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

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability, and lifespan of a device, an organic electric device using the same, and an electronic device thereof.

Description

Technology Field

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

[0002] In general, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical devices utilizing organic light emission typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to increase the efficiency and stability of the organic electrical device, and may consist of, 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 layers in organic electrical devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0004] Currently, the portable display market is trending toward larger displays, which requires higher power consumption than that of conventional portable displays. Consequently, for portable displays that rely on the limited power source of batteries, power consumption has become a critical factor, and issues regarding efficiency and lifespan must also be resolved.

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

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

[0007] In other words, to fully realize the excellent characteristics of organic electronic devices, it is essential that the materials forming the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials—be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic electronic devices has not yet been sufficiently achieved. Therefore, the development of new materials continues to be required. The problem to be solved

[0008] In order to solve the problems of the aforementioned background technology, the present invention has identified a compound having a novel structure and has also revealed that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be significantly improved.

[0009] Accordingly, the present invention aims to provide a novel compound, an organic electric device using the same, and an electronic device thereof. means of solving the problem

[0010] The present invention provides a compound represented by the following chemical formula 1.

[0011] Chemical formula 1

[0012]

[0013] In another aspect, the present invention provides an organic electric element and an electronic device comprising a compound represented by the above chemical formula 1. Effects of the invention

[0014] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be significantly improved. Brief explanation of the drawing

[0015] FIGS. 1 to 3 are exemplary diagrams of an organic electroluminescent device according to the present invention. FIG. 4 shows a chemical formula according to one aspect of the present invention. Specific details for implementing the invention

[0016] The present invention will be described in detail below with reference to embodiments thereof. In describing the present invention, if it is determined that a detailed description of related known components or functions may obscure the essence of the invention, such detailed description will be omitted.

[0017] In addition, terms such as first, second, A, B, (a), (b), etc., may be used when describing the components of the present invention. These terms are intended only to distinguish the components from other components, and the essence, order, or sequence of the components is not limited by the terms. Where it is stated that a component is "connected," "combined," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but that another component may also be "connected," "combined," or "connected" between each component.

[0018] As used in this specification and the appended claims, unless otherwise noted, the meanings of the following terms are as follows:

[0019] As used herein, the terms “halo” or “halogen” are fluorine (F), bromine (Br), chlorine (Cl), or iodine (I) unless otherwise noted.

[0020] Unless otherwise explained, the terms “alkyl” or “alkyl group” as used in the present invention refer to radicals of saturated aliphatic functional groups having single bonds of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, and cycloalkyl-substituted alkyl groups.

[0021] Unless otherwise noted, the terms “alkenyl group,” “alkenyl group,” or “alkynyl group” as used in the present invention each have a double or triple bond having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, and include a straight-chain or branched-chain group, but are not limited thereto.

[0022] Unless otherwise noted, the terms “cycloalkyl” or “cycloalkyl” as used in the present invention refer to alkyls forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms, but are not limited thereto.

[0023] The terms “alkyxyl group,” “alkoxy group,” or “alkyloxy group” used in the present invention refer to an alkyl group to which an oxygen radical is attached, and unless otherwise described, have 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, but are not limited thereto.

[0024] The terms “aryloxyl group” or “aryloxy group” used in the present invention refer to an aryl group to which an oxygen radical is attached, and unless otherwise described, have 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, but are not limited thereto.

[0025] Unless otherwise noted, the terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group refers to a single-ring or multi-ring aromatic group and includes an aromatic ring formed by an adjacent substituent participating in bonding or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a naphthyl group, a fluorene group, or a spirofluorene group.

[0026] The prefixes "aryl" or "ar" denote radicals substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and radicals substituted with an aryl group have the number of carbon atoms described in this specification.

[0027] In addition, when prefixes are named consecutively, it means that the substituents are listed in the order in which they were first described. For example, "aryl alkoxy" refers to an alkoxy group substituted with an aryl group; "alkoxyl carbonyl" refers to a carbonyl group substituted with an alkoxyl group; and "aryl carbonyl alkenyl" refers to an alkhenyl group substituted with an aryl carbonyl group, where the aryl carbonyl group is a carbonyl group substituted with an aryl group.

[0028] Unless otherwise described, the term "heterocyclic ring" as used in the present invention comprises one or more heteroatoms, has a carbon number of 2 to 60, 2 to 30, 2 to 25, 2 to 18, or 2 to 12, comprises at least one of a single ring and a multi-ring, and comprises a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by the bonding of adjacent functional groups.

[0029] As used herein, the term "heteroatom" refers to N, O, S, P, or Si unless otherwise noted.

[0030] Furthermore, "heterocyclic group" refers to single-ring types, ring assemblies, conjugated multi-ring systems, spiro compounds, etc., containing heteroatoms. Additionally, compounds containing heterocyclic groups such as SO2 and P=O, as shown below, instead of the ring-forming carbon, may also be included in heterocyclic groups. For example, "heterocyclic groups" include the following compounds.

[0031]

[0032] The term "aliphatic ring" as used in the present invention refers to a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic types, ring assemblies, conjugated multi-ring systems, spiro compounds, etc. Unless otherwise stated, it refers to a ring having 3 to 60 carbon atoms, a ring having 3 to 30 carbon atoms, a ring having 3 to 25 carbon atoms, a ring having 3 to 18 carbon atoms, or a ring having 3 to 12 carbon atoms, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

[0033] Unless otherwise noted, the terms “fluorenyl group,” “fluorenyl group,” or “fluorentriyl group” as used in the present invention refer to a monovalent, divalent, or trivalent functional group in which R, R’, and R’ are all hydrogens in the following structures, respectively; “substituted fluorenyl group,” “substituted fluorenyl group,” or “substituted fluorentriyl group” refer to a case where at least one of the substituents R, R’, and R’ is a substituent other than hydrogen, and includes cases where R and R’ are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In this specification, fluorenyl group, fluorenyl group, and fluorentriyl group may all be referred to as fluoren groups regardless of valence.

[0034]

[0035] The term "spiro compound" used in the present invention refers to a compound having a "spiro union," where a spiro union is a connection formed by two rings sharing only one atom. At this time, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, they are respectively called "monospiro-," "dyspiro-," and "trispiro-" compounds.

[0036] Unless otherwise stated, the term “aliphatic” as used in the present invention means an aliphatic hydrocarbon having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, and “aliphatic ring” means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms.

[0037] Unless otherwise stated, the term “ring” as used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heteroring having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms; or a fused ring formed by a combination thereof, and includes saturated or unsaturated rings.

[0038] Other heterocompounds or heteroradicals other than the aforementioned heterocompounds comprise one or more heteroatoms, but are not limited thereto.

[0039] Additionally, unless explicitly stated otherwise, in the terms "substituted or unsubstituted" as used in this invention, "substituted" refers to deuterium, halogen, amino group, nitrile group, nitro group, C1~C20 alkyl group of, C1~C 20 alkoxyl group of, C1~C 20 alkylamine group of, C1~C 20 alkylthiophene group of, C6~C 20 arylthiophene group, C2~C 20 The Alken Diary, C2~C 20 Alkin's Diary, C3~C 20 cycloalkyl group of, C6~C 20 aryl group, C6~C substituted with deuterium 20 aryl group of, C8~C 20 aryl alkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group of heterocyclic rings, but is not limited to these substituents.

[0040] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be written as the 'name of the group reflecting the valence,' or it may be written as the 'name of the parent compound.' For example, in the case of 'phenanthrene,' a type of aryl group, the group name may be written by distinguishing the valence, such as 'phenanthrile' for the monovalent group and 'phenanthrillene' for the divalent group, but it may also be written as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be written as 'pyrimidine' regardless of the valence, or it may be written as the 'name of the group' corresponding to the valence, such as pyrimidinyl group for monovalent and pyrimidinyllene for divalent. Furthermore, in this specification, numbers or letters indicating position may be omitted when writing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0041] In addition, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied identically to the definitions of substituents by the definitions of the indices of the following chemical formulas.

[0042]

[0043] Here, if a is an integer of 0, the substituent R 1 ... does not exist, and if a is an integer of 1, there is one substituent R 1 It bonds to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it bonds as follows, respectively, where R 1 The atoms may be identical or different from each other, and when a is an integer from 4 to 6, they are bonded to the carbons of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbons forming the benzene ring is omitted.

[0044]

[0045] Additionally, unless otherwise described in this specification, the rings formed by combining adjacent groups are C6~C 60 Aromatic ring; fluorene group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic group of; and C3~C 60 It can be selected from a group consisting of aliphatic rings.

[0046] In this case, unless otherwise stated in this specification, the term "neighboring elements" refers to, with reference to the following chemical formula, R 1 and R 2 Together, R 2 and R 3 Together, R 3 and R 4 Together, R 5 and R 6 Not only between them, but also R that shares a single carbon 7 and R 8 It also includes Kiri, and R 1 and R7 Together, R 1 and R 8 Together or R 4 and R 5 Substituents bonded to ring constituent elements (such as carbon or nitrogen) that are not immediately adjacent, such as ki-ri, may also be included. That is, if there are substituents on ring constituent elements such as immediately adjacent carbon or nitrogen, they can be neighboring groups, but if no substituents are bonded to ring constituent elements at immediately adjacent positions, they can be neighboring groups with the substituent bonded to the next ring constituent element, and also substituents bonded to the same ring constituent carbon can be considered neighboring groups.

[0047] In the following chemical formula, R 7 and R 8 When substituents bonded to the same carbon bond together to form a ring, a compound containing a spiro moiety can be formed.

[0048]

[0049] Additionally, in this specification, the expression "neighboring units may combine to form a ring" is used with the same meaning as "neighboring units selectively combine to form a ring," and refers to the case where at least one pair of neighboring units combine to form a ring.

[0051] Hereinafter, a compound according to one aspect of the present invention and an organic electric device including the same will be described.

[0052] The present invention provides a compound represented by the following chemical formula 1.

[0053] Chemical formula 1

[0054]

[0055] Chemical formula A

[0056]

[0057] In the above chemical formulas 1 and A, each symbol can be defined as follows.

[0058] A and B are substituents represented by the above chemical formula A independently of each other, and

[0059] X is C(R a )(R b ), Si(R c )(R d ), O or S and,

[0060] R 1 , R 2 , R 3 and R 4 Each is in the plural and is identical or different from one another, and is independently deuterium, and

[0061] R 5 and R 6 Each is plural and is identical or different from one another, and independently deuterium; halogen; cyano group; nitro group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C3~C 60 aliphatic ring of; C1~C 50 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 30 alkoxyl groups of; and C6~C 30 Selected from the group consisting of aryloxy groups, or neighboring groups can bond with each other to form a ring,

[0062] The above R 5 and R 6 If it is an aryl group, preferably C6~C 30 The aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12The aryl group of may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, benzophenanthrene, and combinations thereof.

[0063] The above R 5 and R 6 In the case where it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0064] The above R 5 and R 6 In the case of a fused ring, preferably C3~C 30 The aliphatic ring and C6~C 30 A fused ring of the aromatic ring, more preferably C3~C 25 The aliphatic ring and C6~C 25 It can be a fused ring of an aromatic ring.

[0065] The above R 5 and R 6 In the case of an aliphatic ring, preferably C3~C 30 The aliphatic ring of, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be an aliphatic ring, specifically, cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0066] The above R 5 and R 6In the case where it is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 25 , C1~C 18 or C1~C 12 It can be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0067] The above R 5 and R 6 In the case where it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It can be an alkoxyl group.

[0068] The above R 5 and R 6 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It can be an aryloxy group.

[0069] R a , R b , R c and R d C1~C are independent of each other 50 It is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 25 , C1~C 18 or C1~C 12 It can be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0070] a is an integer from 0 to 5; b, c, d, and e are integers from 0 to 4; f is an integer from 0 to 3; and,

[0071] means the combined position,

[0072] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenyllene group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxyl group, and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group of; C1~C 20 alkoxyl group of; C6~C 20 aryloxy group of; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C6~C 20 aryl group; fluorene group; C2~C 20 The heterocyclic ring of; C3~C 20 of the aliphatic ring; C7~C 20 arylalkyl group of; C8~C 20 The aryl alkene group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; additionally, the hydrogens of these substituents may be further substituted with one or more deuterium atoms; additionally, these substituents may bond with each other to form a ring, wherein 'ring' refers to C3~C 60 aliphatic ring of or C6~C 60 aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes saturated or unsaturated rings.

[0074] As another example, the present invention comprises a compound represented by any one of the following formulas A-1 to A-4, wherein formula A is a compound represented by formulas A-1 to A-4.

[0075] Chemical formula A-1 Chemical formula A-2 Chemical formula A-3 Chemical formula A-4

[0076]

[0077] {In the above chemical formulas A-1 to A-4, X, R 5 , R 6 , e, f and is the same as defined in the above chemical formula A.

[0079] Specifically, the compound represented by the above chemical formula 1 may preferably be any one of the following compounds P-1 to P-80, but is not limited thereto.

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0101] In addition, in another aspect, the present invention provides a method for reusing a compound represented by Formula 1, comprising the steps of: depositing an organic light-emitting material containing a compound represented by Formula 1 in a manufacturing process of an organic light-emitting device; removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; recovering the removed impurities; and purifying the recovered impurities to a purity of 99.9% or higher.

[0102] The step of removing impurities from the unpurified organic light-emitting material recovered from the above deposition apparatus may preferably include performing a preliminary purification process to obtain a purity of 98% or higher by recrystallizing under a recrystallization solvent.

[0103] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0104] The above recrystallization solvent can preferably be used by mixing a polar solvent with a polarity of 5.5 to 7.2 and a non-polar solvent with a polarity of 2.0 to 4.7.

[0105] When the above recrystallization solvent is used by mixing a polar solvent and a non-polar solvent, the non-polar solvent may be used at a ratio of 15% (v / v) or less relative to the polar solvent.

[0106] The above recrystallization solvent is preferably a single solvent of methylpyrrolidone (N-Methylpyrrolidone; NMP); or a mixed polar solvent in which any one selected from the group consisting of dimethylimidazolidinone (1,3-Dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-Dimethyl formamide), dimethylacetamide, and dimethyl sulfoxide is mixed with the methylpyrrolidone; or a single solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone; or a mixed nonpolar solvent. Alternatively, a mixture of polar and non-polar solvents can be used.

[0107] The above preliminary purification process may include a step of dissolving an unpurified organic light-emitting material recovered from a deposition apparatus in a polar solvent at 90°C to 120°C and then cooling it to 0°C to 5°C to precipitate crystals.

[0108] The above preliminary purification process may include the step of dissolving an unpurified organic light-emitting material recovered from a deposition apparatus in a polar solvent at 90°C to 120°C, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C to precipitate crystals.

[0109] The above preliminary purification process may include a step of dissolving an unpurified organic light-emitting material recovered from a deposition apparatus in a non-polar solvent, then concentrating the solvent and removing the non-polar solvent while precipitating crystals.

[0110] The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

[0111] The step of purifying the above-mentioned recovered impurities to a purity of 99.9% or higher may include performing an adsorption separation process to adsorb and remove impurities by adsorbing them onto an adsorbent.

[0112] The above adsorbent may be activated carbon, silica gel, alumina, or a known material for adsorption purposes.

[0113] The step of purifying the above-mentioned recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0115] Referring to FIG. 1, the organic electric device (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer between the first electrode (110) and the second electrode (170) comprising a single compound represented by Chemical Formula 1 or two or more compounds. At this time, the first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode; in the case of an invert type, the first electrode may be a cathode and the second electrode may be an anode.

[0116] The organic layer may sequentially include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). At this time, the remaining layers, excluding the light-emitting layer (140), may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150), etc., may serve as a hole blocking layer. (See FIG. 2)

[0117] Additionally, an organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). Such a light efficiency improvement layer may be formed on the surface of the first electrode that does not come into contact with the organic layer or on the surface of the second electrode that does not come into contact with the organic layer. A compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (120), a hole transport layer (130), a light emission assist layer (220), an electron transport assist layer, an electron transport layer (150), an electron injection layer (160), a light emission layer (140), or as a material for the light efficiency improvement layer. Preferably, for example, a compound according to Formula 1 of the present invention may be used as a material for the hole transport layer.

[0118] The organic layer may include two or more stacks comprising a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (See FIG. 3)

[0119] Meanwhile, even with the same core, the band gap, electrical properties, and interfacial properties can vary depending on which substituent is attached at which location; therefore, the selection of the core and the combination of sub-substituents attached to it are also very important. In particular, long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between each organic layer, as well as the intrinsic properties of the material (mobility, interfacial properties, etc.), form an optimal combination.

[0120] An organic electroluminescent device according to one embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, it can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) thereon, and then depositing a material that can be used as a cathode thereon.

[0121] In addition, the present invention provides an organic electric device characterized in that the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic layer comprises the compound as an electron transport material.

[0122] As another specific example, the present invention provides an organic electric device characterized by using a homogeneous or heterogeneous compound of the compound represented by Chemical Formula 1 mixed in the organic layer.

[0123] In addition, the present invention provides a hole transport layer composition comprising a compound represented by the above chemical formula 1, and an organic electric device comprising the hole transport layer.

[0124] In addition, the present invention provides an electronic device comprising: a display device including the above-described organic electric element; and a control unit for driving the display device.

[0125] In another aspect, the present invention provides an electronic device characterized in that the organic electrical element comprises at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive material, an organic transistor, and a monochromatic or white lighting device. In this case, the electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, various computers, watches, tablets, and virtual reality (VR) devices.

[0127] Hereinafter, examples of synthesis of a compound represented by Chemical Formula 1 according to the present invention and examples of manufacturing an organic electric device will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[0128] [Synthetic Example]

[0129] The compound (final product) represented by Chemical Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

[0130] <Reaction Equation 1>

[0131]

[0132] In the above reaction scheme 1,

[0133] Hal is I, Br, or Cl, and

[0134] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a, b, c, d, e, and f are the same as defined in Chemical Formula 1 and Chemical Formula A above, and

[0135] X 1 and X 2 is identical to the definition of X in the above chemical formula A, and

[0136] R 7 and R8 is R of the above chemical formula A 5 Identical to the definition of,

[0137] g is an integer from 0 to 3, and h is an integer from 0 to 4.

[0139] I. Example of Sub 1

[0140] Meanwhile, compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub 1.

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] compound FD-MS compound FD-MS Sub 1-1 m / z=401.21(C 30 H 27 N=401.55) Sub 1-2 m / z=553.28(C 42 H 35 N=553.75) Sub 1-3 m / z=513.34(C 38 H 43 N=513.77) Sub 1-4 m / z=553.28(C 42 H 35 N=553.75) Sub 1-5 m / z=577.28(C 44 H 35 N=577.77) Sub 1-6 m / z=493.28(C 37 H 35 N=493.69) Sub 1-7 m / z=429.25(C 32 H 31 N=429.61) Sub 1-8 m / z=577.28(C 44 H 35 N=577.77) Sub 1-9 m / z=501.25(C 38 H 31 N=501.67) Sub 1-10 m / z=429.25(C 32 H 31 N=429.61) Sub 1-11 m / z=534.31(C 40 H 26 D7N=534.75) Sub 1-12 m / z=603.29(C 46 H 37 N=603.81) Sub 1-13 m / z=553.28(C 42 H 35 N=553.75) Sub 1-14 m / z=705.34(C 54 H 43 N=705.95) Sub 1-15 m / z=611.36(C 46 H 45 N=611.87) Sub 1-16 m / z=477.25(C 36 H 31 N=477.65) Sub 1-17 m / z=627.29(C 48 H 37 N=627.83) Sub 1-18 m / z=755.36(C 58 H 45 N=756.00) Sub 1-19 m / z=489.25(C 37 H 31 N=489.66) Sub 1-20 m / z=527.22(C 39 H 29 NO=527.67) Sub 1-21 m / z=501.21(C 37 H 27 NO=501.63) Sub 1-22 m / z=469.19(C 33 H 27 NS=469.65) Sub 1-23 m / z=555.26(C 41 H 33 NO=555.72) Sub 1-24 m / z=425.18(C 31 H 23 NO=425.53) Sub 1-25 m / z=460.25(C 33 H 16 D9NO=460.62) Sub 1-26 m / z=491.17(C 35 H 25 NS=491.65) Sub 1-27 m / z=425.18(C 31 H 23 NO=425.53) Sub 1-28 m / z=517.19(C 37 H 27 NS=517.69) Sub 1-29 m / z=541.20(C 39 H 27 NO2=541.65) Sub 1-30 m / z=431.22(C 31 H 29 NO=431.58) Sub 1-31 m / z=577.24(C 43 H 31 NO=577.73) Sub 1-32 m / z=649.19(C 45 H 31 NS2=649.87) Sub 1-33 m / z=541.20(C 39 H 27 NO2=541.65) Sub 1-34 m / z=512.28(C 37 H 16 D 11 NO=512.70) Sub 1-35 m / z=465.17(C 33 H 23 NO2=465.55) Sub 1-36 m / z=531.17(C 37 H 25 NOS=531.67) Sub 1-37 m / z=491.22(C 36 H 29 NO=491.63) Sub 1-38 m / z=555.26(C 41 H 33 NO=555.72) Sub 1-39 m / z=601.24(C 45 H 31 NO=601.75) Sub 1-40 m / z=349.11(C 24 H 15 NO2=349.39) Sub 1-41 m / z=529.20(C 38 H 27 NO2=529.64) Sub 1-42 m / z=393.12(C 26 H 19 NOS=393.50) Sub 1-43 m / z=541.15(C 38 H 23 NOS=541.67) Sub 1-44 m / z=532.22(C 38 H 16 D7NO2=532.65) Sub 1-45 m / z=507.11(C 34 H 21 NS2=507.67) Sub 1-46 m / z=685.19(C 48 H 31 NS2=685.90) Sub 1-47 m / z=501.17(C 36 H 23 NO2=501.59) Sub 1-48 m / z=501.17(C 36 H 23 NO2=501.59) Sub 1-49 m / z=677.24(C 50 H 31 NO2=677.80) Sub 1-50 m / z=501.17(C 36 H 23 NO2=501.59) Sub 1-51 m / z=553.24(C 38 H 35 NOS=553.76) Sub 1-52 m / z=761.22(C 54 H 35 NS2=762.00) Sub 1-53 m / z=489.14(C 34 H 19 NO3=489.53) Sub 1-54 m / z=475.16(C 34 H 21 NO2=475.55) Sub 1-55 m / z=677.28(C 48 H 39 NOS=677.91) Sub 1-56 m / z=545.18(C 38 H 27 NOS=545.70) Sub 1-57 m / z=593.25(C 43 H 35 NSi=593.84) Sub 1-58 m / z=557.13(C 38 H 23 NS2=557.73) Sub 1-59 m / z=609.16(C 42 H 27 NS2=609.80) Sub 1-60 m / z=500.27(C 35 H 24 D7NSi=500.77) Sub 1-61 m / z=507.24(C 36 H 33 NSi=507.75) Sub 1-62 m / z=593.25(C 43 H 35 NSi=593.84) Sub 1-63 m / z=571.27(C 41 H 37 NSi=571.84) Sub 1-64 m / z=593.25(C 43 H 35 NSi=593.84) Sub 1-65 m / z=507.24(C 36 H 33 NSi=507.75) Sub 1-66 m / z=569.25(C 41 H 35 NSi=569.82) Sub 1-67 m / z=619.27(C 45 H 37 NSi=619.88) Sub 1-68 m / z=557.18(C 38 H 27 NO2Si=557.72) Sub 1-69 m / z=635.21(C 44 H 33 NSSi=635.90) Sub 1-70 m / z=619.23(C 44 H 33 NOSi=619.84) Sub 1-71 m / z=607.23(C 43 H 33 NOSi=607.83) Sub 1-72 m / z=577.15(C 38 H 27 NOS2=577.76) Sub 1-73 m / z=543.20(C 38 H 29 NOSi=543.74) Sub 1-74 m / z=557.16(C 38 H 27 NSSi=557.79) Sub 1-75 m / z=517.19(C 36 H 27 NOSi=517.70) Sub 1-76 m / z=585.23(C 40 H 35 NSi2=585.90) Sub 1-77 m / z=433.17(C 28 H 27 NSi2=433.70) Sub 1-78 m / z=559.22(C 38 H 33 NSi2=559.86) Sub 1-79 m / z=643.22(C 42 H 37 NSSi2=644.00)

[0163] II. Examples of Sub 2

[0164] Meanwhile, compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub 2.

[0165]

[0166] compound FD-MS compound FD-MS Sub 2-1 m / z=384.05(C 24 H 17 Br=385.30) Sub 2-2 m / z=357.21(C 24 D 17 Cl=357.95) Sub 2-3 m / z=345.13(C 24 H 12 D5Cl=345.88) Sub 2-4 m / z=344.13(C 24 H 13 D4Cl=344.87) Sub 2-5 m / z=349.16(C 24 H8D9Cl=349.90)

[0168] III. Final Product Synthesis

[0169] 1. Examples of P-1 synthesis

[0170]

[0171] (1) Synthesis of Sub 1-1

[0172] Sub 1-1-1 (30.0 g, 109.82 mmol) was placed in a round-bottom flask and dissolved in 300 mL of toluene, after which Sub 1-1-2 (25.28 g, 120.80 mmol), Pd2(dba)3 (3.02 g, 2.52 mmol), P( t -Bu)3 (1.33 g, 6.59 mmol) and NaOt-Bu (21.11 g, 219.64 mmol) were added and stirred at 50°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 37.5 g of product (yield: 85%).

[0173] (2) Synthesis of P-1

[0174] Sub 1-1 (37.5 g, 93.39 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 375 mL of toluene, after which Sub 2-1 (35.98 g, 93.39 mmol) and Pd2(dba)3 (2.57 g, 2.80 mmol), P( t -Bu)3 (1.13 g, 5.60 mmol) and NaO t -Bu (17.95 g, 186.78 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 48.1 g of product (yield: 73%).

[0176] 2. Examples of P-14 synthesis

[0177]

[0178] Sub 1-1 (30.0 g, 74.71 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 300 mL of toluene, after which Sub 2-3 (25.84 g, 74.71 mmol) and Pd2(dba)3 (2.05 g, 2.24 mmol), P( t -Bu)3 (0.91 g, 4.48 mmol) and NaO t -Bu (14.36 g, 149.42 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 40.4 g of product (yield: 76%).

[0180] 3. Examples of P-25 synthesis

[0181]

[0182] (1) Synthesis of Sub 1-24

[0183] Sub 1-24-1 (25.0 g, 84.13 mmol) was placed in a round-bottom flask and dissolved in 250 mL of toluene, after which Sub 1-1-2 (19.37 g, 92.55 mmol), Pd2(dba)3 (2.31 g, 2.52 mmol), P( t -Bu)3 (1.02 g, 5.05 mmol) and NaOt-Bu (16.17 g, 168.27 mmol) were added and stirred at 50°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 26.9 g of product (yield: 75%).

[0184] (2) Synthesis of P-25

[0185] Sub 1-24 (26.9 g, 63.22 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 270 mL of toluene, after which Sub 2-1 (24.36 g, 63.22 mmol) and Pd2(dba)3 (1.74 g, 1.90 mmol), P( t -Bu)3 (0.77 g, 3.79 mmol) and NaO t -Bu (12.15 g, 126.43 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 32.8 g of product (yield: 71%).

[0187] 4. P-41 Synthesis Example

[0188]

[0189] (1) Synthesis of Sub 1-40

[0190] Sub 1-40-1 (20.0 g, 80.94 mmol) was placed in a round-bottom flask and dissolved in 200 mL of toluene, after which Sub 1-40-2 (16.31 g, 89.04 mmol), Pd2(dba)3 (2.22 g, 2.43 mmol), P( t -Bu)3 (0.98 g, 4.86 mmol) and NaOt-Bu (15.56 g, 161.88 mmol) were added and stirred at 70°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 23.2 g of product (yield: 82%).

[0191] (2) Synthesis of P-41

[0192] Sub 1-40 (23.2 g, 66.40 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 230 mL of toluene, after which Sub 2-5 (23.23 g, 66.40 mmol) and Pd2(dba)3 (1.82 g, 1.99 mmol), P( t -Bu)3 (0.81 g, 3.98 mmol) and NaO t -Bu (12.76 g, 132.80 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 30.8 g of product (yield: 70%).

[0194] 5. Examples of P-52 synthesis

[0195]

[0196] (1) Synthesis of Sub 1-51

[0197] Sub 1-51-1 (30.0 g, 76.74 mmol) was placed in a round-bottom flask and dissolved in 300 mL of toluene. Then, Sub 1-51-2 (16.82 g, 84.41 mmol), Pd2(dba)3 (2.11 g, 2.30 mmol), X-Phos (2.19 g, 4.60 mmol), and NaOt-Bu (14.75 g, 153.47 mmol) were added, and the mixture was stirred at 70°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 28.0 g of product (yield: 66%).

[0198] (2) Synthesis of P-52

[0199] Sub 1-51 (28.0 g, 50.56 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 280 mL of toluene, after which Sub 2-1 (19.48 g, 50.56 mmol) and Pd2(dba)3 (1.39 g, 1.52 mmol), P( t -Bu)3 (0.61 g, 3.03 mmol) and NaO t -Bu (9.72 g, 101.13 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 29.5 g of product (yield: 68%).

[0201] 6. Examples of P-61 synthesis

[0202]

[0203] (1) Synthesis of Sub 1-60

[0204] Sub 1-60-1 (25.0 g, 99.27 mmol) was placed in a round-bottom flask and dissolved in 250 mL of toluene. Then, Sub 1-60-2 (31.16 g, 109.20 mmol), Pd2(dba)3 (2.73 g, 2.98 mmol), X-Phos (2.84 g, 5.96 mmol), and NaOt-Bu (19.08 g, 198.54 mmol) were added, and the mixture was stirred at 50°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 40.3 g of product (yield: 81%).

[0205] (2) Synthesis of P-61

[0206] Sub 1-60 (40.3 g, 160.02 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 400 mL of toluene, after which Sub 2-1 (45.67 g, 160.02 mmol) and Pd2(dba)3 (4.40 g, 4.80 mmol), P( t -Bu)3 (1.94 g, 9.60 mmol) and NaO t -Bu (30.76 g, 320.04 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 88.9 g of product (yield: 69%).

[0208] 7. Examples of P-71 synthesis

[0209]

[0210] (1) Synthesis of Sub 1-70

[0211] Sub 1-70-1 (20.0 g, 46.41 mmol) was placed in a round-bottom flask and dissolved in 200 mL of toluene. Then, Sub 1-70-2 (11.51 g, 51.05 mmol), Pd2(dba)3 (1.28 g, 1.39 mmol), X-Phos (1.33 g, 2.78 mmol), and NaOt-Bu (8.92 g, 92.82 mmol) were added, and the mixture was stirred at 70°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 20.1 g of product (yield: 70%).

[0212] (2) Synthesis of P-71

[0213] Sub 1-70 (20.1 g, 32.42 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 200 mL of toluene, after which Sub 2-1 (12.49 g, 32.42 mmol) and Pd2(dba)3 (0.89 g, 0.97 mmol), P( t -Bu)3 (0.39 g, 1.95 mmol) and NaO t -Bu (6.23 g, 64.86 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 15.9 g of product (yield: 79%).

[0215] 8. Examples of P-77 synthesis

[0216]

[0217] (1) Synthesis of Sub 1-76

[0218] Sub 1-76-1 (20.0 g, 62.33 mmol) was placed in a round-bottom flask and dissolved in 200 mL of toluene. Then, Sub 1-76-2 (20.67 g, 68.56 mmol), Pd2(dba)3 (1.71 g, 1.87 mmol), X-Phos (1.78 g, 3.74 mmol), and NaOt-Bu (11.98 g, 124.65 mmol) were added, and the mixture was stirred at 70°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 23.7 g of product (yield: 65%).

[0219] (2) Synthesis of P-77

[0220] Sub 1-76 (23.7 g, 40.45 mmol) obtained from the above synthesis was placed in a round-bottom flask and dissolved in 240 mL of toluene, after which Sub 2-1 (17.14 g, 44.50 mmol) and Pd2(dba)3 (1.11 g, 1.21 mmol), P( t -Bu)3 (0.49 g, 2.43 mmol) and NaO t -Bu (7.77 g, 80.89 mmol) was added and stirred at 120°C. After the reaction was complete, the mixture was extracted with toluene and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 23.0 g of product (yield: 64%).

[0222] Meanwhile, the FD-MS values ​​of compounds P-1 to P-80 of the present invention prepared according to the synthesis example above are as shown in Table 3 below.

[0223] compound FD-MS compound FD-MS P-1 m / z=705.34(C 54 H 43 N=705.95) P-2 m / z=857.40(C 66 H 51 N=858.14) P-3 m / z=817.46(C 62 H 59 N=818.16) P-4 m / z=857.40(C 66 H 51 N=858.14) P-5 m / z=881.40(C 68 H 51 N=882.16) P-6 m / z=797.40(C 61 H 51 N=798.09) P-7 m / z=733.37(C 56 H 47 N=734.00) P-8 m / z=881.40(C 68 H 51 N=882.16) P-9 m / z=805.37(C 62 H 47 N=806.06) P-10 m / z=750.48(C 56 H 30 D 17 N=751.10) P-11 m / z=838.43(C 64 H 42 D7N=839.15) P-12 m / z=907.42(C 70 H 53 N=908.20) P-13 m / z=857.40(C 66 H 51 N=858.14) P-14 m / z=710.37(C 54 H 38 D5N=710.98) P-15 m / z=1009.46(C 78 H 59 N=1010.34) P-16 m / z=915.48(C 70 H 61 N=916.27) P-17 m / z=781.37(C 60 H 47 N=782.04) P-18 m / z=931.42(C 72 H 53 N=932.22) P-19 m / z=1059.48(C 82 H 61 N=1060.40) P-20 m / z=793.37(C 61 H 47 N=794.05) P-21 m / z=831.35(C 63 H 45 NO=832.06) P-22 m / z=805.33(C 61 H 43 NO=806.02) P-23 m / z=773.31(C 57 H 43 NS=774.04) P-24 m / z=859.38(C 65 H 49 NO=860.11) P-25 m / z=729.30(C 55 H 39 NO=729.92) P-26 m / z=764.38(C 57 H 32 D9NO=765.02) P-27 m / z=795.30(C 59 H 41 NS=796.04) P-28 m / z=729.30(C 55 H 39 NO=729.92) P-29 m / z=821.31(C 61 H 43 NS=822.08) P-30 m / z=845.33(C 63 H 43 NO2=846.04) P-31 m / z=735.35(C 55 H 45 NO=735.97) P-32 m / z=881.37(C 67 H 47 NO=882.12) P-33 m / z=953.31(C 69 H 47 NS2=954.26) P-34 m / z=845.33(C 63 H 43 NO2=846.04) P-35 m / z=820.43(C 61 H 28 D 15 NO=821.11) P-36 m / z=769.30(C 57 H 39 NO2=769.94) P-37 m / z=835.29(C 61 H 41 NOS=836.06) P-38 m / z=795.35(C 60 H 45 NO=796.03) P-39 m / z=859.38(C 65 H 49 NO=860.11) P-40 m / z=905.37(C 69 H 47 NO=906.14) P-41 m / z=662.29(C 48 H 22 D9NO2=662.84) P-42 m / z=833.33(C 62 H 43 NO2=834.03) P-43 m / z=697.24(C 50 H 35 NOS=697.90) P-44 m / z=845.28(C 62 H 39 NOS=846.06) P-45 m / z=836.34(C 62 H 32 D7NO2=837.04) P-46 m / z=811.24(C 58 H 37 NS2=812.06) P-47 m / z=989.31(C 72 H 47 NS2=990.29) P-48 m / z=805.30(C 60 H 39 NO2=805.98) P-49 m / z=805.30(C 60 H 39 NO2=805.98) P-50 m / z=981.36(C 74 H 47 NO2=982.20) P-51 m / z=805.30(C 60 H 39 NO2=805.98) P-52 m / z=857.37(C 62 H 51 NOS=858.16) P-53 m / z=1065.35(C 78 H 51 NS2=1066.39) P-54 m / z=793.26(C 58 H 35 NO3=793.92) P-55 m / z=779.28(C 58 H 37 NO2=779.94) P-56 m / z=981.40(C 72 H 55 NOS=982.30) P-57 m / z=849.31(C 62 H 43 NOS=850.09) P-58 m / z=911.29(C 66 H 41 NO2S=912.12) P-59 m / z=861.25(C 62 H 39 NS2=862.12) P-60 m / z=913.28(C 66 H 43 NS2=914.20) P-61 m / z=804.39(C 59 H 40 D7NSi=805.16) P-62 m / z=897.38(C 67 H 51 NSi=898.24) P-63 m / z=897.38(C 67 H 51 NSi=898.24) P-64 m / z=875.39(C 65 H 53 NSi=876.23) P-65 m / z=897.38(C 67 H 51 NSi=898.24) P-66 m / z=811.36(C 60 H 49 NSi=812.14) P-67 m / z=873.38(C 65 H 51 NSi=874.21) P-68 m / z=923.39(C 69 H 53 NSi=924.27) P-69 m / z=861.31(C 62 H 43 NO2Si=862.12) P-70 m / z=939.34(C 68 H 49 NSSi=940.29) P-71 m / z=923.36(C 68 H 49 NOSi=924.23) P-72 m / z=911.36(C 67 H 49 NOSi=912.22) P-73 m / z=881.28(C 62 H 43 NOS2=882.15) P-74 m / z=847.33(C 62 H 45 NOSi=848.13) P-75 m / z=861.29(C 62 H 43 NSSi=862.18) P-76 m / z=821.31(C 60 H 43 NOSi=822.10) P-77 m / z=889.36(C 64 H 51 NSi2=890.29) P-78 m / z=737.29(C 52 H 43 NSi2=738.09) P-79 m / z=863.34(C 62 H 49 NSi2=864.25) P-80 m / z=947.34(C 66 H 53 NSSi2=948.39)

[0225] Meanwhile, although exemplary synthetic examples of the present invention represented by Chemical Formula 1 or reference literature have been described above, these are all Buchwald-Hartwig cross-coupling reactions, Miyaura boration reactions, Suzuki cross-coupling reactions, 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. Based on 2005, 70, 5014, etc., it will be easily understood by those skilled in the art that the above reaction proceeds even if other substituents defined in Chemical Formula 1 are bonded in addition to the substituents specified in the specific synthesis examples.

[0227] [Example 1] Green organic electroluminescent device (hole transport layer)

[0228] A hole injection layer with a thickness of 10 nm was formed by using compound P-1 of the present invention and compound B on an ITO layer (anode) formed on a glass substrate, and then vacuum depositing compound P-1 of the present invention with a thickness of 110 nm on the hole injection layer.

[0229] Next, a emitting auxiliary layer was formed by vacuum depositing compound CG to a thickness of 40 nm on the hole transport layer. Subsequently, a emitting layer with a thickness of 30 nm was formed by using compound DG as the host material for the emitting layer and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as 'Ir(ppy)3') as the dopant material, doping the dopants in a weight ratio of 90:10.

[0230] Next, compound E was vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and an electron transport layer with a thickness of 30 nm was formed on the hole-blocking layer using a mixture of compound F and compound G mixed in a weight ratio of 5:5. Subsequently, compound G was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0232] Compound B :4,4',4''-((1 E ,1' E ,1'' E )-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0233] Compound CG : N -([1,1'-biphenyl]-2-yl)- N -(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine

[0234] Compound DG: 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-7,7-dimethyl-5,7-dihydroindeno[2,1- b ]carbazole

[0235] Compound E : 2-(4'-(9,9-dimethyl-9) H -fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0236] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0237] Compound G: (8-quinolinolato)lithium

[0239] [Examples 2] to [Examples 9]

[0240] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound of the present invention listed in Table 4 below was used instead of the compound P-1 of the present invention as the hole transport layer material.

[0242] [Comparative Example 1] to [Comparative Example 5]

[0243] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that comparative compounds A to E were used instead of compound P-1 of the present invention as the hole transport layer material.

[0244] [Comparison Compound A] [Comparison Compound B] [Comparison Compound C]

[0245]

[0246] [Comparison Compound D] [Comparison Compound E]

[0247]

[0249] A forward-bias DC voltage was applied to the organic electroluminescent devices of the examples and comparative examples prepared as described above, and the electroluminescent (EL) characteristics were measured using a PR-650 from Photoresearch; the measurement result was 5000 cd / m² 2 T95 lifetime was measured at reference brightness using a lifetime measurement device manufactured by MaxScience. Table 4 below shows the results of device fabrication and evaluation.

[0250] This measuring device can evaluate the performance of a new material by comparing it with a comparative compound under the same conditions, without being affected by the possibility of daily fluctuations in deposition rate, vacuum quality, or other parameters.

[0251] When evaluating, one batch contains four identically prepared OLEDs including a comparison compound, and since the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this way show statistical significance.

[0252] compound Driving voltage (V) Current (mA / cm²) 2 ) Efficiency (cd / A) T(95) Comparative Example 1 Comparative compound A 5.3 11.8 42.4 91.4 Comparative Example 2 Comparative compound B 5.3 11.5 43.6 94.5 Comparative Example 3 Comparative compound C 5.1 11.0 45.3 103.2 Comparative Example 4 Comparative compound D 5.1 12.4 40.4 82.1 Comparative Example 5 Comparative compound E 5.2 12.0 41.5 86.8 Example 1 Compound (P-1) 4.5 9.0 55.4 143.9 Example 2 Compound (P-2) 4.6 9.2 54.3 139.9 Example 3 Compound (P-3) 4.6 9.2 54.1 136.7 Example 4 Compound (P-10) 4.8 9.4 53.4 132.4 Example 5 Compound (P-14) 4.5 9.0 55.6 144.2 Example 6 Compound (P-26) 4.7 9.7 51.4 124.0 Example 7 Compound (P-41) 4.8 10.0 50.2 122.4 Example 8 Compound (P-61) 4.8 9.5 52.6 126.9 Example 9 Compound (P-77) 4.7 9.4 53.1 128.3

[0253] As can be seen in Table 4 above, when a green organic electroluminescent device is fabricated using the organic electroluminescent device material of the present invention as a hole transport layer material, the compound of the present invention exhibits significantly superior characteristics in device performance compared to cases using comparative compounds A to E. In particular, it can be confirmed that it exhibits excellent characteristics in terms of lifespan.

[0254] Compared to Comparative Compounds A to E, the compound of the present invention differs in the substituents of the amine group. In the case of the present invention, two dialkylfluorene, dibenzofuran, dibenzothiophene, or dialkyldibenzosilol groups are substituted, and The composition differs from comparative compounds in that it is characterized by the substitution of a specific quaternyl group represented by . It is believed that this structural difference may affect the physical properties of the compound, and when the specific quaternyl of the present invention is substituted into an amine group, HOMO-LUMO may be localized, and as a result, the lifespan characteristics of the device appear to be excellent.

[0255] In addition, although not described as a comparative example in the specification of the present invention, it can be seen that a device using the compound of the present invention will exhibit significantly superior device characteristics compared to a device using a compound having a structure similar to the compound of the present invention or a simple structural isomer compound.

[0256] In conclusion, even for compounds with similar molecular components, the characteristics of the compound—such as hole properties, photoelectric efficiency, energy levels, hole injection and mobility, hole-electron charge balance, volume density, and intermolecular distance—can vary significantly and unpredictably depending on the presence and position of substituents. Furthermore, this suggests that device performance may vary due to complex factors rather than a single configuration affecting the overall device outcome.

[0257] In the case of the hole transport layer, the relationship with the light-emitting layer (host) must be understood, so even if a similar core is used, it would be very difficult for a person skilled in the art to infer the characteristics exhibited by the hole transport layer using the compound according to the present invention.

[0258] In addition, although the evaluation results of the aforementioned device fabrication described the device characteristics when the compound of the present invention was applied only to the hole transport layer, the compound of the present invention can be applied to the light-emitting auxiliary layer or to both the hole transport layer and the light-emitting auxiliary layer.

[0259] The foregoing description is merely illustrative of the present invention, and those skilled in the art will be able to make various modifications within the scope of the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to illustrate, not limit, the present invention, and the spirit and scope of the present invention are not limited by such embodiments. The scope of protection of the present invention shall be interpreted by the claims below, and all technology within an equivalent scope shall be interpreted as being included within the scope of rights of the present invention. Explanation of the symbols

[0260] 100, 200, 300 : Organic electric device 110 : First electrode 120 : Hole injection layer 130 : Hole transport layer 140: Emitting layer 150: Electron transport layer 160: Electron injection layer 170: Second electrode 180: Light efficiency improvement layer 210: Buffer layer 220: Light-emitting auxiliary layer 320: First hole injection layer 330: First hole transport layer 340: First light-emitting layer 350: First electron transport layer 360: First charge generation layer 361: Second charge generation layer 420: Second hole injection layer 430: Second hole transport layer 440: Second light-emitting layer 450: Second electron transport layer CGL: Charge generation layer ST1: 1st Stack ST2: 2nd Stack

Claims

Claim 1 Compound represented by the following chemical formula 1 Chemical formula 1 Chemical formula A {In the above Chemical Formula 1 and Chemical Formula A, A and B are substituents represented by the above Chemical Formula A independently of each other, and X is C(R a )(R b ), Si(R c )(R d ), O or S and,R 1 , R 2 , R 3 and R 4 are each plural, identical or different from one another, independently deuterium, and R 5 and R 6 Each is in the plural and is identical or different from one another, and independently deuterium; C6~C 25 aryl group; fluorenyl group; C2~C containing either a heteroatom of O and S 25 The heterocyclic ring of; C3~C 25 The aliphatic ring of; and C1~C 20 Selected from the group consisting of alkyl groups; or adjacent groups may bond to each other to form a ring, R a , R b , R c and R d C1~C are independent of each other 20 The alkyl group is, where a is an integer from 0 to 5; b, c, d, and e are integers from 0 to 4; f is an integer from 0 to 3; and, represents the bonding position, where the aryl group, heterocyclic group, fluorenyl group, and alkyl group are each deuterium; C1~C 20 alkyl group of; C6~C 20 aryl group; fluorene group; C2~C 20 The heterocyclic group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of arylalkyl groups, and the hydrogens of these substituents may be further substituted with one or more deuterium atoms. Claim 2 In claim 1, the compound is characterized in that the above chemical formula A is represented by any one of the following chemical formulas A-1 to A-4. Chemical formula A-1 Chemical formula A-2 Chemical formula A-3 Chemical formula A-4 {In the above chemical formulas A-1 to A-4, X, R 5 , R 6 , e, f and is the same as defined in Claim 1 above. Claim 3 In claim 1, the compound represented by the above chemical formula 1 is characterized by being represented by any one of the following compounds P-1 to P-80. Claim 4 An organic electric device comprising an anode, a cathode, and an organic layer formed between the anode and the cathode, wherein the organic layer comprises a single compound represented by Chemical Formula 1 of Claim 1 or two or more compounds. Claim 5 An organic electric device according to claim 4, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emission assist layer, a light emission layer, an electron transport assist layer, an electron transport layer, and an electron injection layer. Claim 6 An organic electric device according to claim 4, characterized in that the organic layer is a hole transport layer. Claim 7 An organic electric device according to claim 4, further comprising a light efficiency improving layer formed on at least one surface of the anode and cathode opposite to the organic layer. Claim 8 An organic electric device according to claim 4, wherein the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on an anode. Claim 9 An organic electric device according to claim 8, wherein the organic layer further comprises a charge generating layer formed between the two or more stacks. Claim 10 An electronic device comprising: a display device including an organic electric element of claim 4; and a control unit for driving the display device. Claim 11 An electronic device according to claim 10, wherein the organic electric device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photosensitive material (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting. Claim 12 In claim 10, the electronic device is characterized as being any one of a wired communication terminal, a wireless mobile communication terminal, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game console, a TV, a computer, a watch, a tablet, and a virtual reality (VR) device. Claim 13 A method for reusing a compound represented by Formula 1 according to Claim 1, comprising: a step of depositing an organic light-emitting material containing a compound represented by Formula 1 of Claim 1 in a manufacturing process of an organic light-emitting device; a step of removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; a step of recovering the removed impurities; and a step of purifying the recovered impurities to a purity of 99.9% or higher.

Images