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

Abstract

The present invention provides a novel compound, an organic electrical element using the same, and an electronic device using the same, the novel compound allowing an increase in luminous efficiency, stability, and lifespan of an element.

Description

Technical Field

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

[0002] Generally, organic luminescence refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic electronic device using the organic luminescence phenomenon generally has a structure including an anode, a cathode, and an organic material layer disposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is usually composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like.

[0003] The materials used as the organic material layer in the organic electronic device 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, and the like.

[0004] The biggest problems of organic light-emitting diodes are their service life and efficiency, and as the display size increases, these efficiency and service life problems must be solved.

[0005] Efficiency, service life, and driving voltage are related to each other. When the efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, the crystallization of the organic material due to Joule heating generated during driving decreases, and thus the service life tends to increase.

[0006] 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.

[0007] In addition, recently, in an organic electroluminescent device, in order to solve the light-emitting problem in the hole transport layer, a light-emitting auxiliary layer must be present between the hole transport layer and the light-emitting layer, and different light-emitting auxiliary layers need to be developed according to each light-emitting layer (R, G, B). Generally, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, so that excitons are generated by recombination.

[0008] However, the materials for the hole transport layer have a low HOMO value and thus generally have a low T1 value. Therefore, the excitons generated in the light-emitting layer are transferred to the hole transport layer, resulting in charge imbalance in the light-emitting layer and light emission at the interface of the hole transport layer.

[0009] When light emission occurs at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device decrease, and the service life is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer having a high T1 value and a HOMO level between the HOMO level of the hole transport layer and the HOMO level of the light-emitting layer.

[0010] Meanwhile, it is necessary to develop a hole injection layer material having stable characteristics, namely a high glass transition temperature, to resist Joule heating generated during driving of the device, 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 the organic electronic device. 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 decreases, 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.

[0011] That is, in order to fully exhibit the excellent characteristics of the organic electronic device, the materials used to form the organic material layer (such as hole injection material, hole transport material, light-emitting material, electron transport material, electron injection material, light-emitting auxiliary layer material) in the device should be stable and effective materials. However, such stable and effective organic material layer materials for organic electronic devices have not been fully developed. Therefore, there is a continuous need to develop new materials, and specifically, there is an urgent need to develop materials for the light-emitting auxiliary layer. Summary of the Invention

[0012] To solve the problems of the above-mentioned background art, the present invention discloses a compound having a new structure, and when the compound is applied to an organic electronic device, the light-emitting efficiency, stability, and service life of the device are greatly improved.

[0013] Therefore, an object of the present invention is to provide a new compound, an organic electronic device using the new compound, and an electronic device thereof.

[0014] [Technical Solution]

[0015] The present invention provides a compound represented by Formula 1.

[0016] [Formula 1]

[0017]

[0018] On the other hand, the present invention provides an organic electronic device and an electronic device thereof containing the compound represented by Formula 1.

[0019] [Advantages of the Invention]

[0020] By using the compounds according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and service life of the device can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figures 1 to 3 Examples of organic electronic devices according to the present invention are illustrated.

[0022] Figure 4 A formula according to one aspect of the present invention is shown.

[0023] 100, 200, 300: Organic electronic device 110: First electrode

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

[0025] 140: Light emitting layer 150: Electron transport layer

[0026] 160: Electron injection layer 170: Second electrode

[0027] 180: Light efficiency enhancement layer 210: Buffer layer

[0028] 220: Light emission assisting layer 320: First hole injection layer

[0029] 330: First hole transport layer 340: First light emitting layer

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

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

[0032] 430: Second hole transport layer 440: Second light emitting layer

[0033] 450: Second electron transport layer CGL: Charge generation layer

[0034] ST1: First stack ST2: Second stack DETAILED DESCRIPTION

[0035] Hereinafter, some embodiments of the present invention will be described in detail. In addition, in the following description of the present invention, when the detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, such detailed description will be omitted.

[0036] 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 define the essence, order or sequence of the corresponding components, but only 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 joined to the other component, but another component may be "connected", "coupled" or "joined" between the components.

[0037] As used in the specification and the appended claims, unless otherwise specified, the following are the meanings of the following terms.

[0038] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0039] 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 straight-chain alkyl groups, branched-chain alkyl groups, alkyl groups, cycloalkyl groups (alicyclic), cycloalkyl groups substituted with alkyl groups or alkyl groups substituted with cycloalkyl groups.

[0040] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes straight-chain or branched-chain groups.

[0041] Unless otherwise specified, the term "cycloalkyl" as used herein means an alkyl group forming a ring of 3 to 60 carbon atoms, but is not limited thereto.

[0042] Unless otherwise specified, the term "alkoxy group", "alkoxyl group" or "alkyloxy group" as used herein means an oxygen group connected to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

[0043] Unless otherwise specified, the term "aryloxy group" or "aryloxyl group" as used herein means an oxygen group connected to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

[0044] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. Herein, the aryl group or arylene group means a monocyclic and polycyclic aromatic group, and includes an aromatic ring formed by adjacent substituents participating in bonding or reaction. Examples of the "aryl group" may include a phenyl group, a biphenyl group, a fluorene group or a spirofluorene group.

[0045] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, arylalkyl can be an alkyl group substituted with an aryl group, and arylalkenyl can be an alkenyl group substituted with an aryl group, and the group substituted with an aryl group has the number of carbon atoms as defined herein.

[0046] In addition, when the prefixes are named in sequence, this means listing the substituents in the order first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, where arylcarbonyl can be a carbonyl group substituted with an aryl group.

[0047] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes either monocyclic or polycyclic rings, and may include heteroaliphatic rings and / or heteroaromatic rings. In addition, it can also combine with adjacent groups to form a heterocyclic group.

[0048] Unless otherwise specified, the term "heteroatom" as used herein represents at least one of N, O, S, P, or Si.

[0049] In addition, the term "heterocyclic group" can include a ring containing SO2 in place of the carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0050]

[0051] 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" are all hydrogen in the following structure, 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.

[0052]

[0053] The term "spiro compound" as used herein has "spiro linkage", and spiro linkage means a connection 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.

[0054] 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.

[0055] 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 a combination thereof, and includes a saturated ring or an unsaturated ring.

[0056] In addition to the hetero-compounds mentioned above, other hetero-compounds or hetero-groups contain one or more heteroatoms, but are not limited thereto.

[0057] Unless otherwise specified, as used herein, the term "substituted or unsubstituted" means that the substitution is 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 20 heterocyclic group, but not limited thereto.

[0058] Unless otherwise explicitly stated, as used herein, the formulas for the present invention are applied in the same manner as the definitions of the substituents according to the exponents of the following formulas.

[0059]

[0060] wherein, when a is an integer of zero, 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 of 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.

[0061]

[0062] Hereinafter, compounds according to aspects of the present invention and organic electronic elements containing the compounds will be described.

[0063] The present invention provides a compound represented by Formula 1.

[0064] <Formula 1>

[0065]

[0066] Wherein:

[0067] A is a C3-C 60 cycloalkyl group,

[0068] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 and R 7 are each independently selected from: hydrogen; deuterium; halogen; cyano group; nitro group; 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 aliphatic ring and C6-C 60 fused ring group of aromatic ring; C1-C 60 alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 alkoxy group; and C6-C 60 aryloxy group; or may be bonded to each other to form a ring.

[0069] Wherein when R 1 、R 2 、R 3 、R 4 、R 5 、R 6 and R 7 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, naphthyl, etc.

[0070] Wherein when R 1 、R 2 、R 3 、R 4 、R 5 、R 6 and R 7 is a heterocyclic group, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 25Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0071] Wherein when R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are fused ring groups, they are preferably fused ring groups of C3-C 30 aliphatic rings and C6-C 30 aromatic rings, and more preferably fused ring groups of C3-C 24 aliphatic rings and C6-C 24 aromatic rings.

[0072] Wherein when R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are alkyl groups, it can preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0073] Wherein when R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are alkenyl groups, it can preferably be a C2-C 30 alkenyl group, and more preferably a C2-C 24 alkenyl group.

[0074] Wherein when R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are alkynyl groups, it can preferably be a C2-C 30 alkynyl group, and more preferably a C2-C 24 alkynyl group.

[0075] Wherein when R 1 , R 2 , R3 , R 4 , R 5 , R 6 and R 7 is an alkoxy group, it may preferably be a C1-C 30 alkoxy group, and more preferably a C1-C 24 alkoxy group.

[0076] Wherein when R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is an aryloxy group, it may preferably be a C6-C 30 aryloxy group, and more preferably a C6-C 24 aryloxy group.

[0077] R 8 and R 9 are each independently a C1-C 60 alkyl group, preferably a C1-C 30 alkyl group, more preferably a C1-C 24 alkyl group.

[0078] L 1 , L 2 and L 3 are each independently selected from: a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C containing at least one heteroatom selected from O, N, S, Si or P 60 heterocyclic group; and a C3-C 60 aliphatic ring and a C6-C 60 fused ring group of an aromatic ring.

[0079] Wherein when L 1 , L 2 and L 3 is an aryloxy group, it may preferably be a C6-C 30 arylene group, more preferably a C6-C 20 arylene group, for example, a phenylene group, a biphenylene group, a naphthylene group, a terphenyl group, etc.

[0080] Wherein when L 1 , L 2 and L 3When it is a fluorenylene group, it can be 9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene, 9,9'-spirobifluorenylene, etc.

[0081] Wherein when L 1 、L 2 and L 3 is a heterocyclic group, it can preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 20 heterocyclic group, for example, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc.

[0082] Wherein when L 1 、L 2 and L 3 is a fused-ring group, it is preferably a fused-ring group of a C3-C 30 aliphatic ring and a C6-C 30 aromatic ring, and more preferably a fused-ring group of a C3-C 24 aliphatic ring and a C6-C 24 aromatic ring.

[0083] Ar is selected from: a C1-C 60 alkyl group; a C3-C 60 cycloalkyl group; a C6-C 60 aryl group; a fluorenyl group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; a C3-C 60 aliphatic ring; and a C3-C 60 aliphatic ring and a C6-C 60 fused-ring group of an aromatic ring;

[0084] Wherein when Ar is an alkyl group, it is preferably a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0085] Wherein when Ar is a cycloalkyl group, it is preferably a C3-C 30 cycloalkyl group, and more preferably a C3-C 24 cycloalkyl group.

[0086] Wherein when Ar is an aryl group, it can preferably be a C6-C 30 aryl group, and more preferably a C6-C25 An aryl group, for example, it can be phenyl, biphenyl, terphenyl, naphthyl, etc.,

[0087] wherein when Ar is a heterocyclic group, it can preferably be C2-C 30 heterocyclic group, and more preferably C2-C 25 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, etc.,

[0088] wherein when Ar is an aliphatic group: it can preferably be C3-C 30 aliphatic ring, and more preferably C3-C 24 aliphatic ring,

[0089] wherein when Ar is a fused ring group, it can preferably be C3-C 30 aliphatic ring and C6-C 30 fused ring group of aromatic ring, more preferably C3-C 24 aliphatic ring and C6-C 24 fused ring group of aromatic ring.

[0090] Wherein, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, cycloalkyl 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 aryl group 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; and the substituents can 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 heterocyclic group or a fused ring formed by their combination.

[0091] In addition, A of Formula 1 is represented by any one of the following Formulas A-1 to A-5:

[0092]

[0093] in:

[0094] R 10 , R 11 and R 12 are independently the same or different and are independently selected from: hydrogen; deuterium; halogen; 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; and C8-C 20 arylalkenyl groups;

[0095] a and b are independently integers from 0 to 11, c is an integer from 0 to 15,

[0096] Refers to the bonding position.

[0097] In addition, Ar in Formula 1 is represented by the following formula Ar-1 or formula Ar-2

[0098]

[0099] in,

[0100] X is NR', O, S, CR'R'' or SiR'R''

[0101] Ar' is selected from: C1-C 60 Alkyl 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; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups;

[0102] Where Ar' is an alkyl group, it may preferably be C1-C 30 alkyl group, and more preferably C1-C 24Alkyl group.

[0103] Where Ar' is an aryl group, it may preferably be C6-C 30 aryl group, and more preferably C6-C 25 Aryl groups, for example, may be phenyl, biphenyl, terphenyl, naphthyl, etc.,

[0104] Where Ar' is a heterocyclic group, it may preferably be C2-C 30 A heterocyclic group, and more preferably a C2-C 25 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, etc.

[0105] Where Ar' is an aliphatic cyclic group, it may preferably be C3-C 30 aliphatic ring, and more preferably C3-C 24 Aliphatic ring.

[0106] When Ar' is a fused ring group, it may preferably be C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring condensed ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0107] R 13 , R 14 , R 15 , R 16 and R 17 With R 10 The definition of R is the same, or multiple adjacent R 13 or multiple R 14 or multiple R 15 or multiple R 16 or multiple R 17 can be bonded to each other to form a ring,

[0108] d is an integer from 0 to 3, e, f, g and h are independently an integer from 0 to 4,

[0109] R' and R" are each independently selected from: hydrogen; deuterium; C1-C 60 Alkyl group; C1-C substituted by deuterium 60 Alkyl group; C6-C 60 An aryl group; and a C2-C 60 Heterocyclic groups;

[0110] Alternatively, R' and R'' may be bonded to each other to form a ring,

[0111] wherein when R' and R'' are alkyl groups, it may preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0112] wherein when R' and R'' 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, naphthyl, etc.,

[0113] wherein when R' and R'' are heterocyclic groups, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 25 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, etc.,

[0114] * indicates the bonding position.

[0115] In addition, Ar in Formula 1 is represented by any one of the following Formulas Ar-1-1 to Ar-1-4:

[0116]

[0117] wherein X, R 13 , R 14 , d, e and * are the same as those defined in Formula Ar-1.

[0118] In addition, Ar in Formula 1 is represented by any one of the following Formulas Ar-1-5 to Ar-1-12:

[0119]

[0120] wherein R 13 , R 14 , d, e, R', R'' and * are the same as those defined in Formula Ar-1.

[0121] In addition, Ar in Formula 1 is represented by any one of the following Formulas Ar-2-1 to Ar-2-3:

[0122]

[0123] wherein R 15 , R16 , R 17 , f, g, h, Ar', and * are the same as defined in Formula Ar-2.

[0124] Specifically, the compound represented by Formula 1 can be any one of the following Compounds P-1 to P-184, but is not limited thereto.

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] On the other hand, the present invention provides a method for reusing the compound represented by Formula 1, including:

[0137] recovering a crude organic light-emitting material containing the compound represented by Formula 1 from a deposition apparatus used in a process for depositing an organic light-emitting material to fabricate an organic light-emitting device;

[0138] removing impurities from the crude organic light-emitting material;

[0139] recovering the impurities; and

[0140] purifying the recovered impurities to a purity of 99.9% or higher.

[0141] 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 by recrystallization in a recrystallization solvent to obtain a purity of 98% or higher.

[0142] The recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0143] The recrystallization solvent can preferably be used by mixing a polar solvent having a polarity index value of 5.5 to 7.2 and a nonpolar solvent having a polarity index value of 2.0 to 4.7.

[0144] When using a mixture of a polar solvent and a nonpolar solvent, the recrystallization solvent can be used in an amount of 15% (v / v) or less of the nonpolar solvent to the polar solvent.

[0145] The recrystallization solvent is preferably 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; or a single nonpolar solvent selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and methyl ethyl ketone; or a mixed nonpolar solvent; or a mixture of a polar solvent and a nonpolar solvent.

[0146] 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.

[0147] 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.

[0148] The pre-purification process can include the step of dissolving the crude organic light-emitting material recovered from the deposition device in a nonpolar solvent and then precipitating crystals while concentrating the solvent and removing the nonpolar solvent.

[0149] The pre-purification process can include the step of re-crystallizing with a nonpolar solvent after first re-crystallizing with a polar solvent.

[0150] The step of purifying the recovered impurities to a purity of 99.9% or higher can include an adsorption separation process of adsorbing and removing impurities by adsorption on an adsorbent.

[0151] The adsorbent can be activated carbon, silica gel, alumina, or a material for known adsorption purposes.

[0152] The step of purifying the recovered impurities to a purity of 99.9% or higher can include performing sublimation purification.

[0153] 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. Among them, 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.

[0154] The organic material layer may sequentially include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). Here, the remaining layers except the light-emitting layer (140) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150), etc. may be used as a hole blocking layer (see Figure 2 ).

[0155] In addition, the organic electronic device according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancement layer (180). Among them, the light efficiency enhancement layer may be formed on one surface of the two surfaces of the first electrode that does not contact the organic material layer, or formed on one surface of the two surfaces of the second electrode that does not contact the organic material layer. The compound 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 light-emitting auxiliary layer (220), the electron transport auxiliary layer, the electron transport layer (150), the electron injection layer (160), the light-emitting layer (140), or a material for the light efficiency enhancement layer. Preferably, for example, the compound of Formula 1 according to the present invention may be used as a material for the light-emitting auxiliary layer.

[0156] The organic material layer may include two or more stacked bodies, the stacked bodies 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 stacked bodies (see Figure 3 ).

[0157] In addition, even when using the same core, the band gap, electrical properties, interface properties, etc. may vary depending on the position where the substituent is bonded. Therefore, the selection of the combination of the core and the associated sub-substituents is also very important. In particular, when achieving the optimal combination of the energy levels and T1 values of each organic material layer and the unique properties of the material (mobility, interface properties, etc.), long service life and high efficiency can be achieved simultaneously.

[0158] 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 metal oxide or an alloy thereof having conductivity is deposited on a substrate to form a cathode, and an organic material layer including a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) is formed thereon, and then a material that can be used as a cathode is deposited thereon.

[0159] 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 contains a compound as an electron transport material.

[0160] As another specific example, the same or different types of compounds represented by Formula 1 are mixed and used in the organic material layer.

[0161] In addition, the present invention provides a light emission assisting layer composition containing the compound represented by Formula 1, and provides an organic electronic device including the light emission assisting layer.

[0162] In addition, the present invention also provides an electronic device, which includes: a display device; and a control unit for driving the display device, and the display device includes an organic electronic device.

[0163] 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 covers all kinds of electronic devices, including mobile communication terminals such as portable phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMP), remote controllers, navigation units, game consoles, various TVs, and various computers.

[0164] Hereinafter, the synthesis examples of the compound represented by Formula 1 of the present invention and the preparation examples of the organic electronic devices of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0165] [Synthesis Example 1]

[0166] The compound (end product) represented by Formula 1 according to the present invention is synthesized by reacting Sub1 and Sub2 as shown in Reaction Scheme 1, but is not limited thereto.

[0167] <Reaction Scheme 1>

[0168]

[0169] Synthesis of Sub 1

[0170] Sub 1 in Reaction Scheme 1 can be synthesized through the reaction pathway of Reaction Scheme 2, but not limited thereto.

[0171] <Reaction Scheme 2>

[0172]

[0173] 1. Synthesis Example of Sub1-2

[0174]

[0175] After dissolving 2-bromo-9,9-dimethyl-9H-9-silafluorene (40 g, 138.9 mmol) in THF (360 ml) in a round-bottom flask, (2-chlorophenyl)boronic acid (26.0 g, 166.7 mmol), Pd(PPh3)4 (4.8 g, 4.2 mmol), NaOH (16.7 g, 416.7 mmol), and water (120 mL) were added and stirred at 75 °C. When the reaction was completed, extraction was performed with an organic solvent and water was removed with MgSO4. The solvent was concentrated, and the resulting compound was purified by column chromatography and recrystallization to obtain the product (36.5 g, yield: 82%).

[0176] 2. Synthesis Example of Sub1-8

[0177]

[0178] Using the synthesis method of Sub 1-2, the product (24.4 g, yield: 66%) was obtained by adding 2-bromo-9,9-dimethyl-9H-9-silafluorene (25.0 g, 86.8 mmol), (8-chlorodibenzo[b,d]thiophen-1-yl)boronic acid (27.3 g, 104.2 mmol), Pd(PPh3)4 (3.0 g, 2.6 mmol), and NaOH (10.4 g, 260.4 mmol) in a round-bottom flask.

[0179] 3. Synthesis Example of Sub1-19

[0180]

[0181] The product (23 g, yield: 76%) was obtained by adding 7-bromo-3-chloro-9,9-dimethyl-9H-dibenzo[b,d]silole (30.0 g, 93.2 mmol), (phenyl-d5)boronic acid (14.2 g, 295.9 mmol), Pd(PPh3)4 (3.2 g, 2.8 mmol), and NaOH (11.2 g, 279.5 mmol) to a round-bottom flask using the synthesis method of Sub 1-2.

[0182] 4. Synthesis Example of Sub1-23

[0183]

[0184] The product (21.4 g, yield: 77%) was obtained by adding 3-bromo-9,9-bis(methyl-d3)-9H-dibenzo[b,d]silole (25 g, 85.0 mmol), (3-chlorophenyl)boronic acid (15.9 g, 102 mmol), Pd(PPh3)4 (2.9 g, 2.6 mmol), and NaOH (10.2 g, 255.1 mmol) to a round-bottom flask using the synthesis method of Sub 1-2.

[0185] Meanwhile, the compound belonging to Sub 1 can be, but is not limited to, the following compounds, and Table 1 shows the FD-MS (field desorption - mass spectrometry) values of the compounds belonging to Sub 1.

[0186]

[0187] [Table 1]

[0188]

[0189]

[0190] II. Synthesis of Sub 2

[0191] Sub 2 in Reaction Scheme 1 is the same as that in Reaction Scheme 3 or Reaction Scheme 4, but is not limited thereto.

[0192] <Reaction Scheme 3>

[0193]

[0194] <Reaction Scheme 4>

[0195]

[0196] Synthesis examples of specific compounds belonging to Sub 2 are as follows.

[0197] 1. Synthesis Example of Sub 2-2

[0198]

[0199] After dissolving 2-bromo-9,9-dimethyl-9H-fluorene (20.0 g, 73.5 mmol) in toluene (250 ml) in a round-bottom flask, 4-cyclohexylaniline (15.5 g, 88.2 mmol), Pd2(dba)3 (2.0 g, 2.2 mmol), 50% P(t-Bu)3 (1.8 ml, 4.4 mmol), and NaOt-Bu (14.1 g, 147.0 mmol) were added and stirred at 110 °C. When the reaction was complete, the mixture was extracted with an organic solvent and water, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was subjected to column chromatography and recrystallization to obtain the product (18.9 g, yield: 70%).

[0200] 2. Synthesis Example of Sub 2-51

[0201]

[0202] Using the synthesis method of Sub 2-2, 2-(4'-chloro-[1,1'-biphenyl]-2-yl)bicyclo[2.2.1]heptane (15.0 g, 53.2 mmol), 9,9-diphenyl-9H-fluoren-3-amine (21.3 g, 63.8 mmol), Pd2(dba)3 (1.5 g, 1.6 mmol), 50% P(t-Bu)3 (1.3 ml, 3.2 mmol), and NaOt-Bu (10.2 g, 106.3 mmol) were added to a round-bottom flask to obtain the product (25.6 g, yield: 83%).

[0203] 3. Synthesis Example of Sub 2-54

[0204]

[0205] Using the synthesis method of Sub 2-2, 2-bromo-9,9-dimethyl-3-phenyl-9H-fluorene (20.0 g, 57.5 mmol), 4-(bicyclo[2.2.1]heptan-2-yl)aniline (12.9 g, 69.0 mmol), Pd2(dba)3 (1.6 g, 1.7 mmol), 50% P(t-Bu)3 (1.4 ml, 3.4 mmol), and NaOt-Bu (11.0 g, 114.9 mmol) were added to a round-bottom flask to obtain the product (23 g, yield: 88%).

[0206] 4. Synthesis Example of Sub 2-62

[0207]

[0208] Using the synthesis method of Sub 2-2, 2-bromo-9,9-dimethyl-9H-9-silafluorene (15.0 g, 52.1 mmol), 4-(adamantan-1-yl)aniline (14.2 g, 62.5 mmol), Pd2(dba)3 (1.4 g, 1.6 mmol), 50% P(t-Bu)3 (1.3 ml, 3.1 mmol), and NaOt-Bu (10.0 g, 104.2 mmol) were added to a round-bottom flask to obtain the product (18.4 g, yield: 81%).

[0209] 5. Synthesis Example of Sub 2-81

[0210]

[0211] Using the synthesis method of Sub 2-2, 1-(bicyclo[2.2.1]heptan-2-yl)-5-chloronaphthalene (20.0 g, 78.1 mmol), dibenzo[b,d]thiophen-1-amine (18.7 g, 93.7 mmol), Pd2(dba)3 (2.1 g, 2.3 mmol), 50% P(t-Bu)3 (1.9 ml, 4.7 mmol), and NaOt-Bu (15.0 g, 156.2 mmol) were added to a round-bottom flask to obtain the product (25.2 g, yield: 77%).

[0212] 6. Synthesis Example of Sub 2-95

[0213]

[0214] Using the synthesis method of Sub 2-2, 4-chloro-6-phenyldibenzo[b,d]furan (20.0 g, 71.9 mmol), 4-(adamantan-1-yl)aniline (19.6 g, 86.3 mmol), Pd2(dba)3 (2.0 g, 2.2 mmol), 50% P(t-Bu)3 (1.7 ml, 4.3 mmol), and NaOt-Bu (13.8 g, 143.9 mmol) were added to a round-bottom flask to obtain the product (27 g, yield: 80%).

[0215] 7. Synthesis Example of Sub 2-99

[0216]

[0217] Using the synthesis method of Sub 2-2, 3-bromo-9-phenyl-9H-carbazole (18.0 g, 56.1 mmol), 4-(adamantan-1-yl)aniline (15.3 g, 67.3 mmol), Pd2(dba)3 (1.5 g, 1.7 mmol), 50% P(t-Bu)3 (1.4 ml, 3.4 mmol), and NaOt-Bu (10.8 g, 112.1 mmol) were added to a round-bottom flask to obtain the product (23.4 g, yield: 86%).

[0218] 8. Synthesis Example of Sub 2-101

[0219]

[0220] Using the synthesis method of Sub 2-2, 9-(2-bromophenyl)-9-phenyl-9H-fluorene (20.0 g, 50.5 mmol), 4-(bicyclo[2.2.1]heptan-2-yl)aniline (11.3 g, 60.6 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), 50% P(t-Bu)3 (1.2 ml, 3.0 mmol), and NaOt-Bu (9.7 g, 101.0 mmol) were added to a round-bottom flask to obtain the product (20.6 g, yield: 81%).

[0221] Compounds belonging to Sub 2 may include but are not limited to the following compounds, and Table 2 shows the FD-MS (field desorption-mass spectrometry) values of the compounds belonging to Sub 2.

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] [Table 2]

[0230]

[0231]

[0232]

[0233] Synthesis Examples of End Products

[0234] 1. Synthesis Example of P-10

[0235]

[0236] After dissolving Sub 1-1 (15.0 g, 52.1 mmol) in toluene (175 ml) in a round-bottom flask, Sub 2-10 (19.8 g, 52.1 mmol), Pd2(dba)3 (1.4 g, 1.6 mmol), 50% P(t-Bu)3 (1.3 ml, 3.1 mmol), and NaOt-Bu (10.0 g, 104.2 mmol) were added and stirred at 110 °C. When the reaction was complete, the mixture was extracted with an organic solvent and water, the organic layer was dried over MgSO4 and concentrated, and the resulting compound was subjected to column chromatography and recrystallization to obtain the product (25.4 g, yield: 83%).

[0237] 2. Synthesis Example of P-52

[0238]

[0239] Sub 1-1 (12.0 g, 41.7 mmol), Sub 2-92 (19.6 g, 41.7 mmol), Pd2(dba)3 (1.1 g, 1.3 mmol), 50% P(t-Bu)3 (1.0 ml, 2.5 mmol), and NaOt-Bu (8.0 g, 83.3 mmol) were added to a round-bottom flask, and 28.2 g of the product (yield: 80%) was obtained using the synthesis method of P-10.

[0240] 3. Synthesis Example of P-70

[0241]

[0242] Sub 1-1 (10.0 g, 34.7 mmol), Sub 2-42 (17.2 g, 34.7 mmol), Pd2(dba)3 (1.0 g, 1.0 mmol), 50% P(t-Bu)3 (0.8 ml, 2.1 mmol), and NaOt-Bu (6.7 g, 69.4 mmol) were added to a round-bottom flask, and 18.1 g of the product (yield: 74%) was obtained using the synthesis method of P-10.

[0243] 4. Synthesis Example of P-73

[0244]

[0245] Sub 1-8 (15.0 g, 35.1 mmol), Sub 2-10 (16.0 g, 44.2 mmol), Pd2(dba)3 (1.0 g, 1.1 mmol), 50% P(t-Bu)3 (0.9 ml, 2.1 mmol), and NaOt-Bu (6.8 g, 70.3 mmol) were added to a round-bottom flask, and 18.4 g of the product was obtained using the synthesis method of P-10 (yield: 68%).

[0246] 5. Synthesis Example of P-80

[0247]

[0248] Sub 1-2 (10.0 g, 31.2 mmol), Sub 2-69 (12.0 g, 31.2 mmol), Pd2(dba)3 (0.9 g, 0.9 mmol), 50% P(t-Bu)3 (0.8 ml, 1.9 mmol), and NaOt-Bu (6.0 g, 62.5 mmol) were added to a round-bottom flask, and 16.3 g of the product was obtained using the synthesis method of P-10 (yield: 78%).

[0249] 6. Synthesis Example of P-86

[0250]

[0251] Sub 1-1 (10.0 g, 34.6 mmol), Sub 2-65 (17.7 g, 41.5 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), 50% P(t-Bu)3 (0.8 ml, 2.1 mmol), and NaOt-Bu (6.6 g, 69.1 mmol) were added to a round-bottom flask, and 16.2 g of the product was obtained using the synthesis method of P-10 (yield: 74%).

[0252] 7. Synthesis Example of P-95

[0253]

[0254] Sub 1-14 (9.0 g, 36.9 mmol), Sub 2-7 (16.3 g, 36.9 mmol), Pd2(dba)3 (1.0 g, 1.1 mmol), 50% P(t-Bu)3 (0.9 ml, 2.2 mmol), and NaOt-Bu (7.1 g, 73.8 mmol) were added to a round-bottom flask, and 19.5 g of the product was obtained using the synthesis method of P-10 (yield: 73%).

[0255] 8. Synthesis Example of P-130

[0256]

[0257] Sub 1-14 (8.0 g, 32.8 mmol), Sub 2-59 (16.8 g, 32.8 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), 50% P(t-Bu)3 (0.8 ml, 2.0 mmol), and NaOt-Bu (6.3 g, 65.6 mmol) were added to a round-bottom flask, and 17.7 g of the product was obtained using the synthesis method of P-10 (yield: 75%).

[0258] 9. Synthesis Example of P-147

[0259]

[0260] Sub 1-14 (18.0 g, 73.5 mmol), Sub 2-103 (44.4 g, 32.8 mmol), Pd2(dba)3 (2.0 g, 2.2 mmol), 50% P(t-Bu)3 (1.8 ml, 4.4 mmol), and NaOt-Bu (14.1 g, 147.1 mmol) were added to a round-bottom flask, and 38.2 g of the product was obtained using the synthesis method of P-10 (yield: 73%).

[0261] 10. Synthesis Example of P-149

[0262]

[0263] Sub 1-14 (8.0 g, 32.8 mmol), Sub 2-96 (19.0 g, 32.8 mmol), Pd2(dba)3 (0.9 g, 1.0 mmol), 50% P(t-Bu)3 (0.8 ml, 3.2 mmol), and NaOt-Bu (6.3 g, 65.6 mmol) were added to a round-bottom flask, and 18.6 g of the product was obtained using the synthesis method of P-10 (yield: 72%).

[0264] 11. Synthesis Example of P-162

[0265]

[0266] Sub 1-21 (10.0 g, 22.0 mmol), Sub 2-2 (8.1 g, 22.0 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), 50% P(t-Bu)3 (0.6 ml, 1.3 mmol), and NaOt-Bu (4.2 g, 44.0 mmol) were added to a round-bottom flask, and 11.4 g of the product was obtained using the synthesis method of P-10 (yield: 70%).

[0267] 12. Synthesis Example of P-176

[0268]

[0269] Sub 1-24 (15.0 g, 40.7 mmol), Sub 2-110 (23.7 g, 48.8 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), 50% P(t-Bu)3 (1.0 ml, 2.4 mmol), and NaOt-Bu (7.8 g, 81.3 mmol) were added to a round-bottom flask, and 25.3 g of the product was obtained using the synthesis method of P-10 (yield: 76%).

[0270] Meanwhile, the FD-MS values of Compounds P-1 to P-184 of the present invention prepared according to the above synthesis examples are shown in Table 3.

[0271] [Table 3]

[0272]

[0273]

[0274]

[0275]

[0276] Manufacturing Evaluation of Organic Electroluminescent Device

[0277] [Example 1] Red Organic Electroluminescent Device (Luminescence-Assisting Layer)

[0278] First, 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to a thickness of 70 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer, and then N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter NPB) was vacuum deposited as a hole transporting compound on the hole injection layer to a thickness of 70 nm to form a hole transporting layer. Subsequently, the compound P-2 of the present invention was vacuum deposited on the hole transporting layer to a thickness of 20 nm to form a light-emission assisting layer. Then, a light-emitting layer was formed by doping 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) as a host material and bis-(1-phenylisoquinolinato)iridium(III) acetylacetonate (hereinafter abbreviated as (piq)2Ir(acac)) as a dopant material in a weight ratio of 95:5 on the light-emission assisting layer by vacuum deposition to a thickness of 40 nm. Then, (1,1'-biphenyl-4-ylidene)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited on the light-emitting layer to a thickness of 10 nm to form a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as “BeBq2”) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transporting layer. Thereafter, alkali metal halide LiF was deposited on the electron transporting layer to a thickness of 0.2 nm to form an electron injection layer, and then a cathode was formed by depositing Al having a thickness of 150 nm on the electron injection layer to fabricate an organic light-emitting device.

[0279] [Example 2] to [Example 16]

[0280] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that a compound of the present invention described in Table 4 was used instead of the compound P-2 of the present invention as the light-emission assisting layer material.

[0281] [Comparative Example 1] or [Comparative Example 2]

[0282] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound A or Comparative Compound B was used instead of the compound P-2 of the present invention as the light-emission assisting layer material.

[0283]

[0284] The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated in this way were measured using a PR-650 from PhotoResearch by applying a forward bias DC voltage to the device. As a result of the measurement, using a lifetime measurement device manufactured by Max Science at 2500 cd / m 2Standard brightness measurement T95 service life. Table 4 shows the results of device fabrication and evaluation.

[0285] [Table 4]

[0286]

[0287]

[0288] From the results in Table 4, it can be seen that when manufacturing a red organic electroluminescent device using the materials for an organic electroluminescent device, it can be confirmed that the luminous efficiency of the organic electroluminescent device is significantly improved in the examples using the compound of the present invention compared to the comparative examples using Comparative Compound A or Comparative Compound B as the light-emitting auxiliary layer. To explain in more detail, the difference between Comparative Compound A and the compound of the present invention lies in the presence or absence of a cycloalkyl group substitution on the substituent of the amine group. When a cycloalkyl group is introduced as a substituent, the refractive index can be reduced compared to a general aryl group, and this seemingly leads to an increase in the external quantum efficiency of the device.

[0289] In addition, when comparing Comparative Compound B and the compound of the present invention, the difference lies in the presence or absence of dibenzothiophene.

[0290] The calculated reorganization energy (RE) values of Comparative Compound B and P-184 are described in Table 5.

[0291] The RE values listed in Table 5 represent the values calculated by RE 空穴 Calculated values.

[0292] [Table 5]

[0293] compound recombinant energy (RE) comparative compound B 0.123 P-184 0.134

[0294] From the above, it can be confirmed that the RE value of the compound P-184 of the present invention is lower than that of Comparative Compound B. From Comparative Example 2 and Example 16 in Table 4, it can be seen that the driving voltage of Example 16 is lower, so the hole transport characteristics of the compound of the present invention seemingly are better, but due to the low RE value, the hole injection characteristics seemingly are poorer. Due to the unique hole transport characteristics and hole injection characteristics of the dibenzothiophene group, the turn-on voltage of the device is reduced, resulting in light emission in the narrow region of the interface between the light-emitting auxiliary layer and the host. It is considered that this narrow light-emitting region actually has the effect of increasing the luminous efficiency. That is to say, from the above, it can be confirmed that the presence or absence of the cycloalkyl group and dibenzothiophene has a great influence on the performance of the device. When substituted with a cycloalkyl group and dibenzothiophene, the driving voltage or efficiency of the device is greatly affected, and it seems that the device performance of the compound of the present invention is maximized due to this.

[0295] In the case of the light-emitting auxiliary layer, it is necessary to understand the relationship between the hole transport layer and the light-emitting layer (host). Therefore, even when using a similar parent nucleus, it is difficult for those skilled in the art to infer the characteristics exhibited in the light-emitting auxiliary layer in which the compound of the present invention is used.

[0296] In addition, the evaluation results of the above device manufacturing explain the device characteristics in which the compound of the present invention is only applied to the light-emitting auxiliary layer, but the compound of the present invention can be used by applying it to the hole transport layer or by applying it to both the hole transport layer and the light-emitting auxiliary layer.

[0297] Although 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 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. The scope of the present invention should be construed based on the appended claims and should be construed to include all technical concepts within the scope equivalent to the claims as belonging to the present invention.

[0298] [Industrial Applicability]

[0299] According to the present invention, an organic device having excellent device characteristics of high brightness, high luminescence, and long life can be manufactured, and thus has industrial applicability.

Claims

1. A compound represented by Formula 1: <Formula 1> Wherein: A is a C3-C 60 cycloalkyl group, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 and R 7 each independently selected from: hydrogen; deuterium; halogen; cyano group; nitro group; 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 aliphatic ring and C6-C 60 fused ring group of aromatic rings; C1-C 60 alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 alkoxy group; and C6-C 60 aryloxy group; or may be bonded to each other to form a ring, R 8 and R 9 each independently is a C1-C 60 alkyl group, L 1 、L 2 and L 3 each independently selected from: a single bond; a C6-C 60 arylene group; a fluorene group; a C2-C containing at least one heteroatom selected from O, N, S, Si or P 60 heterocyclic group; and a C3-C 60 aliphatic ring and a C6-C 60 fused ring group of an aromatic ring; Ar is selected from C1-C 60 alkyl group; C3-C 60 cycloalkyl group; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom selected from O, N, S, Si or P 60 heterocyclic group; C3-C 60 aliphatic ring; and C3-C 60 aliphatic ring and C6-C 60 fused ring group of an aromatic ring; wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic ring group, the fused ring group, the cycloalkyl group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group and the aryloxy group may 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 with 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; and the substituents may also be bonded to each other to form a saturated or unsaturated ring, wherein 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 a combination thereof.

2. The compound according to claim 1, wherein A is represented by any one of the following Formulas A-1 to A-5: Wherein: R 10 , R 11 and R 12 are each independently the same or different and are each independently selected from: hydrogen; deuterium; halogen; 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 aryl group substituted with deuterium; 20 fluorenyl group; C2-C 20 heterocyclic group; C3-C 20 cycloalkyl group; C7-C 20 arylalkyl group; and C8-C 20 arylalkenyl group; a and b are independently integers from 0 to 11, and c is an integer from 0 to 15, Refers to the bonding position.

3. The compound according to claim 1, wherein Ar is represented by the following Formula Ar-1 or Formula Ar-2: Wherein; X is NR', O, S, CR'R” or SiR'R”, Ar' is selected from: C1-C 60 alkyl group; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom selected from O, N, S, Si or P 60 heterocyclic group; C3-C 60 aliphatic ring; C3-C 60 aliphatic ring and C6-C 60 fused ring group of an aromatic ring; R 13 、R 14 、R 15 、R 16 and R 17 has the same definition as R in claim 2, or multiple adjacent R 10 or multiple R 13 or multiple R 14 or multiple R 15 or multiple R 16 or multiple R 17 may be bonded to each other to form a ring, d is an integer from 0 to 3, and e, f, g and h are independently integers from 0 to 4, R' and R” are each independently selected from: hydrogen; deuterium; C1-C 60 alkyl groups; C1-C alkyl groups substituted with deuterium 60 aryl groups; and C2-C 60 heterocyclic groups containing at least one heteroatom selected from O, N, S, Si or P; 60 ​ or R' and R” may be bonded to each other to form a ring, * indicates the bonding position.

4. The compound according to claim 1, wherein the compound represented by Formula 1 may be any one of the following Compounds P-1 to P-184:

5. An organic electronic device, comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer contains the single compound represented by Formula 1 of claim 1 or two or more compounds.

6. The organic electronic device according to claim 5, wherein the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

7. The organic electronic device according to claim 5, wherein the organic material layer is a light-emitting auxiliary layer.

8. The organic electronic device according to claim 5, further comprising a light efficiency enhancement layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.

9. The organic electronic device according to claim 5, wherein the organic material layer includes two or more stacked bodies, and the stacked bodies include a hole transport layer, a light-emitting layer, and an electron transport layer formed in sequence on the anode.

10. The organic electronic device according to claim 9, wherein the organic material layer further includes a charge generation layer formed between the two or more stacked bodies.

11. An electronic device, comprising a display device including the organic electronic device according to claim 5; and a control unit for driving the display device.

12. The electronic device according to claim 11, wherein the organic electronic device is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochromatic or white illumination.

13. A method for recycling the compound represented by Formula 1 of claim 1, comprising: recovering a crude organic light-emitting material containing the compound represented by Formula 1 of claim 1 from a deposition device used in the process of depositing an organic light-emitting material to prepare an organic light-emitting device; removing impurities from the crude organic light-emitting material; recovering the impurities; and purifying the recovered impurities to a purity of 99.9% or higher.

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