterium; halogen; cyano group; nitro group; silane group; C6~C 60 Aryl group of; Fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of ; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 A fused ring group of an aliphatic ring; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of ; C2~C 20 Alkyne group of ; C1~C 20 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups, and adjacent groups can be combined with each other to form a ring, a and b are integers from 0 to 3, respectively. The above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, silane group, alkoxy group, aryloxy group, and the ring formed by bonding adjacent groups to each other are each deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; Cyano group; Nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 Alkyl group of; C2-C 20 Alkenyl group of ; C2-C 20 Alkyne group of ; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It can be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and adjacent substituents can be combined with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

2. In paragraph 1, Above Ar 1 and Ar 2 A compound characterized in that at least one of the compounds is selected from the group consisting of the following chemical formulae Ar-1 to Ar-12: <Chemical Formula Ar-1> <Chemical Formula Ar-2> <Chemical Formula Ar-3> <Chemical Formula Ar-4> <Chemical Formula Ar-5> <Chemical Formula Ar-6> <Chemical Formula Ar-7> <Chemical Formula Ar-8> <Chemical Formula Ar-9> <Chemical Formula Ar-10> <Chemical Formula Ar-11> <Chemical Formula Ar-12> In the above chemical formulas Ar-1 to Ar-12, V is O, S, C(R1)(R2) or N(R3), provided that V is L 1 or L 2 When combined, V is C(R1) or N, R 5 Inland R 11 , R1 to R3 are independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; Cyano group; Nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 Alkyl group of; C2-C 20 Alkenyl group of ; C2-C 20 Alkyne group of ; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 is selected from the group consisting of heterocyclic groups, and adjacent groups can be bonded to each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium, c and g are each integers from 0 to 5, d is an integer from 0 to 7, e is an integer from 0 to 9, and f, h, and i are each integers from 0 to 4.

3. In paragraph 1, The above chemical formula 1-1 is a compound characterized by being represented by one of the following chemical formulas Q-1 to Q-13: <Chemical Formula Q-1> <Chemical Formula Q-2> <Chemical Formula Q-3> <Chemical Formula Q-4> <Chemical Formula Q-5> <Chemical Formula Q-6> <Chemical Formula Q-7> <Chemical Formula Q-8> <Chemical Formula Q-9> <Chemical Formula Q-10> <Chemical Formula Q-11> <Chemical Formula Q-12> <Chemical Formula Q-13> In the chemical formulas Q-1 to Q-13 above, Z is as defined in the first term, and R 12 Inland R 16 is hydrogen or deuterium, j, l, and m are each integers from 0 to 2, and k and n are each integers from 0 to 4.

4. In paragraph 1, The above chemical formula A is a compound characterized by being selected from the group consisting of the following chemical formulas C-1 to C-9: <Chemical Formula C-1> <Chemical Formula C-2> <Chemical Formula C-3> <Chemical Formula C-4> <Chemical Formula C-5> <Chemical Formula C-6> <Chemical Formula C-7> <Chemical Formula C-8> <Chemical Formula C-9> In the chemical formulas C-1 to C-9, X, L a, Q, R 1 , R 2 , a, b are as defined in paragraph 1.

5. In paragraph 1, L 1 , L 2 , L 3 and L a A compound characterized in that at least one of them is selected from the group consisting of a single bond or chemical formulae L-1 to L-20: <Chemical Formula L-1> <Chemical Formula L-2> <Chemical Formula L-3> <Chemical Formula L-4> <Chemical Formula L-5> <Chemical Formula L-6> <Chemical Formula L-7> <Chemical Formula L-8> <Chemical Formula L-9> <Chemical Formula L-10> <Chemical Formula L-11> <Chemical Formula L-12> <Chemical Formula L-13> <Chemical Formula L-14> <Chemical Formula L-15> <Chemical Formula L-16> <Chemical Formula L-17> <Chemical Formula L-18> <Chemical Formula L-19> <Chemical Formula L-20> In the chemical formulas L-1 to L-20 above, W is O, S, C(R 11 )(R 12 ) or N(R 13 ), but when combined through W, W is C(R 11 ) or N, R 17 Inland R 22 , R 11 Inland R 13 are independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; Cyano group; Nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 Alkyl group of; C2-C 20 Alkenyl group of ; C2-C 20 Alkyne group of ; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 is selected from the group consisting of heterocyclic groups, and adjacent groups can be bonded to each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium, o, q, r, s, and t are integers from 0 to 4, respectively, and p is an integer from 0 to 6.

6. In paragraph 1, A compound represented by the above chemical formula 1 is characterized in that it is one of the following compounds: .

7. Material for organic electric devices containing the compound of paragraph 1 and a compound represented by the following chemical formula I: <Chemical Formula I> In the above chemical formula I, X A Inland X C is N or C(R'), at least one of which is N, Ar A Inland Ar C 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 group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of aromatic ring; and C1~C 30 is selected from the group consisting of alkyl groups, L A Inland L C are independently a single bond; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of ; C3~C 60 Aliphatic ring group of; and C3~C 60 Aliphatic ring and C6~C 60 is selected from the group consisting of a fused ring group of an aromatic ring, The above R' is hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 Aryl group of; Fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of ; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 A fused ring group of an aliphatic ring; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of ; C2~C 20 Alkyne group of ; C1~C 20 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups, The above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group are each deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; Cyano group; Nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio group of; C1-C 20 Alkyl group of; C2-C 20 Alkenyl group of ; C2-C 20 Alkyne group of ; C6-C 30 Aryl group of; Fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It can be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and adjacent substituents can be combined with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

8. In an organic electric device including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, An organic electric device characterized in that the organic layer comprises the compound of claim 1 or the material for an organic electric device of claim 7.

9. In paragraph 8, An organic electric device characterized in that the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of claim 1 or the material for an organic electric device of claim 7.

10. In paragraph 8, An organic electric device characterized in that the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.

11. A display device including the organic electric element of clause 8; and An electronic device including a control unit that drives the display device.

12. A step of depositing an organic layer material including a compound represented by the chemical formula 1 of paragraph 1; A step of recovering the organic layer material attached to the deposition equipment; and A method for recovering a compound, characterized by including a step of purifying the recovered organic layer material to obtain a compound represented by the chemical formula 1 having a purity of 99.9% or higher.

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