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

Abstract

The present invention provides: a novel compound capable of improving the luminous efficiency, stability, and lifespan of an element; compositions comprising the compounds; 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 the priority and benefit of U.S. Patent Application No. 18 / 400,275, the entire content of which is incorporated herein by reference. Technical field

[0003] The present invention relates to compounds for organic electronic components, organic electronic components using the compounds, and electronic devices thereof. Technical background

[0004] Generally, organic luminescence refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic electronic components using organic luminescence usually have 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 component, the organic material layer is usually composed of a multi - layer structure, which is composed of different materials and may include, for example, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, etc.

[0005] The materials used as the organic material layer in organic electronic components can be classified into luminescent materials and charge - transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0006] The most intractable problems of organic electroluminescent devices are lifetime and efficiency, and as the display area increases, these efficiency and lifetime problems must be solved.

[0007] Efficiency, service life, and driving voltage are interrelated. When the efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heat generated during driving decreases, and thus the service life tends to increase.

[0008] However, the efficiency cannot be simply maximized by improving the organic material layer. This is because long service life and high efficiency can be achieved simultaneously only when the energy levels and T1 values between the organic material layers and the inherent properties of the materials (mobility, interface properties, etc.) are optimally combined.

[0009] In addition, recently, in organic electroluminescent devices, in order to solve the emission problem in the hole transport layer, an emission - assisting layer must be present between the hole transport layer and the emission layer, and different emission - assisting layers need to be developed according to each emission layer (R, G, B).

[0010] Generally, electrons transfer from the electron transport layer to the emission layer, and holes transfer from the hole transport layer to the emission layer, so that excitons are generated by recombination.

[0011] However, the material for the hole transport layer has a low HOMO value and thus mainly has a low T1 value. Therefore, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge imbalance in the emission layer and luminescence at the interface of the hole transport layer.

[0012] When luminescence occurs at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device are reduced, and the service life is shortened. Therefore, there is an urgent need to develop an emission auxiliary layer having a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the emission layer.

[0013] At the same time, it is necessary to develop a hole injection layer material having stable characteristics, namely a high glass transition temperature, to resist the Joule heat generated during device driving, while delaying the penetration of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the reasons for shortening the service life of organic electronic devices. The low glass transition temperature of the hole transport layer material has the following characteristics: when driving the device, the uniformity of the film surface is reduced, which is reported to have a great impact on the service life of the device. In addition, OLED devices are mainly formed by a deposition method, and it is necessary to develop a material that can withstand long-term deposition, that is, a material having high heat resistance characteristics.

[0014] That is, in order to fully exhibit the excellent characteristics of organic electronic devices, the materials (such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, emission auxiliary layer materials) used to form the organic material layer in the device should be supported by stable and effective materials. However, such materials for stable and effective organic material layers for organic electronic devices have not been fully developed. Therefore, it is necessary to continuously develop new materials.

[0015] Therefore, it is necessary to continuously develop new materials, and in particular, there is an urgent need to develop materials for the emission auxiliary layer. Summary of the Invention

[0016] In order to solve the problems of the above-mentioned background art, the present invention has disclosed a compound having a new structure, and when the compound is applied to an organic electronic device, the luminescence efficiency, stability and service life of the device are greatly improved.

[0017] Therefore, an object of the present invention is to provide a new compound, an organic electronic device using the compound, and an electronic device thereof.

[0018] Technical Solution

[0019] The present invention provides a compound represented by formula (1).

[0020] Formula (1)

[0021]

[0022] On the other hand, the present invention provides an organic electronic element and an electronic device including a compound represented by the formula (1).

[0023] Advantages of the Invention

[0024] 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 significantly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figures 1 to 3 Examples of the organic electronic element according to the present invention are illustrated.

[0026] Figure 4 A formula according to an aspect of the present invention is shown. DETAILED DESCRIPTION

[0027] Hereinafter, some embodiments of the present invention will be described in detail. Further, 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.

[0028] In addition, when describing 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 define the essence, order, or sequence of the corresponding components, but is only used to distinguish the corresponding components from other components. It should be noted that if a component is described as "connected", "coupled", or "joined" to another component, the component may be directly connected or connected to other components, but another component may be "connected", "coupled", or "joined" between the components.

[0029] As used in the specification and the appended claims, unless otherwise specified, the following are the meanings of the following terms.

[0030] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0031] 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 with an alkyl group, or an alkyl group substituted with a cycloalkyl group.

[0032] 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.

[0033] Unless otherwise specified, as used herein, the term "cycloalkyl" means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0034] Unless otherwise specified, as used herein, the term "alkoxy", "alkoxy group" or "alkyloxy group" means an oxygen atom connected to an alkyl group having 1 to 60 carbon atoms, but is not limited thereto.

[0035] Unless otherwise specified, as used herein, the term "aryloxy group" or "aroxy group" means an oxygen atom connected to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

[0036] Unless otherwise specified, as used herein, the term "aryl group" or "arylene group" has 6 to 60 carbon atoms, but is not limited thereto. In this document, an aryl group or an arylene group means a monocyclic and polycyclic aromatic group, and may also be formed by combining with adjacent groups. Examples of "aryl group" may include a phenyl group, a biphenyl group, a fluorene group or a spirofluorene group.

[0037] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl may be an alkyl group substituted by an aryl group, and arylalkenyl may be an alkenyl group substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0038] In addition, when the prefixes are named in sequence, this means that the substituents are listed in the order described first. 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, where arylcarbonyl may be a carbonyl group substituted by an aryl group.

[0039] Unless otherwise specified, as used herein, the term "heterocyclic group" contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes either a monocyclic or polycyclic ring, and may include a heteroaliphatic ring and / or a heteroaromatic ring. In addition, it may also be formed by combining with adjacent groups to form a heterocyclic group.

[0040] Unless otherwise specified, as used herein, the term "heteroatom" means at least one of N, O, S, P or Si.

[0041] In addition, the term "heterocyclic group" may include a ring containing SO2 in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

[0042]

[0043] Unless otherwise specified, as used herein, the term "fluorenyl group" or "fluorenylene group" 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.

[0044]

[0045] As used herein, the term "spiro compound" has "spiro linkage", and spiro linkage means a linkage in which two rings share only one atom. At this time, the atom shared in the two rings is called a "spiro atom", and these compounds are respectively called "monospiro-", "dispiro-", and "trispiro-" according to the number of atoms in the compound.

[0046] Unless otherwise specified, as used herein, the term "aliphatic" 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.

[0047] Unless otherwise specified, as used herein, the term "ring" 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 fused ring formed by their combination, and includes a saturated ring or an unsaturated ring.

[0048] In addition to the heterocompounds mentioned above, other heterocompounds or heterogroups contain one or more heteroatoms, but are not limited thereto.

[0049] Unless otherwise specified, as used herein, the term "substituted or unsubstituted" means that the substitution is substituted by at least one substituent selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 alkyl group, C1-C 20 alkoxy group, C1-C 20 alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C3-C 20 cycloalkyl group, C6-C 20 aryl group, C6-C substituted with deuterium 20 aryl group, C8-C 20 arylalkenyl group, silyl group, boron group, germanium group and C2-C 20Heterocyclic groups, but not limited thereto.

[0050] Unless otherwise specifically stated, the formulas used herein for the present invention apply in the same manner as the definitions of substituents according to the definitions of the exponents of the following formulas.

[0051]

[0052] Wherein, when a is an integer of 0, the substituent R 1 does not exist, when a is an integer of 1, the only substituent R 1 is attached to any one of the carbons constituting the benzene ring, when a is an integer of 2 or 3, each substituent R 1 can be the same or different, when a is an integer from 4 to 6, it is attached to the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0053]

[0054] Hereinafter, compounds according to aspects of the present invention and organic electronic elements containing the compounds will be described.

[0055] The present invention provides a compound represented by formula (1).

[0056] Formula (1)

[0057]

[0058] In formula (1), each symbol can be defined as follows.

[0059] R 1 , R 2 , R 3 and R 4 are each independently the same or different, and are each independently selected from: hydrogen; deuterium; halogen; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; C3-C 60 alicyclic ring and C6-C 60 fused ring group of aromatic ring; C3-C 60 alicyclic ring; C1-C 50 alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy group; and C6-C 30 aryloxy group,

[0060] Wherein if R 1 , R 2 , R3 and R 4 is an aryl group, which can preferably be C6-C 30 aryl group, and more preferably be C6-C 25 aryl group, for example, it can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0061] wherein if R 1 、R 2 、R 3 and R 4 is a heterocyclic group, which can preferably be C2-C 30 heterocyclic group, and more preferably be C2-C 24 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.,

[0062] wherein if R 1 、R 2 、R 3 and R 4 is a fused ring group, which can preferably be a fused ring group of C3-C 30 aliphatic ring and C6-C 30 aromatic ring, more preferably be a fused ring group of C3-C 24 aliphatic ring and C6-C 24 aromatic ring,

[0063] wherein if R 1 、R 2 、R 3 and R 4 is an aliphatic ring group, which can preferably be C3-C 30 aliphatic ring, and more preferably be C3-C 24 aliphatic ring,

[0064] wherein if R 1 、R 2 、R 3 and R 4 is an alkyl group, which can preferably be C1-C 30 alkyl group, and more preferably be C1-C 24 alkyl group,

[0065] wherein if R 1 、R 2 、R 3 and R 4 is an alkoxy group, which can preferably be C1-C 24An alkoxy group,

[0066] wherein if R 1 , R 2 , R 3 and R 4 are aryloxy groups, it may preferably be a C6-C 24 aryloxy group.

[0067] a, b, c and d are each independently an integer from 0 to 3.

[0068] R', R” and Ar 1 are each independently selected from: C6-C 60 aryl groups; fluorenyl groups; C2-C 60 heterocyclic groups containing at least one heteroatom of O, N, S, Si or P; C3-C 60 alicyclic and C6-C 60 fused ring groups of aromatic rings; C1-C 50 alkyl groups; C2-C 20 alkenyl groups; C2-C 20 alkynyl groups; C1-C 30 alkoxy groups; and C6-C 30 aryloxy groups; or R' and R” may combine with each other to form a ring, and Ar 2 is each independently selected from: hydrogen; deuterium; C6-C 60 aryl groups; fluorenyl groups; C2-C 60 heterocyclic groups containing at least one heteroatom of O, N, S, Si or P; C3-C 60 alicyclic and C6-C 60 fused ring groups of aromatic rings; C1-C 50 alkyl groups; C2-C 20 alkenyl groups; C2-C 20 alkynyl groups; C1-C 30 alkoxy groups; and C6-C 30 aryloxy groups,

[0069] wherein if R', R”, Ar 1 and Ar 2 are aryl groups, it may preferably be a C6-C 30 aryl group, and more preferably a C6-C 25 aryl group, for example, it may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.,

[0070] wherein if R', R”, Ar 1 and Ar 2 are heterocyclic groups, it may preferably be a C2-C 30heterocyclic group, and more preferably a C2-C 24 heterocyclic group, such as pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.,

[0071] wherein if R', R", Ar 1 and Ar 2 is a fused ring group, it may preferably be 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 24 aliphatic ring and a C6-C 24 aromatic ring,

[0072] wherein if R', R", Ar 1 and Ar 2 is an alkyl group, it may preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group,

[0073] wherein if R', R", Ar 1 and Ar 2 is an alkoxy group, it may preferably be a C1-C 24 alkoxy group,

[0074] wherein if R', R", Ar 1 and Ar 2 is an aryloxy group, it may preferably be a C6-C 24 aryloxy group.

[0075] Ar 3 is a C6-C 60 aryl group; fluorenyl group; or a substituent represented by any one of Formula Ar-1 to Formula Ar-6 below,

[0076] wherein if Ar 3 is an aryl group, it may preferably be a C6-C 30 aryl group, and more preferably a C6-C 25 aryl group, for example, it may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0077] X is O or S.

[0078] L 3 each independently selected from: a single bond; a C6-C 60Arylene group; fluorenylene group; a C2-C containing at least one heteroatom selected from O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Fused ring group of an aromatic ring.

[0079] Wherein if L 3 is an arylene group, it may preferably be a C6-C 30 arylene group, more preferably a C6-C 25 arylene group, for example, phenylene, biphenylene, naphthylene, terphenylene, anthrylene, etc.,

[0080] Wherein if L 3 is a heterocyclic group, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.,

[0081] Wherein if L 3 is a fused ring group, it may preferably be a C3-C 30 fused ring group of an aliphatic ring and a C6-C 30 aromatic ring, more preferably a C3-C 24 fused ring group of an aliphatic ring and a C6-C 24 aromatic ring.

[0082]

[0083] Wherein:

[0084] R 11 、R 12 、R 13 、R 14 、R 15 and R 16 have the same definition as R 1 ,

[0085] m is an integer from 0 to 5, n, p, q and r are each independently an integer from 0 to 4, and o is an integer from 0 to 3,

[0086] Y is O, S, CR x R y or NR Z ,

[0087] Ra , R b , R x , R y and R z is defined the same as R', or R a and R b or R x and R y can be bonded to each other to form a ring,

[0088] * indicates the position of the bond,

[0089] wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group can be substituted by one or more substituents selected from: deuterium; halogen; silyl group; siloxy 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; and C8-C 20 arylalkenyl group; moreover, the hydrogen of these substituents can be further substituted by one or more deuteriums; and the substituents can be bonded to each other to form a saturated or unsaturated ring, where the term "ring" means a C3-C 60 aliphatic ring or a C6-C 60 aromatic ring or a C2-C 60 heterocyclic group or a fused ring formed by their combination.

[0090] In addition, the compound represented by formula (1) is represented by any one of formulas (2) to (5):

[0091]

[0092]

[0093] wherein, R 1 , R 2 , R 3 , R 4 , R', R'', Ar 1 , Ar 2 , Ar3 , L 3 , a, b, c, and d are the same as defined in formula (1).

[0094] In addition, Ar 3 is represented by any one of formulas Ar-1 to Ar-6.

[0095] In addition, L 3 is represented by any one of formulas L-1 to L-3.

[0096]

[0097] Wherein,

[0098] R 17 is the same as the definition of R in formula (1) 1 ,

[0099] s is an integer from 0 to 4,

[0100] * indicates the bonding position.

[0101] Specifically, the compound represented by formula (1) can be any one of the following compounds P1-1 to compound P1-51, but is not limited thereto.

[0102]

[0103]

[0104]

[0105] On the other hand, the present invention provides a method for reusing the compound represented by formula (1), the method comprising:

[0106] recovering the crude organic light-emitting material containing the compound represented by formula (1) from the deposition equipment used in the process of depositing an organic light-emitting material to prepare an organic light-emitting device;

[0107] removing impurities from the crude organic light-emitting material;

[0108] recovering the organic light-emitting material after removing the impurities; and

[0109] purifying the recovered organic light-emitting material to a purity of 99.9% or higher.

[0110] The step of removing impurities from the crude organic light-emitting material recovered from the deposition equipment may preferably include performing a pre-purification process to obtain a purity of 98% or higher by recrystallization in a recrystallization solvent.

[0111] The recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0112] The recrystallization solvent can preferably be 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.

[0113] When using a mixture of a polar solvent and a nonpolar solvent, the recrystallization solvent can be used in an amount such that the nonpolar solvent is 15% (v / v) or less relative to the polar solvent.

[0114] The recrystallization solvent can preferably be: a single solvent of N-methylpyrrolidone (NMP); 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 nonpolar solvent selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and methyl ethyl ketone; or a mixture of a polar solvent and a nonpolar solvent.

[0115] The pre-purification process can include the 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.

[0116] The pre-purification process can include the step of dissolving the crude organic light-emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C, then cooling to 35°C to 40°C, adding a nonpolar solvent, and then cooling to 0°C to 5°C to precipitate crystals.

[0117] The pre-purification process can include the step of precipitating crystals while concentrating the solvent and removing the nonpolar solvent after dissolving the crude organic light-emitting material recovered from the deposition device in a nonpolar solvent.

[0118] The pre-purification process can include the step of recrystallizing with a nonpolar solvent after the first recrystallization with a polar solvent.

[0119] The step of purifying the recovered organic light-emitting material to a purity of 99.9% or higher can include an adsorption separation process of adsorbing and removing impurities by adsorption on an adsorbent.

[0120] The adsorbent can be activated carbon, silica gel, alumina, or a material for known adsorption purposes.

[0121] The step of purifying the recovered organic light-emitting material to a purity of 99.9% or higher can include performing sublimation purification.

[0122] Reference Figure 1, the organic electronic device (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 represented by Formula (1) or two or more compounds. Here, 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 device, the first electrode may be a cathode, and the second electrode may be an anode.

[0123] The organic material layer may sequentially include a hole injection layer (120), a hole transport layer (130), an emission layer (140), an electron transport layer (150), and an electron injection layer (160) formed in sequence on the first electrode (110). Here, the remaining layers except the emission layer (140) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, an emission assisting 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 ).

[0124] In addition, the organic electronic device according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancing layer (180). The light efficiency enhancing layer may be formed on a surface of the first electrode that does not contact the organic material layer among two surfaces, or on a surface of the second electrode that does not contact the organic material layer among two surfaces. The compound or material for an organic electronic device according to an embodiment of the present invention applied to the organic material layer may be used as a host or a dopant for the hole injection layer (120), the hole transport layer (130), the emission assisting layer (220), the electron transport assisting layer, the electron transport layer (150), the electron injection layer (160), the emission layer (140), or a material for the light efficiency enhancing layer. Preferably, for example, the compound according to Formula (1) of the present invention may be used as a material for the emission assisting layer.

[0125] The organic material layer may include two or more stacks, the stack including a hole transport layer, an emission layer, and an electron transport layer formed in sequence on the anode, and may further include a charge generation layer formed between two or more stacks (see Figure 3 ).

[0126] In addition, even when using the same core, the bandgap, electrical properties, interface properties, etc. may vary depending on which substituents are bonded where, so the selection of the combination of the core and the sub-substituents connected thereto is also very important, and in particular, when achieving an optimal combination of the energy levels and T1 values of each organic material layer and the unique properties (mobility, interface properties, etc.) of the material, long service life and high efficiency can be achieved simultaneously.

[0127] The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (Physical Vapor Deposition) method. For example, a metal or a conductive 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), an emission 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, whereby the organic electroluminescent device according to an embodiment of the present invention can be manufactured.

[0128] In addition, the present invention provides an organic electronic device, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process, and the organic material layer provides an organic electronic device containing the compound as an electron transport material.

[0129] As another specific example, the present invention provides an organic electronic device that uses the same or different compounds represented by the formula (1) by mixing them into the organic material layer.

[0130] In addition, the present invention provides a composition for an emission auxiliary layer containing the compound represented by the formula (1), and provides an organic electronic device including the emission auxiliary layer.

[0131] In addition, the present invention also provides an electronic device, which includes a display device including an organic electronic device; and a control unit for driving the display device.

[0132] According to another aspect, the present invention provides a display device, wherein the organic electronic device is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor (organic TFT), and an element for monochromatic or white illumination. Here, the electronic device can be a wired / wireless communication terminal currently in use or to be used in the future, and encompasses all kinds of electronic devices, including mobile communication terminals such as mobile phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various televisions, and various computers.

[0133] Hereinafter, synthesis examples of the compound represented by the formula (1) and preparation examples of the organic electronic device of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0134] [Synthesis Example 1]

[0135] The compound (final product) represented by the formula (1) according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1, but is not limited thereto.

[0136] <Reaction Scheme 1>

[0137]

[0138] wherein,

[0139] Hal is I, Br or Cl,

[0140] R 1 、R 2 、R 3 、R 4 、R', R'', Ar 1 、Ar 2 、Ar 3 、L 3 、a, b, c and d are the same as defined in formula (1).

[0141] Synthesis of I.Sub 1

[0142] Compound Sub 1 of Reaction Scheme 1 can be synthesized through the reaction pathway of Reaction Scheme 2, but not limited thereto.

[0143] <Reaction Scheme 2>

[0144]

[0145] Synthesis examples of specific compounds belonging to Sub 1 are as follows.

[0146] Synthesis Example of Sub 1-131

[0147]

[0148] (1) Synthesis of Sub 1-131a

[0149] After dissolving dibenzo[b,d]furan-2-ylboronic acid (20.0 g, 94.34 mmol) in 240 mL of THF in a round-bottom flask, 3-bromoaniline (17.85 g, 103.77 mmol), Pd(PPh3)4 (3.27 g, 2.83 mmol), NaOH (7.55 g, 188.67 mmol) and 80 mL of water were added, and the mixture was stirred at 80 °C. When the reaction was completed, it was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized from a silica gel column to obtain 17.6 g of the product (yield: 72%).

[0150] (2) Synthesis of Sub 1-131

[0151] The obtained Sub 1-131a (17.6 g, 67.87 mmol) was placed in a round-bottom flask and dissolved in 230 mL of toluene. Then, 2-chloro-9,9-dimethyl-6-phenyl-9H-fluorene (20.69 g, 67.87 mmol), Pd2(dba)3 (1.87 g, 2.04 mmol), P(t-Bu)3 (0.82 g, 4.07 mmol), and NaOt-Bu (13.05 g, 135.74 mmol) were added, and the mixture was stirred at room temperature. When the reaction was completed, it was extracted with toluene and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 25.1 g of the product (yield: 70%).

[0152] Synthesis Example of Sub 1-136

[0153]

[0154] (1) Synthesis of Sub 1-136a

[0155] After dissolving (9,9-dimethyl-9H-fluoren-3-yl)boronic acid (20.0 g, 84.00 mmol) in 210 mL of THF in a round-bottom flask, 3-bromoaniline (15.90 g, 92.40 mmol), Pd(PPh3)4 (2.91 g, 2.52 mmol), NaOH (6.72 g, 168.00 mmol), and 70 mL of water were added, and the mixture was stirred at 80 °C. When the reaction was completed, it was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 16.4 g of the product (yield: 68%).

[0156] (2) Synthesis of Sub 1-136

[0157] The obtained Sub 1-136a (16.4 g, 57.47 mmol) was placed in a round-bottom flask and dissolved in 190 mL of toluene. Then, 2-chloro-9,9-dimethyl-6-phenyl-9H-fluorene (17.52 g, 57.47 mmol), Pd2(dba)3 (1.58 g, 1.72 mmol), P(t-Bu)3 (0.70 g, 3.45 mmol), and NaOt-Bu (11.05 g, 114.93 mmol) were added, and the mixture was stirred at room temperature. When the reaction was completed, it was extracted with toluene and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 23.2 g of the product (yield: 73%).

[0158] Synthesis Example of Sub 1-126

[0159]

[0160] After dissolving 4-(bicyclo[2.2.1]heptan-2-yl)aniline (20 g, 106.79 mmol) in 356 mL of THF in a round-bottom flask, 2-chloro-9,9-dimethyl-6-phenyl-9H-fluorene (32.55 g, 106.77 mmol), Pd2(dba)3 (2.93 g, 3.20 mmol), P(t-Bu)3 (1.30 g, 6.41 mmol), and NaOt-Bu (20.53 g, 213.57 mmol) were added, and the mixture was stirred at room temperature. When the reaction was complete, it was extracted with toluene and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 37.7 g of the product (yield: 77%).

[0161] Examples of Sub 1 are as follows, but are not limited thereto.

[0162]

[0163]

[0164] [Table 1]

[0165]

[0166]

[0167] II. Synthesis of Sub 2

[0168] Sub 2 of Reaction Scheme 1 can be synthesized by Reaction Scheme 3, but is not limited thereto.

[0169] <Reaction Scheme 3>

[0170]

[0171] Wherein,

[0172] Hal is I, Br, or Cl,

[0173] R 3 、R 4 、X, Ar 2 、c, and d are the same as those defined in formula (1).

[0174] Synthesis examples of specific compounds belonging to Sub 2 are as follows.

[0175] Synthesis Example of Sub 2-82

[0176]

[0177] After dissolving 7-bromo-1-chlorodibenz[b,d]furan (34.79 g, 123.57 mmol) in 280 mL of THF in a round-bottom flask, (4-(tert-butyl)phenyl)boronic acid (20 g, 112.33 mmol), Pd(PPh3)4 (3.89 g, 3.37 mmol), NaOH (8.99 g, 224.67 mmol) and 94 mL of water were added, and the mixture was stirred at 80 °C. When the reaction was completed, it was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized on a silica gel column to obtain 24.7 g of the product (yield: 59%).

[0178] Synthesis Example of Sub 2-89

[0179]

[0180] After dissolving 1-bromo-9-chlorodibenz[b,d]thiophene (33.06 g, 111.09 mmol) in 250 mL of THF in a round-bottom flask, [1,1'-biphenyl]-2-ylboronic acid (20 g, 100.99 mmol), Pd(PPh3)4 (3.50 g, 3.03 mmol), NaOH (8.08 g, 202.00 mmol) and 85 mL of water were added, and the mixture was stirred at 80 °C. When the reaction was completed, it was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized on a silica gel column to obtain 23.8 g of the product (yield: 63%). Examples of Sub 2 are as follows, but are not limited thereto.

[0181]

[0182]

[0183]

[0184]

[0185] [Table 2]

[0186]

[0187]

[0188] Synthesis Examples of the Final Product Synthesis Example of P1-2

[0189] After dissolving Sub 1-116 (20.0 g, 44.29 mmol) in 150 mL of THF in a round-bottom flask, Sub2-14 (12.35 g, 44.29 mmol), Pd2(dba)3 (1.22 g, 1.33 mmol), P(t-Bu)3 (0.54 g, 2.66 mmol), and NaOt-Bu (8.51 g, 88.58 mmol) were added, and the mixture was stirred at 110 °C. When the reaction was completed, it was extracted with toluene and water. The organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized on a silica gel column to obtain 22.8 g of the product (yield: 74%).

[0190] Synthesis Example of P1-14

[0191]

[0192] (1) Synthesis of P1-14'

[0193] After dissolving Sub 1-115 (20.0 g, 44.29 mmol) in toluene (150 mL) in a round-bottom flask, Sub 2-13 (12.35 g, 44.29 mmol), Pd2(dba)3 (1.22 g, 1.33 mmol), P(t-Bu)3 (0.54 g, 2.66 mmol), and NaOt-Bu (8.51 g, 88.58 mmol) were added, and 23.1 g of the product was obtained using the synthesis method of P1-2 (yield: 75%).

[0194] (2) Synthesis of P1-14

[0195] P1-14' (23.0 g, 33.15 mmol) obtained in the above synthesis was dissolved in benzene-d6 (680 mL) in a round-bottom flask, then CF3SO3H (5.86 mL, 66.30 mmol) was slowly added, and the mixture was stirred at room temperature for 16 hours. When the reaction was completed, Na2CO3 (10.54 g, 99.45 mmol) dissolved in D2O was added to neutralize. After the reaction with toluene and D2O was completed, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was recrystallized on a silica gel column to obtain 22.5 g of the product (yield: 93%).

[0196] Synthesis Example of P1-45

[0197]

[0198] After dissolving Sub 1-130 (20.0 g, 45.70 mmol) in toluene (150 mL) in a round-bottom flask, Sub 2-95 (18.78 g, 45.70 mmol), Pd2(dba)3 (1.26 g, 1.37 mmol), P(t-Bu)3 (0.56 g, 2.74 mmol), and NaOt-Bu (8.79 g, 91.41 mmol) were added, and 26.8 g of the product was obtained using the synthesis method of P1-2 (yield: 72%).

[0199] [Table 3]

[0200] Compound FD-MS Compound FD-MS P1-1 <![CDATA[m / z = 693.27 (C 51 H 35 NO2 = 693.85)]]> P1-2 <![CDATA[m / z = 693.27 (C 51 H 35 NO2 = 693.85)]]> P1-3 <![CDATA[m / z = 693.27 (C 51 H 35 NO2 = 693.85)]]> P1-4 <![CDATA[m / z = 719.32 (C 54 H 41 NO = 719.93)]]> P1-5 <![CDATA[m / z = 693.27 (C 51 H 35 NO2 = 693.85)]]> P1-6 <![CDATA[m / z = 693.27 (C 51 H 35 NO2 = 693.85)]]> P1-7 <![CDATA[m / z = 693.27 (C 51 H 35 NO2 = 693.85)]]> P1-8 <![CDATA[m / z = 679.29 (C 51 H 37 NO = 679.86)]]> P1-9 <![CDATA[m / z = 603.26 (C 45 H 33 NO2 = 603.76)]]> P1-10 <![CDATA[m / z = 603.26 (C 45 H 33 NO2 = 603.76)]]> P1-11 <![CDATA[m / z = 735.35 (C 55 H 45 NO = 735.97)]]> P1-12 <![CDATA[m / z = 701.31 (C 51 H 43 NS = 701.97)]]> P1-13 <![CDATA[m / z = 597.30 (C 44 H 39 NO = 597.80)]]> P1-14 <![CDATA[m / z = 728.49 (C 51 D 35 NO2 = 729.06)]]> P1-15 <![CDATA[m / z = 621.30 (C 46 H 39 NO = 621.82)]]> P1-16 <![CDATA[m / z = 639.30 (C 46 H 41 NS = 639.90)]]> P1-17 <![CDATA[m / z = 728.49 (C 51 D 35 NO2 = 729.06)]]> P1-18 <![CDATA[m / z = 704.34 (C 51 H 24 D 11 NO2 = 704.91)]]> P1-19 <![CDATA[m / z = 673.30 (C 49 D 39 NO2 = 673.86)]]> P1-20 <![CDATA[m / z = 673.30 (C 49 D 39 NO2 = 673.86)]]> P1-21 <![CDATA[m / z = 843.35 (C 64 H 45 NO = 844.07)]]> P1-22 <![CDATA[m / z = 843.35 (C 64 H 45 NO = 844.07)]]> P1-23 <![CDATA[m / z = 843.35 (C 64 H 45 NO = 844.07)]]> P1-24 <![CDATA[m / z = 719.32 (C 54 H 41 NO = 719.93)]]> P1-25 <![CDATA[m / z = 719.32 (C 54 H 41 NO = 719.93)]]> P1-26 <![CDATA[m / z = 805.33 (C 61 H 43 NO = 806.02) <!-- 22 -->]]> P1-27 <![CDATA[m / z = 779.32 (C 59 H 41 NO = 799.98)]]> P1-28 <![CDATA[m / z = 771.30 (C 57 H 41 NS = 772.02)]]> P1-29 <![CDATA[m / z = 631.25 (C 46 H 33 NO2 = 631.77)]]> P1-30 <![CDATA[m / z = 631.25 (C 46 H 33 NO2 = 631.77)]]> P1-31 <![CDATA[m / z = 647.23 (C 46 H 33 NOS = 647.84)]]> P1-32 <![CDATA[m / z = 647.23 (C 46 H 33 NOS = 647.84)]]> P1-33 <![CDATA[m / z = 743.28 (C 55 H 37 NO2 = 743.91)]]> P1-34 <![CDATA[m / z = 743.28 (C 55 H 37 NO2 = 743.91)]]> P1-35 <![CDATA[m / z = 749.33 (C 55 H 43 NO2 = 749.95)]]> P1-36 <![CDATA[m / z = 769.33 (C 58 H 43 NO = 769.99)]]> P1-37 <![CDATA[m / z = 769.30 (C 57 H 39 NO2 = 769.94)]]> P1-38 <![CDATA[m / z = 785.28 (C 57 H 39 NOS = 786.00)]]> P1-39 <![CDATA[m / z = 769.30 (C 57 H 39 NO2 = 769.94)]]> P1-40 <![CDATA[m / z = 785.28 (C 57 H 39 NOS = 786.00)]]> P1-41 <![CDATA[m / z = 683.31 (C 51 H 33 D4NO = 683.89)]]> P1-42 <![CDATA[m / z = 527.22 (C 39 H 29 NO = 527.67)]]> P1-43 <![CDATA[m / z = 769.30 (C 57 H 39 NO2 = 769.94)]]> P1-44 <![CDATA[m / z = 801.25 (C 57 H 39 NS2 = 802.07)]]> P1-45 <![CDATA[m / z = 811.33 (C 60 H 45 NS = 812.09)]]> P1-46 <![CDATA[m / z = 871.38 (C 66 H 49 NO = 872.12)]]> P1-47 <![CDATA[m / z = 795.35 (C 60 H 45 NO = 796.03)]]> P1-48 <![CDATA[m / z = 811.33 (C 60 H 45 NS = 812.09)]]> P1-49 <![CDATA[m / z = 819.30 (C 61 H 41 NS = 820.07)]]> P1-50 <![CDATA[m / z = 643.29 (C 48 H 37 NO = 643.83)]]> P1-51 <![CDATA[m / z = 709.24 (C 51 H 35 NOS = 709.91)]]>

[0201] In the above, exemplary synthesis examples of the compound represented by formula (1) have been described, but these are all based on Buchwald-Hartwig cross-coupling reaction, Miyaura boration reaction, Suzuki cross-coupling, 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 will be readily understood by those skilled in the art that the reaction will proceed even when combined with other substituents defined in formula (1) in addition to the substituents specified in the specific synthesis examples.

[0202] [Example 1] Green organic light-emitting device (emission auxiliary layer)

[0203] On the ITO layer (anode) formed on a glass substrate, using Compound A and Compound B, a hole injection layer with a thickness of 10 nm was formed by doping Compound B at a weight ratio of 98:2, and Compound A was vacuum-deposited on the hole injection layer to a thickness of 110 nm to form a hole transport layer. Next, the compound P1-1 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 10 nm to form an emission auxiliary layer. After that, Compounds D-G were used as the host material of the emission layer, and tris(2-phenylpyridine)-iridium (hereinafter referred to as 'Ir(ppy)3') was used as the dopant material, and the dopant was doped at a weight ratio of 90:10 to form an emission layer with a thickness of 30 nm.

[0204] Next, compound E was vacuum deposited on the emission layer to form a hole blocking layer with a thickness of 10 nm, and a mixture of compound F and compound G with a weight ratio of 5:5 was used to form an electron transport layer with a thickness of 30 nm on the hole blocking layer. Thereafter, compound G was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0205] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0206] Compound B: 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-triyltris(cyanomethylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0207] Compound D-G: 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole

[0208] Compound E: 2-(4'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0209] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0210] Compound G: Lithium 8-hydroxyquinoline

[0211] [Example 2] to [Example 14]

[0212] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 was used instead of the compound P1-1 of the present invention as the emission auxiliary layer material.

[0213] [Comparative Example 1] to [Comparative Example 4]

[0214] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that comparative compounds E to comparative compounds H were used instead of the compound P1-1 of the present invention as the emission auxiliary layer material.

[0215]

[0216]

[0217] A forward bias DC voltage was applied to the organic electroluminescent devices of the examples and comparative examples fabricated in this manner, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch. As a result of the measurement, the T95 lifetime was measured by a lifetime measurement device manufactured by McScience at a standard brightness of 5000 cd / m 2 The results of device fabrication and evaluation are shown in Table 4.

[0218] The measurement device 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.

[0219] During the evaluation, one batch contained 4 identically prepared OLEDs containing the comparative compound, and the performance of a total of 12 OLEDs was evaluated in 3 batches. Therefore, the values of the experimental results obtained indicate statistical significance.

[0220] [Table 4]

[0221]

[0222]

[0223] As can be seen from the results in Table 4, when the material for the organic electroluminescent device of the present invention is used as the material for the emission auxiliary layer to fabricate a green organic electroluminescent device, the compound of the present invention shows significant performance in terms of device performance compared to the comparative examples using comparative compounds E to H.

[0224] As can be seen from the above, comparing the comparative compound E and the compound of the present invention, the compound of the present invention is dibenzofuran or dibenzothiophene having an amino group bonded to position 1, while the comparative compound E is dibenzothiophene having an amino group bonded to position 2.

[0225] In other words, the bonding positions of dibenzofuran or dibenzothiophene are different. This difference can be confirmed by Table 5.

[0226] Table 5 shows the data measured for the comparative compound E and the compound P1-49 of the present invention by the DFT method (B3LYPE-31g(D)) using the Gaussian program.

[0227] [Table 5]

[0228] Comparative Compound E P1-49 HOMO (eV) -4.84 -4.96 LUMO (eV) -1.13 -1.19 T1 (eV) 2.60 2.67

[0229] If Table 5 is described in detail, the compound P1-49 of the present invention has a deeper HOMO value and a higher T1 than the comparative compound E. That is, due to the deep HOMO, the hole injection property moving to the host is excellent, which leads to an increase in efficiency. In other words, the hole injection into the host is accelerated, thereby improving the efficiency. Specifically, in the first case of dibenzofuran or dibenzothiophene, it can be seen that the lifetime is excellent, and this seems to be the effect that occurs with the increase of T1.

[0230] Secondly, when comparing the comparative compound F with the compound of the present invention, the comparative compound F has an oxanthrene structure bonded within the structure, while the compound of the present invention is different in that an aryl group, a fluorene group, dibenzofuran or dibenzothiophene is bonded instead of oxanthrene. In addition, when comparing the comparative compound G with the compound of the present invention, the comparative compound G has a substituent bonded to the 5th position of fluorene, while the compound of the present invention is different in that the substituent is bonded to the 6th position of fluorene. Finally, when comparing the comparative compound H with the compound of the present invention, the comparative compound H has an amino group bonded to the 4th position of fluorene, while the compound of the present invention is different in that the amino group is bonded to the 2nd position of fluorene. Regarding this point, we confirm this difference through Table 6.

[0231] Table 6 describes the calculated reorganization energy values of comparative compounds F to comparative compound H, P1-41, P1-50, and P1-51.

[0232] The RE value shown in Table 6 refers to the calculated RE hole value.

[0233] [Table 6]

[0234] Reorganization Energy (eV) Comparative Compound F 0.199 Comparative Compound G 0.176 Comparative Compound H 0.186 P1-41 0.167 P1-50 0.154 P1-51 0.168

[0235] It can be seen from Table 6 that the compounds of the present invention have lower RE values compared with comparative compounds F to comparative compound H. This means that compared with comparative compounds F to comparative compound H, it can be seen that the compounds of the present invention have higher hole transfer properties, and therefore, it is believed that both fast driving voltage and high efficiency are exhibited. That is, the combination of specific substituents of the substituted amine shows a positive effect on the overall charge mobility, which seems to show a significantly improved overall result. Therefore, it can be confirmed that even within the same skeleton, this property is significantly different due to the type and position of the substituents.

[0236] That is to say, as can be seen from the results in Tables 4 to 6, compared with the comparative compounds having a composition similar to the structure of the compounds of the present invention, the compounds satisfying all the structural features and compositions disclosed in the present invention show remarkable effects in organic electronic elements, and this indicates that the compounds of the present invention satisfying all specific compositions show remarkable effects compared with other comparative compounds not described in this specification.

[0237] These results indicate that even among compounds with similar molecular components, depending on the type and substitution position of the substituents being substituted, properties of the compounds such as hole characteristics, light efficiency characteristics, energy levels, hole injection and migration characteristics, charge balance of holes and electrons, volume density, and intermolecular distance may change significantly to the extent that they are difficult to predict, and the composition of a compound does not affect the results of the entire element, but the performance of the element may vary due to complex factors.

[0238] In the case of the emission auxiliary layer, since the correlation between the hole transport layer and the emission layer (host) must be understood, and even when using a similar core, it is difficult for those skilled in the art to infer the characteristics exhibited by the emission auxiliary layer using the compounds of the present invention.

[0239] Furthermore, in the evaluation results of the above-mentioned element manufacturing, the element characteristics are explained by applying only the compounds of the present invention to the emission auxiliary layer, but the compounds of the present invention can be used by applying them to the hole transport layer or both the hole transport layer and the emission auxiliary layer.

[0240] Although the exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and gist 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.

[0241] The scope of the present invention should be interpreted based on the appended claims and should be interpreted to include all technical concepts within the scope equivalent to the claims as belonging to the present invention. Brief Description of the Drawings

[0243] 100, 200, 300: Organic electronic elements 110: First electrode

[0244] 120: Hole injection layer 130: Hole transport layer

[0245] 140: Emission layer 150: Electron transport layer

[0246] 160: Electron injection layer 170: Second electrode

[0247] 180: Light efficiency enhancement layer 210: Buffer layer

[0248] 220: Emission assist layer 320: First hole injection layer

[0249] 330: First hole transport layer 340: First emission layer

[0250] 350: First electron transport layer 360: First charge generation layer

[0251] 361: Second charge generation layer 420: Second hole injection layer

[0252] 430: Second hole transport layer 440: Second emission layer

[0253] 450: Second electron transport layer CGL: Charge generation layer

[0254] ST1: First stack ST2: Second stack.

Claims

1. A compound represented by formula (1): Formula (1) in: R 1 , R 2 , R 3 and R 4 are independently the same or different and are independently selected from: hydrogen; deuterium; halogen; 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 group; C3-C 60 Aliphatic ring; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 Aryloxy groups; a, b, c and d are each independently an integer from 0 to 3, R', R" and Ar 1 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 group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 aryloxy group; or R' and R" may be combined with each other to form a ring, Ar 2 Each independently selected from: hydrogen; deuterium; 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 group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; and C6-C 30 Aryloxy groups; Ar 3 It is C6-C 60 An aryl group; a fluorenyl group; or a substituent represented by any one of the following formulae Ar-1 to Ar-6; X is O or S, L 3 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 groups; in: R 11 , R 12 , R 13 , R 14 , R 15 and R 16 With R 1 The definition is the same as m is an integer from 0 to 5, n, p, q and r are each independently an integer from 0 to 4, o is an integer from 0 to 3, Y is O, S, CR x R y or NR Z , R a , R b , R x , R y and R z Same definition as R', or R a and R b or R x and R y can be bonded to each other to form a ring, *Refers to L 3 The part where the bond is located, The aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenyl group, condensed ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from the group consisting of: 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; and C8-C 20 Moreover, the hydrogen of these substituents may be further replaced by one or more deuterium, and 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 combining them.

2. The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of formula (2) to formula (5): Where R 1 , R 2 , R 3 , R 4 , R', R", Ar 1 ,Ar 2 ,Ar 3 , L 3 , a, b, c and d are the same as defined in claim 1.

3. The compound of claim 1, wherein Ar 3 It is represented by any one of Formulae Ar-1 to Ar-6.

4. The compound of claim 1, wherein L 3 Represented by any one of Formula L-1 to Formula L-3: in: R 17 The same as in claim 1 1 The definition is the same as S is an integer from 0 to 4, *Indicates the position of bonding.

5. The compound according to claim 1, wherein the compound represented by formula (1) can be any one of the following compounds P1-1 to P1-51:

6. Organic electronic components, including: anode; cathode; and an organic material layer between the anode and the cathode, wherein the organic material layer comprises a single compound or two or more compounds represented by formula (1) according to claim 1. 7 . The organic electronic element of claim 6 , wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emission auxiliary layer, an emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. The organic electronic element according to claim 6 , wherein the organic material layer is an emission assisting layer. 9 . The organic electronic element of claim 6 , further comprising a light efficiency enhancing layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer. 10 . The organic electronic element according to claim 6 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode. 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 6; 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 a compound of formula (1) according to claim 1, comprising: Recovering a crude organic light-emitting material comprising a compound of formula (1) according to claim 1 from a deposition apparatus 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; as well as The recovered organic light emitting material is purified to have a purity of 99.9% or more.

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