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

Abstract

Provided are a compound for improving the luminous efficiency, stability, and lifespan of an organic electronic element, an organic electronic element employing the same, and an electronic device thereof.

Description

TECHNICAL FIELD

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

[0002] In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic electronic element using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is generally composed of a multi-layer structure composed of different materials, and can include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc.

[0003] A material used as an organic material layer in an organic electronic element can be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc., according to its function. Also, the light emitting material can be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and the light emitting material can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to a light emitting mechanism. Further, the light emitting material can be classified into a blue light emitting material, a green light emitting material, and a red light emitting material according to an emission color, and a yellow light emitting material and an orange light emitting material necessary for realizing a better natural color.

[0004] However, when only one material is used as a light emitting material, due to intermolecular interaction, the maximum emission wavelength moves to a longer wavelength, and there is a problem that color purity is lowered or device efficiency is lowered due to an emission decay effect, and thus, in order to increase color purity and increase light emitting efficiency by energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of a dopant having a smaller band gap than a host forming a light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transferred to the dopant to emit light with high efficiency. Here, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant used.

[0005] Currently, the portable display market is a large display, and its size is increasing day by day, and thus, a greater power consumption than that required for the existing portable display is required. Accordingly, for a portable display having a limited power supply such as a battery, power consumption becomes a very important factor, and the problems of efficiency and service life must also be solved.

[0006] Efficiency, service life, and driving voltage are related to each other, and when efficiency increases, the driving voltage is relatively lowered, and as the driving voltage is lowered, crystallization of an organic material due to Joule heat generated during driving is reduced, and thus service life tends to increase. However, efficiency cannot be maximized simply by improving the organic material layer. This is because, when energy levels and T1 values between the respective organic material layers and inherent properties (mobility, interface properties, etc.) of the materials are optimally combined, long service life and high efficiency can be simultaneously achieved.

[0007] Therefore, although penetration and diffusion of metal oxides from an anode electrode (ITO) into an organic layer are delayed, which is one of the reasons for shortening service life of an organic electronic element, it should have a stable property against Joule heat generated during driving of a device, and an OLED device is mainly formed by a deposition method, and it is necessary to develop a material which can withstand deposition for a long time, that is, a material having strong heat resistance.

[0008] That is, in order to fully exhibit excellent properties of an organic electronic element, a material which is stable and effective should be prioritized to constitute an organic material layer in a device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. However, development of a stable and effective organic material layer material for an organic electronic element has not been sufficiently achieved. Therefore, there is a continuous need for development of a new material, and in particular, there is an urgent need for development of a host material for a light emitting layer. SUMMARY

[0009] To solve the problems of the above background art, the present application discloses a compound having a new structure, and it is also found that when the compound is applied to an organic electronic element, luminous efficiency, stability, and service life of the element can be greatly improved.

[0010] Therefore, an object of the present application is to provide a new compound, an organic electronic element using the same, and an electronic device thereof.

[0011] TECHNICAL SOLUTION

[0012] The present application provides a compound represented by Formula 1.

[0013] Formula 1

[0014]

[0015] In another aspect, the present application provides a composition for an organic electronic element, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 or Formula 3.

[0016]

[0017] In another aspect, the present application provides an organic electronic element or a composition for an organic electronic element comprising a compound represented by Formula 1, and an electronic device thereof.

[0018] Effects of the Invention

[0019] By using the compound according to the present application, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and color purity and service life of the element can be greatly improved. BRIEF DESCRIPTION OF DRAWINGS

[0020] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present application.

[0021] Figure 4 shows a formula according to one aspect of the present application.

[0022] Numerical Description

[0023] 100, 200, 300: organic electronic element 110: first electrode

[0024] 120: hole injection layer 130: hole transport layer

[0025] 140: light-emitting layer 150: electron transport layer

[0026] 160: electron injection layer 170: second electrode

[0027] 180: light efficiency enhancement layer 210: buffer layer

[0028] 220: light-emitting auxiliary layer 320: first hole injection layer

[0029] 330: first hole transport layer 340: first light-emitting layer

[0030] 350: first electron transport layer 360: first charge generation layer

[0031] 361: second charge generation layer 420: second hole injection layer

[0032] 430: second hole transport layer 440: second light-emitting layer

[0033] 450: second electron transport layer CGL: charge generation layer

[0034] ST1: first stack ST2: second stack DETAILED DESCRIPTION

[0035] Hereinafter, some embodiments of the present application will be described in detail. Also, in the following description of the present application, a detailed description of known functions and configurations incorporated herein can be omitted when it can make the subject matter of the present application rather unclear.

[0036] Also, when components of the present application are described, terms such as first, second, A, B, (a), (b), etc. can be used herein. Each of these terms is not used to define a substantial, sequential or ordinal order of corresponding components but is used only to distinguish the corresponding components from other components. It should be noted that if a component is described as being "connected", "coupled", or "connected" to another component, the component can be directly connected or coupled to the other component, but another component can be "connected", "coupled", or "connected" between each of the components.

[0037] As used in the specification and the appended claims, the following is the meaning of the following terms unless otherwise indicated.

[0038] The term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine unless otherwise indicated.

[0039] The term "alkyl" or "alkyl group" as used herein has 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, 1 to 12 carbon atoms of a single bond, and means a saturated aliphatic functional group, including straight chain alkyl groups, branched alkyl groups, cycloalkyl groups (alicyclic), cycloalkyl groups substituted with alkyl, or alkyl groups substituted with cycloalkyl.

[0040] The term "alkenyl" or "alkynyl" as used herein 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 of a double bond or a triple bond, but is not limited thereto, and includes straight chain or branched chain groups.

[0041] The term "cycloalkyl" as used herein means 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, but is not limited thereto.

[0042] The term "alkoxy group", "alkoxy group", or "alkoxy group" as used herein means an alkyl group bonded to an oxy group and has 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 is not limited thereto.

[0043] The term "aryloxy group" or "aryloxy group" as used herein, unless otherwise specified, means an aryl group bonded to an oxy group, and has 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 is not limited thereto.

[0044] The terms "aryl group" and "arylene group" as used herein, unless otherwise specified, 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, respectively, but are not limited thereto. In the present invention, the aryl group or the arylene group means a monocyclic or polycyclic aromatic, and includes an aromatic ring formed by connecting or participating in a reaction of adjacent substituents.

[0045] For example, the aryl group can be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0046] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, and an arylalkenyl group is an alkenyl group substituted with an aryl group, and the group substituted with an aryl group has the number of carbons as described in this specification.

[0047] Further, when the prefix is named in turn, this means that the substituents are listed in the order of being described first. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, in which the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0048] The term "heterocyclic group" as used herein, unless otherwise specified, 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, including any of monocyclic and polycyclic, and can include a heteroaliphatic ring and a heteroaromatic ring. Further, it can also be combined with adjacent groups to form a heterocyclic group.

[0049] The term "heteroatom" as used herein, unless otherwise specified, means at least one of N, O, S, P, or Si.

[0050] Further, the "heterocyclic group" refers to a monocyclic, a cyclic aggregate, a plurality of fused ring systems, a spiro compound, or the like, containing a heteroatom.

[0051] Further, compounds containing a heteroatom group such as SO2, P=O, or the like, which forms a ring by substitution of carbon, such as the following compounds, can also be included in the heterocyclic group. For example, the "heterocyclic group" includes the following compounds.

[0052]

[0053] The term "aliphatic ring" used in the present application means a ring hydrocarbon excluding aromatic hydrocarbon, and includes a monocyclic ring, a ring aggregate, a plurality of fused ring systems, a spiro compound, etc., and means 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 unless otherwise specified, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it is an aliphatic ring.

[0054] Unless otherwise specified, the term "fluorenyl group", "fluorenylidene group", or "fluorenyltrisyl group" means a monovalent, divalent, or trivalent functional group in which R, R', and R" are all hydrogen in the following structure, and the term "substituted fluorenyl group", "substituted fluorenylidene group", or "substituted fluorenyltrisyl group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes a case in which R and R' are bonded to each other to form a spiro compound together with the carbons to which they are bonded. In the present specification, the fluorenyl group, the fluorenylidene group, and the fluorenyltrisyl group can all be referred to as a fluorenyl group regardless of the valence.

[0055]

[0056] The term "spiro compound" as used herein has "spiro connection", and the spiro connection means a connection in which 2 rings share only one atom. Here, the atom shared in the 2 rings is referred to as a "spiro atom", and these compounds are referred to as "mono-spiro-", "bi-spiro-", and "tri-spiro-", respectively, depending on the number of spiro atoms in the compound.

[0057] Unless otherwise specified, the term "aliphatic" as used herein 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 the term "aliphatic ring" as used herein 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.

[0058] The term "ring" as used herein, unless otherwise indicated, 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 heterocyclic ring 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.

[0059] In addition to the above-mentioned hetero compounds, other hetero compounds or hetero groups include, but are not limited to, one or more hetero atoms.

[0060] Further, the term "substituted or unsubstituted" in the term "substituted or unsubstituted" as used herein, unless expressly stated otherwise, means substituted with one or more substituents selected from the group consisting of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a C1-C 20 alkylamine group, a C1-C 20 alkylthiophene group, a C6-C 20 arylthiophene group, a C2-C 20 alkenyl group, a C2-C 20 alkynyl group, a C3-C 20 cycloalkyl group, a C6-C 20 aryl group, a C6-C 20 aryl group, a C8-C 20 arylalkenyl group, a silane group, a boron group, a germanium group, and a C2-C 20 heterocyclic group, but are not limited to these substituents.

[0061] In the present specification, "group name" corresponding to aryl group, arylene group, heterocyclic group, and the like, as an example of each symbol and its substituent, can be written as "name of group reflecting valence", but also as "name of parent compound". For example, in the case of "phenanthrene", which is a type of aryl group, the name of the group can be written by distinguishing the valence, such as "phenanthryl" for a monovalent group and "phenanthrylene" for a divalent group, but it can be written as "phenanthrene" as the name of the parent compound without considering the valence. Similarly, in the case of pyrimidine, it can be written as "pyrimidine" without considering the valence, or it can be written as 'name of group of valence', such as pyrimidinyl group in the case of a monovalent group, pyrimidinylene group in the case of a divalent group, and the like.

[0062] Additionally, in the present specification, when a compound name or a substituent name is described, a number or a letter indicating a position can be omitted.

[0063] For example, pyrido[4,3-d]pyrimidine can be described as pyridopyrimidine, benzofuran[2,3-d]pyrimidine can be described as benzofuranopyrimidine, 9,9-dimethyl-9H-fluorene can be described as dimethylfluorene, and the like. Thus, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

[0064] Further, unless explicitly explained, the formula used in the present application is the same as the definition of the substituent by the following exponent definition.

[0065]

[0066] Here, when a is an integer of 0, the substituent R 1 is not present, when a is an integer of 1, the only substituent R 1 is bonded to any one of the carbons constituting the benzene ring, when a is an integer of 2 or 3, each in the following combination, wherein R 1 may be the same as or different from each other, when a is an integer of 4 to 6, it is bonded to the carbons of the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0067]

[0068] Unless explicitly specified otherwise, the terms "ortho", "meta", and "para" used in the present application refer to the substitution position of all substituents, and the ortho position indicates the position of the substituent immediately adjacent to the compound, for example, when benzene is used, it means the 1 -position or the 2-position, and the meta position is the next substitution position to the adjacent substitution position, when benzene is used as an example, it represents the 1 -position or the 3 -position, and the para position is the next substitution position to the meta position, when benzene is used as an example, it means the 1 -position and the 4 -position. More detailed examples of the substitution position are as follows, and it can be confirmed that the ortho position and the meta position are substituted by a non-linear type and the para position is substituted by a linear type.

[0069] [Examples of the ortho position]

[0070]

[0071] [Examples of the meta position]

[0072]

[0073] [Examples of the para position]

[0074]

[0075] As used herein, the term "composition" is meant to broadly include compounds as well as solutions, dispersions, liquids and solid mixtures (mixtures, admixtures). The composition of the present application can include a single compound of the present application, or the compounds can be included in combinations of 2 or more different types, or the compounds can be included in combinations of 2 or more types with other compounds. In other words, the composition can include a compound corresponding to Formula 1 alone, a mixture of 2 or more compounds of Formula 1, or a mixture of a compound of Formula 1 and a compound not corresponding to the present application. Among them, the compound not corresponding to the present application can be a single compound, and can be 2 or more types of compounds. Here, when the compound is included in a combination of 2 or more types of other compounds, the other compounds can be known compounds of each organic material layer, or can be compounds to be developed in the future. Here, the compound contained in the organic material layer can consist only of the same type of compound, but can also be a mixture of 2 or more types of different compounds represented by Formula 1.

[0076] Hereinafter, a compound, a composition for an organic electronic element, and an organic electronic element including the same according to aspects of the present application will be described.

[0077] The present application provides a compound represented by Formula 1.

[0078] Formula 1

[0079]

[0080] wherein:

[0081] Ar 1 is a C6-C 12 aryl group, Ar 1 may be further substituted by one or more deuterium,

[0082] Ar 2 is a phenyl; biphenyl; or naphthyl; wherein Ar 2 may be further substituted by one or more deuterium,

[0083] Ar 3 is a phenyl; biphenyl; or C7-C 18 heterocyclic group; wherein Ar 3 may be further substituted by one or more substituents selected from the group consisting of deuterium; C6-C 20 aryl group; and C6-C 20 aryl group substituted with deuterium.

[0084] L 1is a single bond; phenylene; or naphthylene; wherein L 1 may be further substituted by one or more deuterium,

[0085] R 1 and R 2 each are the same or different and each is independently hydrogen; deuterium;

[0086] a and b are each independently an integer from 0 to 6.

[0087] Further, Ar 1 is represented by any one of the following formulae Ar1-1 to Ar1-6:

[0088]

[0089]

[0090] wherein:

[0091] R 3 , R 4 , R 5 and R 6 each are the same or different and each is independently hydrogen; deuterium; c and f are independently an integer from 0 to 5, d is an integer from 0 to 7, e is an integer from 0 to 4,

[0092] * means the position to be bonded.

[0093] Further, Ar 2 is represented by any one of the following formulae Ar2-1 to Ar2-6:

[0094]

[0095] wherein:

[0096] R 7 , R 8 , R 9 and R 10 each are the same or different and each is independently hydrogen; or deuterium; g and i are an integer from 0 to 5, h is an integer from 0 to 4, j is an integer from 0 to 7,

[0097] * means the position to be bonded.

[0098] Further, Ar 3 is represented by any one of the following formulae Ar3-1 to Ar3-10:

[0099]

[0100]

[0101] wherein:

[0102] X and Y are each independently O or S,

[0103] R 11 , R 12 , R 13 , R 16 , R 17 , R 18 , and R 19 are each the same or different and are each independently hydrogen; or deuterium; or can form a benzene ring by bonding with a plurality of adjacent R 18 groups,

[0104] However, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , and R 19 cannot form a ring by bonding with adjacent groups.

[0105] R 14 and R 15 are each the same or different and are independently hydrogen; deuterium; a C6-C 20 aryl group substituted with deuterium or unsubstituted;

[0106] k, m, and s are each independently an integer of 0 to 5, l, n', o, q, and r are independently an integer of 0 to 4, n and r' are independently an integer of 0 to 3, p is an integer of 0 to 2,

[0107] * means a position to be bonded.

[0108] Further, L 1 is a single bond or is represented by any one of the following formulae L1-1 to L1-13:

[0109]

[0110]

[0111] wherein:

[0112] R 20 and R 21 are each the same or different and are each independently hydrogen; or deuterium;

[0113] t is an integer of 0 to 4, u is an integer of 0 to 6,

[0114] * means a position to be bonded.

[0115] Additionally, the compound represented by formula 1 contains at least one deuterium.

[0116] Specifically, the compound represented by Formula 1 can be any one of the following compounds P-1 to P-112, but is not limited thereto.

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] In another aspect, the present application provides a composition for an organic electronic element, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 or Formula 3.

[0123]

[0124] wherein:

[0125] L 11 , L 12 , L 13 , and L 14 are each independently selected from a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si, or P; and a C3-C 60 aliphatic ring; and a C6-C 60 aromatic ring;

[0126] When L 11 , L 12 , L 13 , and L 14 is an arylene group, it is preferably a C6-C 30 arylene group, more preferably a C6-C 25 arylene group, a C6-C 18 arylene group, or a C6-C 12 arylene group, for example, it can be a phenylene group, a biphenylene group, a naphthylene group, a terphenylene group, an anthrylene group, etc.

[0127] When L 11 , L 12 , L 13 , and L 14 is a heterocyclic group, it is preferably a C2-C 30 heterocyclic group, more preferably a C2-C 25heterocyclic group, C2-C 18 heterocyclic group or C2-C 12 heterocyclic group, for example, it can be pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuro-pyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, and the like.

[0128] when L 11 , L 12 , L 13 and L 14 is a fused ring group, it is preferably a fused ring group of a C3-C 30 aliphatic ring and a C6-C 30 aromatic ring, more preferably a fused ring group of a C3-C 25 aliphatic ring and a C6-C 25 aromatic ring.

[0129] Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a C6-C 60 aryl group; a fluorenyl group; a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si or P; a fused ring group of a C3-C 60 aliphatic ring and a C6-C 60 aromatic ring; a C3-C 60 aliphatic ring; a C1-C 50 alkyl group; a C2-C 20 alkenyl group; a C2-C 20 alkynyl group; a C1-C 30 alkoxy group; and a C6-C 30 aryloxy group;

[0130] when Ar 11 , Ar 12 and Ar 13 is an aryl group, it is preferably a C6-C 30 aryl group, more preferably a C6-C 25 aryl group, a C6-C 18 aryl group or a C6-C 12 aryl group, for example, it can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, and the like.

[0131] when Ar 11 , Ar 12 and Ar13 is a heterocyclic group, it is preferably a C2-C 30 is a heterocyclic group, it is preferably a C2-C 25 is a heterocyclic group, it is preferably a C2-C 18 is a heterocyclic group, it is preferably a C2-C 12 is a heterocyclic group, it is preferably a C2-C

[0132] When Ar 11 , Ar 12 and Ar 13 is a fused ring group, it is preferably a C3-C 30 aliphatic ring and a C6-C 30 aromatic ring, more preferably a C3-C 25 aliphatic ring and a C6-C 25 aromatic ring.

[0133] When Ar 11 , Ar 12 and Ar 13 is an aliphatic ring group, it is preferably a C3-C 30 aliphatic ring group, more preferably a C3-C 25 aliphatic ring group, a C3-C 18 aliphatic ring group and a C3-C 12 aliphatic ring group. Specifically, it can be a cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl group, etc.

[0134] When Ar 11 , Ar 12 and Ar 13 is an alkyl group, it is preferably a C1-C 30 alkyl group, more preferably a C1-C 25 alkyl group, a C1-C 18 alkyl group or a C1-C 12 alkyl group. For example, it can be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, etc.

[0135] When Ar 11 , Ar 12 and Ar 13 is an alkoxy group, it is preferably a C1-C 25 alkoxy group, a C1-C 18alkoxy group or C1-C 12 alkoxy group.

[0136] when Ar 11 , Ar 12 and Ar 13 is an aryloxy group, it is preferably a C6-C 25 aryloxy group, a C6-C 18 aryloxy group or a C6-C 12 aryloxy group.

[0137] Ar 14 is each independently selected from the group consisting of a C6-C 60 aryl group; a fluorenyl group; a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si or P; a C3-C 60 aliphatic ring and a C6-C 60 aromatic ring; and -L'-N(R')(R");

[0138] when Ar 14 is an aryl group, it is preferably a C6-C 30 aryl group, more preferably a C6-C 25 aryl group, a C6-C 18 aryl group or a C6-C 12 aryl group, for example, it can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0139] when Ar 14 is a heterocyclic group, it is preferably a C2-C 30 heterocyclic group, more preferably a C2-C 25 heterocyclic group, a C2-C 18 heterocyclic group or a C2-C 12 heterocyclic group, for example, it can be pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuro-pyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0140] when Ar 14 is a fused ring group, it is preferably a C3-C 30 aliphatic ring and a C6-C 30 aromatic ring, more preferably a C3-C 25 aliphatic ring and a C6-C 25 aromatic ring.

[0141] Z is O, S, C(R 51 )(R 52 ) or NR 53 ,

[0142] Ring A is a C6-C 20 aryl group,

[0143] wherein L' is a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si or P; and a C3-C 60 aliphatic ring;

[0144] wherein L' is an arylene group, which is preferably a C6-C 30 arylene group, more preferably a C6-C 25 arylene group, a C6-C 18 arylene group, or a C6-C 12 arylene group, for example, it can be a phenylene group, a biphenylene group, a naphthylene group, a terphenylene group, an anthrylene group, etc.

[0145] When L' is a heterocyclic group, it is preferably a C2-C 30 heterocyclic group, more preferably a C2-C 25 heterocyclic group, a C2-C 18 heterocyclic group, or a C2-C 12 heterocyclic group, for example, it can be a pyrazine, a thiophene, a pyridine, a pyrimidine, a quinoline, a pyrimidoindole, a 5-phenyl-5H-pyrimido[5,4-b]indole, a quinazoline, a quinoxaline, a benzochinazoline, a carbazole, a dibenzochinazoline, a benzofuran, a benzothiophene, a dibenzofuran, a dibenzothiophene, a benzothienopyrimidine, a benzofuranopyrimidine, a phenothiazine, a phenylphenothiazine, a naphthobenzofuran, a naphthobenzothiophene, etc.

[0146] When L' is an aliphatic ring, it is preferably a C3-C 30 aliphatic ring; more preferably a C3-C 25 aliphatic ring; a C3-C 18 aliphatic ring; or a C3-C 12 aliphatic ring; specifically, it can be a cyclobutane, a cyclopentane, a cyclohexane, a bicycloheptane, an adamantyl group, etc.

[0147] wherein R 51 , R 52 , R 53 , R' and R" are the same as the definition of Ar 11 , or R 51 and R 52 may be bonded to each other to form a spiro,

[0148] R 22 and R 23 They may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen; cyano group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; 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 group; or multiple adjacent R groups 22 or multiple R 23 They can bond together to form a ring.

[0149] When R 22 and R 23 When it is an aryl group, it is preferably C6-C. 30 Aryl groups, more preferably C6-C 25 aryl group, C6-C 18 aryl group or C6-C 12 The aryl group, for example, can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc. wait.

[0150] When R 22 and R 23 When it is a heterocyclic group, it is preferably C2-C. 30 Heterocyclic groups, more preferably C2-C 25 Heterocyclic groups, C2-C 18 Heterocyclic groups or C2-C 12 Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidindole, 5-phenyl-5H-pyrimidin[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0151] When R 22 and R 23 When it is a fused ring group, it is 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 25a fused ring group of aromatic rings.

[0152] when R 22 and R 23 are alkyl groups, it is preferably a C1-C 30 alkyl group, more preferably a C1-C 25 alkyl group, a C1-C 18 alkyl group, or a C1-C 12 alkyl group. For example, it can be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0153] when R 22 and R 23 are alkoxy groups, it is preferably a C1-C 25 alkoxy group, a C1-C 18 alkoxy group, or a C1-C 12 alkoxy group.

[0154] when R 22 and R 23 are aryloxy groups, it is preferably a C6-C 25 aryloxy group, a C6-C 18 aryloxy group, or a C6-C 12 aryloxy group.

[0155] aa and ab are each independently an integer from 0 to 4,

[0156] wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylidene group, the fused ring group, the aliphatic ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, and the aryloxy group can be substituted with one or more substituents selected from the group consisting of deuterium; a halogen; a silyl group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C1-C 20 alkylthio group; a C1-C 20 alkoxy group; a C1-C 20 alkyl group; a C2-C 20 alkenyl group; a C2-C 20 alkynyl group; a C6-C 20 aryl group; a C6-C 20 aryl group substituted with deuterium; a fluorenyl group; a C2-C 20 heterocyclic group; a C3-C 20 aliphatic ring; a C7-C 20 arylalkyl group; a C8-C 20 arylalkenyl group; a C7-C 20Alkyl aryl groups; and -L'-N(R')(R"); furthermore, the hydrogens of these substituents may be further substituted with one or more deuteriums, and additionally, 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.

[0157] Preferably, the composition for organic electronic components can be used as the host of the light-emitting layer.

[0158] Equation 2 can be represented by any of the following equations 2-1 to 2-3.

[0159]

[0160] in:

[0161] Ar 12 Ar 13 L 11 L 12 and L 13 Same as defined in Equation 2,

[0162] X 11 X 12 and X 13 The definition of Z is the same as in Equation 3.

[0163] R 24 R 25 R 26 R 27 R 28 and R 29 Each may be the same or different, and each is independently hydrogen; deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkyl thio group; C1-C 20 alkoxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl groups; C7-C 20 arylalkyl group; C8-C 20 aryl alkenyl groups; and C7-C 20 alkylaryl group; or multiple adjacent R groups 24 or multiple R25 or multiple R 26 or multiple R 27 or multiple R 28 or multiple R 29 They can bond together to form a ring.

[0164] ac, af, and ag are each integers from 0 to 4, and ad, ae, and ah are each integers from 0 to 3.

[0165] Equation 3 can be represented by any of the following equations 3-1 to 3-6.

[0166]

[0167] in:

[0168] Z, Ar 14 L 14 R 22 R 23 aa and ab are the same as those defined in Equation 3.

[0169] R 30 With R 22 Multiple Rs with the same definition or adjacent values 30 They can bond together to form a ring, where ai is an integer from 0 to 2.

[0170] Equation 3 can be represented by any of the following equations 3-7 to 3-9.

[0171]

[0172] in:

[0173] Z, Ring A, Ar 14 L 14 R 23 ab is the same as that defined in Equation 3.

[0174] R 31 With R 22 Multiple Rs with the same definition or adjacent values 31 They can be bonded together to form a ring, where aj is an integer from 0 to 6.

[0175] Equation 3 can be represented by any of the following equations 3-10 to 3-12.

[0176]

[0177]

[0178] in:

[0179] Z, Ring A, Ar 14 L14 R 22 aa is the same as that defined in Equation 3.

[0180] R 32 With R 22 Multiple Rs with the same definition or adjacent values 32 They can bond together to form a ring, where ak is an integer from 0 to 6.

[0181] Equation 3 can be represented by any of the following equations 3-13 to 3-18.

[0182]

[0183]

[0184] in:

[0185] Z, Ar 14 L 14 R 22 R 23 aa and ab are the same as those defined in Equation 3.

[0186] R 30 R 31 and R 32 With R 22 Multiple Rs with the same definition or adjacent values 30 Multiple R 31 or multiple R 32 They can bond together to form a ring.

[0187] ai is an integer from 0 to 2, and aj and ak are each integers from 0 to 6.

[0188] Equation 3 can be represented by Equation 3-19.

[0189]

[0190] in:

[0191] Ar 14 L 14 R 53 R 23 ab is the same as that defined in Equation 3.

[0192] R 30 and R 31 With R 22 Multiple Rs with the same definition or adjacent values 30 or multiple R 31 They can bond together to form a ring.

[0193] ai is an integer from 0 to 2, and aj is an integer from 0 to 6.

[0194] Specifically, the compound represented by Formula 2 can be a compound represented by any one of the following compounds N-1 to compound N-128, but is not limited thereto.

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] Specifically, the compound represented by Formula 3 can be a compound represented by any one of the following compounds S-1 to compound S-120, but is not limited thereto.

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] Further, in another aspect, the present application provides an organic electronic element including a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; wherein the organic material layer contains a compound represented by Formula 1 or a composition for an organic electronic element.

[0211] In another aspect, the present application provides a method for reusing a compound of Formula 1, the method comprising:

[0212] recovering a crude organic light emitting material containing a compound of Formula 1 from a deposition apparatus used in a process for depositing an organic light emitting material to prepare an organic light emitting device;

[0213] removing impurities from the crude organic light emitting material;

[0214] recovering the organic light emitting material after removing impurities; and

[0215] purifying the recovered organic light emitting material to have a purity of 99.9% or more.

[0216] The step of removing impurities from the crude organic light emitting material recovered from the deposition apparatus can preferably include a pre-purification process by recrystallization in a recrystallization solvent to obtain a purity of 98% or more.

[0217] The recrystallization solvent can preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0218] 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.

[0219] When using a mixture of a polar solvent and a non-polar solvent, the recrystallization solvent can be used in an amount of 15% (v / v) or less of the non-polar solvent compared to the polar solvent.

[0220] The recrystallization solvent can preferably be used by mixing: an N-methyl pyrrolidone (NMP) single solvent; or a polar solvent selected from 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide, and dimethyl sulfoxide mixed into N-methyl pyrrolidone; or a single non-polar solvent; or a mixed non-polar solvent; selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone; or a polar solvent and a non-polar solvent.

[0221] The pre-purification process can include a step of precipitating crystals by cooling to 0°C to 5°C after dissolving the crude organic light emitting material recovered from the deposition apparatus in a polar solvent at 90°C to 120°C.

[0222] The pre-purification process can include a step of precipitating crystals by cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C after dissolving the crude organic light emitting material recovered from the deposition apparatus in a polar solvent at 90°C to 120°C.

[0223] The pre-purification process can include a step of precipitating crystals while concentrating the solvent and removing the non-polar solvent after dissolving the crude organic light emitting material recovered from the deposition apparatus in a non-polar solvent.

[0224] The pre-purification process can include a step of recrystallizing again with a non-polar solvent after first recrystallizing with a polar solvent.

[0225] The step of purifying the recovered impurities to a purity of 99.9% or more can include performing an adsorption separation process by adsorption on an adsorbent to adsorb and remove the impurities.

[0226] The adsorbent can be activated carbon, silica gel, alumina, or a material used for known adsorption purposes.

[0227] The step of purifying the recovered impurities to a purity of 99.9% or more can include performing a sublimation purification.

[0228] Reference Figure 1 An organic electronic element (100) according to the present application includes a first electrode (110), a second electrode (170), and an organic material layer including a single compound represented by Formula 1 or two or more compounds between the first electrode (110) and the second electrode (170). Among them, the first electrode (110) can be an anode or a positive electrode, and the second electrode (170) can be a cathode or a negative electrode. In the case of an inverted organic electronic element, the first electrode can be a cathode, and the second electrode can be an anode.

[0229] The organic material layer can 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) sequentially formed on the first electrode (110). Here, the remaining layers other than the light-emitting layer (140) can not be formed. The organic material layer can 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) or the like can be used as a hole blocking layer (see Figure 2 ).

[0230] In addition, the organic electronic element according to the embodiment of the present application can further include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer can be formed on a surface of two surfaces of the first electrode which does not contact the organic material layer or on a surface of two surfaces of the second electrode which does not contact the organic material layer. The compound or material for an organic electronic element according to the embodiment of the present application, which is suitable for the organic material layer, can be used as a material for a hole injection layer (120), a hole transport layer (130), a light-emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a light-emitting layer (140), a host or a dopant, or a light efficiency enhancement layer. Preferably, for example, a composition for an organic electronic element including a compound according to Formula 1 of the present application or a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 or Formula 3 can be used as a host material for a light-emitting layer.

[0231] The organic material layer can include 2 or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer formed in this order on an anode, and can further include a charge generation layer formed between the 2 or more stacks (see Figure 3

[0232] In addition, even if the same core is used, the band gap, electrical properties, interface properties, and the like can vary depending on the position at which the substituent is bonded, and thus the selection of the core and the combination of the sub-substituents associated therewith are also very important, and particularly, when an optimal combination of the energy level and T1 value of each organic material layer and the unique properties (mobility, interface properties, and the like) of the material are achieved, long service life and high efficiency can be simultaneously achieved.

[0233] The organic electroluminescent device according to the embodiments of the present application can be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a metal oxide or an alloy thereof having electrical conductivity is deposited on a substrate to form a cathode, and an organic material 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) is formed thereon, and then a material usable as a cathode is deposited thereon, whereby the organic electroluminescent device according to the embodiments of the present application can be manufactured.

[0234] Further, the present application provides an organic electronic element 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 provides an organic electronic element containing a compound or a composition for an organic electronic element as an electron transport material.

[0235] As another specific example, the present application provides an organic electronic element using the same or different compounds represented by Formula 1 mixed to an organic material layer. Preferably, the organic material layer contains a light emitting layer, wherein the light emitting layer contains a composition for an organic electronic element containing a compound represented by Formula 1 or a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 or Formula 3.

[0236] Further, the present application provides a composition for an organic electronic element containing a compound represented by Formula 1 or a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 or Formula 3, and provides an organic electronic element containing the composition.

[0237] Further, the present application also provides an electronic device including a display device containing an organic electronic element; and a control unit for driving the display device.

[0238] ​According to another aspect, the present application provides a display device, wherein 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 a mobile communication terminal such as a portable phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game machine, various televisions (TVs), and various computers.

[0239] Hereinafter, the synthesis example of the compound represented by Formula 1, Formula 2, and Formula 3 of the present application and the preparation example of the organic electronic element of the present application will be described in detail through Examples, but are not limited to the following Examples.

[0240] [Synthesis Example 1]

[0241] The compound represented by Formula 1 according to the present application can be synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1, but is not limited thereto.

[0242] [Reaction Scheme 1]

[0243]

[0244] I. Synthesis of Sub 1

[0245] Sub 1 of Reaction Scheme 1 can be synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto.

[0246] [Reaction Scheme 2]

[0247]

[0248] 1. Synthesis Example of Sub 1-2

[0249]

[0250] 1) Synthesis Example of Sub 1-2A

[0251] After Sub 1-2A-1 (10.0 g, 41.4 mmol) was dissolved in THF (104 mL) and water (36 mL) in a round bottom flask, Sub 1-2A-2 (5.3 g, 41.4 mmol), Pd(PPh3)4(1.4 g, 1.2 mmol), K2CO3(11.4 g, 82.8 mmol) were added and the reaction was performed at 60°C. When the reaction was completed, extraction was performed with CH2Cl2and water, the organic layer was dried with MgSO4, concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 7.7 g of the product. (Yield: 76.3%)

[0252] 2) Synthesis example of Sub 1-2

[0253] After Sub 1-2A (7.7 g, 31.6 mmol) was dissolved in toluene (105 mL) in a round bottom flask, bis(pinacolato)diboron (B2Pin2) (16.0 g, 63.2 mmol), Pd2(dba)3(0.6 g, 0.6 mmol), X-phos (0.6 g, 1.3 mmol), KOAc (9.3 g, 94.8 mmol) were added and the reaction was performed at 110°C. When the reaction was completed, extraction was performed with CH2Cl2and water, the organic layer was dried with MgSO4, concentrated. Thereafter, the resulting organic material was recrystallized using a silica gel column to obtain 5.8 g of the product. (Yield 54.8%)

[0254] 2) Synthesis example of Sub 1-4

[0255]

[0256] 1) Synthesis example of Sub 1-4A

[0257] After Sub 1-4A-1 (10.0 g, 41.4 mmol) was dissolved in THF (104 mL) and water (36 mL) in a round bottom flask, Sub 1-4A-2 (7.1 g, 41.4 mmol), Pd(PPh3)4(1.4 g, 1.2 mmol), K2CO3(11.4 g, 82.8 mmol) were added and 8.9 g of the product was obtained using the synthesis method of Sub 1-2A. (Yield 74.4%)

[0258] 2) Synthesis example of Sub 1-4

[0259] After Sub 1-4A (8.9 g, 30.8 mmol) was dissolved in toluene (103 mL) in a round bottom flask, bis(pinacolato)diboron (B2Pin2) (15.7 g, 61.6 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), X-phos (0.6 g, 1.2 mmol), KOAc (9.1 g, 92.5 mmol) were added and the synthesis method of Sub 1-2 was used to obtain 6.3 g of product. (Yield 53.8%)

[0260] 3. Synthesis example of Sub 1-10

[0261]

[0262] 1) Synthesis example of Sub 1-10A

[0263] After Sub 1-10A-1 (10.0 g, 41.4 mmol) was dissolved in THF (104 mL) and water (36 ml) in a round bottom flask, Sub 1-10A-2 (8.2 g, 41.4 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), K2CO3 (11.4 g, 82.8 mmol) were added and the synthesis method of Sub 1-2A was used to obtain 9.8 g of product. (Yield 75.2%)

[0264] 2) Synthesis example of Sub 1-10

[0265] After Sub 1-10A (9.8 g, 31.1 mmol) was dissolved in toluene (103 mL) in a round bottom flask, bis(pinacolato)diboron (B2Pin2) (15.8 g, 62.2 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), X-phos (0.6 g, 1.2 mmol), KOAc (9.2 g, 93.3 mmol) were added and the synthesis method of Sub 1-2 was used to obtain 7.1 g of product. (Yield 56.1%)

[0266] 4. Synthesis example of Sub 1-13

[0267]

[0268] 1) Synthesis example of Sub 1-13A

[0269] After Sub 1-13A-1 (10.0 g, 41.4 mmol) was dissolved in THF (104 mL) and water (36 ml) in a round-bottom flask, Sub 1-13A-2 (8.6 g, 41.4 mmol), Pd(PPh3)4(1.4 g, 1.2 mmol), K2CO3(11.4 g, 82.8 mmol) were added, and 9.5 g of the product was obtained using the synthesis method of Sub 1-2A. (Yield 70.8%)

[0270] 2) Synthesis example of Sub 1-13

[0271] After Sub 1-13A (9.5 g, 29.3 mmol) was dissolved in toluene (98 mL) in a round-bottom flask, bis(pinacolato)diboron (B2Pin2) (14.9 g, 58.7 mmol), Pd2(dba)3(0.5 g, 0.6 mmol), X-phos (0.6 g, 1.2 mmol), KOAc (8.6 g, 88.0 mmol) were added, and 6.3 g of the product was obtained using the synthesis method of Sub 1-2. (Yield 51.7%)

[0272] The compound belonging to Sub 1 can be the following compounds, but is not limited thereto, and the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1.

[0273]

[0274]

[0275] [Table 1]

[0276] Compound FD-MS Compound FD-MS Sub 1-1 m / z = 330.18 (C 22 H 23 BO2= 330.23)]]> Sub 1-2 m / z = 335.21 (C 22 H 18 D5BO2= 335.26)]]> Sub 1-3 m / z = 340.24 (C 22 H 13 D 10 BO2= 340.3)]]> Sub 1-4 m / z = 380.19 (C 26 H 25 BO2= 380.29)]]> Sub 1-5 m / z = 386.23 (C 26 H 19 D6BO2= 386.33)]]> Sub 1-6 m / z = 387.24 (C 26 H 18 D7BO2= 387.34)]]> Sub 1-7 m / z = 393.28 (C 26 H 12 D 13 BO2= 393.37)]]> Sub 1-8 m / z = 380.19 (C 26 H 25 BO2= 380.29)]]> Sub 1-9 m / z = 387.24 (C 26 H 18 D7BO2= 387.34)]]> Sub 1-10 m / z = 406.21 (C 28 H 27 BO2= 406.33)]]> Sub 1-11 m / z = 411.24 (C 28 H 22 D5BO2= 411.36)]]> Sub 1-12 m / z = 406.21 (C 28 H 27 BO2= 406.33)]]> Sub 1-13 m / z = 415.27 (C 28 H 18 D9BO2= 415.39)]]> Sub 1-14 m / z = 420.3 (C 28 H 13 D 14 BO2= 420.42)]]> Sub 1-15 m / z = 406.21 (C 28 H 27 BO2= 406.33)]]>

[0277] II. Synthesis of Sub 2

[0278] Sub 2 of Reaction Scheme 1 can be synthesized by the reaction scheme of Scheme 3, but is not limited thereto.

[0279] <Reaction Scheme 3>

[0280]

[0281] 1. Synthesis example of Sub 2-1

[0282]

[0283] After Sub 2-1A (10.0 g, 40.3 mmol) was dissolved in THF (101 mL) and water (34 mL) in a round bottom flask, Sub 2-1B (18.2 g, 80.6 mmol), Pd(PPh3)4(1.4 g, 1.2 mmol), K2CO3(11.1 g, 80.6 mmol) were added and reacted at 60°C. When the reaction was completed, extraction was performed with CH2Cl2and water, the organic layer was dried with MgSO4, concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 11.8 g of the product. (Yield: 74.3%)

[0284] 2. Synthesis example of Sub 2-8

[0285]

[0286] After Sub 2-8A (10.0 g, 33.5 mmol) was dissolved in THF (84 mL) and water (28 mL) in a round bottom flask, Sub 2-8B (15.2 g, 67.1 mmol), Pd(PPh3)4(1.2 g, 1.0 mmol), K2CO3(9.3 g, 67.1 mmol) were added, and the synthesis method of Sub 2-1 was used to obtain 11.1 g of the product. (Yield 74.5%)

[0287] 3. Synthesis example of Sub 2-23

[0288]

[0289] After Sub 2-23A (10.0 g, 39.5 mmol) was dissolved in THF (99 mL) and water (33 mL) in a round bottom flask, Sub 2-23B (25.0 g, 79.0 mmol), Pd(PPh3)4(1.4 g, 1.2 mmol), K2CO3(10.9 g, 79.0 mmol) were added, and the synthesis method of Sub 2-1 was used to obtain 14.5 g of the product. (Yield 75.2%)

[0290] 4. Synthesis example of Sub 2-27

[0291]

[0292] After Sub 2-27A (10.0 g, 40.3 mmol) was dissolved in THF (101 mL) and water (34 mL) in a round bottom flask, Sub 2-27B (31.6 g, 80.6 mmol), Pd(PPh3)4(1.4 g, 1.2 mmol), K2CO3(11.1 g, 80.6 mmol) were added, and the synthesis method of Sub 2-1 was used to obtain 15.8 g of product. (Yield 70.1%)

[0293] 5. Synthesis example of Sub 2-47

[0294]

[0295] After Sub 2-47A (10.0 g, 30.8 mmol) was dissolved in THF (77 mL) and water (26 mL) in a round bottom flask, Sub 2-47B (21.7 g, 61.7 mmol), Pd(PPh3)4(1.1 g, 0.9 mmol), K2CO3(8.5 g, 61.7 mmol) were added, and the synthesis method of Sub 2-1 was used to obtain 12.4 g of product. (Yield 67.6%)

[0296] 6. Synthesis example of Sub 2-51

[0297]

[0298] 1) Synthesis example of Sub 2-51A-2

[0299] After Sub 2-51A-1 (10.0 g, 48.4 mmol) was dissolved in THF (120 mL) and water (40 mL) in a round bottom flask, 3-bromo-1,1'-biphenyl (11.3 g, 48.4 mmol), Pd(PPh3)4(1.7 g, 1.5 mmol), K2CO3(13.4 g, 96.9 mmol) were added and reacted at 60°C. When the reaction was completed, extraction was performed with CH2Cl2and water, the organic layer was dried with MgSO4, concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 11.8 g of product. (Yield: 77.2%)

[0300] 2) Synthesis example of Sub 2-51A

[0301] After Sub 2-51A-2 (11.8 g, 37.5 mmol) was dissolved in toluene (125 mL) in a round bottom flask, bis(pinacolato)diboron (B2Pin2) (19.0 g, 75.0 mmol), Pd2(dba)3 (0.7 g, 0.7 mmol), X-phos (0.7 g, 1.5 mmol), KOAc (11.0 g, 112.4 mmol) were added and reacted at 110°C. When the reaction was completed, extraction was performed with CH2Cl2and water, the organic layer was dried with MgSO4, and concentrated. Thereafter, the resulting organic matter was recrystallized using a silica gel column to obtain 8.4 g of product. (Yield 55.2%)

[0302] 3) Synthesis Example of Sub 2-51

[0303] After Sub 2-51A (8.4 g, 20.7 mmol) was dissolved in THF (52 mL) and water (17 mL) in a round bottom flask, Sub 2-51B (12.5 g, 41.3 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), K2CO3 (5.7 g, 41.3 mmol) were added, and 7.1 g of product was obtained using the synthesis method of Sub 2-1. (Yield 62.7%)

[0304] 7) Synthesis Example of Sub 2-68

[0305]

[0306] 1) Synthesis Example of Sub 2-68A-2

[0307] After Sub 2-68A-1 (10.0 g, 47.1 mmol) was dissolved in THF (118 mL) and water (39 mL) in a round bottom flask, 2-bromonaphthalene (9.73 g, 47.1 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), K2CO3 (13.0 g, 94.1 mmol) were added, and 10.8 g of product was obtained using the synthesis method of Sub 2-51A-2. (Yield 77.6%)

[0308] 2) Synthesis Example of Sub 2-68A

[0309] After Sub 2-68A-2 (10.8 g, 36.6 mmol) was dissolved in toluene (122 mL) in a round-bottom flask, 2 bis(pinacolato)diboron (B2Pin2) (18.6 g, 73.3 mmol), Pd2(dba)3 (0.7 g, 0.7 mmol), X-phos (0.7 g, 1.5 mmol), KOAc (10.8 g, 109.9 mmol) were added and 7.9 g of the product was obtained using the synthetic method of Sub 2-51A. (Yield 56.7%)

[0310] 3) Synthesis example of Sub 2-68

[0311] After Sub 2-68A (7.9 g, 20.8 mmol) was dissolved in THF (52 mL) and water (17 mL) in a round-bottom flask, Sub 2-68B (16.3 g, 41.5 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), K2CO3 (5.7 g, 41.5 mmol) were added and 8.4 g of the product was obtained using the synthetic method of Sub 2-1. (Yield 65.4%)

[0312] 8) Synthesis example of Sub 2-70

[0313]

[0314] After Sub 2-70A (10.0 g, 33.5 mmol) was dissolved in THF (84 mL) and water (28 mL) in a round-bottom flask, Sub 2-70B (24.6 g, 67.1 mmol), Pd(PPh3)4 (1.2 g, 1.0 mmol), K2CO3 (9.3 g, 67.1 mmol) were added and 14.5 g of the product was obtained using the synthetic method of Sub 2-1. (Yield 74.2%)

[0315] The compounds belonging to Sub 2 can be the following compounds, but are not limited thereto, and the FD-MS values of the following compounds are shown in Table 2.

[0316]

[0317]

[0318]

[0319]

[0320] [Table 2]

[0321]

[0322]

[0323] III. Synthesis of final product

[0324] 1. Synthesis of P-1

[0325]

[0326] After Sub 1-1 (5.0 g, 15.1 mmol) was dissolved in THF (38 mL) and water (13 mL) in a round bottom flask, Sub 2-1 (6.0 g, 15.1 mmol), Pd(PPh3)4(0.5 g, 0.5 mmol), NaOH (1.2 g, 30.3 mmol) were added and reacted at 75°C. When the reaction was completed, extraction was performed with CH2Cl2and water, the organic layer was dried with MgSO4, and concentrated. Thereafter, the resulting organic matter was recrystallized using a silica gel column to obtain 6.6 g of the product. (Yield 77.6%)

[0327] 2. Synthesis example of P-24

[0328]

[0329] After Sub 1-10 (5.0 g, 12.3 mmol) was dissolved in THF (31 mL) and water (10 mL) in a round bottom flask, Sub 2-6 (5.8 g, 12.3 mmol), Pd(PPh3)4(0.4 g, 0.4 mmol), NaOH (1.0 g, 24.6 mmol) were added and 6.9 g of the product was obtained using the synthesis method of P-1. (Yield 78.2%)

[0330] 3. Synthesis example of P-32

[0331]

[0332] After Sub 1-14 (5.0 g, 11.9 mmol) was dissolved in THF (30 mL) and water (10 mL) in a round bottom flask, Sub 2-8 (5.3 g, 11.9 mmol), Pd(PPh3)4(0.4 g, 0.4 mmol), NaOH (1.0 g, 23.8 mmol) were added and 6.4 g of the product was obtained using the synthesis method of P-1. (Yield 76.8%)

[0333] 4. Synthesis example of P-44

[0334]

[0335] After Sub 1-1 (5.0 g, 15.1 mmol) was dissolved in THF (38 mL) and water (13 mL) in a round-bottom flask, Sub 2-22 (7.3 g, 15.1 mmol), Pd(PPh3)4(0.5 g, 0.5 mmol), NaOH (1.2 g, 30.3 mmol) were added, and the synthesis method of P-1 was used to obtain 7.7 g of the product. (Yield 78.4%)

[0336] 5. Synthesis example of P-56

[0337]

[0338] After Sub 1-1 (5.0 g, 15.1 mmol) was dissolved in THF (38 mL) and water (13 mL) in a round-bottom flask, Sub 2-22 (7.3 g, 15.1 mmol), Pd(PPh3)4(0.5 g, 0.5 mmol), NaOH (1.2 g, 30.3 mmol) were added, and the synthesis method of P-1 was used to obtain 7.7 g of the product. (Yield 78.4%)

[0339] 6. Synthesis example of P-62

[0340]

[0341] After Sub 1-4 (5.0 g, 15.1 mmol) was dissolved in THF (33 mL) and water (11 mL) in a round-bottom flask, Sub 2-16 (6.8 g, 13.1 mmol), Pd(PPh3)4(0.5 g, 0.4 mmol), NaOH (1.1 g, 26.3 mmol) were added, and the synthesis method of P-1 was used to obtain 7.5 g of the product. (Yield 77.1%)

[0342] 7. Synthesis example of P-78

[0343]

[0344] After Sub 1-12 (5.0 g, 12.3 mmol) was dissolved in THF (31 mL) and water (10 mL) in a round-bottom flask, Sub 2-27 (6.9 g, 12.3 mmol), Pd(PPh3)4(0.4 g, 0.4 mmol), NaOH (1.0 g, 24.6 mmol) were added, and the synthesis method of P-1 was used to obtain 7.5 g of the product. (Yield 76.2%)

[0345] 8. Synthesis example of P-88

[0346]

[0347] After Sub 1-2 (5.0 g, 14.9 mmol) was dissolved in THF (37 mL) and water (12 mL) in a round-bottom flask, Sub 2-61 (8.1 g, 14.9 mmol), Pd(PPh3)4(0.5 g, 0.5 mmol), NaOH (1.2 g, 29.8 mmol) were added, and the synthesis method of P-1 was used to obtain 8.3 g of the product. (Yield 77.9%)

[0348] 9. Synthesis Example of P-100

[0349]

[0350] After Sub 1-4 (5.0 g, 13.1 mmol) was dissolved in THF (33 mL) and water (11 mL) in a round-bottom flask, Sub 2-68 (8.1 g, 13.1 mmol), Pd(PPh3)4(0.5 g, 0.4 mmol), NaOH (1.1 g, 26.3 mmol) were added, and the synthesis method of P-1 was used to obtain 8.5 g of the product. (Yield 77.8%)

[0351] 10. Synthesis Example of P-108

[0352]

[0353] After Sub 1-12 (5.0 g, 12.3 mmol) was dissolved in THF (31 mL) and water (10 mL) in a round-bottom flask, Sub 2-45 (6.9 g, 12.3 mmol), Pd(PPh3)4(0.4 g, 0.4 mmol), NaOH (1.0 g, 24.6 mmol) were added, and the synthesis method of P-1 was used to obtain 7.5 g of the product. (Yield 75.6%)

[0354] FD-MS values of the compounds P-1 to P-112 of the present application prepared according to the above synthesis examples are shown in Table 3.

[0355] [Table 3]

[0356]

[0357]

[0358] [Synthesis Example 2]

[0359] The compound represented by Formula 2 or Formula 3 is prepared by referring to known synthetic methods (named reactions) or published patent publications, for example, Korean Patent Registration No. 10-2395819, U.S. Patent Publication No. 2023-0129535, etc., but is not limited thereto.

[0360] FD-MS values of the compounds N-1 to N-128 and the compounds S-1 to S-120 of the present application prepared according to Synthetic Example 2 are shown in Table 4 and Table 5.

[0361] [Table 4]

[0362]

[0363]

[0364] [Table 5]

[0365]

[0366]

[0367]

[0368] In the above, exemplary synthetic examples of the present application represented by Formula 1, Formula 2, and Formula 3 have been described, but these are all based on Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), and it would be easily understood by those skilled in the art that the reaction can proceed even when other substituents defined in Formula 1, Formula 2, and Formula 3 are bonded in addition to the substituents indicated in the specific synthetic examples.

[0369] [Example 1] Red organic light-emitting device (phosphorescent host)

[0370] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0371] Compound B: 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triylidene)tris(2,3,5,6-tetrafluorobenzonitrile)

[0372] Compound C-R: N 7-(dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7 -triphenyldibenzo[b,d]thiophene-2,7-diamine

[0373] Compound E: 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0374] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0375] Compound G: (8-hydroxyquinolinato)lithium

[0376] Compound A and Compound B were used on an ITO layer (anode) formed on a glass substrate, and a hole injection layer having a thickness of 10 nm was formed by doping Compound B at a weight ratio of 98:2, and then Compound A was vacuum-deposited on the hole injection layer to a thickness of 110 nm to form a hole transport layer. Next, Compound C-R was vacuum-deposited on the hole transport layer to a thickness of 10 nm to form a light-emitting auxiliary layer. Thereafter, the host material of the light-emitting layer was formed using Compound P-1 (a compound of the present application) as a first host and Compound N-82 (a compound of the present application) as a second host, and using a mixture of the first host and the second host at a weight ratio of 5:5. Bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate (hereinafter abbreviated as '(piq)2Ir(acac)') was used as a dopant material, and the dopant was doped so that the weight ratio of the host to the dopant was 95:5, to form a light-emitting layer having a thickness of 30 nm.

[0377] Next, Compound E was vacuum-deposited on the light-emitting layer to form a hole blocking layer having a thickness of 10 nm, and Compound F and Compound G were used on the hole blocking layer using a mixture mixed at a weight ratio of 5:5. An electron transport layer having a thickness of 30 nm was formed. Thereafter, Compound G was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.2 nm, and then Al was deposited to form a cathode having a thickness of 150 nm.

[0378] [Example 2] to [Example 34]

[0379] An organic light-emitting device was manufactured in the same manner as in Example 1, but the compounds listed in Table 6 were used as the first host and the second host of the light-emitting layer.

[0380] [Comparative Example 1] to [Comparative Example 5]

[0381] An organic light emitting device was produced in the same manner as in Example 1, but Comparative Compound A to Comparative Compound E were used as the first host material of the light emitting layer.

[0382]

[0383]

[0384] For the organic electroluminescent devices produced according to the examples and comparative examples of the present application, electroluminescence (EL) characteristics were measured by applying a forward bias DC voltage using PR-650 of Photo Research Co. As a result of the measurement, T95 lifetime was measured at a standard luminance of 2,500 cd / m2by a lifetime measuring apparatus produced by McScience. 2 Table 6 shows the results of device production and evaluation.

[0385] The measuring apparatus can evaluate the performance of new materials compared to comparative compounds under the same conditions, without being affected by possible daily fluctuations in deposition rate, vacuum quality, or other parameters.

[0386] During the evaluation, since one batch contained four OLEDs of the same preparation including comparative compounds, and the performance of a total of 12 OLEDs was evaluated in 3 batches, the values of the experimental results obtained in this way showed statistical significance.

[0387] [Table 6]

[0388]

[0389]

[0390]

[0391] As can be seen from the results of Table 6, when a red organic light emitting device was produced using the compound of the present application as a phosphorescent host material, not only the driving voltage of the organic light emitting device could be reduced, but also the luminous efficiency and service life could be significantly improved, compared to the case where Comparative Compound A to Comparative Compound E were used.

[0392] As can be seen from the above, when the host of the light emitting layer is formed by mixing a plurality of compounds, depending on the type of the first compound and the second compound, the properties are different, and when the same compound is applied to the second compound, it can be confirmed that depending on the type of the first compound, there is a significant difference in properties. Similarly, depending on the type of the second compound, there are differences in driving voltage, efficiency, and service life.

[0393] Comparative Compound A to Comparative Compound E have a similar skeleton to the compounds of the present application, but differ in that the skeleton of the compounds of the present application is further substituted with an additional substituent.

[0394] To find the difference in the energy level of the compounds according to the structural difference of the compounds, the energy levels of Comparative Compound A to Comparative Compound E and the similar compound P-1 of the present application were measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program. The measurement results are shown in Table 7.

[0395] [Table 7]

[0396] Compound HOMO (eV) P-1 -5.724 Comparative Compound A -5.704 Comparative Compound B -5.718 Comparative Compound C -5.693 Comparative Compound D -5.664 Comparative Compound E -5.331

[0397] Referring to Table 7, it can be seen that the compounds of the present application have a lower HOMO energy level than the comparative compounds.

[0398] In the case of the compounds of the present application, the first host compound transports electrons in the light-emitting layer and serves to accept and move electrons from the electron transport layer into the light-emitting layer.

[0399] In other words, the fact that the HOMO energy level of the compounds of the present application is lower than that of Comparative Compound A to Comparative Compound E means that the electronic property of the compounds of the present application is higher than that of the comparative compounds, and thus it can be seen that electrons can move more efficiently within the light-emitting layer.

[0400] In detail, if the HOMO energy level of the first host that functions as an electron transport is high, holes flowing from the hole transport layer to the light-emitting layer cannot smoothly move to the second host, and electrons are more likely to be lost (exciton quenching) within the light-emitting layer rather than being transferred to the dopant to form excitons, thereby reducing the light-emitting efficiency.

[0401] Accordingly, the compounds of the present application have a lower HOMO energy level than the comparative compounds, so holes flowing from the hole transport layer can smoothly move to the second host, and the electron mobility within the light-emitting layer is maximized, increasing the charge balance within the light-emitting layer and improving the efficiency and service life.

[0402] As can be seen from Table 6 and Table 7, even if the compounds have similar compositions, the compounds of the present application that satisfy all the complex factors such as the type of substituent and the substitution position of the substituent show a significant effect compared to other comparative compounds in the organic electronic element. From this, it can be seen that the compounds of the present application that satisfy all the specific compositions show a significant effect in the organic electronic element compared to other comparative compounds not described in the present specification.

[0403] These results show that even among compounds having similar molecular components, the properties of the compounds such as 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 depending on the type and substitution position of the substituent, which is difficult to predict, and in addition, it shows that the performance of the element can vary due to complex factors in addition to one configuration that affects the overall result of the element.

[0404] While exemplary embodiments of the present application have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the application as disclosed in the accompanying claims. Therefore, the embodiments disclosed in the present application are intended to illustrate the scope of the technical idea of the present application, and the scope of the present application is not limited by the embodiments. The scope of the present application should be interpreted based on the appended claims, and should be interpreted as including all technical ideas within the scope equivalent to the claims.

Claims

1. Compounds represented by Formula 1: Formula 1 in: Ar 1 It is C6-C 12 The aryl group is optionally substituted with one or more deuterium groups. Ar 2 It is phenyl, biphenyl, or naphthyl, optionally substituted with one or more deuterium groups. Ar 3 It is phenyl, biphenyl, or C7-C. 18 Heterocyclic groups, optionally substituted with one or more substituents selected from deuterium; C6-C 20 aryl groups; and deuterated C6-C 20 aryl group; L 1 It is a single bond, a phenylene or naphthylene group, optionally substituted with one or more deuterium groups. R 1 and R 2 They may be the same or different, and each is independently hydrogen or deuterium; a and b are each an independent integer from 0 to 6.

2. The compound according to claim 1, wherein Ar 1 Any one of the following representations: Ar1-1 to Ar1-6 in: R 3 R 4 R 5 and R 6 They may be the same or different, and each is independently hydrogen or deuterium; c and f are independent integers from 0 to 5, d is an integer from 0 to 7, and e is an integer from 0 to 4. * indicates the position to be bonded.

3. The compound according to claim 1, wherein Ar 2 Any one of the following representations: Ar2-1 to Ar2-6 in: R 7 R 8 R 9 and R 10 They may be the same or different, and each is independently hydrogen or deuterium; g and i are integers from 0 to 5, h is an integer from 0 to 4, j is an integer from 0 to 7, and * indicates the position to be bonded.

4. The compound according to claim 1, wherein Ar 3 Any one of the following representations: Ar3-1 to Ar3-10 in: X and Y are each independently O or S. R 11 R 12 R 13 R 16 R 17 R 18 and R 19 Each may be the same or different, and each is independently hydrogen or deuterium, or is bonded to multiple adjacent R. 18 The group forms a benzene ring under the condition that R 11 R 12 R 13 R 14 R 15 R 16 R 17 and R 19 It does not form a ring by bonding to adjacent groups. R 14 and R 15 Each may be the same or different, and independently is hydrogen, deuterium, or C6-C substituted or unsubstituted with deuterium. 20 aryl group; k, m, and s are each independent integers from 0 to 5; l, n', o, q, and r are each independent integers from 0 to 4; n and r' are each independent integers from 0 to 3; p is an integer from 0 to 2; and * indicates the position to be bonded.

5. The compound according to claim 1, wherein L 1 It is a single bond or any of the representations from equations L1-1 to L1-13: in: R 20 and R 21 They may be the same or different, and each is independently hydrogen or deuterium; t is an integer from 0 to 4, u is an integer from 0 to 6, and * indicates the position to be bonded.

6. The compound according to claim 1, wherein the compound represented by formula 1 comprises at least one deuterium.

7. The compound according to claim 1, wherein the compound represented by formula 1 is selected from compounds P-1 to P-112:

8. A composition for use in organic electronic components, said composition comprising a mixture of the compound of claim 1 represented by formula 1 and a compound represented by formula 2 or 3: in: L 11 L 12 L 13 and L 14 Each is independently selected from a single bond; C6-C 60 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; Ar 11 Ar 12 and Ar 13 Each is independently selected from C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C3-C 60 Aliphatic ring; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy groups; and C6-C 30 aryloxy group; Ar 14 Selected from C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups in aromatic rings; and -L'-N(R')(R"), Z represents O, S, C(R) 51 (R) 52 ) or NR 53 , Ring A is C6-C 20 aryl group, Where L' is a single bond; C6-C 60 arylene group; fluorene group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and C3-C 60 Aliphatic rings; Where R 51 R 52 R 53 、R' and R” with Ar 11 The definitions are the same, or R 51 and R 52 They can bond together to form a screw. R 22 and R 23 They may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen; cyano group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; 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 group; or multiple adjacent R groups 22 or multiple R 23 They can bond together to form a ring. aa and ab are each independent integers from 0 to 4. The aryl group, arylene group, heterocyclic group, fluorene group, fluorene group, fused ring group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be replaced by one or more substituents selected from deuterium; halogen; silyl group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkyl thio group; C1-C 20 alkoxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Aliphatic ring; C7-C 20 arylalkyl group; C8-C 20 Aryl alkenyl group; C7-C 20 Alkyl aryl groups; and -L'-N(R')(R"); furthermore, the hydrogens of these substituents may be 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.

9. The composition for an organic electronic component according to claim 8, wherein the composition for the organic electronic component is used as the body of the light-emitting layer.

10. Organic electronic components, including: First electrode; Second electrode; And an organic material layer formed between the first electrode and the second electrode; The organic material layer thereon comprises the compound represented by Formula 1 as described in claim 1.

11. The organic electronic component of claim 10, further comprising a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, said surface being opposite to the organic material layer.

12. The organic electronic component of claim 10, 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 first electrode.

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

14. An electronic device, comprising a display device including the organic electronic components of claim 10; and a control unit for driving the display device.

15. The electronic device of claim 14, 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.

16. Organic electronic components, including: First electrode; Second electrode; And an organic material layer formed between the first electrode and the second electrode. The organic material layer comprises the composition for organic electronic components as described in claim 8.

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

18. The electronic device of claim 17, 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.

19. A method for reusing the compound of formula 1 according to claim 1, comprising: Recover crude organic light-emitting material containing the compound of Formula 1 from the deposition equipment 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 impurities are removed; as well as The recovered organic light-emitting material is purified to a purity of 99.9% or higher.

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