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

Abstract

The present invention provides a novel compound which can improve the luminous efficiency, stability, and lifespan of an element, a composition comprising the same, and an organic electronic element and an electronic device using the same.

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 light-emitting materials and charge-transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0004] The current portable display market is trending towards larger displays, which in turn requires significantly more power than existing portable displays. Therefore, power consumption has become a critical factor for portable displays with a limited power source called a battery, and issues of efficiency and lifespan must be addressed.

[0005] Efficiency, lifespan, and drive voltage are interrelated, and as efficiency increases, drive voltage decreases relatively. As drive voltage decreases, the crystallization of organic materials due to Joule heating generated during drive decreases, and thus lifespan tends to increase.

[0006] However, efficiency cannot be maximized simply by improving the organic material layers. This is because long service life and high efficiency can only be achieved simultaneously 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] In other words, to fully realize the superior properties of organic electronic components, stable and effective materials should be suitable for forming organic material layers within the components, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and luminescent auxiliary layer materials. However, such stable and effective organic material layer materials for organic electronic components have not yet been fully developed. Therefore, further development of new materials is necessary. Summary of the Invention

[0008] To address the problems mentioned above in the background art, the present invention has disclosed compounds with novel structures, and when these compounds are applied to organic electronic components, they significantly improve the luminous efficiency, stability, and lifespan of the components.

[0009] Therefore, the object of the present invention is to provide new compounds, organic electronic components using said new compounds, and electronic devices thereof.

[0010] Technical solution

[0011] The present invention provides compounds represented by Formula 1.

[0012] <Formula 1>

[0013]

[0014] In another aspect, the present invention provides organic electronic components and electronic devices thereof comprising compounds represented by Formula 1.

[0015] Invention Effects

[0016] 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 significantly improved. Attached Figure Description

[0017] Figures 1 to 3 Examples of organic electronic components according to the present invention are shown.

[0018] Figure 4 An example of one aspect of the invention is shown. Detailed Implementation

[0019] 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.

[0020] 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.

[0021] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0022] Unless otherwise specified, the term “halogenated” or “halogen” as used herein includes fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0023] 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, 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.

[0024] 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, or 2 to 12 carbon atoms, and includes straight-chain or branched groups.

[0025] 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, or 3 to 12 carbon atoms.

[0026] Unless otherwise specified, the terms “alkoxy,” “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.

[0027] 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, or 6 to 12 carbon atoms.

[0028] 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, 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 comprises an aromatic ring formed by the bonding or reaction of adjacent substituents. For example, an aryl group can be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0029] 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.

[0030] 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.

[0031] Unless otherwise specified, the terms "heteroaryl group" or "hybrid aryl group" as used in this invention mean an aryl group or aryl group 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, each containing one or more heteroatoms, but not limited thereto, and including at least one of monocyclic and polycyclic rings, and can be formed by bonding adjacent functional groups.

[0032] 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, or 2 to 12 carbon atoms, and includes any of monocyclic and polycyclic rings, and may include heteroaliphatic and heteroaromatic rings. Furthermore, it may combine with adjacent groups to form heterocyclic groups.

[0033] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0034] Furthermore, "heterocyclic group" refers to monocyclic compounds, cyclic aggregates, fused polycyclic systems, spirochetes, etc., containing heteroatoms. Additionally, compounds containing heteroatom groups (e.g., SO2, P=O, etc.) instead of ring-forming carbon atoms (e.g., the following compounds) can also be included in the category of heterocyclic groups. For example, "heterocyclic group" includes the following compounds.

[0035]

[0036] 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 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, but is not limited thereto. For example, even when benzene, which is an aromatic ring, is fused with cyclohexane, which is a non-aromatic ring, it is still an aliphatic ring.

[0037] Unless otherwise specified, the terms "fluorenyl group," "fluoreneyl group," or "fluorenetrimethyl group" as used herein mean a monovalent, divalent, or trivalent functional group of hydrogen in the following structures, 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.

[0038]

[0039] The term "spiro compound" 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. 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.

[0040] Unless otherwise specified, as used herein, "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.

[0041] Unless otherwise specified, the term "ring" as used herein 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, and includes saturated or unsaturated rings.

[0042] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups contain, but are not limited to, one or more hetero atoms.

[0043] 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.

[0044] In this specification, the “group name” corresponding to aryl groups, arylide groups, heterocyclic groups, etc., is used as an example for each symbol and its substituents. It can be written as “the name of the group reflecting the valence”, but also 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 its valence; for example, a monovalent 'group' is 'phenanthrene' and a divalent group is 'pyrimidine', 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 'group name' of its valence, such as pyrimidinyl group in the case of a monovalent group, and pyrimidinyl group in the case of a divalent group, etc. Furthermore, in this specification, when describing compound names or substituent names, the numbers or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine can be described as pyridopyrimidine, benzofurano[2,3-d]pyrimidine can be described 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.

[0045] Furthermore, unless otherwise explicitly explained, the formulas used in this invention are identical to the definitions of substituents defined by the index in the following formulas.

[0046]

[0047] 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 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 manner, but the indication of the hydrogens bonded to the carbons that form the benzene ring is omitted.

[0048]

[0049] Unless otherwise expressly 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 benzene is used, it means position 1 or 2, and the meta position is the next substitution position after the adjacent substitution position, when benzene is used as an example representing position 1 or 3, and the para position is the next substitution position after the meta position, when benzene is used as an example meaning positions 1 and 4. 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.

[0050] [Examples of adjacent positions]

[0051]

[0052] [Example of interposition]

[0053]

[0054] [Example of alignment]

[0055]

[0056] Below, compounds according to one aspect of the invention and organic electronic components comprising said compounds will be described.

[0057] The present invention provides compounds represented by Formula 1.

[0058] <Formula 1>

[0059]

[0060] in:

[0061] R 1 and R 2 They are either the same as or different from each other, and are independently C1-C that are substituted or unsubstituted with deuterium. 50 Alkyl groups; more preferably C1-C 25 Alkyl groups, C1-C 18 Alkyl or C1-C 12 Alkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, etc.

[0062] R 3 R 4 R5 R 6 and R 7 They may be the same as or different from each other, and are independently selected from hydrogen; deuterium; 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; 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; and C3-C 60 Aliphatic rings; or they can bond to adjacent groups to form aromatic or heteroaromatic rings.

[0063] Where R 3 R 4 R 5 R 6 and R 7 It is an aryl group, preferably C6-C. 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, wait.

[0064] Where R 3 R 4 R 5 R 6 and R 7 It is a heterocyclic group, preferably C2-C. 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, naphthobenzofuran, naphthobenzothiophene, etc.

[0065] Where R 3 R 4 R 5 R 6and R 7 It is a fused ring group, preferably C3-C. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0066] Where R 3 R 4 R 5 R 6 and R 7 It is an alkyl group, preferably C1-C. 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.

[0067] Where R 3 R 4 R 5 R 6 and R 7 It is an alkoxy group, preferably C1-C. 25 alkoxy groups, C1-C 18 alkoxy group or C1-C 12 Alkoxy group.

[0068] Where R 3 R 4 R 5 R 6 and R 7 It is an aryloxy group, preferably C6-C. 25 aryloxy group, C6-C 18 aryloxy group or C6-C 12 Aryloxy group.

[0069] Where R 3 R 4 R 5 R 6 and R 7 It is an aliphatic cyclic group, preferably C3-C. 30 Aliphatic cyclic groups, more preferably C3-C 25 Aliphatic cyclic groups, C3-C 18 Aliphatic cyclic groups and C3-C 12 Aliphatic cyclic groups, specifically cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0070] A is C1-C 50 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.

[0071] L 1 Selected from C6-C 60 arylene group; fluorene group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heteroaryl group; C3-C 60 Aliphatic rings; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings;

[0072] Where L 1 It is an aryl group, preferably C6-C. 30 arylene 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, etc.

[0073] Where L 1 It is a heteroaryl group, preferably C2-C. 30 Heteroaryl groups, more preferably C2-C 25 heteroaryl group, C2-C 18 heteroaryl group or C2-C 12 Hybrid aryl group.

[0074] Where L 1 It is an aliphatic cyclic group, preferably C3-C. 30 Aliphatic cyclic groups, more preferably C3-C 25 Aliphatic cyclic groups, C3-C 18 Aliphatic cyclic groups and C3-C 12 Aliphatic cyclic groups, specifically cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0075] When L 1 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. 25 Aliphatic rings and C6-C 25 Fused ring groups of aromatic rings.

[0076] a and d are independent integers from 0 to 4, b is an integer from 0 to 2, c is an integer from 0 to 7, and e is an integer from 0 to 5.

[0077] The aryl group, arylene group, heteroarylene group, heterocyclic group, fluorenyl group, fluorene group, aliphatic cyclic group, fused cyclic group, 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 Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 Alkyl aryl groups; furthermore, the hydrogens of these substituents may be further replaced by one or more deuteriums, and additionally, the substituents may bond to each other to form saturated or unsaturated rings, wherein the term 'ring' refers to 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 can be represented by Equation 1-1 or Equation 1-2.

[0079]

[0080]

[0081] Where R 1 R 2 R 3 R 4 R 5 R 6 L 1 A, a, b, c, d, and e are the same as those defined in Equation 1.

[0082] Furthermore, A can be represented by any one of the following formulas A-1 to A-3.

[0083]

[0084] Hydrogen can be further replaced by one or more deuterium atoms.

[0085] In addition, L 1 Represented by any one of the following equations L-1 to L-6:

[0086]

[0087] in:

[0088] R 8 R 9 R 10 and R 11 Each may be the same or different, and each is independently selected from hydrogen; deuterium; halogen; cyano group; nitro 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 group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic group; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 alkylaryl group; or multiple adjacent R groups 8 or multiple R 9 or multiple R 10 or multiple R 11 They can bond together to form a ring.

[0089] Y is O, S, NR, or CR'R".

[0090] R, R', and R" are each independently selected from 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 group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic groups; and C3-C 20 Aliphatic rings and C6-C 20 Fused ring groups of aromatic rings;

[0091] f, g, and k are independent integers from 0 to 4, h and i are independent integers from 0 to 3, and j is an integer from 0 to 2.

[0092] * indicates the location to be bonded.

[0093] Specifically, the compound represented by Formula 1 can be any one of the following compounds P-1 to P-80, but is not limited thereto.

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] In another aspect, the present invention provides a method for reusing a compound represented by Formula 1, the method comprising:

[0100] 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;

[0101] Remove impurities from coarse organic light-emitting materials;

[0102] Organic light-emitting materials are recovered after removing impurities; and

[0103] Purify the recovered organic light-emitting materials to a purity of 99.9% or higher.

[0104] 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.

[0105] The recrystallization solvent is preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] The pre-purification process may include a step of recrystallizing with a polar solvent followed by recrystallization with a non-polar solvent.

[0113] 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.

[0114] The adsorbent can be activated carbon, silica gel, alumina, or other materials used for known adsorption purposes.

[0115] The step of purifying the recovered impurities to a purity of 99.9% or higher may include sublimation purification.

[0116] 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 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). The first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode. In the case of an inverted organic electronic component, the first electrode may be a cathode, and the second electrode may be an anode.

[0117] 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 ).

[0118] Furthermore, the organic electronic component according to embodiments 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 according to embodiments of the present invention suitable for 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 compound of formula 1 according to the present invention can be used as a material for the hole transport layer.

[0119] 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 ).

[0120] Furthermore, even when using the same core, band gap, electrical properties, and interfacial properties can vary depending on which substituents are bonded to where. Therefore, the choice of the combination of the core and its associated substituents is 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.

[0121] 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 for use as a cathode can be deposited thereon.

[0122] Furthermore, the present invention provides an organic electronic component in which an 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.

[0123] As another specific example, the same or different types of compounds represented by Formula 1 are mixed and used in an organic material layer.

[0124] Furthermore, the present invention provides a hole transport layer composition comprising a compound represented by Formula 1, and provides an organic electronic device comprising a hole transport layer.

[0125] 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.

[0126] 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.

[0127] The following examples will describe in detail the synthesis examples of the compounds represented by Formula 1 and the preparation examples of the organic electronic components of the present invention, but are not limited to the following examples.

[0128] [Synthesis example 1]

[0129] The compound (final product) according to formula 1 according to the invention can be synthesized by reactions such as those in reaction scheme 1, but is not limited thereto. (Hal) 1 =Cl, I or Cl)

[0130] <Reaction Scheme 1>

[0131]

[0132] Meanwhile, 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.

[0133]

[0134]

[0135]

[0136] [Table 1]

[0137]

[0138]

[0139] Compounds belonging to Sub 2 may include, but are not limited to, the following compounds, and Table 2 shows the FD-MS (field desorption-mass spectrometry) values ​​of compounds belonging to Sub 2.

[0140]

[0141] [Table 2]

[0142]

[0143]

[0144] I. Synthesis of the final product

[0145] 1. Example of P-3 synthesis

[0146]

[0147] 1) Synthesis of Sub 1-3

[0148] Sub 1a-3 (11.5 g, 36.5 mmol), Sub 1b-3 (12.0 g, 40.2 mmol), Pd2(dba)3 (1.0 g, 1.1 mmol), Xphos (8.7 g, 18.3 mmol), NaOt-Bu (7.0 g, 73.1 mmol), and toluene (122 mL) were added to a round-bottom flask and stirred at 60 °C for 4 hours.

[0149] After the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized using a silica gel column to obtain 13.7 g of product (yield: 65%).

[0150] 2) Synthesis of P-3

[0151] Sub 1-3 (13.3 g, 23.0 mmol) was dissolved in toluene (77 mL) in a round-bottom flask, followed by the addition of Sub 2-1 (4.3 g, 23.0 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), Xphos (5.5 g, 11.5 mmol), and NaOt-Bu (4.4 g, 46.0 mmol), and the mixture was stirred at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized from silica gel column to obtain 9.9 g of the product (yield: 59%).

[0152] 2. Example of P-14 synthesis

[0153]

[0154] 1) Synthesis of Sub 1-3

[0155] Sub 1-a13 (10.8 g, 34.3 mmol), Sub 1b-13 (11.3 g, 37.7 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), Xphos (8.2 g, 17.2 mmol), NaOt-Bu (6.6 g, 68.6 mmol), and toluene (114 mL) were added to a round-bottom flask and the product was obtained using the same method as Sub 1-3 (yield: 65%).

[0156] 2) Synthesis of P-14

[0157] Sub 1-13 (11.8 g, 23.5 mmol), Sub 2-1 (4.4 g, 23.5 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), Xphos (5.6 g, 11.8 mmol), NaOt-Bu (4.5 g, 47.0 mmol), and toluene (78 mL) were added to a round-bottom flask and the product was obtained using the P-3 synthesis method (yield: 62%).

[0158] 3. Synthesis example of P-29

[0159]

[0160] 1) Synthesis of Sub 1-28

[0161] Sub 1-a28 (12.7 g, 40.3 mmol), Sub 1b-13 (9.9 g, 44.4 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), Xphos (9.6 g, 20.2 mmol), NaOt-Bu (7.8 g, 80.7 mmol), and toluene (134 mL) were added to a round-bottom flask and the product was obtained using the same method as Sub 1-3 (yield: 67%).

[0162] 2) Synthesis of P-29

[0163] Sub 1-28 (12.8 g, 25.5 mmol), Sub 2-1 (4.8 g, 25.5 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), Xphos (6.1 g, 12.8 mmol), NaOt-Bu (4.9 g, 51.0 mmol), and toluene (85 mL) were added to a round-bottom flask and the product was obtained using the P-3 synthesis method (yield: 60%).

[0164] 4. Synthesis example of P-41

[0165]

[0166] 1) Synthesis of Sub 1-40

[0167] Sub 1-a41 (11.5 g, 48.2 mmol), Sub 1b-41 (12.6 g, 53.0 mmol), Pd2(dba)3 (1.3 g, 1.4 mmol), Xphos (11.5 g, 24.1 mmol), NaOt-Bu (9.3 g, 96.4 mmol), and toluene (161 mL) were added to a round-bottom flask and the product was obtained using the synthetic method of Sub 1-3 (yield: 71%).

[0168] 2) Synthesis of P-41

[0169] Sub 1-40 (14.1 g, 32.1 mmol), Sub 2-1 (6.1 g, 32.1 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), Xphos (7.6 g, 16.0 mmol), NaOt-Bu (6.2 g, 64.1 mmol), and toluene (107 mL) were added to a round-bottom flask and the product was obtained using the P-3 synthesis method (yield: 58%).

[0170] 5. Example of P-64 synthesis

[0171]

[0172] 1) Synthesis of Sub 1-61

[0173] Sub 1-a3 (10.5 g, 33.4 mmol), Sub 1b-13 (8.2 g, 36.7 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), Xphos (8.0 g, 16.7 mmol), NaOt-Bu (6.4 g, 66.7 mmol), and toluene (111 mL) were added to a round-bottom flask and the product was obtained using the same method as Sub 1-3 (yield: 74%).

[0174] 2) Synthesis of P-64

[0175] Sub 1-61 (12.0 g, 23.9 mmol), Sub 2-1 (4.5 g, 23.9 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), Xphos (5.7 g, 12.0 mmol), NaOt-Bu (4.6 g, 47.8 mmol), and toluene (80 mL) were added to a round-bottom flask and the product was obtained using the P-3 synthesis method (yield: 62%).

[0176] 6. Synthesis example of P-72

[0177]

[0178] 1) Synthesis of Sub 1-18

[0179] Sub 2-26 (12.2 g, 51.1 mmol), Sub 1b-13 (12.6 g, 56.2 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), Xphos (12.2 g, 25.6 mmol), NaOt-Bu (9.8 g, 102.2 mmol), and toluene (170 mL) were added to a round-bottom flask and the product was obtained using the same method as Sub 1-3 (yield: 71%).

[0180] 2) Synthesis of P-72

[0181] Sub 1-18 (14.2 g, 33.4 mmol), Sub 2-6 (8.2 g, 33.4 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), Xphos (8.0 g, 16.7 mmol), NaOt-Bu (6.4 g, 66.7 mmol), and toluene (111 mL) were added to a round-bottom flask and the product was obtained using the P-3 synthesis method (yield: 65%).

[0182] 7. Synthesis example of P-80

[0183]

[0184] 1) Synthesis of Sub 1-74

[0185] Sub 2-26 (12.3 g, 51.5 mmol), Sub 1b-74 (17.3 g, 56.7 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), Xphos (12.3 g, 25.8 mmol), NaOt-Bu (9.9 g, 103.1 mmol), and toluene (172 mL) were added to a round-bottom flask and the product was obtained using the same method as Sub 1-3 (yield: 55%).

[0186] 2) Synthesis of P-80

[0187] Sub 1-74 (13.4 g, 26.4 mmol), Sub 2-3 (5.1 g, 26.4 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), Xphos (6.3 g, 13.2 mmol), NaOt-Bu (5.1 g, 52.9 mmol), and toluene (88 mL) were added to a round-bottom flask and the product was obtained using the P-3 synthesis method (yield: 66%).

[0188] Meanwhile, Table 3 shows the FD-MS values ​​of compounds P-1 to P-80 of the present invention prepared according to the synthesis examples described above.

[0189] [Table 3]

[0190]

[0191]

[0192] Meanwhile, exemplary synthetic examples of the present invention represented by Formula 1 have been described, but these are all based on the Buchwald-Hartwig cross-coupling reaction, the Miyaura borylation reaction, the Suzuki cross-coupling reaction, the intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), the Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504.), and the PPh3--mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.). It should be readily understood by those skilled in the art that the reaction proceeds even when other substituents defined in Formula 1 are bonded, in addition to the substituents specified in the specific synthetic examples.

[0193] Manufacturing evaluation of organic electroluminescent devices

[0194] [Example 1] Green organic electroluminescent device (hole transport layer)

[0195] Compound P-1 and compound B of the present invention 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 P-1 of the present invention is vacuum deposited on the hole injection layer with a thickness of 110 nm to form a hole transport layer.

[0196] Next, compound CG was vacuum deposited on the hole transport layer to a thickness of 10 nm to form an emitting auxiliary layer. Subsequently, compound DG was used as the host material of the emitting layer, and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as "Ir(ppy)3") was used as the dopant material, and the dopant was doped at a weight ratio of 90:10 to form an emitting layer with a thickness of 30 nm.

[0197] Next, compound E was vacuum deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and a mixture of compound F and compound G in a 5:5 weight ratio was used to form an electron transport layer with a thickness of 30 nm on the hole-blocking layer.

[0198] 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.

[0199] Compound B: 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanomethylene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0200] Compound CG: N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi[fluorene]-2-amine

[0201] Compound DG: 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-7,7-dimethyl-5,7-dihydroindo[2,1-b]carbazole

[0202] Compound E: 2-(4'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0203] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0204] Compound G: (8-hydroxyquinoline)lithium

[0205] [Examples 2] to [Examples 17] Green Organic Electroluminescent Device (Hole Transport Layer)

[0206] An organic electroluminescent device was manufactured in the same manner as in Example 1, but the compound of the present invention described in Table 4 was used instead of compound P-1 of the present invention as the hole transport layer material.

[0207] Comparative Examples 1 to 3

[0208] The organic electroluminescent device was manufactured in the same manner as in Example 1, but the comparative compounds 1 to 3 described in Table 4 were used instead of the compound P-1 of the present invention as the hole transport layer material.

[0209]

[0210]

[0211] Electroluminescence (EL) characteristics were measured using a PR-650 from PhotoResearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 17 and Comparative Examples 1 to 3 of the present invention. As a result of the measurements, a lifetime measuring device manufactured by Max Science was used at 5000 cd / m². 2 The lifespan of the T95 was measured under standard brightness. Table 4 shows the results of device manufacturing and evaluation.

[0212] The measuring equipment can evaluate the performance of the new material compared to the comparison compound under the same conditions, unaffected by possible daily fluctuations in deposition rate, vacuum quality, or other parameters. During the evaluation, one batch contained four identically prepared OLEDs containing the comparison compound, and the performance of a total of 12 OLEDs was evaluated across three batches, so the experimental results obtained in this manner show statistical significance.

[0213] [Table 4]

[0214]

[0215]

[0216] As can be seen from the results in Table 4, when green organic electroluminescent devices are manufactured using the material of the present invention as a hole transport layer material, it can be seen that, compared with the use of comparative compounds 1 to 3 which have a basic framework similar to the compound of the present invention, not only can the driving voltage of the organic electroluminescent device be reduced, but also the luminous efficiency and lifespan can be improved.

[0217] Comparative compounds 1 to 3 and the compounds of the present invention have similar structures in which the arylamine group is bonded to the fluorene group, but differ in the presence or absence of secondary substituents bonded to specific positions of the fluorene group and the substituents of the amine group.

[0218] As can be seen, the device performance of comparative compound 2 (where the amine group is bonded to the fluorene group at the 2nd position and the phenyl group is additionally substituted at the 3rd position) is improved compared to comparative compound 1 (where only the amine group is bonded to the fluorene group at the 2nd position and no additional substituents are bonded). Furthermore, in the case of comparative compound 3, it is similar to comparative compound 2, but the methyl group is substituted at the 3rd position, and it is characterized by having additional substituents in which a specific aliphatic ring group is fused. Comparative compound 3 shows slightly improved drive voltage and efficiency, but its lifetime is reduced due to the fused aliphatic ring group.

[0219] Furthermore, it can be confirmed that the apparatus results of Examples 1 to 17 produced using the compounds of the present invention are characterized by the fact that the amine group containing a specific aryl moiety is bonded to the 2-position of the fluorene nucleus and the alkyl group is bonded to the 3-position of the fluorene nucleus, exhibiting significantly superior results. It can also be confirmed that the compounds of the present invention represented by Formula 1 have superior apparatus performance than other comparative compounds not described in this specification.

[0220] In summary, even with similar molecular compositions, the properties of compounds (e.g., hole characteristics, light efficiency characteristics, energy levels, hole injection and mobility characteristics, charge balance of holes and electrons, volume density and intermolecular distance) can vary significantly and unpredictably depending on the presence or absence of substituents and their substitution positions. This also indicates that the performance of a device may vary due to complex factors rather than a single component affecting the overall device outcome.

[0221] In the case of a hole transport layer, it is necessary to understand the relationship with the light-emitting layer (substrate), and even with a similar core, it is difficult for those skilled in the art to deduce the characteristics exhibited by a hole transport layer using the compound according to the present invention.

[0222] Furthermore, although the device characteristics in which the compound of the present invention is applied only to one layer of the hole transport layer are described in the evaluation results of the aforementioned device manufacturing, the compound of the present invention can be used by applying the compound of the present invention to both the hole transport layer and the light emission auxiliary layer.

[0223] 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 these embodiments.

[0224] The scope of this invention should be interpreted based on the appended claims, and should be interpreted as including all technical concepts within the scope equivalent to the claims.

[0225] Numerical Explanation

[0226] 100, 200, 300: Organic electronic components; 110: First electrode

[0227] 120: Hole injection layer; 130: Hole transport layer

[0228] 140: Emissive layer; 150: Electron transport layer

[0229] 160: Electron injection layer; 170: Second electrode

[0230] 180: Light efficiency enhancement layer; 210: Buffer layer

[0231] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0232] 330: First hole transport layer; 340: First luminescent layer

[0233] 350: First electron transport layer; 360: First charge generation layer

[0234] 361: Second charge generation layer; 420: Second hole injection layer

[0235] 430: Second hole transport layer; 440: Second luminescent layer

[0236] 450: Second electron transport layer; CGL: Charge generation layer

[0237] ST1: First stack; ST2: Second stack

Claims

1. Compounds represented by Formula 1: <Formula 1> in: R 1 and R 2 They are either the same as or different from each other, and are independently C1-C that are substituted or unsubstituted with deuterium. 50 alkyl groups; R 3 R 4 R 5 R 6 and R 7 They may be the same as or different from each other, and are independently selected from hydrogen; deuterium; 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; 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; and C3-C 60 Aliphatic rings; or they can bond to adjacent groups to form aromatic or heteroaromatic rings. A is C1-C 50 alkyl groups; L 1 Each is independently selected from C6-C 60 arylene group; fluorene group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heteroaryl group; C3-C 60 Aliphatic rings; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; a and d are independent integers from 0 to 4, b is an integer from 0 to 2, c is an integer from 0 to 7, and e is an integer from 0 to 5. The aryl group, arylene group, heteroarylene group, heterocyclic group, fluorene group, fluorene group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be further substituted 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 Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 Alkyl aryl groups; furthermore, the hydrogens of these substituents may be further replaced by one or more deuteriums, and furthermore, 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 their combination.

2. The compound according to claim 1, wherein formula 1 can be represented by formula 1-1 or formula 1-2: in, R 1 R 2 R 3 R 4 R 5 R 6 R 7 L 1 A, a, b, c, d, and e are the same as those defined in claim 1.

3. The compound according to claim 1, wherein A is represented by any one of the following formulas A-1 to A-3: in, Hydrogen can be further replaced by one or more deuterium atoms.

4. The compound according to claim 1, wherein L 1 Represented by any one of the following equations L-1 to L-6: in: R 8 R 9 R 10 and R 11 Each may be the same or different, and each is independently selected from hydrogen; deuterium; halogen; cyano group; nitro 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 group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic group; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 alkylaryl group; or multiple adjacent R groups 8 or multiple R 9 or multiple R 10 or multiple R 11 They can bond together to form a ring. Y is O, S, NR, or CR'R". R, R', and R" are each independently selected from 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 group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic group; C3-C 20 Aliphatic groups; and C3-C 20 Aliphatic rings and C6-C 20 Fused ring groups of aromatic rings; f, g, and k are independent integers from 0 to 4, h and i are independent integers from 0 to 3, and j is an integer from 0 to 2. * 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-80:

6. An organic electronic component comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a single compound or two or more compounds represented by Formula 1 as claimed in claim 1.

7. The organic electronic component according to claim 6, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

8. The organic electronic component according to claim 6, wherein the organic material layer is a hole transport layer.

9. The organic electronic component according to claim 6, 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 the anode.

10. The organic electronic component of claim 9, wherein the organic material layer further comprises a charge-generating layer formed between the two or more stacks.

11. An electronic device, comprising a display device including the organic electronic components of claim 6; and a control unit for driving the display device.

12. The electronic device of claim 11, 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.

13. 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 as claimed in claim 1 is recovered from a deposition apparatus used in the process of 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 removing the impurities; as well as The recovered organic light-emitting material is purified to a purity of 99.9% or higher.

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