Compounds for use in organic electronic elements, organic electronic elements using the compounds and electronic devices having the organic electronic elements

Abstract

Provided are a novel compound that can improve the light-emitting efficiency, stability, and service life of an element, an organic electronic element using the compound, and an electronic device having the organic electronic element.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic components, organic electronic components using said 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 interposed 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 originating from singlet excited states of electrons and phosphorescent materials originating from triplet excited states of electrons. In addition, luminescent materials can be classified according to their emission color into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials 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, leading to problems such as reduced color purity or decreased device efficiency due to emission attenuation. Therefore, to improve 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 to emit light with high efficiency. At this time, because 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-area displays, and their sizes are increasing daily, thus requiring more power than existing portable displays. Therefore, power consumption has become a critical factor for portable displays with limited power sources (such as batteries), and issues of efficiency and lifespan must also be addressed.

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

[0007] Therefore, when delaying 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), the material should have stable properties against the Joule heat generated during device operation. Since OLED devices are mainly formed by deposition methods, it is necessary to develop materials that can withstand long periods of time during deposition, i.e., materials with strong heat resistance.

[0008] In other words, to fully exhibit the superior properties of organic electronic components, the organic material layer within the device should first be supported by stable and efficient materials, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials. However, the development of stable and efficient organic material layer materials for organic electronic components has not been fully realized. Therefore, it is necessary to continuously develop new materials, and specifically, there is an urgent need to develop host materials for the light-emitting layer. Summary of the Invention

[0009] To address the problems mentioned above in the background art, 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.

[0010] Therefore, the object of the present invention is to provide new compounds, organic electronic components using said new compounds, and electronic devices thereof.

[0011] [Technical Solution]

[0012] The present invention provides compounds represented by Formula 1.

[0013] <Formula 1>

[0014] In another aspect, the present invention provides a composition for organic electronic components, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula A.

[0015] <Form A>

[0016] In another aspect, the present invention provides organic electronic components and electronic devices thereof, the organic electronic components and electronic devices comprising compounds represented by Formula 1 or compositions for organic electronic components.

[0017] [Invention Effects]

[0018] By using the compound 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 significantly improved. Attached Figure Description

[0019] Figures 1 to 3 This is an exemplary view of an organic electroluminescent device according to the present invention.

[0020] Figure 4 This is one aspect of the invention.

[0021] 100, 200, 300: Organic electronic components; 110: First electrode

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

[0023] 140: Emissive layer; 150: Electron transport layer

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

[0025] 180: Light efficiency enhancement layer; 210: Buffer layer

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

[0027] 330: First hole transport layer; 340: First luminescent layer

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

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

[0030] 430: Second hole transport layer; 440: Second luminescent layer

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

[0032] ST1: First stack; ST2: Second stack Detailed Implementation

[0033] 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 inclusion would make the subject matter of the invention considerably unclear.

[0034] 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,” “coupled,” or “connected” to another component, then the component may be directly connected to or connected to other components, but may be “connected,” “coupled,” or “connected” to another component between components.

[0035] As used in the specification and appended claims, unless otherwise specified, the following terms shall have the following meanings: Unless otherwise specified, the term “halogenated” or “halogen” as used herein includes fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0036] Unless otherwise specified, 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, 1 to 12 carbon atoms, or 1 to 10 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, and cycloalkyl-substituted alkyl groups.

[0037] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein means having, but is not limited to, 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, 2 to 12 carbon atoms, or 2 to 10 carbon atoms, and includes straight-chain or branched groups.

[0038] Unless otherwise specified, 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, 3 to 12 carbon atoms, or 3 to 10 carbon atoms.

[0039] Unless otherwise specified, the terms “alkoxyl 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, 1 to 12 carbon atoms or 1 to 10 carbon atoms.

[0040] Unless otherwise specified, 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, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms.

[0041] Unless otherwise specified, 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, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 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 comprises 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 substituted with an aryl group. For example, an arylalkyl group can be an aryl-substituted alkyl group, and an arylalyl group can be an aryl-substituted alkenyl group, and the aryl-substituted group has the number of carbon atoms as defined herein. Furthermore, when a prefix is ​​subsequently named, this means that the substituents are listed in the order they are described. For example, arylalkoxy means an aryl-substituted alkoxy group, alkoxycarbonyl means an alkoxy-substituted carbonyl group, and arylcarbonylalkenyl also means an arylcarbonyl-substituted alkenyl group, wherein the arylcarbonyl group can be an aryl-substituted carbonyl group.

[0043] Unless otherwise specified, 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, 2 to 16 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 combine with adjacent groups to form a heterocyclic group.

[0044] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0045] Furthermore, "heterocyclic" can include rings containing carbon atoms that have been replaced by SO2. For example, "heterocyclic" includes the following compounds.

[0046]

[0047] Unless otherwise specified, the terms “fluorenyl group”, “fluoreneyl group” as used herein mean that R, R' and R” are all monovalent, divalent or trivalent functional groups of hydrogen in the following structures, and the terms “substituted fluorenyl group”, “substituted fluoreneyl group” or “substituted fluorenetriyl group” mean that at least one of the substituents R, R', R” is a substituent other than hydrogen, and include those in which R and R' are bonded to each other to form a spiro compound together with the carbons bonded to them.

[0048]

[0049] The term "spiro compound" as used in this invention has the connotation of "spiral connection," and a spiral connection refers to a connection formed by two rings sharing only one atom. The atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms in the compound, they are referred to as "single-spiro," "double-spiro," and "triple-spiro" compounds, respectively.

[0050] Unless otherwise specified, 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, 1 to 12 carbon atoms, or 1 to 10 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, 3 to 12 carbon atoms, or 3 to 10 carbon atoms.

[0051] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms, or 3 to 10 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, 6 to 14 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 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, 2 to 14 carbon atoms, 2 to 12 carbon atoms, or 2 to 10 carbon atoms, or a fused ring formed by combinations thereof, and includes saturated or unsaturated rings.

[0052] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups include, but are not limited to, one or more heteroatoms.

[0053] Furthermore, unless explicitly stated otherwise, the term "substituted or unsubstituted" as used herein means substituted by 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.

[0054] Furthermore, unless otherwise explicitly explained, the formulas used in this invention are identical to the definitions of substituents specified by the exponent definition in the following formulas.

[0055]

[0056] 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 connected to any of the carbons constituting the benzene ring, and when a is an integer of 2 or 3, the combinations are as follows, where R 1They can be the same or different from each other. When a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar way, but the indication of the hydrogens bonded to the carbons that form the benzene ring is omitted.

[0057]

[0058] The term "composition" as used in this invention is intended to be interpreted broadly to include not only compounds but also solutions, dispersions, mixtures and blends of liquids and solids.

[0059] The compositions of the present invention may contain only the compounds of the present invention, or the compounds may be included in a combination of two or more different compounds, or the compounds may be included in a combination of two or more different compounds. That is, the compositions may include a single compound corresponding to Formula 1, a mixture of two or more compounds of Formula 1, and a mixture of a compound of Formula 1 and a compound not corresponding to the present invention. Here, the compound not corresponding to the present invention may be a single compound or two or more compounds. In this case, if the compound is included in a combination of two or more compounds with other compounds, the other compounds may be known compounds of each organic material layer or compounds to be developed in the future. In this case, the compounds included in the organic material layer may consist only of homogeneous compounds, but may also be a mixture of two or more heterogeneous compounds represented by Formula 1.

[0060] Below, compositions of compounds according to one aspect of the invention, phosphorescent layers for organic electronic components, and organic electronic components comprising the same will be described.

[0061] The present invention provides compounds represented by Formula 1.

[0062] <Formula 1>

[0063] <Equation 1-1> <Equation 1-2>

[0064] in: L 1 L 2 and L 3 Independently selected from single bonds; C6-C 60 arylene groups; fluorene groups; and C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups; Where L 1 L 2 and L 3 When it is an arylene group, C6-C is preferred. 30aryl groups, more preferably C6-C 25 arylene group, C6-C 18 arylene group, C6-C 14 arylene group, C6-C 12 arylene group or C6-C 10 Aromatic groups, such as phenylene, biphenylene, naphthylene, terphenylene, anthraceneylene, phenanthrene, etc.

[0065] Where L 1 L 2 and L 3 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups, C2-C 16 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.

[0066] Where L 1 L 2 and L 3 When it is a fused ring group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0067] Ar 1 Independently selected from C6-C 60 An aryl group; or a C2-C group containing at least one heteroatom selected from O, N, S, Si, or P. 60 Heterocyclic groups; 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, C6-C 14 aryl group, C6-C 12 aryl group or C6-C 10 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, phenylene oxide, etc.

[0068] 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 groups, C2-C 18 Heterocyclic groups, C2-C 16 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.

[0069] R is a substituent represented by formula 1-1. C is the substituent represented by formula 1-2. In Equations 1-1 and 1-2, each symbol can be defined as follows.

[0070] Rings A and B are independently C6–C 14 An aryl group, provided that at least one is a C 10 –C 14 aryl group, One of X and Y is N, and the other is O or S. Z is either O or S. R 1 They may be the same as or different from each other, and are independently selected from hydrogen; deuterium; cyano group; 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 Aliphatic ring; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy groups; and C6-C 30 aryloxy group; Where R 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, C6-C 14 aryl group, C6-C 12 aryl group or C6-C10 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, phenylene oxide, etc.

[0071] Where R 1 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups, C2-C 16 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.

[0072] Where R 1 When it is a fused ring group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, and more preferably C3-C 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0073] Where R 1 When it is an aliphatic ring, C3-C is preferred. 30 Aliphatic rings, more preferably C3-C 25 Aliphatic ring, C3-C 18 Aliphatic ring, C3-C 12 Aliphatic rings or C3-C 10 Aliphatic ring.

[0074] Where R 1 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, C1-C 12 alkyl groups or C1-C 10 Alkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, etc.

[0075] Where R 1 When the group is an alkoxy group, C1-C is preferred. 25 Alkoxy groups, more preferably C1-C 18 alkoxy groups, C1-C 12 alkoxy group or C1-C 10Alkoxy group.

[0076] Where R 1 When the group is an aryloxy group, C6-C is preferred. 24 aryloxy groups, more preferably C6-C 18 aryloxy group, C6-C 14 aryloxy group, C6-C 12 aryloxy group or C6-C 10 Aryloxy group.

[0077] a is an integer from 0 to 6. Indicates the location to be bonded. It refers to a single or double key, and The aryl group, arylene group, heterocyclic group, fluorene group, fluorene group, fused ring, aliphatic ring, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be replaced by one or more substituents, wherein the substituents are selected from deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkyl thio group; C1-C 20 alkoxy 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 cycloalkyl ring; C7-C 20 arylalkyl groups; and C8-C 20 The substituents are aryl alkenyl groups, and the hydrogen atoms of these substituents may be further replaced by 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.

[0078] Furthermore, Equation 1 is represented by Equation 2 or Equation 3.

[0079] <Formula 2> <Formula 3>

[0080] in: X, Y, Ar 1 L 1 L 2L 3 , R, R 1 a and Same as defined in Equation 1.

[0081] a' is an integer from 0 to 5. Ar 2 Independently selected from C6-C 60 aryl group; fluorenyl group; or C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; Among them, when Ar 2 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, C6-C 14 aryl group, C6-C 12 aryl group or C6-C 10 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, phenylene oxide, etc.

[0082] Among them, when Ar 2 When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups, C2-C 16 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.

[0083] Furthermore, the A ring of Equation 1-1 is represented by any one of Equations A-1 to A-3.

[0084] <Formula A-1> <Formula A-2> <Formula A-3>

[0085] in: R 2 Independently identical or different from each other, and selected from hydrogen; deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkyl thio group; C1-C 20 alkoxy group; C1-C 20Alkyl 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 Cycloalkyl groups; C7-C 20 arylalkyl groups; and C8-C 20 aryl alkenyl groups; b is an integer from 0 to 3, and c is an integer from 0 to 5. L represents Equation 1 3 The location of the bond, and Indicates the position of contraction.

[0086] Furthermore, the B ring in Equation 1-1 is represented by any one of Equations B-1 to B-3.

[0087] <Formula B-1> <Formula B-2> <Formula B-3>

[0088] in: R 3 With R 2 The definitions are the same. d is an integer from 0 to 4, and e is an integer from 0 to 6. Indicates the position of contraction.

[0089] Preferably, Equation 1-1 is any one of Equations 1-1-1 to 1-1-6.

[0090] <Equation 1-1-1> <Equation 1-1-2> <Equation 1-1-3>

[0091] <Equation 1-1-4> <Equation 1-1-5> <Equation 1-1-6>

[0092] in: Z, R 2 R 3 b, c, d, e and Same as defined above.

[0093] Equation 1-1-1 can be represented by any one of the following equations 1-1-1-a to 1-1-1-d.

[0094] <Equation 1-1-1-a> <Equation 1-1-1-b>

[0095] <Equation 1-1-1-c> <Equation 1-1-1-d>

[0096] in: Z, R 2 R 3 b, e and Same as defined above.

[0097] Equation 1-1-2 is represented by any one of the following equations 1-1-2-a to 1-1-2-d.

[0098] <Equation 1-1-2-a> <Equation 1-1-2-b>

[0099] <Equation 1-1-2-c> <Equation 1-1-2-d>

[0100] in: Z, R 2 R 3 b, e and Same as defined above.

[0101] Equation 1-1-3 is represented by any one of the following equations 1-1-3-a to 1-1-3-d.

[0102] <Equation 1-1-3-a> <Equation 1-1-3-b>

[0103] <Equation 1-1-3-c> <Equation 1-1-3-d>

[0104] in: Z, R 2 R 3 b, e and Same as defined above.

[0105] Equation 1-1-4 is represented by any one of the following equations 1-1-4-a to 1-1-4-f.

[0106] <Equation 1-1-4-a> <Equation 1-1-4-b>

[0107] <Equation 1-1-4-c> <Equation 1-1-4-d>

[0108] <Equation 1-1-4-e> <Equation 1-1-4-f>

[0109] in: Z, R 2 R 3 c, d and Same as defined above.

[0110] Equation 1-1-5 is represented by any one of the following equations 1-1-5-a to 1-1-5-f.

[0111] <Equation 1-1-5-a> <Equation 1-1-5-b>

[0112] <Equation 1-1-5-c> <Equation 1-1-5-d>

[0113] <Equation 1-1-5-e> <Equation 1-1-5-f>

[0114] in: Z, R 2 R 3 c, d and Same as defined above.

[0115] Equation 1-1-6 is represented by any one of the following equations 1-1-6-a to 1-1-6-f.

[0116] <Equation 1-1-6-a> <Equation 1-1-6-b>

[0117] <Equation 1-1-6-c> <Equation 1-1-6-d>

[0118] <Equation 1-1-6-e> <Equation 1-1-6-f>

[0119] in: Z, R 2 R 3 c, d and Same as defined above.

[0120] In addition, L 1 L 2 and L 3 Represented by equations L-1 to L-10.

[0121] <Formula L-1> <Formula L-2> <Formula L-3> <Formula L-4>

[0122] <Formula L-5> <Formula L-6> <Formula L-7>

[0123] <Formula L-8> <Formula L-9> <Formula L-10>

[0124] in: R 4 They are independently identical or different from each other, and are hydrogen; deuterium; or C6-C substituted or unsubstituted with deuterium. 20 aryl group; f is an integer from 0 to 4, g is an integer from 0 to 6, and h is an integer from 0 to 8. Indicates the location to be bonded.

[0125] In addition, Ar 1 Any one of the expressions from c-1 to c-7.

[0126] <Formula c-1> <Formula c-2> <Formula c-3> <Formula c-4>

[0127] <Formula c-5> <Formula c-6> <Formula c-7>

[0128] in: R 5 They are independently identical or different from each other, and are hydrogen; deuterium; or C6-C substituted or unsubstituted with deuterium. 20 aryl group; and i is an integer from 0 to 5, j is an integer from 0 to 7, and k is an integer from 0 to 9. Indicates the location to be bonded.

[0129] Specifically, the compound represented by Formula 1 can be any one of the following compounds P-1 to P-176, but is not limited thereto.

[0130]

[0131] In another aspect, the present invention provides a composition for organic electronic components, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula A.

[0132] <Form A>

[0133] in: X A X B and X C Independently, it is CR' or N; however, X A X B and X C At least two of them are N, and 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 Aliphatic rings; 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, C6-C 14 aryl group, C6-C 12 aryl group or C6-C 10 Aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, phenylene oxide, etc.

[0134] Among them, when Ar A Ar B and Ar C When the group is a heterocyclic group, C2-C is preferred. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups, C2-C 16Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, quinoline, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.

[0135] Among them, when Ar A Ar B and Ar C When it is an aliphatic ring; C3-C is preferred. 30 Aliphatic rings, more preferably C3-C 25 Aliphatic ring, C3-C 18 Aliphatic ring, C3-C 12 Aliphatic rings or C3-C 10 Aliphatic ring.

[0136] Among them, when Ar A Ar B and Ar C When it is a fused ring group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, and more preferably C3-C 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0137] 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 it is an arylene group, C6-C is preferred. 30 aryl groups, more preferably C6-C 25 arylene group, C6-C 18 arylene group, C6-C 14 arylene group, C6-C 12 arylene group or C6-C 10 Aromatic groups, such as phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, hydroxyl, etc.

[0138] 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 groups, C2-C 18 Heterocyclic groups, C2-C 16 Heterocyclic groups or C2-C 12 Heterocyclic groups, such as pyrazine, thiophene, pyridine, quinoline, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.

[0139] Where L A L B and L C When it is a fused ring group, C3-C is preferred. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0140] R' represents hydrogen; or deuterium; The aryl group, arylene group, heterocyclic group, fluorene group, fluorene group, fused ring group, and aliphatic ring may be replaced by one or more substituents, wherein the substituents are 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; 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 groups; and C8-C 20 The substituents are aryl alkenyl groups, and the hydrogen atoms of these substituents may be further replaced by 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 60Heterocyclic groups or fused rings formed by combinations thereof.

[0141] In addition, Ar A Ar B and Ar C At least one of them is represented by any one of the following formulas Ar-a to Ar-d.

[0142] Formula Ar-a Formula Ar-b

[0143] Formula Ar-c Formula Ar-d

[0144] in: Y A Y B and Y C Independently, they are O, S, and NR. 1A or C(R) 1B (R) 1C ), R A R B R C R D R E R F R 1A R 1B and R 1C They are independently the same or different from each other, and are 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 groups, and multiple adjacent groups 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. Indicates the location to be bonded.

[0145] The formula Ar-a is represented by any one of the following formulas Ar-a-1 to Ar-a-4.

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

[0147] <Formula Ar-a-3> <Formula Ar-a-4>

[0148] in: R A R B Y A ,ta,tb and Same as defined in formula Ar-a.

[0149] The formula Ar-b is represented by either formula Ar-b-1 or formula Ar-b-2.

[0150] <Formula Ar-b-1> <Formula Ar-b-2>

[0151] in: R C R D Y B Y C , tc, td and Same as defined in Ar-b.

[0152] The formula Ar-d is represented by the following formulas Ar-d-1 or Ar-d-2.

[0153] <Formula Ar-d-1> <Formula Ar-d-2>

[0154] in: R F , tf and Same as defined in Ar-d.

[0155] L A L B and L C It is independently a single bond or one of the following formulas b-1 to b-13.

[0156] Formula b-1 Formula b-2 Formula b-3 Formula b-4 Formula b-5 Formula b-6

[0157] Formula b-7 Formula b-8 Formula b-9 Formula b-10

[0158] Formula b-11 Formula b-12 Formula b-13

[0159] in: Z 10 It is O, S, NR 1D or C(R) 1E (R) 1F ), Z 49 Z 50 and Z 51 Independently, it is CR 1G Or N, however, Z 49 Z 50 and Z 51 At least one of them is N, R a1 R a2 R a3 R a4 R a5 R a6 R a7 R 1D R 1E and R 1F They are independently the same or different from each other, and are 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 Aryloxy groups; or multiple adjacent groups thereof may bond together to form a ring. R 1G With R A The definitions are the same.

[0160] 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 from 0 to 1. Indicates the location to be bonded.

[0161] Specifically, the compound of formula A can be any one of the following compounds N-1 to N-276, but is not limited thereto.

[0162]

[0163] Preferably, the composition for organic electronic components can be the host for the light-emitting layer.

[0164] Furthermore, in another aspect, the present invention provides 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 a compound represented by Formula 1, or a composition for an organic electronic component comprising a compound represented by Formula 1 and a compound represented by Formula A.

[0165] In another aspect, the present invention provides a method for reusing the compound of formula 1, the method comprising: Crude organic light-emitting materials containing compounds of Formula 1 are recovered from the deposition equipment used in the process of depositing organic light-emitting materials to prepare organic light-emitting devices; 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.

[0166] 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.

[0167] The recrystallization solvent is preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0168] The recrystallization solvent is preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0169] 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.

[0170] When using a mixture of polar and nonpolar solvents, the recrystallization solvent can be used in an amount of nonpolar solvent of 15% (v / v) or less compared to the polar solvent.

[0171] The recrystallization solvent is preferably a single solvent of N-methylpyrrolidone (NMP); or a polar solvent mixed with any one selected from 1,3-dimethyl-2-imidazolium ketone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide and dimethyl sulfoxide; 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.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] The pre-purification process may include a step of recrystallizing with a polar solvent followed by recrystallization with a non-polar solvent.

[0176] 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 onto an adsorbent.

[0177] The adsorbent can be activated carbon, silica gel, alumina, or other materials used for known adsorption purposes.

[0178] The step of purifying the recovered impurities to a purity of 99.9% or higher may include sublimation purification.

[0179] refer to Figure 1 The organic electronic component (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic layer between the first electrode (110) and the second electrode (170) comprising a single compound or two or more compounds represented by Formula 1. 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.

[0180] 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 ).

[0181] Furthermore, the organic electronic component according to an embodiment of the present invention may further 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. The compound or material of the present invention applied to the organic material layer can be used as a host or dopant for the 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 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 A, can be used as the host material for the light emission layer.

[0182] 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 ).

[0183] Furthermore, even when using the same core, band gap, electrical properties, and interfacial properties can vary depending on the location and type of substituents bonded. 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.

[0184] 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 an anode, 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 for use as a cathode can be deposited thereon.

[0185] 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 comprises a compound as an electron transport material or a material for the organic electronic component.

[0186] 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 compounds represented by Formula 1, or may contain a composition for an organic electronic device comprising a mixture of compounds represented by Formula 1 and compounds represented by Formula A as the light-emitting layer.

[0187] Furthermore, the present invention provides a composition for an organic electronic device comprising a compound represented by Formula 1 or a mixture of a compound represented by Formula 1 and a compound represented by Formula A, and provides an organic electronic device comprising the composition.

[0188] Furthermore, the present invention also provides an electronic device, the electronic device comprising a display device including organic electronic components; and a control unit for driving the display device.

[0189] According to another aspect, the present invention provides a display device in which the organic electronic element is at least one of OLED, organic solar cell, organic photoconductor, organic transistor (organic TFT), and elements for monochrome or white lighting. 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.

[0190] The following examples will describe in detail, through embodiments, examples of the synthesis of compounds represented by Formula 1 and Formula A and examples of the preparation of organic electronic components of the present invention, but are not limited to the following examples.

[0191] [Synthesis example]

[0192] The compound (final product) represented by Formula 1 according to the present invention is synthesized by reacting Sub1 and Sub2 as in reaction scheme 1, or by reacting Sub1 and Sub3 as in reaction scheme 2, but is not limited thereto.

[0193] <Reaction Scheme 1>

[0194] <Reaction Scheme 2>

[0195] in: Hal 1 Hal is independently I, Br, or Cl.

[0196] I. Synthesis of Sub1

[0197] Sub1 of reaction scheme 1 is synthesized via the reaction pathway of reaction scheme 3, but is not limited thereto.

[0198] <Reaction Scheme 3>

[0199] in: Hal can be I, Br, or Cl.

[0200] 1. Synthesis example of Sub1-1

[0201] In a round-bottom flask, Sub1a-1 (30.0 g, 100.96 mmol) was dissolved in toluene (340 mL), and Sub1b-1 (14.1 g, 151.44 mmol), Pd2(dba)3 (2.77 g, 3.03 mmol), and P( t -Bu)3 (1.23 g, 6.06 mmol), NaO t -Bu (19.4 g, 201.92 mmol) was stirred at room temperature. 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 applying a silica gel column to give 25.0 g of product (80% yield).

[0202] 2. Synthesis examples of Sub 1-10

[0203] In a round-bottom flask, Sub1a-10 (28.44 g, 95.7 mmol) was dissolved in toluene (320 mL). Using the same method as for Sub 1-1, Sub1b-10 (24.29 g, 143.55 mmol), Pd2(dba)3 (2.63 g, 2.87 mmol), and P( t -Bu)3 (1.16 g, 5.74 mmol), NaO t -Bu (18.39 g, 191.4 mmol), and 28.77 g of product was obtained. (Yield: 78%)

[0204] 3. Synthesis examples of Sub 1-20

[0205] In a round-bottom flask, dissolve Sub1a-20 (30.0 g, 95.7 mmol) in toluene (320 mL). Using the same method as for Sub 1-1, add Sub1b-20 (31.48 g, 143.55 mmol), Pd2(dba)3 (2.63 g, 2.87 mmol), and P( t -Bu)3 (1.16 g, 5.74 mmol), NaO t -Bu (18.39 g, 191.4 mmol), and 36.77 g of product was obtained. (Yield: 85%)

[0206] 4. Synthesis examples of Sub 1-51

[0207] In a round-bottom flask, Sub1a-51 (30.0 g, 118.72 mmol) was dissolved in toluene (400 mL), and Sub1b-51 (39.05 g, 178.08 mmol), Pd2(dba)3 (3.26 g, 3.56 mmol), and P( t -Bu)3 (1.44 g, 7.12 mmol), NaO t -Bu (22.82 g, 237.44 mmol) was added and stirred at 60 °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 36.19 g of product (70% yield).

[0208] 5. Synthesis examples of Sub 1-98

[0209] In a round-bottom flask, dissolve Sub1a-98 (30.0 g, 63.69 mmol) in toluene (210 mL). Using the same method as for Sub1-51, add Sub1b-98 (19.33 g, 95.54 mmol), Pd2(dba)3 (1.75 g, 1.91 mmol), and P( t -Bu)3 (0.77 g, 3.82 mmol), NaO t -Bu (12.24 g, 127.38 mmol), and 33.26 g of product was obtained. (Yield: 82%)

[0210] 6. Synthesis examples of Sub 1-124

[0211] In a round-bottom flask, dissolve Sub1a-124 (30.0 g, 86.4 mmol) in toluene (290 mL). Using the same method as for Sub1-51, add Sub1b-1 (12.07 g, 129.6 mmol), Pd2(dba)3 (2.37 g, 2.59 mmol), and P( t -Bu)3 (1.05 g, 5.18 mmol), NaO t -Bu (16.61 g, 172.8 mmol), and 24.53 g of product was obtained. (Yield: 79%)

[0212] The compounds belonging to Sub1 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 Sub1.

[0213]

[0214] [Table 1]

[0215] II. Synthesis of Sub2

[0216] Sub2 of reaction scheme 1 is synthesized via the reaction pathway of reaction scheme 4, but is not limited thereto.

[0217] <Reaction Scheme 4>

[0218] Hal 1 and Hal 2 It is I, Br, or Cl.

[0219] 1. Synthesis example of Sub2-1

[0220] In a round-bottom flask, Sub2a-1 (30 g, 161.95 mmol) was dissolved in toluene (540 mL), and Sub2b-1 (57.3 g, 242.93 mmol), Pd(OAc)2 (0.36 g, 1.62 mmol), and Cu(OAc)2 were added. H₂O (6.47 g, 32.39 mmol) and K₂CO₃ (44.76 g, 323.9 mmol) were added and stirred 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 silica gel column chromatography to give 41.3 g of product (75% yield).

[0221] 2. Synthesis example of Sub 2-17

[0222] In a round-bottom flask, dissolve Sub2a-17 (30 g, 177.33 mmol) in toluene (590 mL). Using the same method as for Sub 2-17, add Sub2b-17 (76.07 g, 266.0 mmol), Pd(OAc)₂ (0.40 g, 1.77 mmol), and Cu(OAc)₂. The reaction was carried out with H2O (7.08 g, 35.47 mmol) and K2CO3 (49.02 g, 354.66 mmol), yielding 43.14 g of product. (Yield: 65%)

[0223] 3. Synthesis examples of Sub 2-35

[0224] (1) Synthesis example of Sub2a-35

[0225] Sub2c-35 (50 g, 189.29 mmol) was dissolved in THF (630 mL) in a round-bottom flask. Sub2d-35 (51.81 g, 227.15 mmol), NaOH (15.14 g, 378.58 mmol), Pd(PPh3)4 (8.75 g, 7.57 mmol), and water (210 mL) were added, and the mixture was stirred at 60 °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 55.65 g of product (80% yield).

[0226] (2) Synthesis example of Sub2-35

[0227] In a round-bottom flask, dissolve Sub2a-35 (55.65 g, 151.44 mmol) in toluene (500 mL). Using the same method as for Sub 2-1, add Sub2b-1 (53.59 g, 227.16 mmol), Pd(OAc)2 (0.34 g, 1.51 mmol), and Cu(OAc)2. The reaction was carried out with H2O (6.05 g, 30.29 mmol) and K2CO3 (41.86 g, 302.88 mmol), yielding 56.97 g of product. (Yield: 72%)

[0228] 4. Synthesis examples of Sub 2-45

[0229] In a round-bottom flask, dissolve Sub2a-1 (30 g, 161.95 mmol) in toluene (540 mL). Using the same method as for Sub2-45, add Sub2b-45 (81.63 g, 242.93 mmol), Pd(OAc)2 (0.36 g, 1.62 mmol), and Cu(OAc)2. The reaction was carried out with H2O (6.47 g, 32.39 mmol) and K2CO3 (44.76 g, 323.9 mmol), yielding 42.79 g of product. (Yield: 60%)

[0230] 5. Synthesis examples of Sub 2-70

[0231] (1) Synthesis example of Sub2a-70

[0232] Sub2c-70 (50 g, 201.55 mmol) was dissolved in THF (670 mL) in a round-bottom flask. Using the same method as for Sub 2a-35, Sub2d-70 (30.71 g, 241.86 mmol), NaOH (16.12 g, 403.1 mmol), Pd(PPh3)4 (9.32 g, 8.06 mmol), and water (220 mL) were added, yielding 32.1 g of product. (Yield: 62%)

[0233] (2) Synthesis example of Sub2-70

[0234] In a round-bottom flask, dissolve Sub2a-70 (37.84 g, 151.17 mmol) in toluene (500 mL). Using the same method as for Sub 2-1, add Sub2b-1 (53.49 g, 226.76 mmol), Pd(OAc)2 (0.34 g, 1.52 mmol), and Cu(OAc)2. The reaction was carried out with H2O (6.06 g, 30.34 mmol) and K2CO3 (41.94 g, 303.42 mmol), yielding 32.1 g of product. (Yield: 62%)

[0235] The compounds belonging to Sub2 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 Sub2.

[0236]

[0237] [Table 2]

[0238] II. Synthesis of Sub3

[0239] Sub3 of reaction scheme 1 is synthesized via the reaction pathway of reaction scheme 5, but is not limited thereto.

[0240] <Reaction Scheme 5>

[0241] Where Hal is I, Br, or Cl.

[0242] 1. Synthesis example of Sub3-1

[0243] Sub3a-1 (30 g, 120.93 mmol) was dissolved in DMF (240 mL) in a round-bottom flask, and Sub3b-1 (37.01 g, 181.39 mmol), CuI (0.46 g, 2.42 mmol), and Cs₂CO₃ (59.1 g, 181.39 mmol) were added. The mixture was 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. The resulting compound was then recrystallized after column chromatography to give 28.62 g of product (73% yield).

[0244] 2. Synthesis examples of Sub3-6

[0245] Sub3a-6 (30 g, 76.86 mmol) was dissolved in DMF (150 mL) in a round-bottom flask, and Sub3b-6 (39.68 g, 115.3 mmol), CuI (0.29 g, 1.54 mmol), and Cs₂CO₃ (37.57 g, 115.3 mmol) were added. The mixture was 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. The resulting compound was then recrystallized after column chromatography to give 37.76 g of product (81% yield).

[0246] 3. Synthesis example of Sub3-13

[0247] Sub3a-13 (30 g, 120.93 mmol) was dissolved in DMF (240 mL) in a round-bottom flask, followed by the addition of Sub3b-13 (80.6 g, 181.39 mmol), CuI (0.46 g, 2.42 mmol), and Cs₂CO₃ (59.1 g, 181.39 mmol), and the mixture was 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. The resulting compound was then recrystallized after column chromatography to give 47.1 g of the product (69% yield).

[0248] The compounds belonging to Sub3 can be, but are not limited to, the following compounds, and Table 3 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to Sub3.

[0249]

[0250] [Table 3]

[0251] III. Synthesis of the final product

[0252] 1. Example of P-1 synthesis

[0253] In a round-bottom flask, dissolve Sub1-1 (20 g, 64.65 mmol) in toluene (220 mL), then add Sub2-1 (24.2 g, 71.12 mmol), Pd2(dba)3 (1.78 g, 1.94 mmol), and P( t -Bu)3 (0.78 g, 3.88 mmol), NaO t -Bu (12.43 g, 129.3 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 silica gel column chromatography to give 26.47 g of product (72% yield).

[0254] 2. Example of P-12 synthesis

[0255] In a round-bottom flask, dissolve Sub1-10 (20 g, 51.88 mmol) in toluene (170 mL). Using the same method as for P-1, add Sub2-1 (19.42 g, 57.07 mmol), Pd2(dba)3 (1.43 g, 1.56 mmol), and P( t -Bu)3 (0.63 g, 3.11 mmol), NaO t -Bu (9.97 g, 103.76 mmol), and gave 21.07 g of product. (Yield: 63%)

[0256] 3. Example of P-28 synthesis

[0257] In a round-bottom flask, dissolve Sub1-25 (20 g, 41.19 mmol) in toluene (140 mL). Using the same method as for P-1, add Sub2-15 (18.59 g, 45.31 mmol), Pd2(dba)3 (1.13 g, 1.24 mmol), and P( t -Bu)3 (0.50 g, 2.47 mmol), NaO t -Bu (7.92 g, 82.38 mmol), and 23.83 g of product was obtained. (Yield: 71%)

[0258] 4. Synthesis example of P-41

[0259] In a round-bottom flask, dissolve Sub1-36 (20 g, 62.81 mmol) in toluene (210 mL). Using the same method as for P-1, add Sub2-19 (23.86 g, 69.09 mmol), Pd2(dba)3 (1.73 g, 1.88 mmol), and P( t -Bu)3 (0.76 g, 3.77 mmol), NaO t -Bu (12.07 g, 125.62 mmol), and 25.24 g of product was obtained. (Yield: 61%)

[0260] 5. Example of P-58 synthesis

[0261] In a round-bottom flask, dissolve Sub1-52 (20 g, 61.46 mmol) in toluene (200 mL). Using the same method as for P-1, add Sub2-31 (33.83 g, 67.61 mmol), Pd2(dba)3 (1.69 g, 1.84 mmol), and P( t -Bu)3 (0.75 g, 3.69 mmol), NaO t -Bu (11.81 g, 122.92 mmol), and 36.17 g of product was obtained. (Yield: 79%)

[0262] 6. Example of P-77 synthesis

[0263] In a round-bottom flask, dissolve Sub1-68 (20 g, 41.19 mmol) in toluene (140 mL). Using the same method as for P-1, add Sub2-19 (15.64 g, 45.31 mmol), Pd2(dba)3 (1.13 g, 1.24 mmol), and P( t -Bu)3 (0.50 g, 2.47 mmol), NaO t -Bu (7.92 g, 82.38 mmol), and 22.8 g of product was obtained. (Yield: 67%)

[0264] 7. Synthesis example of P-84

[0265] In a round-bottom flask, dissolve Sub1-75 (20 g, 59.79 mmol) in toluene (200 mL). Using the same method as for P-1, add Sub2-52 (29.62 g, 65.77 mmol), Pd2(dba)3 (1.64 g, 1.79 mmol), and P( t -Bu)3 (0.73 g, 3.59 mmol), NaO t -Bu (11.49 g, 119.58 mmol), and 31.14 g of product was obtained. (Yield: 74%)

[0266] 8. Example of P-90 synthesis

[0267] In a round-bottom flask, dissolve Sub1-81 (20 g, 51.08 mmol) in toluene (170 mL). Using the same method as for P-1, add Sub2-1 (19.12 g, 56.19 mmol), Pd2(dba)3 (1.40 g, 1.53 mmol), and P( t -Bu)3 (0.62 g, 3.06 mmol), NaO t -Bu (9.82 g, 102.16 mmol), and 22.94 g of product was obtained. (Yield: 69%)

[0268] 9. Example of P-103 synthesis

[0269] In a round-bottom flask, dissolve Sub1-94 (20 g, 33.8 mmol) in toluene (110 mL). Using the same method as for P-1, add Sub2-4 (12.65 g, 37.18 mmol), Pd2(dba)3 (0.93 g, 1.01 mmol), and P( t -Bu)3 (0.41 g, 2.03 mmol), NaO t -Bu (6.50 g, 67.6 mmol), and gave 21.86 g of product. (Yield: 76%)

[0270] 10. Synthesis example of P-122

[0271] In a round-bottom flask, dissolve Sub1-113 (20 g, 33.40 mmol) in toluene (110 mL). Using the same method as for P-1, add Sub2-6 (11.91 g, 36.74 mmol), Pd2(dba)3 (0.92 g, 1.00 mmol), and P( t -Bu)3 (0.41 g, 2.00 mmol), NaO t -Bu (6.42 g, 66.8 mmol), and 19.97 g of product was obtained. (Yield: 71%)

[0272] 11. Example of P-137 synthesis

[0273] In a round-bottom flask, dissolve Sub1-10 (20 g, 51.88 mmol) in toluene (170 mL). Using the same method as for P-1, add Sub3-1 (18.62 g, 57.07 mmol), Pd2(dba)3 (1.43 g, 1.56 mmol), and P( t -Bu)3 (0.63 g, 3.11 mmol), NaO t -Bu (9.97 g, 103.76 mmol), and 25.52 g of product was obtained. (Yield: 78%)

[0274] 12. Example of P-147 synthesis

[0275] In a round-bottom flask, dissolve Sub1-129 (20 g, 66.59 mmol) in toluene (220 mL). Using the same method as for P-1, add Sub3-3 (31.23 g, 73.25 mmol), Pd2(dba)3 (1.83 g, 2.00 mmol), and P( t -Bu)3 (0.81 g, 4.00 mmol), NaO t -Bu (12.8 g, 133.18 mmol), and 35.36 g of product was obtained. (Yield: 68%)

[0276] 13. Example of P-160 synthesis

[0277] In a round-bottom flask, dissolve Sub1-130 (20 g, 35.61 mmol) in toluene (120 mL). Using the same method as for P-1, add Sub3-5 (19.92 g, 39.17 mmol), Pd2(dba)3 (0.98 g, 1.07 mmol), and P( t -Bu)3 (0.43 g, 2.14 mmol), NaO t -Bu (6.84 g, 71.22 mmol), and 25.71 g of product was obtained. (Yield: 73%)

[0278] Meanwhile, the FD-MS values ​​of compounds P-1 to P-176 of the present invention are shown in Table 4.

[0279] [Table 4]

[0280] Compounds represented by formula A can be prepared by reference to known synthetic methods (referred to as reactions) or published patent disclosures (e.g., Korean Patent Publication Nos. 2020-0129334, 2022-0055392, 2023-000502), but are not limited thereto.

[0281] Meanwhile, the FD-MS values ​​of compounds N-1 to N-276 of the present invention are shown in Table 5.

[0282] [Table 5]

[0283] Meanwhile, exemplary synthetic examples or references of the present invention represented by Formula 1 and Formula A 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 A are bonded, in addition to the substituents specified in the specific synthetic example.

[0284] [Example 1] Red organic electroluminescent device (phosphorescent host)

[0285] Compound A and Compound B are used on an ITO layer (anode) formed on a glass substrate, and Compound B is doped at a weight ratio of 98:2 to form a hole injection layer with a thickness of 10 nm. Then, Compound A is vacuum deposited on the hole injection layer to a thickness of 110 nm to form a hole transport layer.

[0286] Next, compound CR is vacuum deposited on the hole transport layer to a thickness of 15 nm to form a light-emitting auxiliary layer. Subsequently, the host material of the light-emitting layer uses compound P-1 (the compound of the present invention) as the first host and compound N-210 (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 bis-(1-phenylisoquinolinyl)acetylacetonate iridium(III) (hereinafter abbreviated as "(piq)2Ir(acac)") as the dopant material, and the dopant is doped such that the weight ratio of host to dopant is 95:5, thereby forming a light-emitting layer with a thickness of 30 nm.

[0287] Next, compound E was vacuum deposited on the emitting layer to form a hole-blocking layer with a thickness of 10 nm, and a mixture of compounds F and G in a weight ratio of 5:5 was used to form an electron transport layer with a thickness of 30 nm on the hole-blocking layer. Subsequently, compound G was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0288] 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

[0289] Compound B: 4,4',4''-((1 E ,1' E ,1'' E )-Cyclopropane-1,2,3-trimethylenetri(cyanomethylene))tri(2,3,5,6-tetrafluorobenzonitrile)

[0290] Compound CR:N 7-(dibenzo[b,d]thiophen-2-yl)-N 2 N 2 N 7 -triphenyldibenzo[ b,d Thiophene-2,7-diamine

[0291] Compound E: 2-(4'-(9,9-dimethyl-9 H -fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0292] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0293] Compound G: (8-hydroxyquinoline)lithium

[0294] [Example 2] to [Example 24]

[0295] The organic electroluminescent device was manufactured in the same manner as in Example 1, but the compounds of the present invention listed in Table 6 were used instead of compounds P-1 and N-210 of the present invention as the phosphorescent host material.

[0296] Comparative Examples 1 through 5

[0297] The organic electroluminescent device was manufactured in the same manner as in Example 1, but comparative compounds A to E were used instead of comparative compound P-1 of the present invention as the phosphorescent host material.

[0298] [Compare compound A] [Compare compound B] [Compare compound C]

[0299] [Compare compound D] [Compare compound E]

[0300] A forward-biased DC voltage was applied to the organic electroluminescent devices of the embodiments and comparative examples manufactured as described above, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch. As a result of the measurements, a lifetime measuring device manufactured by MaxScience was used at 2500 cd / m². 2 The T95 lifespan was measured at a reference brightness. Table 5 shows the results of device manufacturing and evaluation.

[0301] 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.

[0302] 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 from three batches was evaluated separately, the values ​​of the experimental results obtained in this manner showed statistical significance.

[0303] [Table 6]

[0304] As can be seen from Table 6, when using the organic electroluminescent device material of the present invention as the phosphorescent host material to manufacture a red organic electroluminescent device, the compounds of the present invention exhibit significantly superior characteristics in terms of element performance compared to using comparative compounds A to E, and particularly demonstrate excellent characteristics in terms of efficiency. As can be seen from the above, when the host of the light-emitting layer is formed by mixing multiple compounds, it can be confirmed that there are significant differences in characteristics depending on the type of the first and second compounds. Similarly, depending on the type of the second compound, there are differences in driving voltage, efficiency, and lifespan.

[0305] When comparative compounds A and B are compared with the compounds of the present invention, comparative compounds A and B have structures in which dibenzofuran or dibenzothiophene is bonded, while the compounds of the present invention have structures in which naphthobenzofuran or naphthobenzothiophene is bonded, and therefore there are differences.

[0306] These structural differences may affect the properties of the compounds, as can be seen from Table 7. Table 7 shows the T1 energy levels of comparative compound A, comparative compound B, and compound P-12 of the present invention, measured using the DFT method (B3LYP / 6-31g(D)) with a Gaussian procedure.

[0307] [Table 7]

[0308] As can be seen from the results in Table 7, the T1 of compound P-12 of the present invention is lower than that of comparative compounds A and B. This means that the red dopant has the lowest T1 among the phosphorescent R / G / B compounds, and the T1 bandgap with the red dopant is the lowest. In other words, it shows a very significant difference in efficiency because it can simultaneously transfer excitons from the host P-12 to the dopant or block excitons from the dopant to the hole transport layer.

[0309] Furthermore, when comparing comparative compounds C and D with the compounds of the present invention, the difference lies in that comparative compound D has an attached benzoxazole and comparative compound C has an attached 2,3-naphthoxazole, while the compounds of the present invention have attached 1,2- or 3,4-naphthoxazole. That is, Table 8 shows the HOMO levels of comparative compounds C, comparative compound D, and P-12 measured using a DFT method (B3LYP / 6-31g(D)) with a Gaussian procedure.

[0310] [Table 8]

[0311] As can be seen from the results in Table 8, the HOMO of compound P-12 of the present invention is lower than that of comparative compounds C and D. This indicates that hole transfer between the luminescent auxiliary layer and the host can proceed smoothly, and in particular, the hole transfer to the dopant is expected to be of good performance. Therefore, the compounds of the present invention are highly efficient when applied. Table 9 shows the calculated CN-bond BDE values ​​of the compounds of the examples.

[0312] The weakest BDEs were calculated using the bond-ligand dissociation panel in Schrodinger Materials Science (version 5.0.122, 2023-2). Optimization and CN-bond BDE calculations were performed using the Becke, 3-parameter, Lee-Yang-Parr method (B3LYP method) and 6-31G(d) basis set (which is one of the pople basis sets).

[0313] Here, CN bond BDE refers to the BDE of the CN bond between the amine structure and the naphthoxazazole structure.

[0314] [Table 9]

[0315] The BDE values ​​presented in Table 9 are the results measured in an oxidized state where electrons within the molecule have been removed, and it has been determined that a higher BDE indicates higher structural stability. Therefore, it can be confirmed that the structural stability of the compounds of the present invention is higher than that of the comparative compounds, thus determining that this affects the overall performance of the device. In particular, it is believed to exhibit significantly superior characteristics in terms of service life. Therefore, compared to comparative compounds A to E, the compounds of the present invention exhibit superior characteristics in terms of efficiency or service life.

[0316] 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 should be construed as including all inventive concepts within the scope of equivalent claims.

[0317] [Industrial Applicability]

[0318] According to the present invention, organic devices with excellent device characteristics (e.g., high brightness, high luminosity, and long service life) can be manufactured, thus demonstrating industrial applicability.

Claims

1. Compounds represented by Formula 1: <Formula 1> <Equation 1-1> <Equation 1-2> in: L 1 L 2 and L 3 Independently selected from single bonds; C6-C 60 arylene groups; fluorene groups; and C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups; Ar 1 Independently selected from C6-C 60 An aryl group; or a C2-C group containing at least one heteroatom selected from O, N, S, Si, or P. 60 Heterocyclic groups; R is a substituent represented by formula 1-1. C is a substituent represented by formula 1-2. In Equations 1-1 and 1-2: Rings A and B are independently C6-C 14 An aryl group, provided that at least one of them is a C 10 -C 14 aryl group, One of X and Y is N, and the other is O or S. Z is either O or S. R 1 They may be the same as or different from each other, and are independently selected from hydrogen; deuterium; cyano group; 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 Aliphatic ring; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy groups; and C6-C 30 aryloxy group; a is an integer from 0 to 6. Indicates the location to be bonded. It refers to a single or double key, and The aryl group, arylene group, heterocyclic group, fluorene group, fluorene group, fused ring, aliphatic ring, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be replaced by one or more substituents selected from deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkyl thio group; C1-C 20 alkoxy 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 cycloalkyl ring; C7-C 20 arylalkyl groups; and C8-C 20 The substituents are aryl alkenyl groups, and the hydrogen atoms of these substituents may be further replaced by 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 formula 1 is represented by formula 2 or formula 3: <Formula 2> <Formula 3> in: X, Y, Ar 1 L 1 L 2 L 3 , R, R 1 a and Same as defined in claim 1, a' is an integer from 0 to 5. Ar 2 Independently selected from C6-C 60 aryl group; fluorenyl group; or C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups.

3. The compound according to claim 1, wherein L 1 L 2 and L 3 Equations L-1 to L-10 represent: <Formula L-1> <Formula L-2> <Formula L-3> <Formula L-4> <Formula L-5> <Formula L-6> <Formula L-7> <Formula L-8> <Formula L-9> <Formula L-10> in: R 4 They are independently identical or different from each other, and are hydrogen; deuterium; or C6-C substituted or unsubstituted with deuterium. 20 aryl group; f is an integer from 0 to 4, g is an integer from 0 to 6, and h is an integer from 0 to 8. Indicates the location to be bonded.

4. The compound according to claim 1, wherein Ar 1 Any one of equations c-1 to c-7: <Formula c-1> <Formula c-2> <Formula c-3> <Formula c-4> <Formula c-5> <Formula c-6> <Formula c-7> in: R 5 They are independently identical or different from each other, and are hydrogen; deuterium; or C6-C substituted or unsubstituted with deuterium. 20 aryl group; i is an integer from 0 to 5, j is an integer from 0 to 7, and k is an integer from 0 to 9. Indicates the location to be bonded.

5. 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-176: 。 6. A composition for use in organic electronic components, comprising a mixture of the compound of claim 1 and a compound represented by formula A: <Form A> in: X A X B and X C Independently, it is CR' or N, but X A X B and X C At least two of them are N, and 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 Aliphatic rings; 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' represents hydrogen; or deuterium; The aryl group, arylene group, heterocyclic group, fluorene group, fluorene group, fused ring group, and aliphatic ring 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; 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 Cycloalkyl groups; C7-C 20 arylalkyl groups; and C8-C 20 The substituents are aryl alkenyl groups, and the hydrogen atoms of these substituents may be further replaced by 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.

7. The composition for organic electronic components according to claim 6, wherein the composition is used as a host for a light-emitting layer.

8. The composition for organic electronic components according to claim 6, wherein the above-mentioned 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 C(R) 1B (R) 1C ), R A R B R C R D R E R F R 1A R 1B and R 1C They are independently the same or different from each other, and are 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 groups, and multiple adjacent groups 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. Indicates the location to be bonded.

9. 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 6.

10. The organic electronic component of claim 9, further comprising 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.

11. The organic electronic component according to claim 9, 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.

12. The organic electronic component of claim 11, wherein the organic material layer further comprises a charge-generating layer formed between the two or more stacks.

13. An electronic device comprising a display device including the organic electronic components of claim 9; and a control unit for driving the display device.

14. The electronic device of claim 13, 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 lighting.

15. A method for reusing the compound of formula 1 according to claim 1, comprising: Crude organic light-emitting material comprising the compound of Formula 1 of claim 1 is recovered from a deposition apparatus used in a process for depositing organic light-emitting material 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; as well as The recovered organic light-emitting material is purified to a purity of 99.9% or higher.

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