Compounds for use in organic electronic components, organic electronic components using said compounds, and electronic devices thereof.

Abstract

This invention provides: novel compounds that can improve the luminous efficiency, stability and lifespan of components; organic electrical components using said compounds; and electronic devices thereof.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic components, organic electronic components using the compounds, and electronic devices thereof. Background Technology

[0002] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electronic components utilizing organic light emission generally have a structure comprising an anode, a cathode, and layers of organic material inserted therebetween. To increase the efficiency and stability of the organic electronic components, the organic material layers are typically composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic material layers in organic electronic components can be classified according to their function into luminescent materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Furthermore, luminescent materials can be classified according to molecular weight into high molecular weight and low molecular weight types, and according to their luminescence mechanism into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons. In addition, luminescent materials can be classified according to their emission color into materials that emit blue light, materials that emit green light, and materials that emit red light, as well as materials that emit yellow light and materials that emit orange light, which are necessary for achieving better natural colors.

[0004] However, when only one material is used as the luminescent material, the maximum emission wavelength shifts to a longer wavelength due to intermolecular interactions, and there is a problem of reduced color purity or device efficiency due to emission attenuation effects. Therefore, to increase color purity and luminous efficiency through energy transfer, a host / dopant system can be used as the luminescent material. The principle is that when a small amount of dopant with a smaller band gap than the host forming the luminescent layer is mixed into the luminescent layer, excitons generated in the luminescent layer are transferred to the dopant for efficient luminescence. Here, since the wavelength of the host shifts to the wavelength band of the dopant, light with the desired wavelength can be obtained depending on the type of dopant used.

[0005] Currently, the portable display market is dominated by large displays, and their sizes are increasing daily, thus requiring significantly more power than existing portable displays. Therefore, power consumption becomes a critical factor for portable displays with limited power supplies such as batteries, and issues of efficiency and lifespan must also be addressed.

[0006] Efficiency, lifetime, and drive voltage are interrelated. As efficiency increases, the drive voltage relatively decreases. With a lower drive voltage, the crystallization of the organic material decreases due to Joule heating generated during operation, leading to a tendency for increased lifetime. However, efficiency cannot be maximized simply by improving the organic material layers. This is because long lifetime and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between the organic material layers, as well as the intrinsic properties of the material (mobility, interfacial properties, etc.), are optimally combined.

[0007] Therefore, although it delays the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer (which is one of the reasons for the shortened lifespan of organic electronic components), it should have stable properties to resist the Joule heat generated during device operation. Furthermore, since OLED devices are mainly formed by deposition methods, it is necessary to develop materials that can withstand long-term deposition, i.e., materials with strong heat resistance.

[0008] In other words, to fully realize the superior properties of organic electronic components, priority should be given to materials that are stable and effective in constituting the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials. However, the development of stable and effective organic material layer materials for organic electronic components has not yet been fully realized. Therefore, there is a continuous need to develop new materials, and specifically, there is an urgent need to develop host materials for light-emitting layers. Summary of the Invention

[0009] Overview

[0010] To address the aforementioned problems in the background technology, the present invention has discovered compounds with novel structures, and further found that when these compounds are applied to organic electronic components, they can significantly improve the luminous efficiency, stability, and lifespan of the components.

[0011] Therefore, the object of the present invention is to provide a novel compound, an organic electronic component using the compound, and an electronic device thereof.

[0012] Technical solution

[0013] The present invention provides compounds represented by Formula 1.

[0014] Formula 1

[0015] In another aspect, the present invention provides organic electronic components and electronic devices thereof comprising compounds represented by Formula 1.

[0016] Invention Effects

[0017] By using the compounds according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the element can be achieved, and the color purity and lifespan of the element can be greatly improved. Attached Figure Description

[0018] Figures 1 to 3 This is an exemplary view of an organic electroluminescent device according to the present invention.

[0019] Figure 4 This is one aspect of the invention.

[0020] 100, 200, 300: Organic electronic components; 110: First electrode

[0021] 120: Hole injection layer; 130: Hole transport layer

[0022] 140: Emissive layer; 150: Electron transport layer

[0023] 160: Electron injection layer; 170: Second electrode

[0024] 180: Light efficiency enhancement layer; 210: Buffer layer

[0025] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0026] 330: First hole transport layer; 340: First luminescent layer

[0027] 350: First electron transport layer; 360: First charge generation layer

[0028] 361: Second charge generation layer; 420: Second hole injection layer

[0029] 430: Second hole transport layer; 440: Second luminescent layer

[0030] 450: Second electron transport layer; CGL: Charge generation layer

[0031] ST1: First stack; ST2: Second stack Detailed Implementation

[0032] Some embodiments of the invention will be described in detail below. Furthermore, in the following description of the invention, detailed descriptions of known functions and configurations incorporated herein will be omitted where such descriptions might make the subject matter of the invention quite unclear.

[0033] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b) may be used herein. Each of these terms is not intended to define the substance, order, or sequence of the respective component, but only to distinguish the respective component from other components. It should be noted that if a component is described as “connected,” “linked,” or “attached” to another component, the component may be directly connected to or connected to other components, but may be “connected,” “linked,” or “attached” between components.

[0034] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0035] Unless otherwise stated, the terms “halogenated” or “halogen” as used herein include fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0036] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein means having a single bond of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, and refers to a saturated aliphatic functional group, including straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups (alicyclic), alkyl-substituted cycloalkyl groups, or cycloalkyl-substituted alkyl groups.

[0037] Unless otherwise stated, the term "alkenyl" or "alkynyl" as used herein means, but is not limited to, having a double or triple bond of 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, and includes straight-chain or branched groups.

[0038] Unless otherwise stated, the term "cycloalkyl" as used herein means, but is not limited to, an alkyl group 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.

[0039] Unless otherwise stated, the terms “alkoxy group”, “alkoxy group” or “alkyloxy group” as used herein mean, but are not limited to, an alkyl group bonded to an oxygen group and 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.

[0040] Unless otherwise stated, the term "aryloxy group" or "aryloxy group" as used herein means, but is not limited to, an aryl group bonded to an oxygen group and 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.

[0041] Unless otherwise stated, the terms "aryl group" and "arylene group" as used in this invention refer to groups 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, but are not limited thereto. In this invention, an aryl group or arylene group refers to a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by the bonding or reaction of adjacent substituents. For example, an aryl group can be a phenyl, biphenyl, fluorene, or spirofluorene group.

[0042] The prefix “aryl” or “aromatic” indicates a group that is substituted by an aryl group. For example, an arylalkyl group can be an aryl-substituted alkyl group, and an arylalin group can be an aryl-substituted alkenyl group, and the aryl-substituted group has the number of carbon atoms as defined herein.

[0043] Furthermore, when prefixes are named sequentially, this means that substituents are listed in the order they are first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0044] Unless otherwise stated, the term "heterocyclic group" as used herein contains one or more heteroatoms and has 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, and includes any of monocyclic or polycyclic rings, and may include heteroaliphatic and heteroaromatic rings. Furthermore, it may form a heterocyclic group together with adjacent groups.

[0045] Unless otherwise stated, the term "heteroatom" as used herein means at least one of N, O, S, P, or Si.

[0046] In addition, "heterocyclic group" refers to monocyclic rings, cyclic aggregates, fused polycyclic systems, spirocyclic compounds, etc., containing heteroatoms. Furthermore, compounds containing heteroatom groups (e.g., SO2, P=O, etc.) instead of ring-forming carbon atoms (e.g., the following compounds) may also be included in heterocyclic groups. For example, "heterocyclic group" includes the following compounds.

[0047]

[0048] The term "aliphatic cyclic group" as used in this invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic rings, cyclic aggregates, fused polycyclic systems, spirochetes, etc., and means, but is not limited to, rings 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. For example, even when benzene (an aromatic ring) and cyclohexane (a non-aromatic ring) are fused, it is still an aliphatic ring.

[0049] Unless otherwise stated, the terms "fluorenyl group," "fluoreneyl group," or "fluorenetrimethyl group" as used herein mean a functional group in which R, R', and R'' are all monovalent, divalent, or trivalent hydrogens, and the terms "substituted fluorenyl group," "substituted fluoreneyl group," or "substituted fluorenetrimethyl group" mean that at least one of the substituents R, R', and R'' is a substituent other than hydrogen, including those in which R and R' are bonded to each other to form a spiro compound with the carbon atoms to which they are bonded. In this specification, fluorenyl groups, fluoreneyl groups, and fluorenetrimethyl groups may all be referred to as fluorenyl groups, regardless of their valence.

[0050]

[0051] The term "spirocyclic compound" as used in this invention has the connotation of "spiral connection," and a spiral connection refers to a connection formed by two rings that share only one atom. In this case, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in the compound, they are respectively referred to as "single-spiro," "double-spiro," and "triple-spiro" compounds.

[0052] Unless otherwise stated, as used herein, the term "aliphatic" 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.

[0053] Unless otherwise stated, as used herein, the term "ring" means an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heterocycle having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, or a fused ring formed by combinations thereof, including saturated or unsaturated rings.

[0054] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups contain, but are not limited to, one or more hetero atoms.

[0055] Furthermore, unless explicitly stated otherwise, the term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from deuterium, halogens, amino groups, nitrile groups, nitro groups, C1-C6 groups, and C2-C4 groups. 20 Alkyl groups, C1-C 20 alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 aryl group, deuterated C6-C 20 aryl group, C8-C 20 Aryl alkenyl groups, silyl groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but not limited to these substituents.

[0056] In this specification, the 'group name' corresponding to aryl groups, arylide groups, heterocyclic groups, etc., as an example of each symbol and its substituents, can be written as 'the name of the group reflecting the valence', but it can also be written as 'the name of the parent compound'. For example, in the case of 'phenanthrene' (a type of aryl group), the group name can be written by distinguishing the valence, such as the monovalent 'group' being 'phenanthrene' and the divalent group being 'arypheneyl', but it can be written as the name of the parent compound 'phenanthrene', regardless of its valence. Similarly, in the case of pyrimidine, it can be written as 'pyrimidine', regardless of its valence, or it can be written as 'the name of the group with the valence', such as pyrimidinyl in the case of a monovalent group, pyrimidinyl in the case of a divalent group, etc.

[0057] Additionally, in this specification, numbers or letters indicating positions may be omitted when describing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine is written as pyridopyrimidine, benzofurano[2,3-d]pyrimidine is written as benzofuranopyrimidine, and 9,9-dimethyl-9H-fluorene can be described as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzo[g]quinoxaline.

[0058] Furthermore, unless otherwise explicitly explained, the formulas used in this invention are identical to the definitions of substituents through the following exponent definition.

[0059]

[0060] Here, when a is an integer of 0, the substituent R 1 There is no unique substituent R when a is an integer of 1. 1 When a is an integer of 2 or 3, the carbon atom attached to any one of the carbon atoms forming the benzene ring can be combined in the following ways, where R 1 They can be the same or different from each other. When a is an integer from 4 to 6, they are bonded to the carbons of the benzene ring in a similar manner, but the indication of the hydrogens bonded to the carbons that form the benzene ring is omitted.

[0061]

[0062] Unless otherwise explicitly stated, the terms “ortho,” “meta,” and “para” as used in this invention refer to the substitution positions of all substituents, with the ortho position meaning the position of the substituent immediately adjacent to the compound, for example, when using benzene, it means position 1 or 2, and the meta position is the next substitution position after the adjacent substitution position, representing position 1 or 3 when benzene is used as an example, and the para position is the next substitution position after the meta position, meaning position 1 and 4 when benzene is used as an example. More detailed examples of substitution positions are given below, and it can be confirmed that the ortho and meta positions are substituted in a non-linear manner and the para position is substituted in a linear manner.

[0063] [Examples of adjacent positions]

[0064] [Examples of interposition]

[0065] [Example of alignment]

[0066] The term "composition" as used in this invention is intended to be interpreted broadly as including not only compounds, but also solutions, dispersions, liquids, and solid mixtures (mixtures, admixtures). A composition of this invention may contain only a compound of this invention, or the compound may be contained in a combination of two or more different types, or the compound may be contained in combination with two or more other compounds. In other words, a composition may contain only a compound corresponding to Formula 1, may contain a mixture of two or more compounds of Formula 1, or may contain a mixture of a compound of Formula 1 and a compound not corresponding to this invention. The compound not corresponding to this invention may be a single compound or two or more compounds. When a compound is contained in combination with two or more other compounds, the other compounds may be known compounds of each organic material layer or compounds to be developed in the future. The compounds contained in the organic material layer may consist only of compounds of the same type, but may also be a mixture of two or more types of heterogeneous compounds represented by Formula 1.

[0067] Hereinafter, compounds according to one aspect of the invention and organic electronic components comprising such compounds will be described.

[0068] Formula 1

[0069] Formula A, Formula B, Formula Q

[0070] in: A is the substituent represented by formula A. B is a substituent represented by the formula B.

[0071] Ring C is C 10 -C 60 aryl group, and can be further reacted with one or more R 6 replace, The preferred ring C is C. 10 -C 60 Aryl group, more preferably C 10 -C 25 aryl group, C 10 -C 18 aryl group or C 10 -C 12 Aryl groups, such as naphthalene, phenanthrene, anthracene, benzo[c]phenanthrene, etc.

[0072] Q is a substituent represented by the formula Q, provided that R 4 Or R 5 Connect to L a , L 1 L2 L 3 and L a Independently selected from single bonds; C6-C 60 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; Where L 1 L 2 L 3 and L a When the group is arylene, C6-C is preferred. 30 aryl groups, more preferably C6-C 25 arylene group, C6-C 18 arylene group or C6-C 12 Aromatic groups, such as phenylene group, biphenylene group, naphthylene group, terphenylene group, anthracene group, phenanthrene group, etc.

[0073] Where L 1 L 2 L 3 and L a When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic group, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0074] Where L 1 L 2 L 3 and L a When the group is a fused cyclic group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0075] Ar 1 Independently selected from C6-C 60aryl groups; fluorenyl groups; and C2-C groups containing at least one heteroatom selected from O, N, S, Si, or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; Among them, when Ar 1 When it is an aryl group, C6-C is preferred. 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 18 aryl group or C6-C 12 Aryl groups, such as phenyl groups, biphenyl groups, terphenyl groups, naphthalene, phenanthrene, benzo[c]phenanthrene, anthracene, benzo[c]phenanthrene, etc.

[0076] Among them, when Ar 1 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic group, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0077] When Ar1 is a fused cyclic group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0078] X is O, S, or CR. 30 R 31 , Y is either O or S. Z is O, S, or NR. 32 , R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 Independently selected from hydrogen; deuterium; halogen; C6-C 60aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C3-C 60 Cycloalkyl groups; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 20 alkoxy groups; and C6-C 30 aryloxy group; or multiple adjacent R groups 1 Multiple adjacent R 2 Multiple adjacent R 3 Multiple adjacent R 4 Multiple adjacent R 5 and multiple adjacent R 6 They can bond together to form a ring, or R 30 and R 31 They can bond together to form a helical ring. Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When it is an aryl group, C6-C is preferred. 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 18 aryl group or C6-C 12 Aryl groups, such as phenyl groups, biphenyl groups, terphenyl groups, naphthyl, phenanthrene, etc.

[0079] Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic group, C2-C 18 Heterocyclic groups, or C2-C 12Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0080] Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When the group is a fused cyclic group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0081] Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When the group is a cycloalkyl group, C3-C is preferred. 30 Cycloalkyl groups, more preferably C3-C 25 Cycloalkyl groups, C3-C 18 Cycloalkyl groups or C3-C 12 Cycloalkyl groups, such as cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0082] Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When the group is an alkyl group, C1-C is preferred. 30 Alkyl groups, more preferably C1-C 25 Alkyl groups, C1-C 18 alkyl groups or C1-C 12Alkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, etc.

[0083] Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When the group is an alkoxy group, C1-C is preferred. 25 Alkoxy groups, more preferably C1-C 18 alkoxy group or C1-C 12 alkoxy group, Where R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 When the group is aryloxy group, C6-C is preferred. 25 aryloxy groups, more preferably C6-C 18 aryloxy group or C6-C 12 Aryloxy group.

[0084] a and b are integers from 0 to 3, and c and d are independent integers from 0 to 4. Indicates the position to be bonded. The aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenyl group, the fused cyclic group, the cycloalkyl group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, and the aryloxy group may be substituted by one or more substituents selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 The substituents are alkylaryl groups; and the hydrogen atoms of these substituents may be further substituted with one or more deuterium atoms; and the substituents may bond to each other to form saturated or unsaturated rings, wherein the term "ring" means C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by combinations thereof.

[0085] Furthermore, ring C is represented by any one of the following formulas C-1 to C-15.

[0086] Formula C-1 Formula C-2 Formula C-3 Formula C-4

[0087] Formula C-5, Formula C-6, Formula C-7, Formula C-8

[0088] Formula C-9, Formula C-10, Formula C-11, Formula C-12

[0089] Formula C-13 Formula C-14 Formula C-15

[0090] in: R 7 R 8 R 9 R 10 and R 11 Independently identical or different from each other and independently selected from hydrogen; deuterium; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic rings and C6-C 20 Fused ring groups of aromatic rings; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 20 alkoxy groups; and C6-C 20 An aryloxy group; or multiple adjacent groups thereof may bond together to form a ring. e is an integer from 0 to 6, f and g are independently integers from 0 to 8, and h and i are independently integers from 0 to 10. This indicates the location where bonding is to take place.

[0091] Furthermore, equation A can be represented by any one of the following equations A-1 to A-4.

[0092] Formula A-1 Formula A-2

[0093] Formula A-3 Formula A-4

[0094] in: Rings C, X, R 3 and Same as defined above, c' is an integer from 0 to 3.

[0095] Furthermore, equation B is represented by any one of the following equations B-1 to B-16.

[0096] Formula B-1 Formula B-2

[0097] Formula B-3 Formula B-4

[0098] Type B-5 Type B-6

[0099] Type B-7 Type B-8

[0100] Type B-9 Type B-10

[0101] Type B-11 Type B-12

[0102] Type B-13 Type B-14

[0103] Type B-15 Type B-16

[0104] in: Y, Q, R 1 R 2 L a a, b and Same as defined above.

[0105] Furthermore, Q can be represented by any one of the following formulas, from Q-1 to Q-5.

[0106] Formula Q-1 Formula Q-2 Formula Q-3 Formula Q-4

[0107] Type Q-5

[0108] in: R 4 R 5 Z, d and Same as defined above, R 12 With R 1 The definitions are the same. j is an integer between 0 and 3.

[0109] Furthermore, Ar1 is represented by any one of the following formulas: Ar-1 to Ar-10.

[0110] Formula Ar-1 Formula Ar-2 Formula Ar-3 Formula Ar-4

[0111] Formula Ar-5 Formula Ar-6 Formula Ar-7

[0112] Formula Ar-8 Formula Ar-9 Formula Ar-10

[0113] in: W is O, S, or C(R) 33 (R) 34 ), R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 R 21 R 22 R 23 R 33 and R 34 With R 7 The definitions are the same, or multiple adjacent R 13 Multiple adjacent R 14 Multiple adjacent R 15 Multiple adjacent R 16 Multiple adjacent R 17Multiple adjacent R 18 Multiple adjacent R 19 Multiple adjacent R 20 Multiple adjacent R 21 Multiple adjacent R 22 and multiple adjacent R 23 They can bond together to form a ring, or R 33 With R 34 They can bond together to form a helical ring. R a Selected from C6-C 60 aryl group; C2-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; C1-C 50 Alkyl group; C2-C 20 alkenyl groups; and C2-C 20 alkynyl group; R b Selected from hydrogen; deuterium; C6-C 60 aryl group; C2-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; or R a and R b They can bond together to form a helical ring. Where R a and R b When it is an aryl group, C6-C is preferred. 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 18 aryl group or C6-C 12 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0114] Where R a and R b When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic group, C2-C 18 Heterocyclic groups or C2-C 12Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0115] Where R a and R b When the group is an alkyl group, C1-C is preferred. 30 Alkyl groups, more preferably C1-C 25 Alkyl groups, C1-C 18 alkyl groups or C1-C 12 Alkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, etc.

[0116] k is an integer from 0 to 5, l, p, q, s, t, and u are independently integers from 0 to 4, m is an integer from 0 to 7, n is an integer from 0 to 9, and o and r are independently integers from 0 to 3. This indicates the location where bonding is to take place.

[0117] In addition, L a L 1 L 2 and L 3 Any one of the following expressions L-1 to L-20.

[0118] [Equation L-1] [Equation L-2] [Equation L-3]

[0119] [Equation L-4] [Equation L-5] [Equation L-6]

[0120] [Equation L-7] [Equation L-8] [Equation L-9]

[0121] [Equation L-10] [Equation L-11] [Equation L-12] [Equation L-13]

[0122] [Equation L-14] [Equation L-15] [Equation L-16] [Equation L-17]

[0123] [Equation L-18] [Equation L-19] [Equation L-20]

[0124] in: R 24 R 25 R 26 R 27 R 28 and R 29 With R 7 The definitions are the same. W is the same as above. v, w, x, z, and aa are independent integers from 0 to 4, and y is an integer from 0 to 6. This indicates the location where bonding is to take place.

[0125] Specifically, the compound represented by Formula 1 can be any one of the following compounds P-1 to P-130, but is not limited thereto.

[0126]

[0127] In another aspect, the present invention provides a composition for organic electronic components comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 2.

[0128] <Equation 2>

[0129] in: X A X B and X C Independently is CR a Or N, However, X A X B and X C At least one of them is N, and preferably, at least two are N. Ar A Ar B and Ar C Independently selected from C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Cycloalkyl groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; Among them, when Ar A Ar B and Ar C When it is an aryl group, C6-C is preferred. 30 Aryl groups, more preferably C6-C 25 Aryl group, C6-C 18 aryl group or C6-C 12 When aryl groups are involved, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0130] Among them, when Ar A Ar Band Ar C When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic group, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0131] Among them, when Ar A Ar B and Ar C When the group is a cycloalkyl group, C3-C is preferred. 30 Cycloalkyl groups, more preferably C3-C 24 Cycloalkyl groups.

[0132] Among them, when Ar A Ar B and Ar C When the group is a fused cyclic group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0133] L A L B and L C Independently selected from single bonds; C6-C 60 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; Where L A L B and L C When the group is arylene, C6-C is preferred. 30 aryl groups, more preferably C6-C 25 arylene group, C6-C 18 arylene group or C6-C 12 Aromatic groups, such as phenylene, biphenylene, naphthylene, terphenylene, anthraceneylene, phenanthrene, etc.

[0134] Where L A L B and L C When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic group, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0135] Where L A L B and L C When the group is a fused cyclic group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0136] R a It is hydrogen; or deuterium; The aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorene group, the cycloalkyl group, and the fused cyclic group may be replaced by one or more substituents selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C... 20 Alkyl thio group; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 Alkyl aryl groups; and the hydrogens of these substituents can be further replaced by one or more deuteriums or C6-C atoms. 20The aryl group is substituted; and the substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" means C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by combinations thereof.

[0137] In addition, Ar A Ar B and Ar C At least one of the following is represented by any one of the following formulas: Ar-a to Ar-d.

[0138] Formula Ar-a Formula Ar-b

[0139] Formula Ar-c Formula Ar-d

[0140] in: Y A Y B and Y C Independently, they are O, S, and NR. 1A or CR 1B R 1C , R A R B R C R D R E R F R 1A R 1B and R 1C Independently identical or different from each other and independently selected from hydrogen; deuterium; halogen; cyano group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 20 alkoxy groups; and C6-C 20 aryloxy group; or multiple adjacent R groups A Multiple adjacent R B Multiple adjacent R C Multiple adjacent R D Multiple adjacent R E Multiple adjacent R FThey can bond together to form a ring. ta and tc are independent integers from 0 to 3, tb and td are independent integers from 0 to 4, te is an independent integer from 0 to 5, and tf is an independent integer from 0 to 7. This indicates the location where bonding is to take place.

[0141] The formula Ar-a is represented by any one of the following formulas Ar-a-1 to Ar-a-4.

[0142] <Formula AR-a-1> <Formula AR-a-2>

[0143] <Formula AR-a-3> <Formula AR-a-4>

[0144] in: R A R B Y A ,ta,tb and Same as defined in Ar-a.

[0145] The formula Ar-b is represented by either formula Ar-b-1 or formula Ar-b-2.

[0146] <Formula Ar-b-1> <Formula Ar-b-2>

[0147] in: R C R D Y B Y C , tc, td and Same as defined in Ar-b.

[0148] The formula Ar-d is represented by the following formulas Ar-d-1 or Ar-d-2.

[0149] <Formula Ar-d-1> <Formula Ar-d-2>

[0150] in: R F , tf and Same as defined in Ar-d.

[0151] L in Equation 2 A L B and L C It is represented by a single bond or one of the following formulas b-1 to b-13.

[0152] Formula b-1 Formula b-2 Formula b-3 Formula b-4 Formula b-5 Formula b-6

[0153] Formula b-7 Formula b-8 Formula b-9 Formula b-10

[0154] Formula b-11 Formula b-12 Formula b-13

[0155] in: Z 10 It is O, S, NR 1D or CR 1E R 1F , a”, c”, d”, e”, and i” are independent integers from 0 to 4, b” is an integer from 0 to 6, f” and g” are independent integers from 0 to 3, h” is an integer from 0 to 2, and j” is an integer of 0 or 1. R a1 R a2 R a3 R a4 R a5 R a6 R a7 R 1D R 1E and R 1F Independently identical or different from each other and independently selected from hydrogen; deuterium; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy groups; and C6-C 30 An aryloxy group; or multiple adjacent groups thereof may bond together to form a ring. Z 49 Z 50 and Z 51 Independently is CR 1g Or N, However, Z 49 Z 50 and Z 51 At least one of them is N, and R 1g With R A The definitions are the same.

[0156] This indicates the location where bonding is to take place.

[0157] Specifically, the compound of Formula 2 can be any one of the following compounds N-1 to N-276, but is not limited thereto.

[0158]

[0159] Preferably, the composition for organic electronic components can be the host for the light-emitting layer.

[0160] In another aspect, the present invention provides an organic electronic element comprising a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; wherein the organic material layer comprises a compound represented by Formula 1 or a composition for the organic electronic element, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 2.

[0161] In another aspect, the present invention provides a method for reusing compounds of formula 1, the method comprising: Crude organic light-emitting materials containing compounds of formula 1 are recovered from a deposition apparatus used in a process for depositing organic light-emitting materials to prepare organic light-emitting devices. Remove impurities from coarse organic light-emitting materials; Recovering organic light-emitting materials after removing impurities; and Purify the recovered organic light-emitting materials to a purity of 99.9% or higher.

[0162] The step of removing impurities from the crude organic light-emitting material recovered from the deposition equipment may preferably include a pre-purification process by recrystallization in a recrystallization solvent to obtain a purity of 98% or higher.

[0163] The recrystallization solvent is preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0164] The recrystallization solvent is preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0165] The recrystallization solvent can preferably be used by mixing a polar solvent having a polarity value of 5.5 to 7.2 and a non-polar solvent having a polarity value of 2.0 to 4.7.

[0166] When using a mixture of polar and nonpolar solvents, the recrystallization solvent can be used at 15% (v / v) or less of the nonpolar solvent compared to the polar solvent.

[0167] The recrystallization solvent is preferably a single solvent of N-methylpyrrolidone (NMP); or a polar solvent in which any one selected from 1,3-dimethyl-2-imidazolium ketone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide and dimethyl sulfoxide is mixed into N-methylpyrrolidone; or a single nonpolar solvent; or a mixture of nonpolar solvents; selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate and butanone; or a mixture of polar and nonpolar solvents.

[0168] The pre-purification process may include dissolving the crude organic light-emitting material recovered from the deposition equipment in a polar solvent at 90°C to 120°C, and then precipitating crystals by cooling to 0°C to 5°C.

[0169] The pre-purification process may include dissolving the crude organic light-emitting material recovered from the deposition equipment in a polar solvent at 90°C to 120°C, followed by adding a non-polar solvent and then cooling to 35°C to 40°C to precipitate crystals.

[0170] The pre-purification process may include the steps of precipitating crystals while concentrating and removing the nonpolar solvent after dissolving the crude organic light-emitting material recovered from the deposition device in a nonpolar solvent.

[0171] The pre-purification process may include a step of recrystallizing with a polar solvent followed by recrystallization with a non-polar solvent.

[0172] The step of purifying the recovered impurities to a purity of 99.9% or higher may include an adsorption separation process to adsorb and remove the impurities by adsorption on an adsorbent.

[0173] The adsorbent can be activated carbon, silica gel, alumina, or other materials used for known adsorption purposes.

[0174] The step of purifying the recovered impurities to a purity of 99.9% or higher may include sublimation purification.

[0175] refer to Figure 1 An organic electronic component (100) according to one embodiment of the present invention includes a first electrode (110), a second electrode (120), and an organic material layer comprising a single compound or two or more compounds represented by Formula 1 between the first electrode (110) and the second electrode (170). Here, the first electrode may be an anode or a positive electrode, and the second electrode may be a cathode or a negative electrode. In the case of an inverted organic electronic component, the first electrode may be a cathode, and the second electrode may be an anode.

[0176] The organic material 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). Here, layers other than the light-emitting layer (140) may not be formed. The organic material layer may also 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., can be used as a hole blocking layer (see [reference]). Figure 2 ).

[0177] Furthermore, the organic electronic component according to an embodiment of the present invention may also include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer is formed on one of the two surfaces of the first electrode that is not in contact with the organic material layer, or on one of the two surfaces of the second electrode that is not in contact with the organic material layer. Compounds or materials suitable for the organic material layer according to an embodiment of the present invention for organic electronic components can be used as a host or dopant for hole injection layer (120), hole transport layer (130), light emission auxiliary layer (220), electron transport auxiliary layer, electron transport layer (150), electron injection layer (160), light emission layer (140), or as a material for the light efficiency enhancement layer. Preferably, for example, a composition for organic electronic components comprising a compound according to Formula 1 of the present invention or a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 can be used as the host material for the light emission layer.

[0178] The organic material layer may include two or more stacks, each stack comprising a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on an anode, and may further include a charge-generating layer formed between the two or more stacks (see [link to documentation]). Figure 3 ).

[0179] Furthermore, even when using the same core, band gap, electrical properties, and interfacial properties can vary depending on the position of the substituents. Therefore, the choice of core and the combination of its associated substituents are also very important. In particular, when the optimal combination of the energy level and T1 value of each organic material layer and the unique properties of the material (mobility, interfacial properties, etc.) is achieved, both long service life and high efficiency can be realized simultaneously.

[0180] The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a conductive metal or metal oxide or alloy thereof is deposited on a substrate to form a cathode, and an organic material layer comprising a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) is formed thereon, and then a material that can be used as a cathode is deposited thereon.

[0181] Furthermore, the present invention provides an organic electronic component, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process, and the organic material layer contains a compound or material for the organic electronic component as an electron transport material.

[0182] As another specific example, compounds of the same or different types represented by Formula 1 are mixed and used in an organic material layer. Preferably, the organic material layer comprises a light-emitting layer and may contain a compound represented by Formula 1, or a composition for an organic electrical device containing a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 as the light-emitting layer.

[0183] Furthermore, the present invention provides compositions for organic electronic components, the compositions comprising compounds represented by Formula 1, or mixtures of compounds represented by Formula 1 and compounds represented by Formula 2, and provides organic electronic components comprising the compositions.

[0184] Furthermore, the present invention also provides an electronic device, the electronic device including a display device comprising organic electronic components; and a control unit for driving the display device.

[0185] According to another aspect, the present invention provides a display device in which the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor (organic TFT), and an element for monochrome or white illumination. Here, the electronic device can be a wired / wireless communication terminal currently in use or to be used in the future, and encompasses all kinds of electronic devices, including mobile communication terminals such as portable telephones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMP) devices, remote controllers, navigation units, game consoles, various televisions (TVs), and various computers.

[0186] The following examples will describe in detail, through embodiments, examples of the synthesis of compounds represented by Formulas 1 and 2 and examples of the preparation of organic electronic components of the present invention, but are not limited to the following examples.

[0187] [Synthesis example 1]

[0188] The compound (final product) represented by Formula 1 according to the present invention is synthesized as in reaction scheme 1, but is not limited thereto.

[0189] <Reaction Scheme 1>

[0190] In reaction scheme 1, Hal is I, Br, or Cl.

[0191] I. Synthesis of Sub1

[0192] 1. Synthesis example of Sub 1-2

[0193] In a round-bottom flask, dissolve Sub 1-2a (50.0 g, 159.6 mmol) in toluene (532 mL), then add Sub 1-2b (36.0 g, 159.6 mmol), Pd2(dba)3 (4.4 g, 4.8 mmol), and P( t -Bu)3 (1.9 g, 9.6 mmol), NaO t -Bu (30.7 g, 319.3 mmol) was added and stirred at 120 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting compound was recrystallized after column chromatography to obtain 50.1 g of product (yield 68.7%).

[0194] 2. Synthesis examples of Sub 1-5

[0195] Using the same method as Sub 1-2, in round-bottom flasks, react Sub 1-5a (50.0 g, 168.3 mmol) and Sub 1-5b (16.5 g, 168.3 mmol), Pd2(dba)3 (4.6 g, 5.0 mmol), P( t -Bu)3 (2.0 g, 10.1 mmol), NaO t The experiment was conducted using Bu (32.3 g, 333.5 mmol) and toluene (560 mL), yielding 34.5 g of product. (Yield: 65.4%)

[0196] 3. Synthesis examples of Sub 1-12

[0197] Using the same method as Sub 1-2, in round-bottom flasks, react Sub 1-12a (50.0 g, 168.9 mmol) and Sub 1-12b (15.7 g, 168.9 mmol), Pd2(dba)3 (4.6 g, 5.1 mmol), P( t -Bu)3 (2.1 g, 10.1 mmol), NaO t The experiment was conducted using Bu (32.5 g, 337.9 mmol) and toluene (563 mL), yielding 35.0 g of product. (Yield: 67.1%)

[0198] 4. Synthesis examples in Sub 1-27

[0199] 1) Composition of sub 1-27-int1

[0200] Sub 1-27a (50.0 g, 190.8 mmol) was dissolved in toluene (635 mL) in a round-bottom flask. Sub 1-27b (61.2 g, 209.9 mmol), Pd(PPh3)4 (6.6 g, 5.7 mmol), K2CO3 (39.6 g, 286.2 mmol), ethanol (63 mL), and water (210 mL) were added, and the reaction was carried out at 80 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting compound was recrystallized after column chromatography to give 40.92 g of product (50.1% yield).

[0201] 2) Synthesis of sub 1-27

[0202] Using the same method as Sub 1-2, in a round-bottom flask, the concentrations of Sub 1-27-int1 (40.9 g, 95.6 mmol) and Sub 1-27c (8.9 g, 95.6 mmol), Pd2(dba)3 (2.6 g, 2.9 mmol), and P( t -Bu)3 (1.2g, 5.7 mmol), NaO t The experiment was conducted using Bu (18.4 g, 191.2 mmol) and toluene (318 mL), yielding 44.1 g of product. (Yield: 70.5%)

[0203] 5. Synthesis examples of Sub 1-43

[0204] Using the same method as Sub 1-2, in round-bottom flasks, react Sub 1-43a (50.0 g, 168.3 mmol) and Sub 1-43b (16.5 g, 168.3 mmol), Pd2(dba)3 (4.6 g, 5.0 mmol), P( t -Bu)3 (2.0 g, 10.1 mmol), NaO t The experiment was conducted using Bu (32.3 g, 336.5 mmol) and toluene (560 mL), yielding 36.6 g of product. (Yield: 69.4%)

[0205] 6. Synthesis examples of Sub 1-45

[0206] 1) Composition of sub 1-45-int1

[0207] In a round-bottom flask, Sub 1-45a (100.0 g, 353.1 mmol) was dissolved in benzene-d6 (891.6 mL), followed by the dropwise addition of trifluoromethanesulfonic acid (62.3 mL, 706.3 mmol), and the reaction was carried out at room temperature. When the reaction was complete, the mixture was neutralized with water and Na₂CO₃ (112.3 g, 1059.4 mmol). After neutralization, the mixture was extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated, and then recrystallized using a silica gel column to give 98.1 g of product (yield 94.5%).

[0208] 2) Composition of sub 1-45-int2

[0209] In a round-bottom flask, Sub 1-45-int1 (98.1 g, 304.4 mmol) was dissolved in toluene-DMSO (590 mL), and aN3 (39.58 g, 608.9 mmol), Cu2O (43.5 g, 304.4 mmol), and L-proline (45.6 g, 395.8 mmol) were added. The reaction was carried out at 130 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting compound was recrystallized after column chromatography to give 42.10 g of product (60.1% yield).

[0210] 3) Synthesis of sub 1-45

[0211] Using the same method as Sub 1-2, in a round-bottom flask, react Sub 1-45-int2 (42.1 g, 182.9 mmol) and Sub 1-45b (63.3 g, 182.9 mmol), Pd2(dba)3 (5.0 g, 5.5 mmol), P( t -Bu)3 (2.2 g, 11.0 mmol), NaO t -Bu (35.2 g, 365.8 mmol), toluene (610 mL), yielded 71.1 g of product. (Yield: 78.4%)

[0212] 7. Synthesis examples of Sub 1-51

[0213] 1) Composition of sub 1-51-int1

[0214] Sub 1-51a (100.0 g, 335.6 mmol) was dissolved in benzene-d6 (847.3 mL) in a round-bottom flask, followed by the dropwise addition of trifluoromethanesulfonic acid (59.2 mL, 671.2 mmol), and the reaction was carried out at room temperature. When the reaction was complete, the mixture was neutralized with water and Na₂CO₃ (106.7 g, 1006.8 mmol). After neutralization, 99.31 g of product was obtained using the same method as for sub-1-45-int1. (Yield: 97.0%)

[0215] 2) Composition of sub 1-51-int2

[0216] Following the same method as Sub 1-2, Sub 1-51-int1 (99.3 g, 325.6 mmol), Sub 1-51b (64.8 g, 325.6 mmol), Pd2(dba)3 (8.9 g, 9.8 mmol), and P( t -Bu)3 (4.0 g, 19.5 mmol), NaO t Bu (62.5 g, 651.1 mmol) and toluene (560 mL) were added to a round-bottom flask to give 75.8 g of product. (Yield: 54.9%)

[0217] 8. Synthesis examples of Sub 1-62

[0218] Using the same method as Sub 1-2, in a round-bottom flask, react Sub 1-62a (50.0 g, 168.3 mmol) and Sub 1-62b (41.2 g, 168.3 mmol), Pd2(dba)3 (4.6 g, 5.0 mmol), P(t-Bu)3 (2.0 g, 10.1 mmol), and NaO... t The experiment was conducted using Bu (32.3 g, 336.5 mmol) and toluene (560 mL), yielding 54.3 g of product. (Yield: 70.1%)

[0219] 9. Synthesis examples of Sub 1-73

[0220] 1) Composition of sub 1-73-int1

[0221] After adding Sub 1-73a (38.8 g, 318.0 mmol) to a round-bottom flask and dissolving it in toluene (96 ml), Sub 1-73b (100.0 g, 289.1 mmol), Pd(PPh3)4 (10.0 g, 8.7 mmol), K2CO3 (59.9 g, 433.6 mmol), ethanol (96 ml), and water (321 ml) were tested in the same manner as for sub-1-27-int1 above, to obtain 64.84 g of product. (Yield: 65.2%)

[0222] 2) Synthesis of sub 1-73

[0223] Using the same method as Sub 1-2, in a round-bottom flask, react Sub 1-73-int1 (64.8 g, 216.6 mmol) and Sub 1-73c (42.3 g, 216.6 mmol), Pd2(dba)3 (5.8 g, 6.4 mmol), P(t-Bu)3 (2.6 g, 12.8 mmol), and NaO... t The experiment was conducted using Bu (40.9 g, 425.1 mmol) and toluene (710 mL), yielding 63.5 g of product. (Yield: 70.5%)

[0224] 10. Synthesis examples of Sub 1-79

[0225] Using the same method as Sub 1-2, in round-bottom flasks, react Sub 1-79a (50.0 g, 168.9 mmol), Sub 1-79b (25.2 g, 168.9 mmol), Pd2(dba)3 (4.6 g, 5.1 mmol), P(t-Bu)3 (2.1 g, 10.1 mmol), and NaO... t The experiment was conducted using Bu (32.5 g, 337.9 mmol) and toluene (710 mL), yielding 63.5 g of product. (Yield: 67.5%)

[0226] 11. Synthesis examples of Sub 1-81

[0227] Using the same method as Sub 1-2, in a round-bottom flask, react Sub 1-81a (50.0 g, 144.5 mmol) and Sub 1-81b (35.4 g, 144.5 mmol), Pd2(dba)3 (4.0 g, 4.3 mmol), P(t-Bu)3 (1.8 g, 8.7 mmol), and NaO... t The experiment was conducted using Bu (27.8 g, 289.0 mmol) and toluene (480 mL), yielding 53.7 g of product. (Yield: 72.6%)

[0228] 12. Synthesis Examples of Sub 1-100

[0229] 1) Composition of sub 1-100-int1

[0230] After adding Sub 1-100a (100.0 g, 820.1 mmol) to a round-bottom flask and dissolving it in toluene (2733 ml), Sub 1-100b (299.1 g, 902.2 mmol), Pd(PPh3)4 (28.5 g, 24.6 mmol), K2CO3 (170.0 g, 1230.2 mmol), ethanol (273 ml), and water (911 ml) were tested in the same manner as for sub-1-27-int1 above, to obtain 165.8 g of product. (Yield: 61.5%)

[0231] 2) Synthesis of sub 1-100

[0232] Using the same method as Sub 1-2, in a round-bottom flask, the following were prepared: Sub 1-100-int1 (165.8 g, 504.3 mmol) and Sub 1-100c (97.5 g, 504.3 mmol), Pd2(dba)3 (13.9 g, 15.1 mmol), P(t-Bu)3 (6.1 g, 30.3 mmol), and NaO. t The experiment was conducted using Bu (96.9 g, 1008.5 mmol) and toluene (1680 mL), yielding 155.4 g of product. (Yield: 63.5%)

[0233] The compounds belonging to Sub 1 can be, but are not limited to, the following compounds, and Table 1 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to Sub 1.

[0234]

[0235] Table 1

[0236] II. Composition of Sub 2

[0237] 1. Synthesis example of Sub2-2

[0238] 1) Composition of sub 2-2-int1

[0239] Sub 2-2a (100 g, 364.8 mmol), bis(pinacol)diboron (111.2 g, 437.8 mmol), KOAc (85.9 g, 875.5 mmol), and Pd(dppf)Cl2 (8.0 g, 10.9 mmol) were dissolved in toluene (1220 ml) in a round-bottom flask and stirred at 100 °C for 2 hours. After the reaction was complete, the organic layer was extracted with CH2Cl2 and water, then treated with MgSO4, concentrated, applied to a silica gel column, and recrystallized to give 61.04 g of Sub 1-1 (yield: 5.1%).

[0240] 2) Synthesis of sub 2-2

[0241] Sub 2-2b (49.0 g, 174.0 mmol) was dissolved in toluene (580 mL) in a round-bottom flask. Sub 2-2-int1 (61.5 g, 191.5 mmol), Pd(PPh3)4 (6.0 g, 5.2 mmol), K2CO3 (36.1 g, 261.2 mmol), ethanol (58 mL), and water (190 mL) were then added, and the reaction was carried out at 80 °C. After the reaction was complete, the organic layer was extracted with CH2Cl2 and water, dried over MgSO4, concentrated, and then passed through a silica gel column and recrystallized to obtain 44.50 g of product. (Yield: 64.6%)

[0242] 2. Synthesis examples of Sub 2-5

[0243] 1) Composition of sub 2-5-int1

[0244] Sub 2-5a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 253.9 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as Sub 2-2-int1, yielding 59.0 g of product (yield: 50.8%).

[0245] 2) Synthesis of sub 2-5

[0246] Sub 2-5b (49.3 g, 174.9 mmol) was dissolved in toluene (583 ml) in a round-bottom flask, and then Sub 2-5-int1 (59.0 g, 174.9 mmol), Pd(PPh3)4 (6.1 g, 5.2 mmol), K2CO3 (3631 g, 262.4 mmol), ethanol (58 ml), and water (190 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 49.5 g of product. (Yield: 68.7%)

[0247] 3. Synthesis example of Sub2-12

[0248] 1) Composition of sub 2-12-int1

[0249] Sub 2-5a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 253.9 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as for Sub 2-2-int1, yielding 61.6 g of product (yield: 54.3%).

[0250] 2) Synthesis of sub 2-12

[0251] Sub 2-12-int1 (61.6 g, 155.4 mmol) was dissolved in toluene (518 ml) in a round-bottom flask, and then Sub 2-12b (43.8 g, 155.4 mmol), Pd(PPh3)4 (5.4 g, 4.7 mmol), K2CO3 (32.2 g, 233.2 mmol), ethanol (51 ml), and water (170 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 47.2 g of product. (Yield: 64.5%)

[0252] 4. Synthesis example of Sub2-27

[0253] 1) Composition of sub 2-27-int1

[0254] Sub 2-27a (100.0 g, 236.1 mmol) was dissolved in toluene (787 ml) in a round-bottom flask, and then Sub 2-27b (28.8 g, 236.1 mmol), Pd(PPh3)4 (8.2 g, 7.1 mmol), K2CO3 (49.0 g, 354.2 mmol), ethanol (78 ml), and water (290 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 81.7 g of product. (Yield: 71.1%)

[0255] 2) Composition of sub 2-27-int2

[0256] Sub 2-27c (100 g, 364.8 mmol), bis(pinacol)diboron (111.2 g, 437.8 mmol), KOAc (85.9 g, 875.5 mmol), Pd(dppf)Cl2 (8.0 g, 10.9 mmol), and toluene (1220 ml) were added to a round-bottom flask and the experiment was performed in the same manner as Sub 2-2-int1, yielding 65.9 g of product (yield: 56.3%).

[0257] 3) Synthesis of sub 2-27

[0258] Sub 2-27-int1 (75.0 g, 200.7 mmol) was dissolved in toluene (669 ml) in a round-bottom flask, and then Sub 2-27-int2 (64.5 g, 200.7 mmol), Pd(PPh3)4 (7.0 g, 6.0 mmol), K2CO3 (41.6 g, 301.1 mmol), ethanol (69 ml), and water (223 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 69.6 g of product. (Yield: 71.1%)

[0259] 5. Synthesis example of Sub2-43

[0260] 1) Composition of sub 2-43-int1

[0261] Sub 2-43a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 413.5 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as Sub 2-2-int1, yielding 66.9 g of product (yield: 57.6%).

[0262] 2) Synthesis of sub 2-43

[0263] Sub 2-43b (80.0 g, 237.2 mmol) was dissolved in toluene (790 ml) in a round-bottom flask, and then Sub 2-43-int1 (70.6 g, 237.2 mmol), Pd(PPh3)4 (8.2 g, 7.1 mmol), K2CO3 (49.2 g, 355.8 mmol), ethanol (79 ml), and water (230 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 65.2 g of product. (Yield: 64.3%)

[0264] 6. Synthesis example of Sub2-45

[0265] 1) Composition of sub 2-45-int1

[0266] Sub 2-45a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 413.5 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as for Sub 2-2-int1, yielding 65.1 g of product (yield: 56.1%).

[0267] 2) Synthesis of sub 2-45

[0268] Sub 2-45b (55.0 g, 195.4 mmol) was dissolved in toluene (651 ml) in a round-bottom flask, and then Sub 2-45-int1 (65.9 g, 195.4 mmol), Pd(PPh3)4 (6.8 g, 5.9 mmol), K2CO3 (40.5 g, 293.0 mmol), ethanol (65 ml), and water (218 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 55.7 g of product. (Yield: 69.3%)

[0269] 7. Synthesis example of Sub2-51

[0270] 1) Composition of sub 2-51-int1

[0271] Sub 2-51a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 413.5 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as Sub 2-2-int1, yielding 69.8 g of product (yield: 60.1%).

[0272] 2) Composition of sub 2-51-int2

[0273] Sub 2-51b (100.0 g, 352.7 mmol) was dissolved in benzene-d6 (890.4 mL) in a round-bottom flask, followed by the dropwise addition of trifluoromethanesulfonic acid (62.3 mL, 705.3 mmol), and the reaction was carried out at room temperature. When the reaction was complete, the mixture was neutralized with water and Na₂CO₃ (112.1 g, 1058.0 mmol). After neutralization, the mixture was extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated, and then recrystallized using a silica gel column to give 102.7 g of product (yield 97.6%).

[0274] 3) Synthesis of sub 2-51

[0275] Sub 2-51-int1 (58.0 g, 200.3 mmol) was dissolved in toluene (667 ml) in a round-bottom flask, and then Sub 2-51-int2 (67.5 g, 200.3 mmol), Pd(PPh3)4 (6.9 g, 6.0 mmol), K2CO3 (41.5 g, 300.4 mmol), ethanol (66 ml), and water (222 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 62.7 g of product. (Yield: 76.6%)

[0276] 8. Synthesis example of Sub2-62

[0277] 1) Composition of sub 2-62-int1

[0278] Sub 2-62a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 413.5 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as for Sub 2-2-int1, yielding 68.9 g of product (yield: 59.3%).

[0279] 2) Synthesis of sub 2-62

[0280] Sub 2-62b (73.0 g, 204.1 mmol) was dissolved in toluene (680 ml) in a round-bottom flask, and then Sub 2-62-int1 (68.8 g, 204.1 mmol), Pd(PPh3)4 (7.1 g, 6.1 mmol), K2CO3 (42.3 g, 306.2 mmol), ethanol (68 ml), and water (230 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 58.7 g of product. (Yield: 59.0%)

[0281] 9. Synthesis example of Sub2-73

[0282] 1) Composition of sub 2-73-int1

[0283] Sub 2-73a (100 g, 344.6 mmol), bis(pinacol)diboron (105.0 g, 413.5 mmol), KOAc (81.2 g, 827.1 mmol), Pd(dppf)Cl2 (7.6 g, 10.3 mmol), and toluene (1150 ml) were added to a round-bottom flask and the experiment was performed in the same manner as for Sub 2-2-int1, yielding 78.2 g of product (yield: 67.3%).

[0284] 2) Synthesis of sub 2-73

[0285] Sub 2-73b (80.0 g, 215.1 mmol) was dissolved in toluene (716 ml) in a round-bottom flask, and then Sub 2-73-int1 (72.5 g, 215.1 mmol), Pd(PPh3)4 (7.5 g, 6.5 mmol), K2CO3 (44.6 g, 322.6 mmol), ethanol (71 ml), and water (270 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 56.8 g of product. (Yield: 52.4%)

[0286] 10. Synthesis example of Sub2-79

[0287] 1) Composition of sub 2-79-int1

[0288] Sub 2-79a (100.0 g, 309.8 mmol) was dissolved in toluene (1032 ml) in a round-bottom flask, and then Sub 2-79b (39.3 g, 309.8 mmol), Pd(PPh3)4 (10.7 g, 9.3 mmol), K2CO3 (64.2 g, 464.6 mmol), ethanol (100 ml), and water (333 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 65.9 g of product. (Yield: 76.3%)

[0289] 2) Composition of sub 2-79-int2

[0290] Sub 2-79-int1 (65.9 g, 221.8 mmol), bis(pinacol)diboron (67.6 g, 266.1 mmol), KOAc (52.2 g, 532.3 mmol), Pd(dppf)Cl2 (4.9 g, 6.7 mmol), and toluene (740 ml) were added to a round-bottom flask and the experiment was performed in the same manner as for Sub 2-2-int1, yielding 47.9 g of product (yield: 63.2%).

[0291] 3) Synthesis of sub 2-79

[0292] Sub 2-79-int2 (47.9 g, 139.9 mmol) was dissolved in toluene (466 ml) in a round-bottom flask, and then Sub 2-79c (41.6 g, 139.9 mmol), Pd(PPh3)4 (4.9 g, 4.2 mmol), K2CO3 (29.0 g, 209.9 mmol), ethanol (46 ml), and water (180 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 36.8 g of product. (Yield: 63.2%)

[0293] 11. Synthesis example of Sub2-81

[0294] 1) Composition of sub 2-81-int1

[0295] Sub 2-81a (50.0 g, 182.4 mmol), bis(pinacol)diboron (55.6 g, 218.9 mmol), KOAc (43.0 g, 437.8 mmol), Pd(dppf)Cl2 (4.0 g, 5.5 mmol), and toluene (610 ml) were added to a round-bottom flask and the experiment was performed in the same manner as for Sub 2-2-int1, yielding 34.7 g of product (yield: 59.4%).

[0296] 2) Composition of sub 2-81-int2

[0297] Sub 1-81b (50.0 g, 168.0 mmol) was dissolved in benzene-d6 (424.2 mL) in a round-bottom flask, followed by the dropwise addition of trifluoromethanesulfonic acid (29.6 mL, 336.0 mmol). The reaction was carried out at room temperature. When the reaction was complete, the solution was neutralized with water and Na₂CO₃ (53.4 g, 504.0 mmol). The reaction was performed in the same manner as that for sub 1-51-int2, yielding 48.1 g of product. (Yield: 94.3%)

[0298] 3) Synthesis of sub 2-81

[0299] Sub 2-81-int1 (35.0 g, 109.0 mmol) was dissolved in toluene (363 ml) in a round-bottom flask, and then Sub 2-81-int2 (33.1 g, 109.9 mmol), Pd(PPh3)4 (3.8 g, 3.3 mmol), K2CO3 (22.6 g, 163.5 mmol), ethanol (36 ml), and water (121 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 28.6 g of product. (Yield: 62.9%)

[0300] 12. Synthesis example of Sub2-100

[0301] 1) Composition of sub 2-100-int1

[0302] Sub 2-100a (50.0 g, 183.2 mmol), bis(pinacol)diboron (55.8 g, 219.8 mmol), KOAc (43.1 g, 439.6 mmol), Pd(dppf)Cl2 (4.0 g, 5.5 mmol), and toluene (610 ml) were added to a round-bottom flask and the experiment was performed in the same manner as Sub 2-2-int1, yielding 32.1 g of product (yield: 54.6%).

[0303] 2) Synthesis of sub 2-100

[0304] Sub 2-100b (30.0 g, 100.8 mmol) was dissolved in toluene (336 ml) in a round-bottom flask, and then Sub 2-100-int1 (32.4 g, 100.8 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), K2CO3 (20.9 g, 151.2 mmol), ethanol (33 ml), and water (112 ml) were added. The experiment was performed in the same manner as with Sub 2-2 to obtain 28.4 g of product. (Yield: 68.4%)

[0305] The compounds belonging to Sub 2 can be, but are not limited to, the following compounds, and Table 2 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to Sub 2.

[0306]

[0307] [Table 2]

[0308] III. Synthesis of the final product

[0309] 1. Example of P-2 synthesis

[0310] In a round-bottom flask, dissolve Sub 1-2 (10.0 g, 21.9 mmol) in toluene (72 mL), then add Sub 2-2 (8.6 g, 21.9 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), and P( t -Bu)3 (0.3 g, 1.3 mmol), NaO t -Bu (4.2 g, 43.7 mmol) was added and stirred at 120 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. Then, the resulting compound was recrystallized after column chromatography to give 11.4 g of product (64.0% yield).

[0311] 2. Example of P-5 synthesis

[0312] Combine Sub 1-5 (10.0 g, 31.8 mmol), Sub 2-5 (13.1 g, 31.8 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), P(t-Bu)3 (0.4 g, 1.9 mmol), NaO t Bu (6.1 g, 63.6 mmol) and toluene (110 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 15.2 g of product. (Yield: 69.4%)

[0313] 3. Synthesis of P-12

[0314] Combine Sub 1-12 (10.0 g, 32.3 mmol), Sub 2-12 (15.2 g, 32.3 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), P(t-Bu)3 (0.4 g, 1.9 mmol), NaO tBu (6.2 g, 64.6 mmol) and toluene (110 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 15.0 g of product. (Yield: 62.5%)

[0315] 4. Synthesis of P-27

[0316] Combine Sub 1-27 (10.0 g, 20.6 mmol), Sub 2-27 (10.0 g, 20.6 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 1.2 mmol), NaO t Bu (4.0 g, 41.2 mmol) and toluene (70 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 12.6 g of product. (Yield: 65.3%)

[0317] 5. Synthesis of P-43

[0318] Combine Sub 1-43 (10.0 g, 31.8 mmol), Sub 2-43 (13.6 g, 31.8 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), P(t-Bu)3 (0.4 g, 1.9 mmol), NaO t Bu (6.1 g, 63.6 mmol) and toluene (110 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 13.8 g of product. (Yield: 61.9%)

[0319] 6. Synthesis of P-45

[0320] Combine Sub 1-45 (10.0 g, 20.2 mmol), Sub 2-45 (8.3 g, 20.2 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 1.2 mmol), NaO t Bu (3.9 g, 40.3 mmol) and toluene (70 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 10.3 g of product. (Yield: 58.9%)

[0321] 7. Synthesis of P-51

[0322] Combine Sub 1-51 (10.0 g, 23.6 mmol), Sub 2-51 (9.9 g, 23.6 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), P(t-Bu)3 (0.3 g, 1.4 mmol), NaO t Bu (4.5 g, 47.1 mmol) and toluene (80 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 12.8 g of product. (Yield: 67.5%)

[0323] 8. Synthesis of P-62

[0324] Combine Sub 1-62 (10.0 g, 21.7 mmol), Sub 2-62 (10.6 g, 21.7 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), P(t-Bu)3 (0.3 g, 1.3 mmol), NaO t Bu (4.2 g, 43.4 mmol) and toluene (70 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 11.7 g of product. (Yield: 59.3%)

[0325] 9. Synthesis of P-73

[0326] Combine Sub 1-73 (10.0 g, 24.9 mmol), Sub 2-73 (12.6 g, 24.9 mmol), Pd2(dba)3 (0.7 g, 0.7 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaO t Bu (4.8 g, 49.9 mmol) and toluene (80 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 13.8 g of product. (Yield: 63.8%)

[0327] 10. Synthesis of P-79

[0328] Combine Sub 1-79 (10.0 g, 27.4 mmol), Sub 2-79 (11.4 g, 27.4 mmol), Pd2(dba)3 (0.8 g, 0.8 mmol), P(t-Bu)3 (0.3 g, 1.6 mmol), NaO t Bu (5.3 g, 54.7 mmol) and toluene (90 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 14.0 g of product. (Yield: 69.0%)

[0329] 11. Synthesis of P-81

[0330] Combine Sub 1-81 (10.0 g, 19.5 mmol), Sub 2-81 (8.2 g, 19.5 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 1.2 mmol), NaO t Bu (3.8 g, 39.1 mmol) and toluene (70 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 11.3 g of product. (Yield: 64.5%)

[0331] 12. Synthesis of P-100

[0332] Combine Sub 1-100 (10.0 g, 20.6 mmol), Sub 2-100 (8.5 g, 20.6 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 1.2 mmol), NaO t Bu (4.0 g, 41.2 mmol) and toluene (70 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as for P-2, yielding 17.7 g of product. (Yield: 59.7%)

[0333] Meanwhile, the FD-MS values ​​of compounds P-1 to P-128 of the present invention prepared according to the above synthesis examples are shown in Table 3.

[0334] [Table 3]

[0335] The compound represented by Formula 2 can be prepared by known synthetic methods (named reaction) or by referring to published patents such as Korean Patent Publication Nos. 2020-0129334, 2022-0055392, and 2023-000502, but is not limited thereto.

[0336] Meanwhile, the FD-MS values ​​of compounds N-1 to N-276 of the present invention are shown in Table 4.

[0337] [Table 4]

[0338] Meanwhile, exemplary synthetic examples of the present invention represented by Formulas 1 and 2 have been described, but these are all based on the Buchwald-Hartwig cross-coupling reaction, the Miyaura borylation reaction, the Suzuki cross-coupling reaction, and intramolecular acid-induced cyclization reactions. J. mater. Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction ( Org. Lett .2011, 13, 5504) and PPh3--mediated reductive cyclization reaction ( J. Org. Chem (2005, 70, 5014.), and it will be readily understood by those skilled in the art that the reaction proceeds even when other substituents defined in Formula 1 or Formula 2 are bonded, in addition to the substituents specified in the specific synthetic example.

[0339] Manufacturing and evaluation of organic electroluminescent devices

[0340] [Example 1] Red organic electroluminescent device (phosphor body)

[0341] Compound A and Compound B were used on an ITO layer (anode) formed on a glass substrate, and Compound B was doped at a weight ratio of 98:2 to form a hole injection layer with a thickness of 10 nm. Then, Compound A was vacuum deposited on the hole injection layer to a thickness of 110 nm to form a hole transport layer.

[0342] Then, compound CR was vacuum deposited on the hole transport layer to a thickness of 10 nm to form an emission auxiliary layer. Subsequently, the host material of the luminescent layer used compound P-1 (the compound of the present invention) as the first host and compound N-178 (the compound of the present invention) as the second host, using a mixture of the first host and the second host in a weight ratio of 5:5, and used bis-(1-phenylisoquinolinyl)iridium(III)acetylacetonate (hereinafter abbreviated as '(piq)2Ir(acac)') as the dopant material, and the dopant was doped such that the weight ratio of host to dopant was 95:5, thereby forming a luminescent layer with a thickness of 30 nm.

[0343] Then, compound E is 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 is formed on the hole-blocking layer using a mixture of compound F and compound G in a weight ratio of 5:5. Then, compound G is 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.

[0344] Compound A: N -([1,1'-biphenyl]-4-yl)-9,9-dimethyl- N -(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9 H -fluorene-2-amine

[0345] Compound B: 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-trimethylenetris(cyanomethylene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0346] Compound CR: N 7 -(dibenzo[b,d]thiophen-2-yl)- N 2 , N 2 , N 7 -triphenyldibenzo[ b,d Thiophene-2,7-diamine

[0347] Compound E: 2-(4'-(9,9-dimethyl-9 H -fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0348] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0349] Compound G: (8-hydroxyquinoline)lithium

[0350] [Example 2] to [Example 24]

[0351] The organic light-emitting device was manufactured in the same manner as in Example 1, but the compound of the present invention described in Table 5 was used as the host material for the light-emitting layer.

[0352] [Comparative Example 1] and [Comparative Example 2]

[0353] The organic light-emitting device was manufactured in the same manner as in Example 1, but comparative compound A and comparative compound B were used as the first host material for the light-emitting layer.

[0354] [Compare compound A] [Compare compound B]

[0355] Electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 4 and Comparative Example 1 of the present invention, and lifetime measurement devices manufactured by Maxscience were used at 2500 cd / m². 2 The standard brightness measurement T95 lifetime is used. Table 5 shows the results of device manufacturing and evaluation.

[0356] The measuring equipment can evaluate the performance of new materials compared to comparison compounds under the same conditions, without being affected by possible daily fluctuations in deposition rate, vacuum quality, or other parameters.

[0357] During the evaluation period, each batch contained four identically prepared OLEDs containing the comparison compound, and since the performance of a total of 12 OLEDs across three batches was evaluated, the values ​​of the experimental results obtained in this manner represent statistical significance.

[0358] [Table 5]

[0359] As can be seen from the results in Table 5, when a red organic electroluminescent device is manufactured using the material of the present invention as the main material of the light-emitting layer, the driving voltage, luminous efficiency and lifetime of the organic electroluminescent device can be improved compared with the comparative examples using comparative compound A or comparative compound B, which have a basic framework similar to the compound of the present invention.

[0360] Comparative compounds A and B are similar to the compounds of the present invention in that they are tertiary amine compounds in which the oxazole moiety is substituted on the 3-fused ring. However, the compounds of the present invention differ from the comparative compounds in that at least one of the substituents in the amine group is a substituent represented by formula A.

[0361] To confirm the energy level differences in the compounds caused by these differences, the data measured using the DFT method (B3LYP / 6-31 g(D)) with the Gaussian procedure are shown in Table 6.

[0362] [Table 6]

[0363] As can be seen from the results in Table 6, the energy level formation modes of the compounds of the present invention and the comparative compounds are different.

[0364] To explain in more detail, the T1 level of the compounds of the present invention is lower than that of comparative compounds A and B. This is believed to be because the compounds of the present invention include a portion represented by formula A in their structure, thus forming a longer intramolecular conjugation length than that of the comparative compounds. Therefore, when the compounds of the present invention having a lower T1 level than the comparative compounds are applied to a device, it is determined that energy transfer from the host to the dopant is facilitated, thereby reducing damage during energy transfer from the host to the dopant, and also significantly improving the drive voltage, efficiency, and lifetime of the device.

[0365] In other words, as can be seen from the results in Tables 5 and 6, even though the compounds have similar structures, it can be confirmed that the compounds of the present invention, which satisfy all the complex factors (e.g., the type of specific substituent and the substitution position of the substituent), exhibit significant effects compared to other comparative compounds in organic electrical devices. And from this, it can be seen that the compounds of the present invention exhibit significant effects in organic electronic components compared to simple structural isomers or compounds with similar structures not described in this specification.

[0366] These results indicate that even with similar molecular components, the properties of compounds, such as hole characteristics, light efficiency characteristics, energy levels, hole injection and migration characteristics, charge balance of holes and electrons, volume density and intermolecular distance, can differ significantly to some extent. This difference is difficult to predict depending on the type and position of the substituents, and the performance of the device can vary not only due to a single component but also due to complex factors.

[0367] While exemplary embodiments of the invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and spirit of the invention as disclosed in the appended claims. Therefore, the embodiments disclosed herein are intended to illustrate the scope of the inventive concept, and the scope of the invention is not limited by the embodiments. The scope of the invention should be interpreted based on the appended claims, and the scope of the invention should be construed as including all inventive concepts within the scope of equivalents to the claims.

[0368] [Industrial Applicability]

[0369] According to the present invention, organic devices with excellent device characteristics such as high brightness, high luminescence and long life can be manufactured, thus proving industrial applicability.

Claims

1. Compounds represented by Formula 1: Formula 1 Formula A, Formula B, Formula Q in: A is a substituent represented by formula A. B is a substituent represented by the formula B. Ring C is C 10 -C 60 aryl group, and can be further reacted with one or more R 6 replace, Q is a substituent represented by the formula Q, provided that R 4 or R 5 Connect to L a , L 1 L 2 L 3 and L a Independently selected from single bonds; C6-C 60 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; Ar 1 Independently selected from C6-C 60 aryl groups; fluorenyl groups; and C2-C groups containing at least one heteroatom selected from O, N, S, Si, or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; X is O, S, or CR. 30 R 31 , Y is either O or S. Z is O, S, or NR. 32 , R 1 R 2 R 3 R 4 R 5 R 6 R 30 R 31 and R 32 Independently selected from hydrogen; deuterium; halogen; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C3-C 60 Cycloalkyl groups; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 20 alkoxy groups; and C6-C 30 aryloxy group; or multiple adjacent R groups 1 Multiple adjacent R 2 Multiple adjacent R 3 Multiple adjacent R 4 Multiple adjacent R 5 and multiple adjacent R 6 They can bond together to form a ring, or R 30 and R 31 They can bond together to form a helical ring. a and b are independent integers from 0 to 3, and c and d are independent integers from 0 to 4. Indicates the position to be bonded. The aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenyl group, the fused cyclic group, the cycloalkyl group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, and the aryloxy group may be substituted by one or more substituents selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 The substituents are alkylaryl groups; and the hydrogen atoms of these substituents may be further substituted with one or more deuterium atoms; and the substituents may bond to each other to form saturated or unsaturated rings, wherein the term "ring" means C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by combinations thereof.

2. The compound according to claim 1, wherein the ring C is represented by any one of the following formulas C-1 to C-15: Formula C-1 Formula C-2 Formula C-3 Formula C-4 Formula C-5, Formula C-6, Formula C-7, Formula C-8 Formula C-9, Formula C-10, Formula C-11, Formula C-12 Formula C-13 Formula C-14 Formula C-15 in: R 7 R 8 R 9 R 10 and R 11 Independently identical or different from each other and independently selected from hydrogen; deuterium; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic rings and C6-C 20 Fused ring groups of aromatic rings; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 20 alkoxy groups; and C6-C 20 An aryloxy group; or multiple adjacent groups thereof may bond together to form a ring. e is an integer from 0 to 6, f and g are independently integers from 0 to 8, and h and i are independently integers from 0 to 10. This indicates the location where bonding is to take place.

3. The compound according to claim 1, wherein formula A is represented by any one of the following formulas A-1 to A-4: Formula A-1 Formula A-2 Formula A-3 Formula A-4 in: Rings C, X, R 3 and Same as defined in claim 1, c' is an integer from 0 to 3.

4. The compound according to claim 1, wherein formula B is represented by any one of formulas B-1 to B-16: Formula B-1 Formula B-2 Formula B-3 Formula B-4 Type B-5 Type B-6 Type B-7 Type B-8 Type B-9 Type B-10 Type B-11 Type B-12 Type B-13 Type B-14 Type B-15 Type B-16 in: Y, Q, R 1 R 2 L a a, b and Same as defined in claim 1.

5. The compound according to claim 1, wherein Q is represented by any one of the following formulas Q-1 to Q-5: Formula Q-1 Formula Q-2 Formula Q-3 Formula Q-4 Type Q-5 in: R 4 R 5 Z, d and Same as defined in claim 1, R 12 With claim 1, R 1 The definitions are the same. j is an integer between 0 and 3.

6. The compound according to claim 1, wherein Ar 1 Represented by any one of the following formulas Ar-1 to Ar-10: Formula Ar-1 Formula Ar-2 Formula Ar-3 Formula Ar-4 Formula Ar-5 Formula Ar-6 Formula Ar-7 Formula Ar-8 Formula Ar-9 Formula Ar-10 in: W is O, S, or C(R) 33 (R) 34 ), R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 R 21 R 22 R 23 R 33 and R 34 With claim 2, R 7 The definitions are the same, or multiple adjacent R 13 Multiple adjacent R 14 Multiple adjacent R 15 Multiple adjacent R 16 Multiple adjacent R 17 Multiple adjacent R 18 Multiple adjacent R 19 Multiple adjacent R 20 Multiple adjacent R 21 Multiple adjacent R 22 and multiple adjacent R 23 They can bond together to form a ring, or R 33 With R 34 They can bond together to form a helical ring; R a Selected from C6-C 60 aryl group; C2-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; C1-C 50 Alkyl group; C2-C 20 alkenyl groups; and C2-C 20 alkynyl group; R b Selected from hydrogen; deuterium; C6-C 60 aryl group; C2-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; or R a and R b They can bond together to form a helical ring. k is an integer from 0 to 5, l, p, q, s, t, and u are independently integers from 0 to 4, m is an integer from 0 to 7, n is an integer from 0 to 9, and o and r are independently integers from 0 to 3. This indicates the location where bonding is to take place.

7. The compound according to claim 1, wherein L a L 1 L 2 and L 3 Represented by any one of the following equations L-1 to L-20: [Equation L-1] [Equation L-2] [Equation L-3] [Equation L-4] [Equation L-5] [Equation L-6] [Equation L-7] [Equation L-8] [Equation L-9] [Equation L-10] [Equation L-11] [Equation L-12] [Equation L-13] [Equation L-14] [Equation L-15] [Equation L-16] [Equation L-17] [Equation L-18] [Equation L-19] [Equation L-20] in: R 24 R 25 R 26 R 27 R 28 and R 29 With claim 2, R 7 The definitions are the same. W is the same as that defined in claim 5. v, w, x, z, and aa are independent integers from 0 to 4, and y is an integer from 0 to 6. This indicates the location where bonding is to take place.

8. The compound according to claim 1, wherein the compound represented by formula 1 can be any one of the following compounds P-1 to P-130: 。 9. A composition for use in organic electronic components, comprising a mixture of the compound represented by Formula 1 according to claim 1 and the compound represented by Formula 2: <Formula 2> in: X A X B and X C Independently is CR a Or N, However, X A X B and X C At least one of them is N, and preferably, at least two are N. Ar A Ar B and Ar C Independently selected from C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Cycloalkyl groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; L A L B and L C Independently selected from single bonds; C6-C 60 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; R a It is hydrogen; or deuterium; The aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorene group, the cycloalkyl group, and the fused cyclic group may be replaced by one or more substituents selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C... 20 Alkyl thio group; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 Alkyl aryl groups; and the hydrogens of these substituents can be further replaced by one or more deuteriums or C6-C atoms. 20 The aryl group is substituted; and the substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" means C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by combinations thereof.

10. The composition for an organic electronic component according to claim 9, wherein the composition serves as the host of the light-emitting layer.

11. The composition for organic electronic components according to claim 9, wherein Ar A Ar B and Ar C At least one of the following is represented by any one of the following formulas: Ar-a to Ar-d: Formula Ar-a Formula Ar-b Formula Ar-c Formula Ar-d in: Y A Y B and Y C Independently, they are O, S, and NR. 1A or CR 1B R 1C , R A R B R C R D R E R F R 1A R 1B and R 1C Independently identical or different from each other and independently selected from hydrogen; deuterium; halogen; cyano group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 20 alkoxy groups; and C6-C 20 aryloxy group; or multiple adjacent R groups A Multiple adjacent R B Multiple adjacent R C Multiple adjacent R D Multiple adjacent R E Multiple adjacent R F They can bond together to form a ring. ta and tc are independent integers from 0 to 3, tb and td are independent integers from 0 to 4, te is an independent integer from 0 to 5, and tf is an independent integer from 0 to 7. This indicates the location where bonding is to take place.

12. An organic electronic component comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode; wherein the organic material layer comprises the compound of claim 1 or the composition of claim 9.

13. The organic electronic component of claim 12 further comprises a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, said surface being opposite to the organic material layer.

14. The organic electronic component of claim 12, wherein the organic material layer comprises two or more stacks, the stacks comprising a hole transport layer, a light-emitting layer and an electron transport layer sequentially formed on a first electrode.

15. The organic electronic component of claim 14, wherein the organic material layer further comprises a charge-generating layer formed between the two or more stacks.

16. An electronic device, comprising a display device including the organic electronic components of claim 12; and a control unit for driving the display device.

17. The electronic device of claim 16, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochrome or white illumination.

18. A method for reusing Formula 1 according to claim 1, the method comprising: The crude organic light-emitting material comprising Formula 1 as described in claim 1 is recovered from the deposition equipment used in the process of depositing organic light-emitting materials to prepare an organic light-emitting device; Remove impurities from the crude organic light-emitting material; The organic light-emitting material is recovered after the impurities are removed; and The recovered organic light-emitting material is purified to a purity of 99.9% or higher.

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