Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof

Abstract

The present invention provides: a novel compound capable of improving light-emission efficiency, stability and lifetime of a device; an organic electronic device using same; and an electronic apparatus thereof.

Description

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

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

[0002] In general, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical devices utilizing organic light emission typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the organic electrical device; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic layers in organic electrical devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0004] The biggest issues regarding organic electroluminescent devices are lifespan and efficiency, and as displays become larger in size, these efficiency and lifespan problems must be resolved.

[0005] Efficiency, lifespan, and driving voltage are interrelated; as efficiency increases, the driving voltage relatively decreases, and as the driving voltage drops, the crystallization of organic materials caused by Joule heating during operation is reduced, resulting in a tendency for increased lifespan.

[0006] However, simply improving the aforementioned organic layers does not guarantee maximum efficiency. This is because both a long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between the organic layers, along with the intrinsic properties of the materials (mobility, interfacial characteristics, etc.), form an optimal combination.

[0007] Furthermore, in order to solve the light emission problem in the hole transport layer of organic electroluminescent devices, an auxiliary light emission layer must exist between the hole transport layer and the light-emitting layer, and it is now necessary to develop different auxiliary light emission layers according to each light-emitting layer (R, G, B).

[0008] Generally, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated by recombination.

[0009] However, materials used in the hole transport layer must have a low HOMO value, so most of them have a low T1 value. As a result, excitons generated in the emissive layer move into the hole transport layer, causing charge unbalance within the emissive layer and consequently emitting light at the hole transport layer interface.

[0010] When light is emitted at the interface of the hole transport layer, problems arise such as reduced color purity and efficiency of the organic device and a shortened lifespan. Therefore, there is an urgent need to develop an emitting auxiliary layer that has a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the emitting layer.

[0011] Meanwhile, there is a need to develop hole injection layer materials that possess high glass transition temperatures, which delay the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer—one of the causes of shortened lifespan in organic electronic devices—while also exhibiting stable characteristics against Joule heating generated during device operation. It has been reported that the low glass transition temperatures of hole transport layer materials degrade the uniformity of the thin film surface during device operation, which significantly impacts device lifespan. Furthermore, as OLED devices are primarily formed by deposition methods, there is a need to develop materials capable of withstanding prolonged deposition, specifically materials with strong heat resistance.

[0012] In other words, to fully realize the excellent characteristics of organic electronic devices, it is essential that the materials constituting the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials—be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic electronic devices has not yet been sufficiently achieved. Consequently, the development of new materials continues to be required, and there is a particularly urgent need for the development of materials for the light-emitting auxiliary layer.

[0013] In order to solve the problems of the aforementioned background technology, the present invention has identified a compound having a novel structure and has also revealed that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be significantly improved.

[0014] Accordingly, the present invention aims to provide a novel compound, an organic electric device using the same, and an electronic device thereof.

[0015] The present invention provides a compound represented by the following chemical formula 1.

[0016] <Chemical Formula 1>

[0017]

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

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

[0020] FIGS. 1 to 3 are exemplary diagrams of an organic electroluminescent device according to the present invention.

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

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

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

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

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

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

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

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

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

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

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

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

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

[0034] The present invention will be described in detail below with reference to embodiments thereof. In describing the present invention, if it is determined that a detailed description of related known components or functions may obscure the essence of the invention, such detailed description will be omitted.

[0035] In addition, terms such as first, second, A, B, (a), (b), etc., may be used when describing the components of the present invention. These terms are intended only to distinguish the components from other components, and the essence, order, or sequence of the components is not limited by the terms. Where it is stated that a component is "connected," "combined," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but that another component may also be "connected," "combined," or "connected" between each component.

[0036] As used in this specification and the appended claims, unless otherwise noted, the meanings of the following terms are as follows:

[0037] As used herein, the terms “halo” or “halogen” are fluorine (F), bromine (Br), chlorine (Cl), or iodine (I) unless otherwise noted.

[0038] Unless otherwise explained, the terms “alkyl” or “alkyl group” as used in the present invention refer to radicals of saturated aliphatic functional groups having single bonds of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, and cycloalkyl-substituted alkyl groups.

[0039] Unless otherwise noted, the terms “alkenyl group,” “alkenyl group,” or “alkynyl group” as used in the present invention each have a double or triple bond having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, and include a straight-chain or branched-chain group, but are not limited thereto.

[0040] Unless otherwise noted, the terms “cycloalkyl” or “cycloalkyl” as used in the present invention refer to alkyls forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms, but are not limited thereto.

[0041] The terms “alkyxyl group,” “alkoxy group,” or “alkyloxy group” used in the present invention refer to an alkyl group to which an oxygen radical is attached, and unless otherwise described, have 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, but are not limited thereto.

[0042] The terms “aryloxyl group” or “aryloxy group” used in the present invention refer to an aryl group to which an oxygen radical is attached, and unless otherwise described, have 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, but are not limited thereto.

[0043] Unless otherwise noted, the terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group refers to a single-ring or multi-ring aromatic group and includes an aromatic ring formed by an adjacent substituent participating in bonding or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a naphthyl group, a fluorene group, or a spirofluorene group.

[0044] The prefixes "aryl" or "ar" denote radicals substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and radicals substituted with an aryl group have the number of carbon atoms described in this specification.

[0045] In addition, when prefixes are named consecutively, it means that the substituents are listed in the order in which they were first described. For example, "aryl alkoxy" refers to an alkoxy group substituted with an aryl group; "alkoxyl carbonyl" refers to a carbonyl group substituted with an alkoxyl group; and "aryl carbonyl alkenyl" refers to an alkhenyl group substituted with an aryl carbonyl group, where the aryl carbonyl group is a carbonyl group substituted with an aryl group.

[0046] Unless otherwise described, the term "heterocyclic ring" as used in the present invention comprises one or more heteroatoms, has a carbon number of 2 to 60, 2 to 30, 2 to 25, 2 to 18, or 2 to 12, comprises at least one of a single ring and a multi-ring, and comprises a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by the bonding of adjacent functional groups.

[0047] As used herein, the term "heteroatom" refers to N, O, S, P, or Si unless otherwise noted.

[0048] Furthermore, "heterocyclic group" refers to single-ring types, ring assemblies, conjugated multi-ring systems, spiro compounds, etc., containing heteroatoms. Additionally, compounds containing heterocyclic groups such as SO2 and P=O, as shown below, instead of the ring-forming carbon, may also be included in heterocyclic groups. For example, "heterocyclic groups" include the following compounds.

[0049]

[0050] The term "aliphatic ring" as used in the present invention refers to a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic types, ring assemblies, conjugated multi-ring systems, spiro compounds, etc. Unless otherwise stated, it refers to a ring having 3 to 60 carbon atoms, a ring having 3 to 30 carbon atoms, a ring having 3 to 25 carbon atoms, a ring having 3 to 18 carbon atoms, or a ring having 3 to 12 carbon atoms, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

[0051] Unless otherwise noted, the terms “fluorenyl group,” “fluorenyl group,” or “fluorentriyl group” as used in the present invention refer to a monovalent, divalent, or trivalent functional group in which R, R’, and R’ are all hydrogens in the following structures, respectively; “substituted fluorenyl group,” “substituted fluorenyl group,” or “substituted fluorentriyl group” refer to a case where at least one of the substituents R, R’, and R’ is a substituent other than hydrogen, and includes cases where R and R’ are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In this specification, fluorenyl group, fluorenyl group, and fluorentriyl group may all be referred to as fluoren groups regardless of valence.

[0052]

[0053] The term "spiro compound" used in the present invention refers to a compound having a "spiro union," where a spiro union is a connection formed by two rings sharing only one atom. At this time, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, they are respectively called "monospiro-," "dyspiro-," and "trispiro-" compounds.

[0054] Unless otherwise stated, the term “aliphatic” as used in the present invention means an aliphatic hydrocarbon having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, and “aliphatic ring” means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms.

[0055] Unless otherwise stated, the term “ring” as used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heteroring having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms; or a fused ring formed by a combination thereof, and includes saturated or unsaturated rings.

[0056] Other heterocompounds or heteroradicals other than the aforementioned heterocompounds comprise one or more heteroatoms, but are not limited thereto.

[0057] Additionally, unless explicitly stated otherwise, in the terms "substituted or unsubstituted" as used in this invention, "substituted" refers to deuterium, halogen, amino group, nitrile group, nitro group, C1~C 20 alkyl group of, C1~C 20 alkoxyl group of, C1~C 20 alkylamine group of, C1~C 20 alkylthiophene group of, C6~C 20 arylthiophene group, C2~C 20 The Alken Diary of, C2~C 20 Alkin's Diary, C3~C 20 cycloalkyl group of, C6~C 20 aryl group, C6~C substituted with deuterium20 aryl group of, C8~C 20 aryl alkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group of heterocyclic rings, but is not limited to these substituents.

[0058] 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 written as the 'name of the group reflecting the valence,' or it may be written as the 'name of the parent compound.' For example, in the case of 'phenanthrene,' a type of aryl group, the group name may be written by distinguishing the valence, such as 'phenanthrile' for the monovalent group and 'phenanthrillene' for the divalent group, but it may also be written as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be written as 'pyrimidine' regardless of the valence, or it may be written as the 'name of the group' corresponding to the valence, such as pyrimidinyl group for monovalent and pyrimidinyllene for divalent. Furthermore, in this specification, numbers or letters indicating position may be omitted when writing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0059] In addition, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied identically to the definitions of substituents by the definitions of the indices of the following chemical formulas.

[0060]

[0061] Here, if a is an integer of 0, the substituent R 1 ... does not exist, and if a is an integer of 1, there is one substituent R 1It bonds to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it bonds as follows, respectively, where R 1 The atoms may be identical or different from each other, and when a is an integer from 4 to 6, they are bonded to the carbons of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbons forming the benzene ring is omitted.

[0062]

[0063] In addition, unless explicitly stated otherwise, the terms "ortho," "meta," and "para" used in the present invention refer to the substitution positions of all substituents. The ortho position indicates the compound immediately adjacent to the substituent position, for example, in the case of benzene, it refers to the 1st and 2nd positions. The meta position indicates the substitution position following the immediately adjacent substitution position, for example, in the case of benzene, it refers to the 1st and 3rd positions. The para position indicates the substitution position following the meta position, for example, in the case of benzene, it refers to the 1st and 4th positions. A more detailed explanation of examples of substitution positions is as follows, and it can be confirmed that the ortho- and meta- positions are of a non-linear type, and the para- positions are of a linear type.

[0064] [Example of ortho-position]

[0065]

[0066] [Example of meta-location]

[0067]

[0068] [Example of para-position]

[0069]

[0070]

[0071] Hereinafter, a compound according to one aspect of the present invention and an organic electric device including the same will be described.

[0072] The present invention provides a compound represented by the following chemical formula 1.

[0073] Chemical formula 1

[0074]

[0075] In the above chemical formula 1, each symbol can be defined as follows.

[0076] X 1 and X 2 are independently O or S, and

[0077] R 1 , R 2 , R 3 and R 4 Each is identical or different from each other, and independently deuterium; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C1~C 50 Selected from the group consisting of alkyl groups; or multiple adjacent groups may bond to each other to form a ring,

[0078] The above R 1 , R 2 , R 3 and R 4 If it is an aryl group, preferably C6~C 30 The aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group of can be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0079] The above R 1 , R 2 , R 3 and R 4 In the case where it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 25, C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0080] The above R 1 , R 2 , R 3 and R 4 In the case of an aliphatic ring, preferably C3~C 30 The aliphatic ring of, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be an aliphatic ring, specifically, cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0081] The above R 1 , R 2 , R 3 and R 4 In the case where it is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 25 , C1~C 18 or C1~C 12 It can be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0082] R 5 is deuterium, and

[0083] a, c, and e are independent integers from 0 to 4, and b and d are independent integers from 0 to 3, and

[0084] Ar 1 and Ar2 C6~C are independent of each other 60 aryl group of; or C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic of, and,

[0085] The above Ar 1 and Ar 2 If it is an aryl group, preferably C6~C 30 The aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group of can be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0086] The above Ar 1 and Ar 2 If it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0087] Here, the aryl group, heterocyclic group, fluorenyl group, aliphatic cyclic group, and alkyl group are, respectively, deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group of; C1~C 20 alkoxyl group of; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C6~C 20 aryl group of; C6~C substituted with deuterium20 aryl group; fluorene group; C2~C 20 The heterocyclic ring of; C3~C 20 of the aliphatic ring; C7~C 20 arylalkyl group of; C8~C 20 The aryl alkene group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; additionally, the hydrogens of these substituents may be further substituted with one or more deuterium atoms; additionally, these substituents may bond with each other to form a ring, wherein 'ring' refers to C3~C 60 aliphatic ring of or C6~C 60 aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes saturated or unsaturated rings.

[0088]

[0089] In addition, the present invention relates to Ar of the above chemical formula 1. 1 and Ar 2 At least one of the following provides a compound represented by any one of the following chemical formulas A to F.

[0090] Chemical formula A Chemical formula B Chemical formula C

[0091]

[0092] Chemical formula D Chemical formula E Chemical formula F

[0093]

[0094] In the above chemical formulas A to F,

[0095] 1) R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14They are each identical or different from one another, and independently deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group of; C1~C 20 alkoxyl group of; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C6~C 20 aryl group of; C6~C substituted with deuterium 20 aryl group; fluorene group; C2~C 20 The heterocyclic ring of; C3~C 20 of the aliphatic ring; C7~C 20 arylalkyl group of; C8~C 20 The aryl alkene group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and the hydrogens of these substituents may be further substituted with one or more deuterium atoms.

[0096] 2) X 3 is O; S; or CR a R b ; and,

[0097] 3) R a and R b C6~C are independent of each other 20 aryl group of; C2~C 20 The heterocyclic group of; or C1~C 20 The alkyl group of; and R a and R b They can combine with each other to form a ring,

[0098] 4) g, h, j, k and m are independent integers from 0 to 4, f is an integer from 0 to 3, and i, l and n are independent integers from 0 to 5, and

[0099] * indicates the position where N is joined.

[0100]

[0101] Here, the above chemical formula A can be represented by the following chemical formula A-1 or chemical formula A-2.

[0102] Chemical formula A-1 Chemical formula A-2

[0103]

[0104] In the above chemical formulas A-1 and A-2,

[0105] R 6 , R 7 , X 3 , f, and g are the same as those defined in the above chemical formula A, and

[0106] Ar 3 and Ar 4 C1~C are independent of each other 20 alkyl group of; C6~C 20 aryl group of; C6~C substituted with deuterium 20 aryl group; fluorene group; C2~C 20 The heterocyclic group of; or C3~C 20 of aliphatic ring; and,

[0107] g' is an integer from 0 to 3, and f' is an integer from 0 to 2, and

[0108] * indicates the part where N is joined.

[0109]

[0110] In addition, the above chemical formula A can be represented by any one of the following chemical formulas A-1-1 to A-1-4.

[0111] Chemical formula A-1-1 Chemical formula A-1-2

[0112]

[0113] Chemical formula A-1-3 Chemical formula A-1-4

[0114]

[0115] In the above chemical formulas A-1-1 to A-1-4,

[0116] R 6 , R 7 , X3 , f is the same as that defined in the above chemical formula A, and

[0117] Ar 3 and g' are the same as defined in the above chemical formula A-1, and

[0118] * indicates the part where N is joined.

[0119]

[0120] In addition, in the present invention, the above formula A may be represented by any one of the following formulas A-2-1 to A-2-4.

[0121] Chemical formula A-2-1 Chemical formula A-2-2

[0122]

[0123] Chemical formula A-2-3 Chemical formula A-2-4

[0124]

[0125] In the above chemical formulas A-2-1 to A-2-4,

[0126] R 6 , R 7 , X 3 , g is the same as defined in the above chemical formula A, and

[0127] Ar 4 , f' is the same as defined above, and

[0128] * indicates the part where N is joined.

[0129]

[0130] As another example, in the present invention, the formula A may be represented by any one of the following formulas A-1-1-1 to A-1-4-4 and formulas A-2-1-1 to A-2-4-3.

[0131] Chemical formula A-1-1-1 Chemical formula A-1-1-2 Chemical formula A-1-1-3 Chemical formula A-1-1-4

[0132]

[0133] Chemical formula A-1-2-1 Chemical formula A-1-2-2 Chemical formula A-1-2-3 Chemical formula A-1-2-4

[0134]

[0135] Chemical formula A-1-3-1 Chemical formula A-1-3-2 Chemical formula A-1-3-3 Chemical formula A-1-3-4

[0136]

[0137] Chemical formula A-1-4-1 Chemical formula A-1-4-2 Chemical formula A-1-4-3 Chemical formula A-1-4-4

[0138]

[0139] Chemical formula A-2-1-1 Chemical formula A-2-1-2 Chemical formula A-2-1-3 Chemical formula A-2-2-1

[0140]

[0141] Chemical formula A-2-2-2 Chemical formula A-2-2-3 Chemical formula A-2-3-1 Chemical formula A-2-3-2

[0142]

[0143] Chemical formula A-2-3-3 Chemical formula A-2-4-1 Chemical formula A-2-4-2 Chemical formula A-2-4-3

[0144]

[0145] In the above chemical formulas A-1-1-1 to A-1-4-4,

[0146] R 6 , R 7 , X 3 , f is the same as that defined in the above chemical formula A, and

[0147] Ar 3 , g' is the same as that defined in the above chemical formula A-1, and

[0148] In the above chemical formulas A-2-1-1 to A-2-4-3,

[0149] R 6 , R 7 , X3 , g is the same as defined in the above chemical formula A, and

[0150] Ar 4 , f' is the same as that defined in the above chemical formula A-2.

[0151] * indicates the part where N is joined.

[0152]

[0153] In addition, in the present invention, the above chemical formula B may be represented by any one of the following chemical formulas B-1 to B-3.

[0154] Chemical formula B-1 Chemical formula B-2 Chemical formula B-3

[0155]

[0156] In the above chemical formulas B-1 to B-3, R 8 , R 9 , R 10 , R 11 , h, i, j, k are the same as defined in the above chemical formula B, and * indicates the part where N is bonded.

[0157]

[0158] Specifically, the compound represented by the above chemical formula 1 may be any one of the following compounds P-1 to P-134, but is not limited thereto.

[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]

[0190]

[0191]

[0192]

[0193]

[0194] In addition, in another aspect, the present invention provides a method for reusing a compound represented by Formula 1, comprising the steps of: depositing an organic light-emitting material containing a compound represented by Formula 1 in a manufacturing process of an organic light-emitting device; removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; recovering the removed impurities; and purifying the recovered impurities to a purity of 99.9% or higher.

[0195] The step of removing impurities from the unpurified organic light-emitting material recovered from the above deposition apparatus may preferably include performing a preliminary purification process to obtain a purity of 98% or higher by recrystallizing under a recrystallization solvent.

[0196] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0197] The above recrystallization solvent can preferably be used by mixing a polar solvent with a polarity of 5.5 to 7.2 and a non-polar solvent with a polarity of 2.0 to 4.7.

[0198] When the above recrystallization solvent is used by mixing a polar solvent and a non-polar solvent, the non-polar solvent may be used at a ratio of 15% (v / v) or less relative to the polar solvent.

[0199] The above recrystallization solvent is preferably a single solvent of methylpyrrolidone (N-Methylpyrrolidone; NMP); or a mixed polar solvent in which any one selected from the group consisting of dimethylimidazolidinone (1,3-Dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-Dimethyl formamide), dimethylacetamide, and dimethyl sulfoxide is mixed with the methylpyrrolidone; or a single solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone; or a mixed nonpolar solvent. Alternatively, a mixture of polar and non-polar solvents can be used.

[0200] The above preliminary purification process may include a step of dissolving an unpurified organic light-emitting material recovered from a deposition apparatus in a polar solvent at 90°C to 120°C and then cooling it to 0°C to 5°C to precipitate crystals.

[0201] The above preliminary purification process may include the step of dissolving an unpurified organic light-emitting material recovered from a deposition apparatus 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 crystals.

[0202] The above preliminary purification process may include a step of dissolving an unpurified organic light-emitting material recovered from a deposition apparatus in a non-polar solvent, then concentrating the solvent and removing the non-polar solvent while precipitating crystals.

[0203] 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.

[0204] The step of purifying the above-mentioned recovered impurities to a purity of 99.9% or higher may include performing an adsorption separation process to remove impurities by adsorbing them onto an adsorbent.

[0205] The above adsorbent may be activated carbon, silica gel, alumina, or a known material for adsorption purposes.

[0206] The step of purifying the above-mentioned recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0207]

[0208] Referring to FIG. 1, the organic electric device (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer between the first electrode (110) and the second electrode (170) comprising a single compound represented by Chemical Formula 1 or two or more compounds. At this time, the first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode; in the case of an invert type, the first electrode may be a cathode and the second electrode may be an anode.

[0209] The organic layer may sequentially include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). At this time, the remaining layers, excluding the light-emitting layer (140), may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150), etc., may serve as a hole blocking layer. (See FIG. 2)

[0210] Additionally, an organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). Such a light efficiency improvement layer may be formed on the surface of the first electrode that does not come into contact with the organic layer or on the surface of the second electrode that does not come into contact with the organic layer. A compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (120), a hole transport layer (130), a light-emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a light-emitting layer (140), or as a material for the light efficiency improvement layer. Preferably, for example, a compound according to Formula 1 of the present invention may be used as a material for the light-emitting auxiliary layer.

[0211] The organic layer may include two or more stacks comprising a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (See FIG. 3)

[0212] Meanwhile, even with the same core, the band gap, electrical properties, and interfacial properties can vary depending on which substituent is attached at which location; therefore, the selection of the core and the combination of sub-substituents attached to it are also very important. In particular, long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between each organic layer, as well as the intrinsic properties of the material (mobility, interfacial properties, etc.), form an optimal combination.

[0213] An organic electroluminescent device according to one embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, it can be manufactured by forming an anode 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 thereon.

[0214] In addition, the present invention provides an organic electric device characterized in that the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic layer comprises the compound as an electron transport material.

[0215] As another specific example, the present invention provides an organic electric device characterized by using a homogeneous or heterogeneous compound of the compound represented by Chemical Formula 1 mixed in the organic layer.

[0216] In addition, the present invention provides a light-emitting auxiliary layer composition comprising a compound represented by the above chemical formula 1, and an organic electric device comprising the above light-emitting auxiliary layer.

[0217] In addition, the present invention provides an electronic device comprising: a display device including the above-described organic electric element; and a control unit for driving the display device.

[0218] In another aspect, the present invention provides an electronic device characterized in that the organic electrical device comprises at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive material, an organic transistor, and a device for monochromatic or white lighting. 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 mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, various computers, watches, tablets, and virtual reality (VR) devices.

[0219]

[0220] Hereinafter, examples of synthesis of a compound represented by Chemical Formula 1 according to the present invention and examples of manufacturing an organic electric device will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[0221]

[0222] [Synthetic Example]

[0223] The compound represented by Chemical Formula 1 according to the present invention (Final Products) is synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

[0224] <Reaction Equation 1>

[0225]

[0226] In the above reaction scheme 1, X 1 , X 2 , R 1 , R 2 , R 3 , R 4 , R 5 , Ar 1 , Ar 2 , a, b, c, d, and e are the same as defined in Chemical Formula 1 above.

[0227]

[0228] I. Example of Sub 1

[0229] Sub 1 of the above reaction scheme 1 can be synthesized by the reaction route of the following reaction scheme 2, but is not limited thereto.

[0230] <Reaction Equation 2>

[0231]

[0232] In the above reaction scheme 2, X 1 , X 2 , R 1 , R 2 , R 3 , R 4 , R 5 , a, b, c, d, and e are the same as defined in Chemical Formula 1 above, and Hal is Br, I, or Cl.

[0233]

[0234] Compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub 1.

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] 화합물FD-MS화합물FD-MSSub 1-1m / z=459.10 (C 30 H 18 ClNO2=459.93)Sub 1-2m / z=535.13 (C 36 H 22 ClNO2=536.03)Sub 1-3m / z=539.17 (C 36 H 26 ClNO2=540.06)Sub 1-4m / z=611.17 (C 42 H 26 ClNO2=612.12)Sub 1-5m / z=611.17 (C 42 H 26 ClNO2=612.12)Sub 1-6m / z=611.17 (C 42 H 26 ClNO2=612.12)Sub 1-7m / z=509.12 (C 34 H 20 ClNO2=509.99)Sub 1-8m / z=585.15 (C 40 H 24 ClNO2=586.09)Sub 1-9m / z=585.15 (C 40 H 24 ClNO2=586.09)Sub 1-10m / z=585.15 (C 40 H 24 ClNO2=586.09)Sub 1-11m / z=558.14 (C 39 H 23 ClNO2=559.06)Sub 1-12m / z=475.08 (C 30 H 18 ClNOS=475.99)Sub 1-13m / z=551.11 (C 36 H 22 ClNOS=552.09)Sub 1-14m / z=565.13 (C 37 H 24 ClNOS=566.12)Sub 1-15m / z=489.10 (C 31 H 20 ClNOS=490.02)Sub 1-16m / z=551.11 (C 36 H 22ClNOS=552.09)Sub 1-17m / z=551.11 (C 36 H 22 ClNOS=552.09)Sub 1-18m / z=561.19 (C 36 H 32 ClNOS=562.17)Sub 1-19m / z=601.13 (C 40 H 24 ClNOS=602.15)Sub 1-20m / z=601.13 (C 40 H 24 ClNOS=602.15)Sub 1-21m / z=601.13 (C 40 H 24 ClNOS=602.15)Sub 1-22m / z=525.10 (C 34 H 20 ClNOS=526.05)Sub 1-23m / z=529.13 (C 34 H 24 ClNOS=530.08)Sub 1-24m / z=601.13 (C 40 H 24 ClNOS=602.15)Sub 1-25m / z=601.13 (C 40 H 24 ClNOS=602.15)Sub 1-26m / z=575.11 (C 38 H 22 ClNOS=576.11)Sub 1-27m / z=491.06 (C 30 H 18 ClNS2=492.05)Sub 1-28m / z=547.12 (C 34 H 16 ClNS2=548.16)Sub 1-29m / z=567.09 (C 36 H 22 ClNS2=568.15)Sub 1-30m / z=643.12 (C 42 H 26 ClNS2=644.25)Sub 1-31m / z=622.23 (C 42 H 15 D 11 ClNO2=623.19)Sub 1-32m / z=621.23 (C 42 H 16 D10 ClNO2=622.19)Sub 1-33m / z=571.11 (C 36 H 18 D4ClNS2=572.17)Sub 1-34m / z=558.15 (C 36 H 15 D7ClNOS=559.13)Sub 1-35m / z=534.15 (C 34 H 11 D9ClNOS=535.10)Sub 1-36m / z=573.25 (C 36 D 22 ClNOS=574.22)Sub 1-37m / z=475.20 (C 30 D 18 ClNO2=476.02)Sub 1-38m / z=540.17 (C 36 H 17 D5ClNO2=541.06)

[0247]

[0248] II. Examples of Sub 2

[0249] Compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub 2.

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272] 화합물FD-MS화합물FD-MSSub 2-1m / z=169.09 (C 12 H 11 N = 169.23) Sub 2-2m / z = 245.12 (C 18 H 15 N = 245.32) Sub 2-3m / z = 245.12 (C 18 H 15 N = 245.32) Sub 2-4m / z = 245.12 (C 18 H 15 N = 245.32) Sub 2-5 m / z = 321.15 ( C 24 H 19 N = 321.42) Sub 2-6m / z = 321.15 (C 24 H 19 N = 321.42) Sub 2-7 m / z = 251.17 ( C 18 H 21 N = 251.37) Sub 2-8m / z = 345.15 (C 26 H 19 N = 345.44) Sub 2-9m / z = 345.15 (C 26H 19 N=345.44)Sub 2-10m / z=259.10 (C 18 H 13 NO=259.31)Sub 2-11m / z=259.10 (C 18 H 13 NO=259.31)Sub 2-12m / z=259.10 (C 18 H 13 NO=259.31)Sub 2-13m / z=335.13 (C 24 H 17 NO=335.41)Sub 2-14m / z=335.13 (C 24 H 17 NO=335.41)Sub 2-15m / z=335.13 (C 24 H 17 NO=335.41)Sub 2-16m / z=487.19 (C 36 H 25 NO=487.60)Sub 2-17m / z=411.16 (C 30 H 21 NO=411.50)Sub 2-18m / z=391.19 (C 28 H 25 NO=391.51)Sub 2-19m / z=467.22 (C 34 H 29 NO=467.61)Sub 2-20m / z=417.21 (C 30 H 27 NO=417.55)Sub 2-21m / z=363.13 (C 25 H 17 NO2=363.42)Sub 2-22m / z=363.13 (C 25 H 17 NO2=363.42)Sub 2-23m / z=405.17 (C 28 H 23 NO2=405.50)Sub 2-24m / z=425.14 (C 30 H 19 NO2=425.49)Sub 2-25m / z=309.12 (C 22 H 15 NO=309.37)Sub 2-26m / z=435.16 (C 32 H 21NO=435.53)Sub 2-27m / z=351.11 (C 24 H 17 NS=351.47)Sub 2-28m / z=427.14 (C 30 H 21 NS=427.56)Sub 2-29m / z=351.11 (C 24 H 17 NS=351.47)Sub 2-30m / z=357.16 (C 24 H 23 NS=357.52)Sub 2-31m / z=503.17 (C 36 H 25 NS=503.66)Sub 2-32m / z=393.16 (C 27 H 23 NS=393.55)Sub 2-33m / z=365.09 (C 24 H 15 NOS=365.45)Sub 2-34m / z=441.12 (C 30 H 19 NOS=441.55)Sub 2-35m / z=379.10 (C 25 H 17 NOS=379.48)Sub 2-36m / z=455.13 (C 31 H 21 NOS=455.57)Sub 2-37m / z=471.17 (C 32 H 25 NOS=471.62)Sub 2-38m / z=517.15 (C 36 H 23 NOS=517.65)Sub 2-39m / z=441.12 (C 30 H 19 NOS=441.55)Sub 2-40m / z=285.15 (C 21 H 19 N=285.39)Sub 2-41m / z=335.17 (C 25 H 21 N=335.45)Sub 2-42m / z=361.18 (C 27 H 23 N=361.49)Sub 2-43m / z=493.28 (C 37 H 35N=493.69)Sub 2-44m / z=375.16 (C 27 H 21 NO=375.47)Sub 2-45m / z=451.19 (C 33 H 25 NO=451.57)Sub 2-46m / z=451.19 (C 33 H 25 NO=451.57)Sub 2-47m / z=527.22 (C 39 H 29 NO=527.67)Sub 2-48m / z=425.18 (C 31 H 23 NO=425.53)Sub 2-49m / z=441.16 (C 31 H 23 NS=441.59)Sub 2-50m / z=517.19 (C 37 H 27 NS=517.69)Sub 2-51m / z=409.18 (C 31 H 23 N=409.53)Sub 2-52m / z=485.21 (C 37 H 27 N=485.63)Sub 2-53m / z=567.29 (C 43 H 37 N=567.78)Sub 2-54m / z=561.25 (C 43 H 31 N=561.73)Sub 2-55m / z=553.28 (C 42 H 35 N=553.75)Sub 2-56m / z=611.26 (C 47 H 33 N=611.79)Sub 2-57m / z=541.28 (C 41 H 35 N=541.74)Sub 2-58m / z=527.26 (C 40 H 33 N=527.71)Sub 2-59m / z=575.22 (C 43 H 29 NO=575.71)Sub 2-60m / z=631.29 (C 47 H 37NO=631.82)Sub 2-61m / z=515.17 (C 37 H 25 NS=515.67)Sub 2-62m / z=591.20 (C 43 H 29 NS=591.77)Sub 2-63m / z=529.19 (C 38 H 27 NS=529.70)Sub 2-64m / z=605.22 (C 44 H 31 NS=605.80)Sub 2-65m / z=681.21 (C 49 H 31 NOS=681.85)Sub 2-66m / z=681.21 (C 49 H 31 NOS=681.85)Sub 2-67m / z=641.22 (C 47 H 31 NS=641.83)Sub 2-68m / z=565.19 (C 41 H 27 NS=565.73)Sub 2-69m / z=677.31 (C 52 H 39 N=677.89)Sub 2-70m / z=254.18 (C 18 H6D9N=254.38)Sub 2-71m / z=264.13 (C 18 H8D5NO=264.34)Sub 2-72m / z=490.25 (C 37 H 22 D5N=490.66)Sub 2-73m / z=381.20 (C 27 H 15 D6NO=381.51)Sub 2-74m / z=448.16 (C 30 H 12 D7NOS=448.59)Sub 2-75m / z=395.29 (C 27 HD 20 NO=395.59)Sub 2-76m / z=511.34 (C 36 HD 24 NO=511.75)Sub 2-77m / z=411.16 (C 30 H 21NO=411.50)Sub 2-78m / z=335.13 (C 24 H 17 NO=335.41)Sub 2-79m / z=465.21 (C 34 H 27 NO=465.60)Sub 2-80m / z=441.12 (C 30 H 19 NOS=441.55)Sub 2-81m / z=591.20 (C 43 H 29 NS=591.77)Sub 2-82m / z=477.25 (C 36 H 31 N=477.65)

[0273]

[0274] III. Product Synthesis

[0275] 1. Examples of P-2 synthesis

[0276]

[0277]

[0278]

[0279] (1) Composition of Sub 1-1'

[0280] Sub 1-1'-1 (30.0 g, 121.14 mmol) was dissolved in 400 mL of toluene in a round-bottom flask, after which Sub 1-1'-2 (26.69 g, 145.70 mmol), Pd2(dba)3 (3.34 g, 3.64 mmol), P(t-Bu)3 (1.47 g, 7.28 mmol), and NaOt-Bu (23.34 g, 242.83 mmol) were added and stirred at 65°C. After the reaction was completed, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 29.6 g of product (yield: 70%).

[0281] (2) Synthesis of Sub 1-1

[0282] Sub 1-1' (29.6 g, 84.72 mmol) was dissolved in 280 mL of toluene in a round-bottom flask, after which Sub 1-1'-3 (19.46 g, 101.66 mmol), Pd2(dba)3 (2.33 g, 2.54 mmol), P(t-Bu)3 (1.03 g, 5.08 mmol), and NaOt-Bu (16.29 g, 169.44 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 25.3 g of product (yield: 65%).

[0283] (3) Synthesis of P-2

[0284] Sub 1-1 (25.3 g, 55.01 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 183 mL of toluene. Then, Sub 2-2 (13.50 g, 55.01 mmol), Pd2(dba)3 (1.51 g, 1.65 mmol), P(t-Bu)3 (0.67 g, 3.30 mmol), and NaOt-Bu (10.57 g, 110.02 mmol) were added, and the mixture was stirred at 120°C. After the reaction was completed, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 27.2 g of product (yield: 74%).

[0285]

[0286] 2. Examples of P-11 synthesis

[0287]

[0288] (1) Synthesis of P-11

[0289] Sub 1-1 (25.0 g, 54.36 mmol) was placed in a round-bottom flask and dissolved in toluene (180 mL), then Sub 2-11 (14.10 g, 54.36 mmol), Pd2(dba)3 (1.49 g, 1.63 mmol), P(t-Bu)3 (0.66 g, 3.26 mmol), and NaOt-Bu (10.45 g, 108.71 mmol) were added, and 26.0 g of product (yield: 70%) was obtained using the synthesis method of P-2 above.

[0290]

[0291] 3. Examples of P-23 synthesis

[0292]

[0293]

[0294] (1) Synthesis of Sub 2-23

[0295] Sub 2-23-1 (25.0 g, 82.45 mmol) was dissolved in 275 mL of toluene in a round-bottom flask, after which Sub 2-23-2 (18.13 g, 98.94 mmol), Pd2(dba)3 (2.27 g, 2.47 mmol), P(t-Bu)3 (1.00 g, 4.95 mmol), and NaOt-Bu (15.85 g, 164.91 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 21.8 g of product (yield: 65%).

[0296] (2) Synthesis of P-23

[0297] Sub 1-1 (24.7 g, 53.70 mmol) was placed in a round-bottom flask and dissolved in toluene (179 mL), then Sub 2-23 (21.8 g, 53.70 mmol), Pd2(dba)3 (1.48 g, 1.61 mmol), P(t-Bu)3 (0.65 g, 3.22 mmol), and NaOt-Bu (10.32 g, 107.41 mmol) were added, and 31.6 g of product (yield: 71%) was obtained using the synthesis method of P-2 above.

[0298]

[0299] 4. Examples of P-38 synthesis

[0300]

[0301]

[0302] (1) Synthesis of Sub 2-61

[0303] Sub 2-61-1 (20.0 g, 50.34 mmol) was dissolved in 168 mL of toluene in a round-bottom flask, after which Sub 2-61-2 (12.04 g, 60.41 mmol), Pd2(dba)3 (1.38 g, 1.51 mmol), P(t-Bu)3 (0.61 g, 3.02 mmol), and NaOt-Bu (9.68 g, 100.68 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 19.5 g of product (yield: 75%).

[0304] (2) Synthesis of P-38

[0305] Sub 1-1 (17.4 g, 37.83 mmol) was placed in a round-bottom flask and dissolved in toluene (177 mL), then Sub 2-61 (19.5 g, 37.83 mmol), Pd2(dba)3 (1.04 g, 1.14 mmol), P(t-Bu)3 (0.46 g, 2.27 mmol), and NaOt-Bu (7.27 g, 75.66 mmol) were added, and 27.7 g of product (yield: 78%) was obtained using the synthesis method of P-2 above.

[0306]

[0307] 5. Examples of P-65 synthesis

[0308]

[0309]

[0310]

[0311] (1) Synthesis of Sub 1-11'

[0312] Sub 1-11'-1 (25.0 g, 84.13 mmol) was dissolved in 280 mL of toluene in a round-bottom flask, after which Sub 1-11'-2 (23.56 g, 100.96 mmol), Pd2(dba)3 (2.31 g, 2.52 mmol), P(t-Bu)3 (1.02 g, 5.05 mmol), and NaOt-Bu (16.17 g, 168.27 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 27.6 g of product (yield: 73%).

[0313] (2) Synthesis of Sub 1-11

[0314] Sub 1-11' (27.6 g, 61.40 mmol) was dissolved in 205 mL of toluene in a round-bottom flask, after which Sub 1-1'-3 (14.11 g, 73.68 mmol), Pd2(dba)3 (1.69 g, 1.84 mmol), P(t-Bu)3 (0.75 g, 3.68 mmol), and NaOt-Bu (11.80 g, 122.80 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 26.2 g of product (yield: 76%).

[0315] (3) Synthesis of P-65

[0316] Sub 1-11 (26.2 g, 46.78 mmol) was placed in a round-bottom flask and dissolved in toluene (156 mL), then Sub 2-1 (7.92 g, 46.78 mmol), Pd2(dba)3 (1.29 g, 1.40 mmol), P(t-Bu)3 (0.57 g, 2.81 mmol), and NaOt-Bu (9.00 g, 93.56 mmol) were added, and 21.5 g of product (yield: 66%) was obtained using the synthesis method of P-2.

[0317]

[0318] 6. Examples of P-79 synthesis

[0319]

[0320]

[0321]

[0322] (1) Synthesis of Sub 1-17'

[0323] Sub 1-17'-1 (25.0 g, 89.69 mmol) was dissolved in 300 mL of toluene in a round-bottom flask, after which Sub 1-17'-2 (21.45 g, 107.63 mmol), Pd2(dba)3 (2.46 g, 2.69 mmol), P(t-Bu)3 (1.09 g, 5.38 mmol), and NaOt-Bu (17.24 g, 179.38 mmol) were added and stirred at 75°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 27.8 g of product (yield: 70%).

[0324] (2) Synthesis of Sub 1-17

[0325] Sub 1-17' (27.8 g, 62.96 mmol) was dissolved in 210 mL of toluene in a round-bottom flask, after which Sub 1-1'-3 (14.46 g, 75.55 mmol), Pd2(dba)3 (1.73 g, 1.89 mmol), P(t-Bu)3 (0.76 g, 3.78 mmol), and NaOt-Bu (12.10 g, 125.92 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 21.6 g of product (yield: 62%).

[0326] (3) Synthesis of P-79

[0327] Sub 1-17 (21.6 g, 39.12 mmol) was placed in a round-bottom flask and dissolved in toluene (130 mL), then Sub 2-23 (15.87 g, 39.12 mmol), Pd2(dba)3 (1.08 g, 1.17 mmol), P(t-Bu)3 (0.48 g, 2.35 mmol), and NaOt-Bu (7.52 g, 78.25 mmol) were added, and 22.7 g of product (yield: 63%) was obtained using the synthesis method of P-2 above.

[0328]

[0329] 7. Examples of P-81 synthesis

[0330]

[0331]

[0332]

[0333]

[0334] (1) Synthesis of Sub 1-9'

[0335] Sub 1-9'-1 (25.0 g, 89.69 mmol) was dissolved in 300 mL of toluene in a round-bottom flask, after which Sub 1-9'-2 (25.11 g, 107.63 mmol), Pd2(dba)3 (2.46 g, 2.69 mmol), P(t-Bu)3 (1.09 g, 5.38 mmol), and NaOt-Bu (17.24 g, 179.38 mmol) were added and stirred at 75°C. After the reaction was completed, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 30.1 g of product (yield: 70.5%).

[0336] (2) Synthesis of Sub 1-9

[0337] Sub 1-9' (30.1 g, 63.30 mmol) was dissolved in 211 mL of toluene in a round-bottom flask, after which Sub 1-1'-3 (14.54 g, 75.95 mmol), Pd2(dba)3 (1.74 g, 1.90 mmol), P(t-Bu)3 (0.77 g, 3.80 mmol), and NaOt-Bu (12.17 g, 126.59 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 25.3 g of product (yield: 68%).

[0338] (3) Synthesis of Sub 2-28

[0339] Sub 2-28-1 (25.0 g, 84.80 mmol) was dissolved in 280 mL of toluene in a round-bottom flask, after which Sub 2-28-2 (17.22 g, 101.76 mmol), Pd2(dba)3 (2.33 g, 2.54 mmol), P(t-Bu)3 (1.03 g, 5.09 mmol), and NaOt-Bu (16.30 g, 169.61 mmol) were added and stirred at 75°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 22.9 g of product (yield: 63%).

[0340] (4) Synthesis of P-81

[0341] Sub 1-9 (25.3 g, 43.17 mmol) was placed in a round-bottom flask and dissolved in toluene (144 mL), then Sub 2-28 (18.46 g, 43.17 mmol), Pd2(dba)3 (1.19 g, 1.30 mmol), P(t-Bu)3 (0.52 g, 2.59 mmol), and NaOt-Bu (8.30 g, 86.33 mmol) were added, and 30.5 g of product (yield: 72%) was obtained using the synthesis method of P-2.

[0342]

[0343] 8. Examples of P-96 synthesis

[0344]

[0345]

[0346]

[0347] (1) Synthesis of Sub 1-19'

[0348] Sub 1-19'-1 (25.0 g, 72.49 mmol) was dissolved in 240 mL of toluene in a round-bottom flask, after which Sub 1-1'-2 (15.94 g, 86.99 mmol), Pd2(dba)3 (1.99 g, 2.17 mmol), P(t-Bu)3 (0.88 g, 4.35 mmol), and NaOt-Bu (13.94 g, 144.99 mmol) were added and stirred at 75°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 25.7 g of product (yield: 72%).

[0349] (2) Synthesis of Sub 1-19

[0350] Sub 1-19' (25.7 g, 52.28 mmol) was dissolved in 174 mL of toluene in a round-bottom flask, after which Sub 1-1'-3 (12.01 g, 62.73 mmol), Pd2(dba)3 (1.44 g, 1.57 mmol), P(t-Bu)3 (0.64 g, 3.14 mmol), and NaOt-Bu (10.05 g, 104.55 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 19.6 g of product (yield: 62%).

[0351] (3) Synthesis of P-96

[0352] Sub 1-19 (19.6 g, 32.55 mmol) was placed in a round-bottom flask and dissolved in toluene (108 mL), then Sub 2-46 (14.70 g, 32.55 mmol), Pd2(dba)3 (0.90 g, 0.98 mmol), P(t-Bu)3 (0.40 g, 1.95 mmol), and NaOt-Bu (6.26 g, 65.10 mmol) were added, and 25.6 g of product (yield: 77%) was obtained using the synthesis method of P-2.

[0353]

[0354] 9. Examples of P-116 synthesis

[0355]

[0356]

[0357]

[0358]

[0359] (1) Synthesis of Sub 1-31''

[0360] Sub 1-31''-1 (25.0 g, 89.69 mmol) was dissolved in Benzene-D6 (318 mL) in a round-bottom flask, after which CF3SO3H (15.85 mL, 179.38 mmol) was slowly added and stirred at room temperature for 16 hours. Once the reaction was complete, Na2CO3 (28.52 g, 269.07 mmol) dissolved in D2O was added to neutralize the mixture. After extraction with toluene and D2O, the organic layer was dried with MgSO4 and concentrated. The resulting compound was then crystalline using a silicagel column to obtain 23.7 g of product (yield: 91%).

[0361] (2) Synthesis of Sub 1-31'

[0362] Sub 1-31'' (23.7 g, 81.78 mmol) was dissolved in 273 mL of toluene in a round-bottom flask, after which Sub 1-31''-2 (25.45 g, 98.14 mmol), Pd2(dba)3 (2.25 g, 2.45 mmol), P(t-Bu)3 (0.99 g, 4.91 mmol), and NaOt-Bu (15.72 g, 163.56 mmol) were added and stirred at 75°C. After the reaction was completed, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 35.2 g of product (yield: 84%).

[0363] (3) Synthesis of Sub 1-31

[0364] Sub 1-31' (35.2 g, 68.66 mmol) was dissolved in 230 mL of toluene in a round-bottom flask, after which Sub 1-1'-3 (15.78 g, 82.40 mmol), Pd2(dba)3 (1.89 g, 2.06 mmol), P(t-Bu)3 (0.83 g, 4.12 mmol), and NaOt-Bu (13.20 g, 137.33 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 29.5 g of product (yield: 69%).

[0365] (4) Synthesis of P-116

[0366] Sub 1-31 (29.5 g, 47.34 mmol) was placed in a round-bottom flask and dissolved in toluene (158 mL), then Sub 2-2 (11.61 g, 47.34 mmol), Pd2(dba)3 (1.30 g, 1.42 mmol), P(t-Bu)3 (0.58 g, 2.84 mmol), and NaOt-Bu (9.10 g, 94.67 mmol) were added, and 31.2 g of product (yield: 79%) was obtained using the synthesis method of P-2.

[0367]

[0368] 10. Examples of P-125 synthesis

[0369]

[0370]

[0371]

[0372] (1) Synthesis of Sub 2-16

[0373] Sub 2-16-1 (25.0 g, 80.85 mmol) was dissolved in 270 mL of toluene in a round-bottom flask, after which Sub 1-31''-2 (25.16 g, 97.02 mmol), Pd2(dba)3 (2.22 g, 2.43 mmol), P(t-Bu)3 (0.98 g, 4.85 mmol), and NaOt-Bu (15.54 g, 161.70 mmol) were added and stirred at 65°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 33.5 g of product (yield: 85%).

[0374] (2) Synthesis of P-16

[0375] Sub 1-1 (31.6 g, 68.70 mmol) was placed in a round-bottom flask and dissolved in toluene (230 mL), then Sub 2-16 (33.5 g, 68.70 mmol), Pd2(dba)3 (1.89 g, 2.06 mmol), P(t-Bu)3 (0.83 g, 4.12 mmol), and NaOt-Bu (13.21 g, 137.41 mmol) were added, and 45.1 g of product (yield: 72%) was obtained using the synthesis method of P-2.

[0376] (1) Synthesis of P-125

[0377] P-16 (45.0 g, 49.39 mmol) was dissolved in Benzene-D6 (1163 mL) in a round-bottom flask, after which CF3SO3H (14.92 mL, 98.78 mmol) was slowly added and stirred at room temperature for 16 hours. Once the reaction was complete, Na2CO3 (15.71 g, 148.18 mmol) dissolved in D2O was added to neutralize the mixture. After extraction with toluene and D2O, the organic layer was dried with MgSO4 and concentrated. The resulting compound was then filtered through a silicagel column and recrystallized to obtain 30.7 g of product (yield: 65%).

[0378]

[0379] Meanwhile, the FD-MS values ​​of compounds P-1 to P-134 of the present invention prepared according to the synthesis example above are as shown in Table 3 below.

[0380] Compound FD-MS Compound FD-MSP-1 m / z=592.22 (C 42 H 28 N2O2=592.70)P-2m / z=668.25 (C 48 H 32 N2O2=668.80)P-3m / z=668.25 (C 48 H 32 N2O2=668.80)P-4m / z=668.25 (C 48 H 32 N2O2=668.80)P-5m / z=744.28 (C 54 H 36 N2O2=744.89)P-6m / z=674.29 (C 48 H 38 N2O2=674.84)P-7m / z=768.28 (C 56 H 38 N2O2=768.92)P-8m / z=768.28 (C 56 H 38 N2O2=768.92)P-9m / z=744.28 (C 54 H 36 N2O2=744.89)P-10m / z=682.23 (C 48 H 30 N2O3=682.78)P-11m / z=682.23 (C 48 H 30 N2O3=682.78)P-12m / z=682.23 (C 48 H 30 N2O3=682.78)P-13m / z=758.26 (C 54 H 34 N2O3=758.88)P-14m / z=758.26 (C 54 H 34 N2O3=758.88)P-15m / z=758.26 (C 54 H 34 N2O3=758.88)P-16m / z=910.32 (C66 H 42 N2O3=911.07)P-17m / z=834.29 (C 60 H 38 N2O3=834.97)P-18m / z=814.32 (C 58 H 42 N2O3=814.98)P-19m / z=732.24 (C 52 H 32 N2O3=732.84)P-20m / z=848.27 (C 60 H 36 N2O4=848.96)P-21m / z=786.25 (C 55 H 34 N2O4=786.89)P-22m / z=786.25 (C 55 H 34 N2O4=786.89)P-23m / z=828.30 (C 58 H 40 N2O4=828.97)P-24m / z=858.29 (C 62 H 38 N2O3=859.00)P-25m / z=850.27 (C 60 H 38 N2O2S=851.04)P-26m / z=774.23 (C 54 H 34 N2O2S=774.94)P-27m / z=774.23 (C 54 H 34 N2O2S=774.94)P-28m / z=926.30 (C 66 H 42 N2O2S=927.13)P-29m / z=780.28 (C 54 H 40 N2O2S=780.99)P-30m / z=816.28 (C 57 H 40 N2O2S=817.02)P-31m / z=788.21 (C 54 H 32 N2O3S=788.92)P-32m / z=864.24 (C 60 H 36 N2O3S=865.02)P-33m / z=802.23 (C 55 H 34N2O3S=802.95)P-34m / z=832.31 (C 61 H 40 N2O2=833.00)P-35m / z=908.34 (C 67 H 44 N2O2=909.10)P-36m / z=984.37 (C 73 H 48 N2O2=985.20)P-37m / z=998.35 (C 73 H 46 N2O3=999.18)P-38m / z=938.30 (C 67 H 42 N2O2S=939.14)P-39m / z=990.42 (C 73 H 54 N2O2=991.25)P-40m / z=1034.39 (C 77 H 50 N2O2=1035.26)P-41m / z=988.31 (C 71 H 44 N2O2S=989.20)P-42m / z=1014.33 (C 73 H 46 N2O2S=1015.24)P-43m / z=976.40 (C 72 H 52 N2O2=977.22)P-44m / z=1100.43 (C 82 H 56 N2O2=1101.36)P-45m / z=708.28 (C 51 H 36 N2O2=708.86)P-46m / z=874.32 (C 63 H 42 N2O3=875.04)P-47m / z=874.32 (C 63 H 42 N2O3=875.04)P-48m / z=784.31 (C 57 H 40 N2O2=784.96)P-49m / z=950.35 (C 69 H 46 N2O3=951.14)P-50m / z=798.29 (C 57 H 38 N2O3=798.94)P-51m / z=848.30 (C61 H 40 N2O3=849.00)P-52m / z=864.28 (C 61 H 40 N2O2S=865.06)P-53m / z=940.31 (C 67 H 44 N2O2S=941.16)P-54m / z=916.40 (C 67 H 63 N2O2=917.17)P-55m / z=844.37 (C 60 H 48 N2O3=845.05)P-56m / z=890.35 (C 64 H 46 N2O3=891.08)P-57m / z=868.28 (C 60 H 40 N2O3S=869.05)P-58m / z=944.31 (C 66 H 44 N2O3S=945.15)P-59m / z=1108.37 (C 79 H 52 N2O3S=1109.36)P-60m / z=1108.37 (C 79 H 52 N2O3S=1109.36)P-61m / z=1032.37 (C 74 H 52 N2O2S=1033.30)P-62m / z=1058.44 (C 77 H 58 N2O3=1059.32)P-63m / z=878.26 (C 61 H 38 N2O3S=879.05)P-64m / z=894.29 (C 62 H 42 N2O3S=895.09)P-65m / z=692.25 (C 50 H 32 N2O2=692.82)P-66m / z=810.27 (C 58 H 38 N2OS=811.01)P-67m / z=820.31 (C 60 H 40 N2O2=820.99)P-68m / z=774.27 (C 55 H 38N2OS=774.98)P-69m / z=794.29 (C 58 H 38 N2O2=794.95)P-70m / z=698.20 (C 48 H 30 N2O2S=698.84)P-71m / z=774.23 (C 54 H 34 N2O2S=774.94)P-72m / z=698.20 (C 48 H 30 N2O2S=698.84)P-73m / z=942.27 (C 66 H 42 N2OS2=943.20)P-74m / z=846.27 (C 58 H 42 N2OS2=847.11)P-75m / z=798.23 (C 56 H 34 N2O2S=798.96)P-76m / z=964.28 (C 68 H 40 N2O3S=965.14)P-77m / z=818.21 (C 55 H 34 N2O2S2=819.01)P-78m / z=938.31 (C 67 H 42 N2O4=939.08)P-79m / z=920.31 (C 64 H 44 N2O3S=921.13)P-80m / z=1010.35 (C 74 H 46 N2O3=1011.19)P-81m / z=976.31 (C 70 H 44 N2O2S=977.19)P-82m / z=900.28 (C 64 H 40 N2O2S=901.10)P-83m / z=922.31 (C 64 H 46 N2OS2=923.21)P-84m / z=832.26 (C 57 H 40 N2OS2=833.08)P-85m / z=924.32 (C 67 H 44 N2OS=925.16)P-86m / z=924.32 (C67 H 44 N2OS=925.16)P-87m / z=984.37 (C 73 H 48 N2O2=985.20)P-88m / z=1174.44 (C 85 H 62 N2S2=1175.57)P-89m / z=1060.40 (C 79 H 52 N2O2=1061.30)P-90m / z=1150.41 (C 85 H 54 N2O3=1151.38)P-91m / z=1044.32 (C 74 H 48 N2OS2=1045.33)P-92m / z=1014.42 (C 75 H 54 N2O2=1015.27)P-93m / z=966.36 (C 70 H 50 N2OS=967.24)P-94m / z=1192.44 (C 88 H 60 N2OS=1193.52)P-95m / z=860.34 (C 63 H 44 N2O2=861.06)P-96m / z=1016.34 (C 73 H 48 N2O2S=1017.26)P-97m / z=1016.34 (C 73 H 48 N2O2S=1017.26)P-98m / z=936.37 (C 69 H 48 N2O2=937.15)P-99m / z=1066.36 (C 77 H 50 N2O2S=1067.32)P-100m / z=890.30 (C 63 H 42 N2O2S=891.10)P-101m / z=974.35 (C 71 H 46 N2O3=975.16)P-102m / z=990.33 (C 71 H 46 N2O2S=991.22)P-103m / z=1082.34 (C 77 H50 N2OS=1083.38)P-104m / z=1058.43 (C 77 H 58 N2OS=1059.38)P-105m / z=942.42 (C 66 H 58 N2O2S=943.26)P-106m / z=978.37 (C 68 H 54 N2OS2=979.31)P-107m / z=944.31 (C 66 H 44 N2O3S=945.15)P-108m / z=960.28 (C 66 H 44 N2O2S2=961.21)P-109m / z=1134.37 (C 81 H 54 N2OS2=1135.46)P-110m / z=1090.40 (C 77 H 58 N2OS2=1091.44)P-111m / z=1030.32 (C 73 H 46 N2O3S=1031.24)P-112m / z=774.27 (C 55 H 38 N2OS=774.98)P-113m / z=982.31 (C 69 H 46 N2OS2=983.26)P-114m / z=677.30 (C 48 H 23 D9N2O2=677.85)P-115m / z=687.81 (C 48 H 25 D5N2O3=687.81)P-116m / z=831.38 (C 60 H 29 D 11 N2O2=832.06)P-117m / z=913.37 (C 67 H 39 D5N2O2=914.13)P-118m / z=946.43 (C 69 H 38 D 10 N2O2=947.22)P-119m / z=896.33 (C 63 H 36D6N2O2S=897.14)P-120m / z=946.30 (C 66 H 38 D4N2OS2=947.22)P-121m / z=872.06 (C 60 H 29 D7N2O3S=872.06)P-122m / z=781.28 (C 54 H 27 D7N2O2S=781.98)P-123m / z=807.29 (C 56 H 25 D9N2O2S=808.01)P-124m / z=932.56 (C 63 D 42 N2O2S=933.36)P-125m / z=952.58 (C 66 D 42 N2O3=953.33)P-126m / z=902.28 (C 64 H 42 N2S2=903.17)P-127m / z=834.29 (C 60 H 38 N2O3=834.97)P-128m / z=834.29 (C 60 H 38 N2O3=834.97)P-129m / z=904.31 (C 64 H 44 N2O2S=905.13)P-130m / z=940.28 (C 66 H 40 N2O3S=941.12)P-131m / z=1090.36 (C 79 H 50 N2O2S=1091.34)P-132m / z=981.43 (C 72 H 37 D5N2O2=982.25)P-133m / z=776.23 (C 54 H 36 N2S2=777.02)P-134m / z=740.23 (C 51 H 36 N2S2=740.98)

[0381]

[0382] Although exemplary synthetic examples of the present invention represented by Chemical Formula 1 have been described above, they are all based on the 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 other substituents defined in Chemical Formula 1 are attached in addition to the substituents specified in the specific synthetic examples.

[0383]

[0384] [Example 1]

[0385] Compound A and compound B were used on an ITO layer (anode) formed on a glass substrate, and compound B was doped in a weight ratio of 98:2 to form a hole injection layer with a thickness of 10 nm, and then compound A was vacuum deposited to a thickness of 110 nm on the hole injection layer to form a hole transport layer.

[0386] Next, a emitting auxiliary layer was formed by vacuum depositing the compound P-1 of the present invention to a thickness of 30 nm on the hole transport layer. Subsequently, a emitting layer with a thickness of 30 nm was formed by using the compound DG as the host material for the emitting layer and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as 'Ir(ppy)3') as the dopant material, doping the dopants in a weight ratio of 90:10.

[0387] Next, compound E was vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and an electron transport layer with a thickness of 30 nm was formed on the hole-blocking layer using a mixture of compound F and compound G mixed in a weight ratio of 5:5. Subsequently, compound G was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0388]

[0389] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0390] Compound B: 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0391] Compound DG: 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole

[0392] Compound E: 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0393] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0394] Compound G: (8-quinolinolato)lithium

[0395]

[0396] [Examples 2] to [Examples 17]

[0397] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound of the present invention listed in Table 4 below was used instead of the compound P-1 of the present invention as the light-emitting auxiliary layer.

[0398]

[0399] [Comparative Example 1] to [Comparative Example 7]

[0400] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Comparative Compounds A to G below were used instead of Comparative Compound P-1 of the present invention as the light-emitting auxiliary layer.

[0401] [Comparison Compound A] [Comparison Compound B] [Comparison Compound C]

[0402]

[0403] [Comparison Compound D] [Comparison Compound E] [Comparison Compound F]

[0404]

[0405] [Comparative Compound G]

[0406]

[0407]

[0408] A forward-bias DC voltage was applied to the organic electroluminescent devices of the examples and comparative examples prepared as described above, and the electroluminescent (EL) characteristics were measured using a PR-650 from Photoresearch; the measurement result was 5000 cd / m² 2 T95 lifetime was measured at reference brightness using a lifetime measurement device manufactured by MaxScience. Table 4 below shows the results of device fabrication and evaluation.

[0409] This measuring device can evaluate the performance of a new material by comparing it with a comparative compound under the same conditions, without being affected by the possibility of daily fluctuations in deposition rate, vacuum quality, or other parameters.

[0410] When evaluating, one batch contains four identically prepared OLEDs including a comparison compound, and since the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this way show statistical significance.

[0411] Compound driving voltage (V) current (mA / cm²) 2 )Efficiency (cd / A)T(95) Comparative Example (1) Comparative Compound A 5.312.739.483.4 Comparative Example (2) Comparative Compound B 5.212.141.291.3 Comparative Example (3) Comparative Compound C 5.312.440.390.4 Comparative Example (4) Comparative Compound D 5.111.842.296.5 Comparative Example (5) Comparative Compound E 5.213.138.281.3 Comparative Example (6) Comparative Compound F 5.111.842.494.2 Comparative Example (7) Comparative Compound G5.412.938.881.7 Example (1) Compound (P-1) 4.89.453.5111.7 Example (2) Compound (P-10) 4.68.956.2124.8 Example (3) Compound (P-11) 4.68.956.0123.5 Example (4) Compound (P-12) 4.68.956.1124. Example 2 (5) Compound (P-13) 4.6 8.9 5 6.4 12 5.5 Example (6) Compound (P-19) 4.9 9.5 5 2.5 10 8.3 Example (7) Compound (P-31) 4.7 9.0 5 5.3 12 0.3 Example (8) Compound (P-34) 4.8 9.3 5 4.0 11 5.9 Example (9) Compound (P-45 )4.79.254.6117.6 Example (10) Compound (P-48)4.79.254.4116.5 Example (11) Compound (P-71)4.79.155.1119.4 Example (12) Compound (P-85)4.89.353.8114.1 Example (13) Compound (P-114)4.89.453 .31 10.9 Example (14) Compound (P-126) 4.9 9.7 5 1.6 10 4.5 Example (15) Compound (P-127) 4.8 9.4 5 3.0 10 9.8 Example (16) Compound (P-133) 4.8 9.4 5 3.1 11 0.4 Example (17) Compound (P-134) 4.7 9.2 5 4.3 11 5.7

[0412] As can be seen in Table 4 above, when the compound of the present invention is used as a light-emitting auxiliary layer material, it can be confirmed that the efficiency is significantly improved compared to when comparative compounds A to F are used. In particular, comparative compounds A to D and the compound of the present invention differ in the binding positions of dibenzofuran or dibenzothiophene, and through this, the physical properties of the compound change. Therefore, it appears that the characteristics of the device change due to these physical properties.

[0413] Table 5 below shows the energy levels of comparative compound D and compound P-133 of the present invention, measured using the Gaussian program's DFT Method (B3LYP / 6-31g(D)).

[0414] Compound HOMO (eV) Comparative Compound D-4.879 P-133-4.938

[0415] As can be seen from the results of Table 5 above, it can be confirmed that the compound P-133 of the present invention has a lower HOMO compared to the comparative compound D. That is, it has a deeper HOMO, which appears to facilitate hole transfer to the phosphorescent host due to the deep HOMO, and thus appears to increase efficiency.

[0416] Table 6 below describes the calculated Reorganization Energy values ​​of Comparative Compound F, Comparative Compound G, and Compound P-134 of the present invention.

[0417] The RE values ​​listed in Table 6 below are RE hole It means the calculated value.

[0418] Compound Reorganization Energy (RE) Comparative Compound F 0.142 Comparative Compound G 0.199 P - 1340.120

[0419] To explain Table 6 in detail above, the compound P-134 of the present invention has a lower RE value compared to comparative compound F and comparative compound G. As a result, it can be confirmed that the hole mobility is very fast. In other words, since it has fast hole mobility, the movement of holes to the host is very smooth, so it appears that the efficiency increases.

[0420] From Tables 4 to 6 above, it can be confirmed that even among compounds with similar compositions, 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 significant effect in organic electrical devices compared to other comparative compounds. Through this, it can be seen that the compound of the present invention, which satisfies all specific compositions, exhibits a significant effect in organic electrical devices compared to other comparative compounds not described in this specification.

[0421] These results suggest that even for compounds with similar molecular components, properties such as hole characteristics, photoelectric efficiency, energy levels, hole injection and mobility characteristics, hole-electron charge balance, volume density, and intermolecular distance can vary significantly and unpredictably depending on the type and position of the substituents. Furthermore, they indicate that device performance may vary due to complex factors rather than being influenced by a single configuration alone.

[0422]

[0423] The foregoing description is merely illustrative of the present invention, and those skilled in the art will be able to make various modifications within the scope of the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to illustrate, not limit, the present invention, and the spirit and scope of the present invention are not limited by such embodiments. The scope of protection of the present invention shall be interpreted by the claims below, and all technology within an equivalent scope shall be interpreted as being included within the scope of rights of the present invention.

[0424] According to the present invention, an organic device having excellent device characteristics of high brightness, high luminescence, and long lifespan can be manufactured, making it industrially applicable.

Claims

1. Compounds represented by the following chemical formula 1 Chemical formula 1 In the above chemical formula 1, X 1 and X 2 are independently O or S, and R 1 , R 2 , R 3 and R 4 Each is identical or different from each other, and independently deuterium; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C1~C 50 Selected from the group consisting of alkyl groups; or multiple adjacent groups may bond to each other to form a ring, R 5 is deuterium, and a, c, and e are independent integers from 0 to 4, and b and d are independent integers from 0 to 3, and Ar 1 and Ar 2 C6~C are independent of each other 60 aryl group of; or C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic of, and, Here, the aryl group, heterocyclic group, fluorenyl group, aliphatic cyclic group, and alkyl group are, respectively, deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group of; C1~C 20 alkoxyl group of; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C6~C 20 aryl group of; C6~C substituted with deuterium 20 aryl group; fluorene group; C2~C 20 The heterocyclic ring of; C3~C 20 of the aliphatic ring; C7~C 20 arylalkyl group of; C8~C 20 The aryl alkene group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; additionally, the hydrogens of these substituents may be further substituted with one or more deuterium atoms; additionally, these substituents may bond with each other to form a ring, wherein 'ring' refers to C3~C 60 aliphatic ring of or C6~C 60 aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes saturated or unsaturated rings.

2. In claim 1, the Ar of the above chemical formula 1 1 and Ar 2 A compound characterized in that at least one of the following is represented by any one of the following chemical formulas A to F. Chemical formula A Chemical formula B Chemical formula C Chemical formula D Chemical formula E Chemical formula F {In the above chemical formulas A to F, 1) R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 They are each identical or different from one another, and independently deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group of; C1~C 20 alkoxyl group of; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C6~C 20 aryl group of; C6~C substituted with deuterium 20 aryl group; fluorene group; C2~C 20 The heterocyclic ring of; C3~C 20 of the aliphatic ring; C7~C 20 arylalkyl group of; C8~C 20 The aryl alkene group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and the hydrogens of these substituents may be further substituted with one or more deuterium atoms, and 2) X 3 is O; S; or CR a R b ; and, 3) R a and R b C6~C are independent of each other 20 aryl group of; C2~C 20 The heterocyclic group of; or C1~C 20 The alkyl group of; and R a and R b They can combine with each other to form a ring, 4) g, h, j, k and m are independent integers from 0 to 4, f is an integer from 0 to 3, and i, l and n are independent integers from 0 to 5, and * indicates the position where N is joined.

3. A compound according to claim 1, characterized in that the compound represented by Chemical Formula 1 is any one of the following compounds.

4. An organic electric device comprising a first electrode; a second electrode; and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a single compound represented by Chemical Formula 1 of Claim 1 or two or more compounds.

5. An organic electrical device according to claim 4, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emission assist layer, a light emission layer, an electron transport assist layer, an electron transport layer, and an electron injection layer.

6. An organic electric device according to claim 4, characterized in that the organic layer is a light-emitting auxiliary layer.

7. An organic electric device according to claim 4, further comprising a light efficiency improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic layer.

8. An organic electric device according to claim 4, wherein 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 a first electrode.

9. An organic electric device according to claim 8, wherein the organic layer further comprises a charge generating layer formed between the two or more stacks.

10. An electronic device comprising: a display device including the organic electric element of claim 4; and a control unit for driving the display device.

11. An electronic device according to claim 10, wherein the organic electric device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photosensitive material (OPC), an organic transistor, a device for monochromatic or white lighting, and a device for a quantum dot display.

12. An electronic device according to claim 10, characterized in that the electronic device is any one of a wired communication terminal, a wireless mobile communication terminal, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game console, a TV, a computer, a watch, a tablet, and a virtual reality (VR) device.

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

Images