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

Abstract

Provided are: a compound capable of improving the luminous efficiency, stability, and lifespan of an element; an organic electronic element using the compound; the invention also provides an electronic device.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of U.S. Patent Application No. 18 / 501,355, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to a compound for an organic electronic element, an organic electronic element using the compound, and an electronic device thereof. Background Art

[0004] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. 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 multilayer structure composed of different materials and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

[0005] Materials used as organic material layers in organic electronic elements can be classified into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. Among them, light-emitting materials can be classified into high molecular weight types and low molecular weight types according to molecular weight, and according to the light-emitting mechanism, light-emitting materials can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons. In addition, light-emitting materials can be classified into blue-emitting materials, green-emitting materials, and red-emitting materials according to emission colors, as well as yellow-emitting materials and orange-emitting materials necessary to achieve more natural colors.

[0006] However, when only one material is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and there is a problem of reduced color purity or reduced device efficiency due to the emission attenuation effect. Therefore, in order to increase color purity and increase luminous efficiency through 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 the band gap of the host forming the light-emitting layer is mixed in the light-emitting layer, the excitons generated in the light-emitting layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light with a desired wavelength can be obtained according to the type of dopant used.

[0007] Currently, the portable display market is large displays, and their size is increasing day by day, therefore, more power consumption is required than that required by existing portable displays. Therefore, for portable displays with limited power supply such as batteries, power consumption becomes a very important factor, and the issues of efficiency and service life must also be addressed.

[0008] Efficiency, service life and driving voltage are related to each other, and when efficiency increases, the driving voltage is relatively reduced, and as the driving voltage decreases, the crystallization of the organic material caused by Joule heating generated during driving decreases, and thus the service life tends to increase. However, efficiency cannot be maximized simply by improving the organic material layer. This is because long service life and high efficiency can only be achieved simultaneously when the energy level and T1 value between each organic material layer and the inherent properties of the material (mobility, interface properties, etc.) are optimally combined.

[0009] Therefore, while delaying the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the reasons for shortening the service life of organic electronic components, it should have stable characteristics against Joule heating generated during device driving, and OLED devices are mainly formed by a deposition method, and it is necessary to develop materials that can withstand long-term deposition, that is, materials with strong heat resistance.

[0010] That is, in order to fully demonstrate the excellent characteristics of organic electronic components, priority should be given to materials that are stable and effective in constituting the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. However, the development of stable and effective organic material layer materials for organic electronic components has not been fully carried out. Therefore, there is a continuous need to develop new materials, and in particular, there is an urgent need to develop host materials for the luminescent layer. Summary of the invention

[0011] In order to solve the above-mentioned problems of the background art, the present invention discloses a compound having a novel structure, and when the compound is applied to an organic electronic element, it has been found that the luminous efficiency, stability and service life of the device can be significantly improved.

[0012] Therefore, an object of the present invention is to provide a novel compound, an organic electronic element using the compound, and an electronic device thereof.

[0013] [Technical solution]

[0014] The present invention provides a compound represented by Formula 1.

[0015] Formula 1

[0016]

[0017] In another aspect, the present invention provides a composition for a phosphorescent light-emitting layer of an organic electronic element, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5.

[0018]

[0019] In another aspect, the present invention provides an organic electronic element including the compound represented by Formula 1 or a composition for a phosphorescent light-emitting layer of the organic electronic element and an electronic device thereof.

[0020] [Effects of the invention]

[0021] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and the color purity and service life of the element can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present invention.

[0023] Figure 4 A formula according to one aspect of the present invention is shown.

[0024] [Explanation of symbols]

[0025] 100, 200, 300: organic electronic element 110: first electrode

[0026] 120: hole injection layer 130: hole transport layer

[0027] 140: Light-emitting layer 150: Electron transport layer

[0028] 160: electron injection layer 170: second electrode

[0029] 180: Light efficiency enhancement layer 210: Buffer layer

[0030] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0031] 330: first hole transport layer 340: first light emitting layer

[0032] 350: first electron transport layer 360: first charge generation layer

[0033] 361: second charge generation layer 420: second hole injection layer

[0034] 430: second hole transport layer 440: second light emitting layer

[0035] 450: Second electron transport layer CGL: Charge generation layer

[0036] ST1: first stack ST2: second stack DETAILED DESCRIPTION

[0037] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, when a detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0038] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to limit the substance, order or sequence of the corresponding component, but is only used to distinguish the corresponding component from other components. It should be noted that if a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected", "coupled" or "connected" between the components.

[0039] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0040] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0041] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms and means a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0042] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes a straight chain or branched chain group.

[0043] Unless otherwise specified, the term "cycloalkyl group" as used herein means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0044] Unless otherwise specified, the term “alkoxy group,” “alkoxy group,” or “alkyloxy group” as used herein means an alkyl group bonded to an oxy group and has 1 to 60 carbon atoms, but is not limited thereto.

[0045] Unless otherwise specified, the term “aryloxy group” or “aryloxy group” as used herein means an aryl group bonded to an oxy group and has 6 to 60 carbon atoms, but is not limited thereto.

[0046] Unless otherwise specified, the terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, but are not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by connecting or reacting adjacent substituents.

[0047] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0048] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl can be an alkyl substituted by an aryl group, and arylalkenyl can be an alkenyl substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0049] In addition, when the prefixes are named sequentially, this means that the substituents are listed in the order first described. For example, arylalkoxy means an alkoxy group substituted by an aryl group, alkoxycarbonyl means a carbonyl group substituted by an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted by an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0050] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, has 2 to 60 carbon atoms, but is not limited thereto, includes any of a monocyclic and polycyclic ring, and may include a heteroaliphatic ring and a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0051] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0052] In addition, the term "heterocyclic group" may include a ring containing SO2 instead of carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0053]

[0054] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R' and R" in the following structure are all hydrogen, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0055]

[0056] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. At this time, the atom shared by the two rings is called a "spiro atom", and these compounds are respectively called "single spiro-", "double spiro-" and "triple spiro-" according to 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, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0058] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

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

[0060] In addition, unless otherwise specified, the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 Alkylthiophene group, C6-C 20 Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 Aryl groups, deuterated C6-C 20 Aryl group, C8-C 20 Arylene groups, silane groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but are not limited to these substituents.

[0061] In addition, unless otherwise specifically explained, the formulae used in the present invention are the same as the definitions of substituents by the following exponent definitions of the formulae.

[0062]

[0063] Here, when a is an integer of 0, the substituent R 1does not exist. When a is an integer equal to 1, the only substituent R 1 Connected to any one of the carbon atoms constituting the benzene ring, when a is an integer of 2 or 3, each is combined as follows, wherein R 1 may be the same as or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, but indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

[0064]

[0065] The term "composition" as used herein is intended to be interpreted broadly, including compounds and solutions, dispersions, liquids and solid mixtures (mixtures, admixtures). The composition of the present invention may contain the compound of the present invention alone, or the compound may be contained in a combination of 2 or more different types, or the compound may be contained in a combination of 2 or more types with other compounds. In other words, the composition may contain a single compound corresponding to Formula 1, 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 invention. Among them, the compound not corresponding to the present invention may be a single compound, or may be a compound of 2 or more types. Here, if the compound is contained in a combination of 2 or more types of other compounds, the other compounds may be known compounds of each organic material layer, or may be compounds to be developed in the future. Here, the compound contained in the organic material layer may consist only of compounds of the same type, but may also be a mixture of 2 or more types of different compounds represented by Formula 1.

[0066] Hereinafter, a compound according to one aspect of the present invention, a composition for a phosphorescent light emitting layer of an organic electronic element, and an organic electronic element including the composition will be described.

[0067] The present invention provides a compound represented by Formula 1.

[0068] Formula 1

[0069]

[0070] in,

[0071] R 1 , R 2 , R 3 , R 4 and R 5 are the same or different and are independently hydrogen; or deuterium;

[0072] In addition, adjacent multiple R 4 or multiple R 5may be bonded to each other to form a benzene ring, wherein the benzene ring may be further substituted with one or more deuteriums,

[0073] a is an integer from 0 to 5, b is an integer from 0 to 6, c and e are independently integers from 0 to 4, d is an integer from 0 to 3,

[0074] Ar 1 is hydrogen; phenyl which may be substituted by deuterium; or naphthyl which may be substituted by deuterium.

[0075] In addition, Formula 1 is represented by Formula 1-1 or Formula 1-2.

[0076]

[0077] Among them, R 1 , R 2 , R 3 , R 4 , R 5 , a, b, c, d, e and Ar 1 As defined in Eq. 1.

[0078] Specifically, the compound of Formula 1 may be any one of the following Compound P-1 to Compound P-32, but is not limited thereto.

[0079]

[0080]

[0081] Furthermore, in another aspect, the present invention provides a composition for a phosphorescent light-emitting layer of an organic electronic element, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5.

[0082]

[0083] in:

[0084] L 12 , L 13 , L 14 and L 15 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups;

[0085] If L 12 , L 13 , L 14 and L 15is an arylene group, which may preferably be C6-C 30 Arylene groups, more preferably C6-C 25 Arylene groups, for example, phenylene, biphenylene, naphthylene, terphenylene, anthracene, etc.,

[0086] If L 12 , L 13 , L 14 and L 15 is a heterocyclic group, which may preferably be C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiazine, benzocarbazole, etc.

[0087] If L 12 , L 13 , L 14 and L 15 is a fused ring group, which may preferably be C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0088] Ar 12 ,Ar 13 and Ar 14 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups;

[0089] Ar 15 Selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-NR'R";

[0090] If Ar 12 ,Ar13 ,Ar 14 and Ar 15 is an aryl group, which may preferably be C6-C 30 aryl group, and more preferably C6-C 25 The aryl group, for example, can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, (chryshen) etc.

[0091] If Ar 12 ,Ar 13 ,Ar 14 and Ar 15 is a heterocyclic group, which may preferably be C2-C 30 A heterocyclic group, and more preferably a C2-C 24 The heterocyclic group, for example, can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiazine, benzocarbazole, etc.

[0092] If Ar 12 ,Ar 13 ,Ar 14 and Ar 15 is a fused ring group, which may preferably be C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group.

[0093] Y 10 O, S, CR 51 R 52 or NR 53 ,

[0094] Ring B is C6-C 20 Aryl groups,

[0095] R 31 and R 32 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; cyano group; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C50 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 31 or multiple R 32 can be bonded to each other to form a ring,

[0096] R 51 , R 52 , R 53 , R' and R" are each independently C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 an aryloxy group; or R 51 and R 52 can be bonded to each other to form a ring,

[0097] If R 31 , R 32 , R 51 , R 52 , R 53 , R' and R" are aryl groups, which may preferably be C6-C 30 aryl group, and more preferably C6-C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0098] If R 31 , R 32 , R 51 , R 52 , R 53 , R' and R" are heterocyclic groups, which may preferably be C2-C 30 A heterocyclic group, and more preferably a C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc.,

[0099] If R 31 , R 32 , R 51 , R 52 , R 53 , R' and R" are fused ring groups, which may preferably be C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0100] If R 31 , R 32 , R 51 , R 52 , R 53 , R' and R" are alkyl groups, which may preferably be C1-C 30 An alkyl group, and more preferably a C1-C 24 Alkyl groups,

[0101] If R 31 , R 32 , R 51 , R 52 , R 53 , R' and R" are alkoxy groups, which may preferably be C1-C 24 Alkoxy groups,

[0102] If R 31 , R 32 , R 51 , R 52 , R 53 , R' and R" are aryloxy groups, which may preferably be C6-C 24 Aryloxy groups,

[0103] ba and bb are each independently an integer from 0 to 4,

[0104] wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group and condensed ring group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Aryl alkenyl group; and -L'-NR'R"; and in addition, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by a combination thereof.

[0105] Preferably, the composition for a phosphorescent light-emitting layer of an organic electronic element may be used as a host of the light-emitting layer.

[0106] Formula 4 is expressed by any one of Formula 4-1 to Formula 4-3.

[0107]

[0108] <Formula 4-3>

[0109]

[0110] in:

[0111] Ar 13 ,Ar 14 , L 12 , L 13 and L 14 As defined in Equation 4,

[0112] X 11 , X 12 and X 13 With Y in formula 5 10 The definition is the same as

[0113] R 33 , R 34 , R 35 , R 36 , R 37 and R 38 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl; or multiple adjacent R 33 or R 34 or R 35 or R 36 or R 37 or R 38 can be bonded to each other to form a ring,

[0114] bc, be, and bg are independently integers from 0 to 4, and bd, bf, and bh are independently integers from 0 to 3.

[0115] Formula 5 is expressed by any one of Formula 5-1 to Formula 5-6:

[0116]

[0117] in:

[0118] Y 10 ,Ar 15 , L 15 , R 31 , R 32 , ba and bb are the same as those defined in Formula 5,

[0119] R 39 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl group; or adjacent multiple R 39 can be bonded to each other to form a ring,

[0120] bi is an integer from 0 to 2.

[0121] Formula 5 can be represented by any one of the following Formulas 5-7 to 5-9.

[0122]

[0123] in:

[0124] Y 10 , Ring B, Ar 15 , L 15 , R 32 and bb are the same as those defined in Equation 5,

[0125] R 40 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl group; or adjacent multiple R 40 can be bonded to each other to form a ring,

[0126] bj is an integer from 0 to 6.

[0127] Formula 5 can be represented by any one of the following Formulas 5-10 to 5-12.

[0128]

[0129] <Formula 5-12>

[0130]

[0131] in:

[0132] Y 10 , Ring B, Ar 15 , L 15 , R 31 and ba are the same as those defined in Equation 5,

[0133] R 41 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C20 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 by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl group; or adjacent multiple R 41 can be bonded to each other to form a ring,

[0134] bk is an integer from 0 to 6.

[0135] Formula 5 can be represented by any one of the following Formulas 5-13 to 5-18.

[0136]

[0137]

[0138] in:

[0139] Y 10 ,Ar 15 , L 15 , R 31 , R 32 , ba and bb are the same as those defined in Formula 5,

[0140] R 39 , R 40 and R 41 are independently the same or different and are independently selected from hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl; or multiple adjacent R 39 or multiple R 40 or multiple R41 can be bonded to each other to form a ring,

[0141] bi is an integer from 0 to 2, and bj and bk are each independently an integer from 0 to 6.

[0142] Formula (5) can be expressed by Formula 5-19.

[0143] <Formula 5-19>

[0144]

[0145] in:

[0146] Ar 15 , L 15 , R 53 , R 32 and bb are the same as defined in Formula 5.

[0147] R 39 and R 40 are the same or different and are each independently selected from hydrogen; deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl; or multiple adjacent R 39 or multiple R 40 or multiple R 41 can be bonded to each other to form a ring,

[0148] bi is an integer from 0 to 2, and bj is an integer from 0 to 6.

[0149] Specifically, the compound represented by Formula 4 may be any one of the following Compound H-1 to Compound H-124, but is not limited thereto.

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] Specifically, the compound represented by Formula 5 may be any one of the following Compounds S-1 to S-116, but is not limited thereto.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] In addition, on the other hand, the present invention relates to an organic electronic element, which includes 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 a phosphorescent light-emitting layer of an organic electronic element containing a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5.

[0165] On the other hand, the present invention provides a method for reusing a compound represented by Formula 1, comprising: recovering a crude organic light-emitting material containing a compound of Formula 1 from a deposition device used in a process for depositing an organic light-emitting material to prepare an organic light-emitting device; removing impurities from the crude organic light-emitting material; recovering the organic light-emitting material after removing the impurities; and purifying the recovered organic light-emitting material to have a purity of 99.9% or higher.

[0166] The step of removing impurities from the crude organic light emitting material recovered from the deposition apparatus may preferably include performing a pre-purification process to obtain a purity of 98% or more by recrystallization in a recrystallization solvent.

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

[0168] The recrystallization solvent may be preferably used by mixing a polar solvent having a polarity index of 5.5 to 7.2 and a nonpolar solvent having a polarity index of 2.0 to 4.7.

[0169] When a mixture of a polar solvent and a non-polar solvent is used, the recrystallization solvent may be used in an amount of 15% (v / v) or less of the non-polar solvent compared to the polar solvent.

[0170] The recrystallization solvent may preferably be: a single solvent of N-methylpyrrolidone (NMP); or a polar solvent in which any one selected from 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide and dimethyl sulfoxide is mixed into N-methylpyrrolidone; a single or mixed non-polar solvent selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate and butanone; or a mixture of a polar solvent and a non-polar solvent.

[0171] The pre-purification process may include a step of dissolving the crude organic light emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C and then precipitating crystals by cooling to 0°C to 5°C.

[0172] The pre-purification process may include the steps of dissolving the crude organic light-emitting material recovered from the deposition device 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.

[0173] The pre-purification process may include the steps of, after dissolving the crude organic light emitting material recovered from the deposition apparatus in a non-polar solvent, precipitating crystals while concentrating the solvent and removing the non-polar solvent.

[0174] The pre-purification process may include a step of recrystallization with a non-polar solvent followed by a first recrystallization with a polar solvent.

[0175] The step of purifying the recovered impurities to a purity of 99.9% or more may include an adsorption separation process of adsorbing and removing the impurities by adsorption on an adsorbent.

[0176] The adsorbent may be activated carbon, silica gel, alumina or a material used for known adsorption purposes.

[0177] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0178] refer to Figure 1The organic electronic element (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer between the first electrode (110) and the second electrode (170) containing a single compound or two or more compounds represented by Formula 1. The first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode. In the case of an inverted organic electronic element, the first electrode may be a cathode, and the second electrode may be an anode.

[0179] The organic material layer may 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) formed on the first electrode (110) in sequence. Here, the remaining layers except the light emitting layer (140) may not be formed. The organic material layer may also include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150) etc. may be used as a hole blocking layer (see Figure 2 ).

[0180] In addition, the organic electronic element according to the embodiment of the present invention may further include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer may be formed on a surface of the two surfaces of the first electrode that is not in contact with the organic material layer or on a surface of the two surfaces of the second electrode that is not in contact with the organic material layer. The compound according to the embodiment of the present invention suitable for the organic material layer may be used as a host or dopant 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), or a material for a light efficiency enhancement layer. Preferably, for example, a compound of formula 1 of the present invention, or a composition comprising a mixture of a compound represented by formula 1 and a compound represented by formula 4 or formula 5 for a phosphorescent light-emitting layer of an organic electronic element may be used as a host material for a light-emitting layer.

[0181] The organic material layer may include two or more stacks, the stack including 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 Figure 3 ).

[0182] In addition, even if the same core is used, the band gap, electrical properties, interface properties, etc. may vary depending on which substituent is bonded at what position, so the selection of the combination of the core and its associated sub-substituents is also very important, and in particular, when the optimal combination of the energy level and T1 value of each organic material layer and the unique properties of the material (mobility, interface properties, etc.) is achieved, long service life and high efficiency can be achieved at the same time.

[0183] The organic electroluminescent device according to the embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a conductive metal or metal oxide or an alloy thereof 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 that can be used as a cathode is deposited thereon, and the organic electroluminescent device according to the embodiment of the present invention can be manufactured.

[0184] In addition, the present invention provides an organic electronic element, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process or a roll-to-roll process, and the organic material layer provides an organic electronic element containing the compound as an electron transport material.

[0185] As another specific example, the present invention provides an organic electronic element, which is used by mixing the same or different compounds among the compounds represented by Formula 1 into an organic material layer. Preferably, the organic material layer includes a light-emitting layer, wherein the light-emitting layer may include a composition for a phosphorescent light-emitting layer of an organic electronic element, the composition comprising a compound represented by Formula 1, or a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5.

[0186] In addition, the present invention provides a composition for a phosphorescent light-emitting layer of an organic electronic element, the composition comprising a compound represented by Formula 1, or a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5, and an organic electronic element comprising the composition.

[0187] In addition, the present invention also provides an electronic device including a display device including an organic electronic element; and a control unit for driving the display device.

[0188] According to another aspect, the present invention 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 lighting. Here, the electronic device may be a wired / wireless communication terminal currently used or to be used in the future, and covers all kinds of electronic devices, including mobile communication terminals such as portable phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various televisions, and various computers.

[0189] Hereinafter, synthesis examples of the compounds represented by Formula 1, Formula 4 and Formula 5 of the present invention and manufacturing examples of the organic electronic element of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0190] Example

[0191] [Synthesis example]

[0192] The compound represented by Formula 1 according to the present invention (final product) may be synthesized by reacting Sub 2 and Sub 2 as in Reaction Scheme 1, but is not limited thereto.

[0193] <Reaction Scheme 1>

[0194]

[0195] I. Synthesis of Sub 1

[0196] Sub 1 of Reaction Scheme 1 is synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto.

[0197] <Reaction Scheme 2>

[0198]

[0199] The synthesis examples of specific compounds belonging to Sub 1 are as follows.

[0200] 1. Synthesis example of Sub 1-1

[0201]

[0202] Sub1-1-1 (40.00 g, 111.34 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (36.75 g, 144.74 mmol), Pd2(dppf)Cl2 (2.44 g, 3.34 mmol), KOAc (21.85 g, 222.67 mmol) were added to DMF (370 mL) in a round-bottom flask and stirred at 150° C. for 2 hours. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silica gel column to obtain 32.57 g (72%) of the product Sub1-1.

[0203] 2. Synthesis example of Sub 1-2

[0204]

[0205] (1) Synthesis of Sub 1-2-1

[0206] Sub1-2-1a (35.00 g, 121.44 mmol), (3-chlorophenyl)boronic acid (18.99 g, 121.44 mmol), Pd(PPh3)4 (4.21 g, 3.64 mmol), K2CO3 (33.57 g, 242.89 mmol) were added to a round-bottom flask, dissolved in 400 mL of anhydrous THF and 133 mL of water, and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 29.13 g (75%) of Sub1-2-1.

[0207] (2) Synthesis of Sub 1-2

[0208] Sub1-2-1 (28.00 g, 87.54 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (28.90 g, 113.81 mmol), Pd2(dba)3 (2.40 g, 2.63 mmol), Xphos (2.50 g, 5.25 mmol), KOAc (17.18 g, 175.09 mmol) were added to DMF (290 mL) in a round-bottom flask and stirred at 150° C. for 2 hours. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silica gel column to obtain 24.48 g (68%) of the product Sub1-2.

[0209] 3. Synthesis example of Sub 1-3

[0210]

[0211] (1) Synthesis of Sub 1-3-1

[0212] Sub1-3-1a (38.00 g, 153.17 mmol), 1-bromo-3-chlorobenzene-d4 (29.94 g, 153.17 mmol), Pd(PPh3)4 (5.31 g, 4.60 mmol), K2CO3 (42.34 g, 306.34 mmol) were placed in a round-bottom flask, dissolved in anhydrous THF (510 mL) and water (170 mL) and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 35.65 g (73%) of Sub1-3-1.

[0213] (2) Synthesis of Sub 1-3

[0214] Sub1-3-1 (32.00 g, 100.36 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (33.13 g, 130.47 mmol), Pd2(dba)3 (2.76 g, 3.01 mmol), Xphos (2.87 g, 6.02 mmol), KOAc (19.70 g, 200.73 mmol) were added to DMF (335 mL) in a round-bottom flask and stirred at 150° C. for 2 hours. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silica gel column to obtain 27.59 g (67%) of the product Sub1-3.

[0215] 4. Synthesis example of Sub 1-4

[0216]

[0217] (1) Synthesis of Sub 1-4-1

[0218] Sub1-4-1a (35.00 g, 118.95 mmol), (3-chlorophenyl)boronic acid (18.60 g, 118.95 mmol), Pd(PPh3)4 (4.13 g, 3.57 mmol), K2CO3 (32.88 g, 237.90 mmol) were placed in a round-bottom flask, dissolved in anhydrous THF (396 mL) and water (132 mL) and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 29.07 g (75%) of Sub1-4-1.

[0219] (2) Synthesis of Sub 1-4

[0220] Sub1-4-1 (26.00 g, 79.78 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (26.34 g, 103.72 mmol), Pd2(dba)3 (2.19 g, 2.39 mmol), Xphos (2.28 g, 4.79 mmol), KOAc (15.66 g, 159.57 mmol) were added to DMF (266 mL) in a round-bottom flask and stirred at 150° C. for 2 hours. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silica gel column to obtain 27.31 g (82%) of the product Sub1-4.

[0221] 5. Synthesis example of Sub 1-6

[0222]

[0223] Sub1-6-1 (40.00 g, 106.85 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (35.27 g, 138.90 mmol), Pd2(dppf)Cl2 (2.35 g, 3.21 mmol), KOAc (20.97 g, 213.70 mmol) were added to DMF (365 mL) in a round-bottom flask and stirred at 150° C. for 2 hours. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silica gel column to obtain 30.62 g (68%) of the product Sub1-6.

[0224] Meanwhile, the compound belonging to Sub 1 may be the following compounds, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub 1.

[0225]

[0226] [Table 1]

[0227] Compound FD-MS Compound FD-MS Sub1-1 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=406.21(C <h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> BO2 = 406.33<h2 style=";text-align:left;direction:ltr"> Sub1-2 <![CDATA[m / z=411.24(C 28 H 22 D5BO2=411.36)]]> Sub1-3 <![CDATA[m / z=410.24(C 28 H 23 D4BO2=410.36)]]> Sub1-4 <![CDATA[m / z=417.28(C 28 H 16 D 11 BO2=417.4)]]> Sub1-5 <![CDATA[m / z=412.25(C 28 H 21 D6BO2=412.37)]]> Sub1-6 <![CDATA[m / z=421.3(C 28 H 12 D 15 BO2=421.42)]]> Sub1-7 <![CDATA[m / z=416.27(C 28 H 17 D 10 BO2=416.39)]]>

[0228] II. Synthesis of Sub 2

[0229] Sub 2 of Reaction Scheme 1 is synthesized through the reaction path of Reaction Scheme 3, but is not limited thereto.

[0230] <Reaction Scheme 3>

[0231]

[0232] The synthesis examples of specific compounds belonging to Sub 2 are as follows.

[0233] 1. Synthesis example of Sub 2-4

[0234]

[0235] Sub2-2-1 (83.34 g, 368.65 mmol), Sub2-2-a (33.00 g, 184.33 mmol), Pd(PPh3)4 (6.39 g, 5.53 mmol), K2CO3 (50.95 g, 368.65 mmol) were added to a round-bottom flask, dissolved in anhydrous THF (615 mL) and water (205 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 25.15 g (42%) of Sub2-2.

[0236] 2. Synthesis example of Sub 2-5

[0237]

[0238] Sub2-5-1 (92.54 g, 335.14 mmol), Sub2-2-a (30.00 g, 167.57 mmol), Pd(PPh3)4 (5.81 g, 5.03 mmol), K2CO3 (46.32 g, 335.14 mmol) were added to a round-bottom flask, dissolved in anhydrous THF (558 mL) and water (186 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 23.87 g (38%) of Sub2-5.

[0239] 3. Synthesis example of Sub 2-10

[0240]

[0241] Sub2-2-1 (39.13 g, 173.09 mmol), Sub2-10-a (20.00 g, 86.54 mmol), Pd(PPh3)4 (3.00 g, 2.60 mmol), K2CO3 (23.92 g, 173.09 mmol) were added to a round-bottom flask, dissolved in anhydrous THF (288 mL) and water (96 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 15.00 g (46%) of Sub2-10.

[0242] 4. Synthesis example of Sub 2-12

[0243]

[0244] Sub2-12-1 (83.26 g, 360.28 mmol), Sub2-12-a (40.00 g, 180.14 mmol), Pd(PPh3)4 (6.25 g, 5.40 mmol), K2CO3 (46.79 g, 360.28 mmol) were added to a round-bottom flask, dissolved in anhydrous THF (600 mL) and water (200 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 28.88 g (43%) of Sub2-12.

[0245] 5. Synthesis example of Sub 2-16

[0246]

[0247] Sub2-16-1 (77.12 g, 279.28 mmol), Sub2-16-a (25.00 g, 139.64 mmol), Pd(PPh3)4 (4.84 g, 4.19 mmol), K2CO3 (38.60 g, 279.28 mmol) were added to a round-bottom flask, dissolved in anhydrous THF (465 mL) and water (155 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2 and water, and then treated with MgSO4. The product produced by concentrating the organic solvent was recrystallized using a silica gel column to obtain 27.22 g (52%) of Sub2-16.

[0248] Meanwhile, the compound belonging to Sub 2 may be the following compounds, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compound belonging to Sub 2.

[0249]

[0250]

[0251] [Table 2]

[0252] Compound FD-MS Compound FD-MS Sub2-1 <![CDATA[m / z=317.07(C 19 A 12 ClN3=317.78)]]> Sub2-2 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=324.12(C <h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> H5D7ClN3 = 324.82<h2 style=";text-align:left;direction:ltr"> Sub2-3 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=322.1(C <h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> H7D5ClN3 = 322.81<h2 style=";text-align:left;direction:ltr"> Sub2-4 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=324.12(C <h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> H5D7ClN3 = 324.82<h2 style=";text-align:left;direction:ltr"> Sub2-5 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=374.13(C <h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> H7D7ClN3 = 374.88<h2 style=";text-align:left;direction:ltr"> Sub2-6 <![CDATA[m / z=381.18(C 23 D 14 ClN3=381.92)]]> Sub2-7 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=374.13(C <h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> H7D7ClN3 = 374.88<h2 style=";text-align:left;direction:ltr"> Sub2-8 <![CDATA[m / z=367.09(C 23 A 14 ClN3=367.84)]]> Sub2-9 <![CDATA[m / z=367.09(C 23 A 14 ClN3=367.84)]]> Sub2-10 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=376.14(C <h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> H5D9ClN3 = 376.89<h2 style=";text-align:left;direction:ltr"> Sub2-11 <![CDATA[m / z=367.09(C 23 A 14 ClN3=367.84)]]> Sub2-12 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=372.12(C <h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> H9D5ClN3 = 372.87<h2 style=";text-align:left;direction:ltr"> Sub2-13 <![CDATA[m / z=417.1(C 27 A 16 ClN3=417.9)]]> Sub2-14 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=424.15(C <h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> H9D7ClN3 = 424.94<h2 style=";text-align:left;direction:ltr"> Sub2-15 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=426.16(C <h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> H7D9ClN3 = 426.95<h2 style=";text-align:left;direction:ltr"> Sub2-16 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=374.13(C <h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> H7D7ClN3 = 374.88<h2 style=";text-align:left;direction:ltr">

[0253] III. Synthesis of Final Product 1. Synthesis Example of P-1

[0254]

[0255] Sub1-1 (15.00 g, 36.92 mmol), Sub2-1 (11.73 g, 36.92 mmol), Pd(PPh3)4 (1.28 g, 1.11 mmol), NaOH (2.95 g, 73.83 mmol), THF (120 mL) and water (40 mL) were added and reacted at 75°C for 8 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Thereafter, the concentrated reactant was recrystallized using a silica gel column to obtain 16.17 g (78%) of product P-1.

[0256] 2. Synthesis Example of P-10

[0257]

[0258] Sub1-1 (18.00 g, 44.30 mmol), Sub2-5 (16.61 g, 44.30 mmol), Pd(PPh3)4 (1.54 g, 1.33 mmol), NaOH (3.54 g, 88.60 mmol), THF (150 mL) and water (50 mL) were added and reacted at 75°C for 8 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Thereafter, the concentrated reactant was recrystallized using a silica gel column to obtain 20.28 g (74%) of the product P-10.

[0259] 3. Synthesis Example of P-13

[0260]

[0261] Sub1-2 (17.00 g, 41.33 mmol), Sub2-8 (15.20 g, 41.33 mmol), Pd(PPh3)4 (1.43 g, 1.24 mmol), NaOH (3.31 g, 82.65 mmol), THF (138 mL) and water (46 mL) were added and reacted at 75°C for 8 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Thereafter, the concentrated reactant was recrystallized using a silica gel column to obtain 17.33 g (68%) of the product P-13.

[0262] 4. Synthesis Example of P-15

[0263]

[0264] Sub1-4 (12.00 g, 28.75 mmol), Sub2-8 (10.58 g, 28.75 mmol), Pd(PPh3)4 (1.00 g, 0.86 mmol), NaOH (2.30 g, 57.50 mmol), THF (96 mL) and water (32 mL) were added and reacted at 75°C for 8 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Thereafter, the concentrated reactant was recrystallized using a silica gel column to obtain 13.61 g (76%) of the product P-15.

[0265] 5. Synthesis Example of P-27

[0266]

[0267] Sub1-1 (14.00 g, 34.54 mmol), Sub2-10 (13.02 g, 34.54 mmol), Pd(PPh3)4 (1.20 g, 1.04 mmol), NaOH (2.76 g, 69.08 mmol), THF (115 mL) and water (38 mL) were added and reacted at 75°C for 8 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Thereafter, the concentrated reactant was recrystallized using a silica gel column to obtain 15.44 g (72%) of the product P-27.

[0268] Meanwhile, the FD-MS values ​​of Compound P-1 to Compound P-32 of the present invention prepared according to the above Synthesis Examples are shown in Table 3.

[0269] [Table 3]

[0270]

[0271]

[0272] The compound represented by Formula 4 or Formula 5 may be prepared by referring to known synthesis methods (named reactions) or disclosed patent publications, such as Korean Patent Publication No. 10-2395819, U.S. Patent Publication No. 2023-0129535, etc., but is not limited thereto.

[0273] Meanwhile, FD-MS values ​​of Compound H-1 to Compound H-124 and Compound S-1 to Compound S-116 of the present invention are shown in Tables 4 and 5.

[0274] [Table 4]

[0275]

[0276]

[0277]

[0278] [Table 5]

[0279]

[0280]

[0281]

[0282] In addition, the synthesis examples of the present invention represented by Formula 1, Formula 4 and Formula 5 have been described, but these are all based on Buchwald-Hartwig cross coupling reaction, Miyaura borylation reaction, Suzuki 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 those skilled in the art will easily understand that the reaction proceeds even when other substituents defined in Formula 1, Formula 4 and Formula 5 other than the substituents specified in the specific synthesis examples are bonded.

[0283] [Organic Electronic Component Manufacturing Evaluation]

[0284] [Example 1] Red organic light-emitting device (phosphorescent host)

[0285] 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.

[0286] Subsequently, compound CR was vacuum deposited on the hole transport layer to a thickness of 10 nm to form a light-emitting auxiliary layer. Thereafter, the main material of the light-emitting layer used the compound P-1 of the present invention as the first main body and the compound H-19 of the present invention as the second main body, and a mixture of the first main body and the second main body in a weight ratio of 5:5 was used, and bis(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as'(piq)2Ir(acac)') was used as a dopant material, and a light-emitting layer having a thickness of 30 nm was formed by doping the dopant so that the weight ratio of the main body to the dopant was 95:5.

[0287] Subsequently, compound E was vacuum-deposited on the light-emitting layer to form a hole blocking layer having a thickness of 10 nm, and an electron transport layer having a thickness of 30 nm was formed on the hole blocking layer using a mixture of compound F and compound G at a weight ratio of 5:5. 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.

[0288] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0289] Compound B: 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0290] Compound CR:N 7 -(Dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7 -Triphenyldibenzo[b,d]thiophene-2,7-diamine

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

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

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

[0294] [Example 2] to [Example 26]

[0295] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds of the present invention shown in Table 6 were used as host materials of the light-emitting layer.

[0296] [Comparative Example 1] and [Comparative Example 2]

[0297] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following Comparative Compound A and Comparative Compound B were used as a first host material of the light-emitting layer.

[0298]

[0299] For the organic electroluminescent devices manufactured by Examples 1 to 26 of the present invention, Comparative Examples 1 and 2, electroluminescent (EL) characteristics were measured using PR-650 manufactured by PhotoResearch Co. by applying a forward bias DC voltage. As a result of the measurement, the lifetime measurement device manufactured by McScience measured the EL characteristics at 2,500 cd / m 2 Table 6 shows the results of device fabrication and evaluation.

[0300] The measurement setup is independent of possible day-to-day variations in deposition rate, vacuum quality or other tool performance parameters and allows the performance of new materials to be evaluated in comparison with comparative compounds under identical conditions.

[0301] At the time of evaluation, each field contained 4 identically prepared OLEDs comprising comparative compounds, and since the performance of each of a total of 12 OLEDs in 3 fields was evaluated, the statistical evaluation of the experimental results obtained clearly showed statistical significance.

[0302] [Table 6]

[0303]

[0304] It can be seen from the results in Table 6 that when the material for an organic light-emitting device of the present invention is used as the main material of the light-emitting layer to manufacture a red organic light-emitting device, the driving voltage, luminous efficiency and service life of the organic electroluminescent device can be improved compared with the comparative example using comparative compound A or comparative compound B having a basic skeleton similar to the compound of the present invention.

[0305] Comparative Compound A and Comparative Compound B have similar compositions to the compound of the present invention, but Comparative Compound A and Comparative Compound B are different from the compound of the present invention in that they contain a heterocyclic group or a cyano group.

[0306] In order to confirm the difference in energy levels of the compounds due to this difference, data measured using a DFT method (B3LYP / 6-31g(D)) using a Gaussian program are shown in Table 7.

[0307] [Table 7]

[0308] Comparative Compound A Comparative Compound B P-8 HOMO(eV) -5.8770 -5.8458 -5.5547 LUMO(eV) -2.0792 -2.2694 -1.9075 T1(eV) 2.4961 2.4729 2.4274

[0309] As can be seen from the results in Table 7, it can be seen that the energy level of the compound of the present invention is formed differently from the energy level of the comparative compound.

[0310] To explain in more detail, comparative compound A and comparative compound B have a structure containing a heterocyclic group or a cyano group, which produces a deep LUMO energy level and causes excessive electron injection into the light-emitting layer, which breaks the charge balance of the element. In contrast, the compound of the present invention has a LUMO energy level that is an intermediate value between the electron transport zone and the dopant of the light-emitting layer, so it can prevent the electrons in the electron transport zone from accumulating directly into the dopant of the light-emitting layer, and easily forms an exciplex between the first host and the second host. In addition, the compound of the present invention having a lower T1 energy level than the comparative compound transfers energy from the host to the dopant more easily than the comparative compound, resulting in less damage when energy is transferred from the host to the dopant, which is considered to significantly improve the device life.

[0311] That is, it can be seen from the results in Tables 6 and 7 that even if the compounds have similar compositions, it can be confirmed that the compounds of the present invention that satisfy all complex factors (such as the type of specific substituents and the substitution positions of the substituents) show significant effects in organic electronic components compared with other comparative compounds, and it can be seen from this that the compounds of the present invention show more significant effects in organic electronic components than simple structural isomers not described in this specification or compounds with similar compositions.

[0312] These results show that even in compounds with similar molecular components, the properties of the compounds (such as the hole characteristics, light efficiency characteristics, energy level characteristics, hole injection and mobility characteristics, charge balance of holes and electrons, volume density and intermolecular distance) can vary significantly to an unpredictable degree depending on the type and substitution position of the substituents substituted, and furthermore, indicate that one configuration does not affect the results of the entire element, but the performance of the element may vary due to complex factors.

[0313] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be appreciated by those skilled in the art that various modifications, additions and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments.

[0314] The scope of the present invention should be interpreted based on the appended claims, and should be interpreted that all technical concepts included in the scope equivalent to the claims belong to the present invention.

Claims

1. A compound represented by Formula 1: Formula 1 in: R 1 , R 2 , R 3 , R 4 and R 5 are the same as or different from each other, are independently hydrogen or deuterium, and multiple adjacent R 4 or multiple adjacent R 5 may be bonded to each other to form a benzene ring, wherein the benzene ring may be further substituted with one or more deuteriums, a is an integer from 0 to 5, b is an integer from 0 to 6, c and e are independently integers from 0 to 4, d is an integer from 0 to 3, Ar 1 It is hydrogen, phenyl which may be substituted by deuterium, or naphthyl which may be substituted by deuterium.

2. The compound according to claim 1, wherein Formula 1 is represented by Formula 1-1 or Formula 1-2: in, R 1 , R 2 , R 3 , R 4 , R 5 , a, b, c, d, e and Ar 1 Same as defined in claim 1.

3. The compound according to claim 1, wherein the compound represented by Formula 1 is any one of Compound P-1 to Compound P-32:

4. A composition for an organic electronic device, comprising a mixture of the compound according to claim 1 and a compound represented by Formula 4 or Formula 5: in: L 12 , L 13 , L 14 and L 15 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups; Ar 12 ,Ar 13 and Ar 14 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring-fused ring groups; Ar 15 Selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-NR'R"; Y 10 O, S, CR 51 R 52 or NR 53 , Ring B is C6-C 20 Aryl groups, R 31 and R 32 are the same as or different from each other and are independently selected from hydrogen; deuterium; halogen; cyano group; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 an aryloxy group; and a plurality of adjacent R 31 or multiple adjacent R 32 can be bonded to each other to form a ring, R 51 , R 52 , R 53 R' and R" are each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 an aryloxy group; or R 51 and R 52 can be bonded to each other to form a ring, ba and bb are each independently an integer from 0 to 4, The aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group and condensed ring group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio 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 by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl group; and -L'-NR'R"; and in addition, the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by a combination thereof. 5 . The composition for an organic electronic device as claimed in claim 4 , wherein the composition is used as a host of a light emitting layer.

6. The composition for an organic electronic device according to claim 4, wherein the compound represented by Formula 4 is represented by any one of Compound H-1 to Compound H-124:

7. The composition for an organic electronic device according to claim 4, wherein the compound represented by Formula 5 is represented by any one of Compound S-1 to Compound S-116: 8 . An organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises the compound according to claim 1 or the composition according to claim 4 . 9 . The organic electronic element of claim 8 , wherein the organic electronic element further comprises a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer. 10 . The organic electronic element according to claim 8 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 11 . The organic electronic element according to claim 10 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies. 12 . An electronic device comprising a display device including the organic electronic element according to claim 8 ; and a control unit for driving the display device. 13 . The electronic device of claim 12 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochrome or white lighting.

14. A method for reusing the compound represented by Formula 1 according to claim 1, comprising: Recovering a crude organic light-emitting material comprising the compound represented by Formula 1 according to claim 1 from a deposition device used in a process of depositing the organic light-emitting material to prepare an organic light-emitting device; removing impurities from the crude organic light-emitting material; recovering the organic light emitting material after removing the impurities; as well as The recovered organic light-emitting material is purified to have a purity of 99.9% or higher.

Images