Organic electric element comprising compound for organic electric element, and electronic device therefor

Abstract

The present invention provides: an organic electric element comprising a positive electrode, a negative electrode, and an organic material layer between the positive electrode and the negative electrode; and an electronic device comprising the organic electric element, and can lower the driving voltage and improve the luminous efficiency and lifespan of the organic electric element.

Description

Organic electric device comprising a compound for organic electric device and electronic device thereof

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

[0002] Organic light emitting diodes (OLEDs) generally refer to the conversion of electrical energy into light energy using organic materials. Organic electronic devices utilizing this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer interposed between them. These organic layers can be multilayered, composed of different materials, to enhance the efficiency and stability of the device.

[0003] The current portable display market is growing in size, with large-area displays. Because portable displays rely on batteries with a limited power supply, they require more efficient power consumption than conventional portable displays. Furthermore, in addition to efficient power consumption, luminous efficiency and lifespan must also be addressed.

[0004] To address power consumption, luminous efficiency, and lifespan issues, research is being conducted on tandem organic electronic devices (OLEDs) comprising two or more stacks (or light-emitting units), each containing a light-emitting layer. In particular, research is being conducted to improve the organic materials contained in the stacks to enhance power consumption, luminous efficiency, and lifespan of OEDs.

[0005] Efficiency, lifespan, and operating voltage are all interrelated. As efficiency increases, the operating voltage relatively decreases, and as the operating voltage decreases, the crystallization of organic materials due to Joule heating generated during operation decreases, which tends to result in an extended lifespan. However, efficiency cannot be maximized simply by improving organic materials. This is because long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​of each organic material, and the inherent properties of the material (mobility, interfacial properties, etc.) are optimally combined. Therefore, the development of materials that have high thermal stability and can efficiently achieve charge balance within the light-emitting layer is necessary.

[0006] In addition, in tandem organic devices, a charge generation layer is required between two or more stacks (or light-emitting units) to increase the current efficiency generated in the light-emitting layer and to facilitate charge distribution. Depending on how smoothly the charge distribution is facilitated in the charge generation layer, it affects the driving voltage of the entire device, and the charge injection characteristics and the lifespan of the device are also affected depending on the energy level difference between the n-type charge generation layer and the p-type charge generation layer, the concentration of the doping material doped in the charge generation layer, etc.

[0007] In other words, the efficiency, lifespan, and operating voltage of tandem organic electronic devices can vary depending on the organic materials used in each layer. However, the development of stable and efficient organic layer materials for tandem organic electronic devices has not yet been sufficiently achieved. Therefore, the development of new materials continues to be required.

[0008] Currently, in tandem organic devices, an organic compound doped with a metal is typically used as the n-type charge generation layer, and lithium (Li) is used as the metal doping material of the organic compound. However, since lithium (Li) has a relatively low resistance among metal materials, when lithium (Li) is used as the doping material of the organic compound of the n-type charge generation layer, the resistance of the n-type charge generation layer decreases, resulting in lateral current leakage and prevents charge distribution to the p-type charge generation layer from occurring smoothly. This causes leakage current between pixels, which results in an imbalance in the charge balance in the light-emitting layer, which significantly reduces the lifespan due to the progressive driving voltage. Therefore, there is a need to improve this problem.

[0009] The present invention provides an organic electroluminescent device including a plurality of stacks, in which an n-type charge generation layer is doped with ytterbium (Yb) having a high resistance in a tandem organic electroluminescent device including a plurality of stacks to minimize leakage current in the n-type charge generation layer, and a p-type charge generation layer (p-CGL) has a lateral resistance of 10Ω / sq to 50Ω / sq, and uses a compound represented by the chemical formula 1, thereby facilitating charge distribution between a plurality of layers forming an organic material layer, improving color purity, lowering the driving voltage of the device, and improving the lifespan, and an electronic device thereof.

[0010] The present invention provides an organic electric device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode; wherein the organic layer comprises a first stack and a second stack, and further comprises a charge generation region between the first stack and the second stack, and the charge generation region comprises an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer is stacked so as to face the first electrode, and the p-type charge generation layer is stacked so as to face the second electrode, and the n-type charge generation layer is doped with ytterbium (Yb), and the p-type charge generation layer comprises a tertiary amine compound, and the tertiary amine compound comprises at least one diphenylfluorene substituent and at least one fluorene substituent.

[0011] <Chemical Formula 1>

[0012]

[0013] The above tertiary amine compound is

[0014] In another aspect, the present invention provides an electronic device including the organic electric element.

[0015] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved.

[0016] Figure 1 is an exemplary diagram of an organic light-emitting device according to the present invention.

[0017] Figure 2 is a drawing showing an experimental setup for measuring the lateral resistance of an organic light-emitting device according to the present invention.

[0018] 300: Organic electric element 110: First electrode

[0019] 170: Second electrode 180: Light efficiency improvement layer

[0020] 320: First hole injection layer 330: First hole transport layer

[0021] 340: First light-emitting layer 350: First electron transport layer

[0022] 360: n-type charge generation layer 361: p-type charge generation layer

[0023] 420: Second hole injection layer 430: Second hole transport layer

[0024] 440: Second light-emitting layer 450: Second electron transport layer

[0025] CGL: Charge generation layer ST1: First stack

[0026] ST2: Second Stack

[0027] Hereinafter, the present invention will be described in detail with reference to embodiments. In describing the present invention, if a detailed description of a related known configuration or function is judged to obscure the gist of the present invention, such detailed description will be omitted.

[0028] Additionally, terms such as first, second, A, B, (a), (b), etc. may be used to describe components of the present invention. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

[0029] As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

[0030] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0031] The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

[0032] The term "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise stated, includes a straight-chain or branched chain group having a double bond or triple bond of 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms or 2 to 12 carbon atoms, but is not limited thereto.

[0033] The term "cycloalkyl" or "cycloalkyl" as used in the present invention means, unless otherwise stated, an alkyl forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms or 3 to 12 carbon atoms, but is not limited thereto.

[0034] The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms.

[0035] The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.

[0036] The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, have, but are not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, respectively. In the present invention, the aryl group or arylene group refers to a single ring or multi-ring aromatic group, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0037] The prefix "aryl" or "ar" refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the aryl-substituted radical has the number of carbon atoms described herein.

[0038] Also, when prefixes are named consecutively, it means that the substituents are listed in the order they were first written. For example, in the case of arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0039] The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by bonding adjacent functional groups.

[0040] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0041] Additionally, the term "heterocyclic group" refers to a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc. containing a heteroatom. In addition, compounds containing a heteroatom group such as SO2, P=O, etc. instead of carbon forming a ring, such as the compounds below, may also be included in the heterocyclic group. For example, the term "heterocyclic group" includes the following compounds.

[0042]

[0043] The term "aliphatic ring" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, means a ring having 3 to 60 carbon atoms, a ring having 3 to 30 carbon atoms, a ring having 3 to 25 carbon atoms, a ring having 3 to 18 carbon atoms, or a ring having 3 to 12 carbon atoms, but is not limited thereto. For example, even when an aromatic ring, benzene, and a non-aromatic ring, cyclohexane, are fused, it is considered an aliphatic ring.

[0044] The term "fluorenyl group", "fluorenylene group" or "fluorenetriyl group" used in the present invention, unless otherwise stated, means a monovalent, divalent or trivalent functional group in which R, R' and R" in the structure below are all hydrogen, and a "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl group" means that at least one of the substituents R, R' and R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In the present specification, regardless of valence, a fluorenyl group, a fluorenylene group and a fluorenetriyl group may all be referred to as a fluorene group.

[0045]

[0046] The term "spiro compound" used in the present invention has a "spiro union," and a spiro union means a connection formed by two rings sharing only one atom. In this case, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are called "monospiro-," "dicepiro-," and "trispiro-" compounds, respectively.

[0047] Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms or 1 to 12 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms or 3 to 12 carbon atoms.

[0048] Unless otherwise stated, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heterocycle having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms; or a fused ring composed of a combination thereof, including a saturated or unsaturated ring.

[0049] Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds include, but are not limited to, one or more heteroatoms.

[0050] Also, unless explicitly stated otherwise, the term "substituted" in the term "substituted or unsubstituted" used in the present invention means deuterium, halogen, amino group, nitrile group, nitro group, C1~C20 Alkyl group of C1~C 20 Alkoxyl group, C1~C 20 Alkylamine group of C1~C 20 Alkylthiophene group, C6~C 20 Arylthiophene group, C2~C 20 Alkenyl group, C2~C 20 Alkyne group, C3~C 20 Cycloalkyl group of C6~C 20 Aryl group of C6~C substituted with deuterium 20 Aryl group of C8~C 20 Arylalkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group consisting of heterocyclic groups, but is not limited to these substituents.

[0051] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', but may also be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, but it may also be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent. In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing the compound name or substituent name. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine can be written as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene can be written as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0052] Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

[0053]

[0054] Here, if a is an integer of 0, the substituent R 1 is absent, and if a is an integer of 1, there is one substituent R 1 is bonded to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, in which case R 1 may be the same or different, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0055]

[0056] In addition, unless explicitly stated otherwise, the terms "ortho", "meta", and "para" used in the present invention mean the substitution positions of all substituents, and the ortho position refers to a compound in which the positions of the substituents are immediately adjacent, for example, in the case of benzene, it refers to the 1st and 2nd positions, the meta position refers to the substitution position next to the immediately adjacent substitution position, and refers to the 1st and 3rd positions in the case of benzene as an example, and the para position refers to the substitution position next to the meta position, and refers to the 1st and 4th positions in the case of benzene as an example. A more detailed description of examples of substitution positions is as follows, and it can be confirmed that the ortho- and meta- positions are substituted in a non-linear type, and the para- position is substituted in a linear type.

[0057] [Example of ortho-position]

[0058]

[0059] [Example of meta-position]

[0060]

[0061] [Example of para-location]

[0062]

[0063]

[0064] Hereinafter, the laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIG. 1.

[0065] When assigning reference numerals to components in each drawing, it should be noted that identical components are assigned the same numerals whenever possible, even if they appear on different drawings. Furthermore, when describing the present invention, if a detailed description of a related known configuration or function is deemed likely to obscure the gist of the present invention, such detailed description will be omitted.

[0066] Figure 1 is an exemplary diagram of an organic electric device according to an embodiment of the present invention.

[0067] Referring to FIG. 1, an organic electric element (300) according to an embodiment of the present invention may have two or more sets of stacks (ST1, ST2) of organic layers formed in multiple layers formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stacks of organic layers.

[0068] Specifically, an organic electric device according to one embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL: Charge Generation Layer), a second stack (ST2), a second electrode (170), and a light efficiency improvement layer (180).

[0069] The first stack (ST1) is an organic layer formed on the first electrode (110), which may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450), and the second hole injection layer (420) of the second stack (ST2) may be omitted if necessary. In this way, the first stack and the second stack may be organic layers having the same stack structure, but may also be organic layers having different stack structures.

[0070] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include an n-type charge generation layer (360) adjacent to the first electron transport layer (350) of the first stack (ST1) and a p-type charge generation layer (361) adjacent to the second hole injection layer (420) of the second stack (ST2). This charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to smoothly distribute charges. In the case of a top emission organic light emitting device, the formation of a light efficiency improvement layer (180) can reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode (170), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer (180) can serve as a buffer for the second electrode (170).

[0071] When a plurality of light-emitting layers are formed by a multilayer stack structure as shown in Fig. 1, not only can an organic light-emitting device be manufactured that emits white light by the mixing effect of the light emitted from each light-emitting layer, but an organic light-emitting device that emits light of various colors can also be manufactured. Although not shown in Fig. 1, a buffer layer and a light-emitting auxiliary layer may be further formed between the hole transport layer and the light-emitting layer of each stack, and an electron transport auxiliary layer may be further formed between the light-emitting layer and the electron transport layer.

[0072] Although FIG. 1 describes a tandem element having two stacks, the organic electric element according to the present invention may be a tandem element having two or more stacks (e.g., a tandem element having three stacks, a tandem element having four stacks).

[0073] Preferably, the compound represented by the chemical formula 1 of the present invention can be used as a charge generation layer (CGL), and more preferably, the compound represented by the chemical formula 1 can be used as a p-type charge generation layer.

[0074] Even if the core is identical or similar, the band gap, electrical properties, and interface properties can vary depending on which substituent is bonded at which position. Therefore, research on the selection of the core and the combination of sub-substituents bonded to it is necessary. In particular, when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

[0075] An organic light-emitting device according to one embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode (110), and a first stack (ST1) sequentially including a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340) and a first electron transport layer (350) is formed thereon, and then a charge generation layer (CGL) sequentially including an n-type charge generation layer (360) and a p-type charge generation layer (361) for connecting two stacks is formed thereon, and a second stack (ST2) sequentially including a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440) and a second electron transport layer (450) is formed thereon. It can be manufactured by forming an electron injection layer and depositing a material that can be used as a cathode (170) thereon. In addition, a buffer layer (not shown) and a light-emitting auxiliary layer (not shown) may be further formed between the hole transport layer and the light-emitting layer of each stack, and an electron transport auxiliary layer (not shown) may be further formed between the light-emitting layer and the electron transport layer, or two or more stack structures may be formed as described above.

[0076] In addition, the organic layer can be manufactured with a smaller number of layers by using various polymer materials and a solution process or solvent process other than a deposition method, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, a screen printing process, or a thermal transfer method. Since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0077] In addition, the organic electric device according to one embodiment of the present invention may be selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, a device for monochrome lighting, and a device for quantum dot display.

[0078] Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as cell phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

[0079]

[0080] Hereinafter, an organic electric device according to one aspect of the present invention will be described.

[0081] According to one embodiment of the present invention, an organic electric device includes: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode; wherein the organic layer includes a first stack and a second stack, and a charge generation region is further included between the first stack and the second stack, and the charge generation region includes an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer is stacked so as to face the first electrode, and the p-type charge generation layer is stacked so as to face the second electrode, and the n-type charge generation layer is doped with ytterbium (Yb), and the p-type charge generation layer includes a tertiary amine compound, and the tertiary amine compound includes at least one diphenylfluorene substituent and at least one fluorene substituent.

[0082] In addition, the present invention provides an organic electric device in which the n-type charge generation layer is doped with ytterbium (Yb), and the ytterbium (Yb) is doped at 0.5 w% to 5 w%.

[0083] In addition, the present invention provides an organic electric device in which the p-type charge generation layer is doped with a doping material of 5 w% to 10 w%.

[0084] In addition, the present invention provides an organic electric device in which the tertiary amine compound is a compound represented by the following chemical formula 1.

[0085] <Chemical Formula 1>

[0086]

[0087] In the above chemical formula 1, each symbol can be defined as follows.

[0088] A is C6~C 60 is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0089] R 1 and R 2 are independently of each other, identical or different, and independently of each other, hydrogen; deuterium; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; and C1~C 30 is selected from the group consisting of an alkoxyl group;

[0090] The above R 1 and R 2 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0091] The above R 1 and R 2If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0092] R 3 , R 4 , R 5 and R 6 are independently of each other, the same or different, and independently of each other, hydrogen; deuterium; C6~C 60 Aryl group of; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group; Fluorenyl group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; or adjacent multiple R 3 R's or multiple R's 4 R's or multiple R's 5 R's or multiple R's 6 They can combine with each other to form rings,

[0093] The above R 3 , R 4 , R 5 and R 6 In this case, aryl group is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0094] The above R 3 , R 4 , R 5 and R 6In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0095] The above R 3 , R 4 , R 5 and R 6 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0096] The above R 3 , R 4 , R 5 and R 6 In this case, it is preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0097] The above R 3 , R 4 , R 5 and R 6 In the case of this alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C12 It may be an alkoxyl group.

[0098] The above R 3 , R 4 , R 5 and R 6 In the case of this aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0099] R 7 and R 8 are independently C1~C 50 alkyl group; and preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0100] a, c and f are each independently an integer from 0 to 4, b is an integer from 0 to 5, d and e are each independently an integer from 0 to 3,

[0101] L 1 , L 2 and L 3 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0102] Above L 1 , L 2 and L 3 In the case of this arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0103] Above L 1 , L 2 and L 3 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0104] Above L 1 , L 2 and L 3 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0105] Ar 1 Silver C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C3~C 60Cycloalkyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups;

[0106] The above Ar 1 In this case, it is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0107] The above Ar 1 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0108] The above Ar 1 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0109] The above Ar 1 In this case, it is preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0110] The above Ar 1 In the case of this cycloalkyl group, preferably C3~C 30 Cycloalkyl group, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0111] The above Ar 1 In the case of this alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0112] The above Ar 1 In the case of this aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0113] Here, the aryl group, arylene group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0114]

[0115] The above chemical formula 1 can be represented by any one of the following chemical formulas 1-A1 to 1-A4.

[0116] <Chemical Formula 1-A1> <Chemical Formula 1-A2>

[0117]

[0118] <Chemical Formula 1-A3> <Chemical Formula 1-A4>

[0119]

[0120] {In the above chemical formulas 1-A1 to 1-A4, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1 is the same as defined in the above chemical formula 1.

[0121]

[0122] The above chemical formula 1 can be represented by any one of the following chemical formulas 1-B1 to 1-B3.

[0123] <Chemical Formula 1-B1> <Chemical Formula 1-B2> <Chemical Formula 1-B3>

[0124]

[0125] {In the above chemical formulas 1-B1 to 1-B3, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1 is the same as defined in the above chemical formula 1.

[0126]

[0127] The above chemical formula 1 can be represented by any one of the following chemical formulas 1-C1 to 1-C4.

[0128] <Chemical Formula 1-C1> <Chemical Formula 1-C2>

[0129]

[0130] <Chemical Formula 1-C3> <Chemical Formula 1-C4>

[0131]

[0132] {In the above chemical formulas 1-C1 to 1-C4, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1is the same as defined in the above chemical formula 1.

[0133]

[0134] The above n-type charge generation layer may include a compound represented by the following chemical formula 2, and the n-type charge generation layer is doped with ytterbium (Yb).

[0135] Chemical Formula 2

[0136]

[0137] In the above chemical formula 2, each symbol can be defined as follows.

[0138] 1) R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are independently the same or different from each other, and independently hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups;

[0139] However, R 15 , R 16 and R 17 At least one of them combines with a* to form a single bond.

[0140] The above R 10 , R 11 , R12 , R 13 , R 14 , R 15 , R 16 and R 17 In this case, aryl group is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0141] The above R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0142] The above R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 In the case of this aliphatic ring, preferably C3~C 30 aliphatic ring, more preferably C3~C 25 , C3~C 18 or C3~C12 It may be an aliphatic ring group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0143] The above R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0144] The above R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 In this case, it is preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0145] The above R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 In the case of this alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0146] The above R10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 In the case of this aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0147] 2) L is C6~C 60 Arylene group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group;

[0148] When the above L is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0149] If the above L is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0150] 3) Ar 10 Silver C6~C 60Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group; and

[0151] The above Ar 10 In this case, it is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0152] The above Ar 10 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 24 In the case of a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0153] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents is C6~C substituted or unsubstituted with one or more deuterium, cyano group, or deuterium. 20 It can be further substituted with an aryl group, and these substituents can also combine with each other to form a ring, where the 'ring' refers to C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0154]

[0155] Specifically, the compound of the above chemical formula 2 may be any one of the following compounds N-1 to N-92, but is not limited thereto.

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] The above p-type charge generation layer can be doped with the following chemical formula 3.

[0181] Chemical Formula 3

[0182]

[0183] In the above chemical formula 3, each symbol can be defined as follows.

[0184] 1) R p1 , R p2 , R p3 , R p4 , R p5 and R p6are independently hydrogen; halogen; cyano group; nitrile group; nitro group; -SO2R; -SOR; -SO2NR2; -SO3R; trifluoromethyl group; -COOR; -CONHR; -CONRR'; -NRR'; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 C2~C substituted or unsubstituted with an alkyl group; cyano group 20 Alkenyl group of; and C1~C 30 is selected from the group consisting of an alkoxyl group;

[0185] The above R p1 , R p2 , R p3 , R p4 , R p5 and R p6 In this case, aryl group is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0186] The above R p1 , R p2 , R p3 , R p4 , R p5 and R p6 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0187] The above R p1 , R p2 , R p3 , R p4 , R p5 and R p6 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0188] The above R p1 , R p2 , R p3 , R p4 , R p5 and R p6 In this case, it is preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0189] The above R p1 , R p2 , R p3 , R p4 , R p5 and R p6 In the case of this alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12It may be an alkoxyl group.

[0190] 2) R and R' are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and C1~C 50 is selected from the group consisting of alkyl groups;

[0191] When the above R and R' are aryl groups, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0192] When the above R and R' are heterocyclic groups, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0193] When the above R and R' are fused ring groups, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0194] When the above R and R' are alkyl groups, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0195]

[0196] The above chemical formula 3 may preferably be any one of the following compounds E-1 to E-5.

[0197]

[0198]

[0199]

[0200] In another example, the p-type charge generation layer may be doped with any one of the following compounds E-6 to E-26.

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] The above p-type charge generation layer may be doped with any one of the compounds E-1 to E-26 at 0.1 w% to 50 w%, preferably at 3 w% to 15 w%, and more preferably at 5 w% to 10 w%.

[0208]

[0209] In addition, in another aspect, the present invention provides an organic electric device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode; wherein the organic layer includes a first stack and a second stack, and further includes a charge generation region between the first stack and the second stack, and the charge generation region includes an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer is stacked so as to face the first electrode and the p-type charge generation layer is stacked so as to face the second electrode, and the n-type charge generation layer is doped with ytterbium (Yb), and the p-type charge generation layer has a lateral resistance of 10Ω / sq to 50Ω / sq.

[0210] In addition, the present invention provides an organic electric device in which a p-type charge generation layer having a lateral resistance of 10Ω / sq to 50Ω / sq includes a compound represented by the following chemical formula 1.

[0211] <Chemical Formula 1>

[0212]

[0213] {In the above chemical formula 1, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1 is the same as defined above.}

[0214]

[0215] Specifically, the compound represented by the above chemical formula 1 may be any one of the following compounds, but is not limited thereto.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] Hereinafter, examples of synthesis of a compound represented by Chemical Formula 1 according to the present invention and examples of manufacturing an organic electric device are described in detail, but the present invention is not limited to the following examples.

[0245] [Synthesis Example 1]

[0246] The compound represented by chemical formula 1 according to the present invention (Final Product 1) is synthesized by reacting Sub1 and Sub2 as shown in the following reaction scheme 1, but is not limited thereto.

[0247] <Reaction Scheme 1>

[0248]

[0249]

[0250] I. Synthesis of the final compound

[0251] 1. P1-1 Synthesis Example

[0252]

[0253] Sub1-1 (10.0 g, 21.1 mmol) was dissolved in toluene (106 mL) in a round-bottomed flask, and then Sub2-1 (6.0 g, 21.1 mmol), Pd2(dba)3 (0.58 g, 0.63 mmol), P(t-Bu)3 (0.26 g, 1.27 mmol), and NaOt-Bu (4.1 g, 42.2 mmol) were added and the reaction was carried out at 80°C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting organic material was then purified by silica gel column chromatography and recrystallization to obtain 11.0 g of the product (yield: 77%).

[0254]

[0255] 2. P1-11 Synthesis Example

[0256]

[0257] After dissolving Sub1-1 (10.0 g, 21.1 mmol) in toluene (106 mL) in a round-bottom flask, Sub2-19 (6.1 g, 21.1 mmol), Pd2(dba)3 (0.58 g, 0.63 mmol), P(t-Bu)3 (0.26 g, 1.27 mmol), and NaOt-Bu (4.1 g, 42.2 mmol) were added, and the experiment was conducted in the same manner as P1-1 to obtain 10.8 g of the product (yield 75%).

[0258]

[0259] 3. P1-25 Synthesis Example

[0260]

[0261] After dissolving Sub1-22 (10.0 g, 21.1 mmol) in toluene (106 mL) in a round-bottom flask, Sub2-1 (6.0 g, 21.1 mmol), Pd2(dba)3 (0.58 g, 0.63 mmol), P(t-Bu)3 (0.26 g, 1.27 mmol), and NaOt-Bu (4.1 g, 42.2 mmol) were added, and the experiment was conducted in the same manner as P1-1 to obtain 10.6 g of the product (yield 74%).

[0262]

[0263] 4. P1-32 Synthesis Example

[0264]

[0265] After dissolving Sub1-22 (10.0 g, 21.1 mmol) in toluene (106 mL) in a round-bottom flask, Sub2-12 (9.5 g, 21.1 mmol), Pd2(dba)3 (0.58 g, 0.63 mmol), P(t-Bu)3 (0.26 g, 1.27 mmol), and NaOt-Bu (4.1 g, 42.2 mmol) were added, and the experiment was conducted in the same manner as P1-1 to obtain 12.7 g of the product (yield 71%).

[0266]

[0267] Meanwhile, although the above-described exemplary synthetic examples of the present invention represented by Chemical Formula 1 are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J.86-60 Org. Chem. 2005, 70, 5014), it will be easily understood by those skilled in the art that the above-described reaction proceeds even if a substituent other than the substituent specified in the specific synthetic example is combined.

[0268]

[0269] [Component Data]

[0270] [Experimental example of measuring lateral resistance]

[0271] The term "lateral resistance" used herein refers to a numerical value that represents the resistance to leakage current in an organic layer. The higher the lateral resistance value, the lower the lateral leakage current. The lateral resistance can be obtained through a value measured using the M6100 Source meter from Maxscience.

[0272]

[0273] (R: resistance, I: current, V: voltage)

[0274]

[0275] Figure 2 is a schematic diagram for the experimental setup as a device for measuring lateral resistance using the Maxscience M6100 Source meter.

[0276] In Fig. 2, a represents an insulator, b1 represents a cathode, b2 represents an anode, d represents the distance between b1 and b2, and L represents the length of the electrodes through which current can flow between b1 and b2 (hereinafter, referred to as the active electrode length). Although only electrodes b1 and b2 are disclosed in Fig. 2, the electrodes may be configured as an even number of electrodes, from 2 to 20. After forming an organic layer between the anode and the cathode, the lateral resistance of the p-type charge generation layer (p-CGL) was measured.

[0277] In the device configured as in Fig. 2, d was set to 40 μm, a voltage of 100 V was applied, and the current was measured. The resistance value was calculated using the resistance-current relationship.

[0278] The resistance value obtained through calculation is multiplied by the number of electrodes in the device. In the experiment, the number of electrodes was set to 20, so the value (A) was obtained by multiplying by 20 (20 pairs, 1 pair of anode and cathode) and then multiplying by the length (L) of the active electrode.

[0279] Afterwards, the experiment is conducted in the same manner as above, but the d value is adjusted to 80 ㎛, 160 ㎛, and 320 ㎛ to obtain the value (A).

[0280] The values ​​(A) obtained by adjusting the d value in this way were used to calculate the resistance value ohm / sq. using the LINEST formula in Excel, and the unit of the resistance value is expressed as Gohm (GΩ) for convenience.

[0281] The lateral resistance of the p-type charge generation layer obtained using the above method is 10 GΩ / sq. or more, preferably 10 to 50 GΩ / sq., and more preferably 10 to 20 GΩ / sq.

[0282]

[0283] [Manufacturing Evaluation of Organic Electronics]

[0284] When the organic electroluminescent device according to the present specification is a front-emitting type and the first electrode is formed on the substrate before the formation of the organic layer and the second electrode, not only a transparent material but also an opaque material with excellent light reflectivity can be used as the first electrode material.

[0285] When the organic electroluminescent device according to the present specification is a back-emitting type and the first electrode is formed on the substrate before the formation of the organic layer and the second electrode, a transparent material must be used as the first electrode material, or an opaque material must be formed into a thin film to the extent that it becomes transparent.

[0286] In this embodiment, a front-emitting tandem organic electroluminescent device is fabricated and the following examples are presented, but the embodiments of the present invention are not limited thereto. A tandem organic electroluminescent device according to one embodiment of the present invention is fabricated by connecting a plurality of stacks through a charge generation layer.

[0287] A tandem organic electroluminescent device according to one embodiment of the present invention uses the same compound in the light-emitting layer and electron transport layer of each of the two stacks, but is not limited thereto.

[0288]

[0289] [Example 1] Tandem organic electroluminescent device with two stacks connected

[0290] A tandem organic electroluminescent device with two stacks connected was manufactured with a structure of first electrode / hole transport region / emission layer / electron transport region / charge generation region / hole transport region / emission layer / electron transport region / electron injection layer / second electrode.

[0291] Specifically, a hole injection layer having a thickness of 60 nm was formed on an ITO layer (first electrode) formed on a glass substrate using N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) and HATCN, and HATCN was doped in a weight ratio of 90:10. A hole transport layer was formed on the hole injection layer by vacuum-depositing N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) to a thickness of 145 nm.

[0292] Next, 4,4'-Bis(2,2-diphenylethenyl)-1,1'-biphenyl (hereinafter abbreviated as DPVBi) was used as a host material of the light-emitting layer on the hole transport layer, and 4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl (hereinafter abbreviated as BCzVBi) was used as a dopant material, and the dopant was doped at a weight ratio of 95:5 to form a light-emitting layer having a thickness of 115 nm.

[0293] Next, on the light-emitting layer, Tris(8-hydroxyquinolinato)aluminium (hereinafter abbreviated as Alq3) was vacuum-deposited to a thickness of 90 nm to form an electron transport layer. (hereinafter, the first stack)

[0294] Next, to connect two stacks, Bathophenanthroline (hereinafter abbreviated as Bphen) and Yb were used, and Yb was doped at a weight ratio of 97:3 to form an n-type charge generation layer having a thickness of 45 nm, and on the n-type charge generation layer, the compound P1-1 of the present invention and HATCN were used, and HATCN was doped at a weight ratio of 93:7 to form a p-type charge generation layer having a thickness of 60 nm.

[0295] On the p-type charge generation layer, a hole transport layer, a light-emitting layer, and an electron transport layer identical to those formed in the first stack were sequentially formed. (Hereinafter, the second stack)

[0296] Afterwards, 8-quinolinolato lithium (hereinafter abbreviated as Liq) was vacuum-deposited to a thickness of 6 nm as an electron injection layer, and then Ag:Mg was deposited to a thickness of 150 nm to form a second electrode, thereby manufacturing a tandem organic electroluminescent device.

[0297]

[0298] [Example 2] to [Example 10]

[0299] An organic electric device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used as p-type charge generation layer materials.

[0300]

[0301] [Comparative Example 1] to [Comparative Example 4]

[0302] An organic electric device was manufactured in the same manner as in Example 1, except that the n-type charge generation layer was doped with Li or the comparative compound 1 or comparative compound 2 was used as the p-type charge generation layer material.

[0303] Comparative Compound 1 Comparative Compound 2

[0304]

[0305]

[0306] The organic electroluminescence devices manufactured in this way were subjected to a direct current bias voltage and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch. The measured result was 1,500 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. Table 1 below shows the results of the device fabrication and evaluation.

[0307] This measuring device can evaluate the performance of new materials compared to reference compounds under identical conditions, regardless of possible daily variations in deposition rate, vacuum quality, or other parameters. Since each batch contains four identically prepared OLEDs containing the reference compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this manner demonstrate statistical significance.

[0308] n-type charge generation layerp-type charge generation layerp-type charge generation layer Lateral resistance (GΩ / sq)Device driving voltage (V)Device current (mA / cm) 2 ) Device luminance (cd / m 2 ) Device efficiency (cd / A) Device T (97) Comparative Example 1 n-CGL: Li Comparative Compound 11.8 14.8 17.6 150 0.08 54 2.7 Comparative Example 2 n-CGL: Yb Comparative Compound 11.8 14.0 17.9 150 0.08 45 0.1 Comparative Example 3 n-CGL: Yb Comparative Compound 23.9 13.5 16.5 150 0.09 15 3.4 Comparative Example 4 n-C GL:LiP1-2519.58.811.01500.013.677.6Example 1n-CGL:YbP1-116.47.410.81500.013.890.5Example 2n-CGL:YbP1-416.27.310.71500.014.092.8Example 3n-CGL:YbP1-1013.57.011.01500.0 13.690.5 Example 4 n-CGL: YbP1-25 19.57.110.7 1500.014.092.8 Example 5 n-CGL: YbP1-27 17.17.111.01 500.013.692.7 Example 6 n-CGL: YbP1-29 18.37.110.9 1500.013.792.3 Example 7 n-CGL: YbP1-31 19.07.211.01500.013.790.6 Example 8n-CGL:YbP1-6615.37.310.91500.013.895.0 Example 9n-CGL:YbP1-7312.27.510.91500.013.894.4 Example 10n-CGL:YbP1-9815.97.010.71500.014.094.9

[0309] As can be seen from the results in Table 1 above, it can be confirmed that the device performance of the tandem organic electric device using ytterbium (Yb) as a doping material of an n-type charge generation layer organic compound and using the compound chemical formula 1 of the present invention, which is a compound having a lateral resistance of 10 to 50 GΩ / sq. as a p-type charge generation layer, is improved. First, although Comparative Examples 1 and 2 have similar device configurations, it can be seen that the device performance of Comparative Example 2 using ytterbium (Yb) is improved in terms of driving voltage and lifespan more than that of Comparative Example 1 using lithium (Li) as an n-type doping material. This can be explained by the difference in resistance values ​​between lithium (Li) and ytterbium (Yb). While the resistance of lithium (Li) is 92.8 n Ω·m, the resistance of ytterbium (Yb) is 250 n Ω·m, which means that the resistance value of ytterbium is much higher than that of lithium. In other words, when lithium is used as a doping material for the n-type charge generation layer, lateral current leakage occurs in the n-type charge generation layer due to lithium having a low resistance value, and charge distribution in the charge generation layer is not smooth. On the other hand, when ytterbium (Yb) is used as a doping material for the n-type charge generation layer, lateral current leakage in the n-type charge generation layer is minimized due to the high resistance of ytterbium, and charge distribution to the p-type charge generation layer is smooth, so it can be confirmed that the driving voltage and lifespan of the device are improved. These results can be confirmed through the fact that Example 1 shows better results than Comparative Example 4 in terms of driving voltage and lifespan in the device results of Example 1 and Comparative Example 4, which both use the compound of the present invention as the p-type charge generation layer, but have different uses of lithium or ytterbium as the doping material for the n-type charge generation layer.

[0310] In addition, although Comparative Examples 2 and 3 use ytterbium (Yb) as an n-type doping material, Comparative Compounds 1 and 2, which have significantly lower lateral resistance, are used as p-type charge generation layer materials, which ultimately causes leakage current to occur in the p-type charge generation layer, and as a result, the charge balance of the entire device is not correct, which can be seen to deteriorate the performance of the device. In particular, although Comparative Compound 2 and the compound of the present invention are similar in that they contain a dimethylfluorene group, it can be seen that the compound of the present invention, which further contains at least one diphenylfluorene having an asymmetrical structure, has higher lateral resistance.

[0311] That is, it was confirmed that the effect of the compound of the asymmetric structure according to the presence of the A substituent in the chemical formula 1, which is a compound of the present invention in which an aryl group is further substituted on the phenyl group of the diphenylfluorene group, shows superior results compared to the comparative compounds.

[0312] If the lateral resistance of the charge generation layer is formed too high, the total amount of holes entering the device decreases, and the holes required for device operation are not sufficiently supplied, so it is important to have an appropriate level of lateral resistance.

[0313] As a result, it can be confirmed that the device performance of Examples 1 to 10, which used ytterbium (Yb) as an n-type doping material and applied the compound of the present invention having a lateral resistance of 10 to 50 GΩ / sq., preferably 10 to 20 GΩ / sq., as a p-type charge generation layer, was very excellent.

[0314] The above description is merely an example of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are intended to illustrate rather than limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all techniques within a scope equivalent thereto should be interpreted as being included in the scope of the rights of the present invention.

[0315] According to the present invention, an organic device having excellent device characteristics such as high brightness, high luminescence, and long lifespan can be manufactured, and thus has industrial applicability.

Claims

1. First electrode; a second electrode; and An organic layer disposed between the first electrode and the second electrode; The organic layer comprises a first stack and a second stack, A charge generation region is further included between the first stack and the second stack, The above charge generation region includes an n-type charge generation layer and a p-type charge generation layer, The n-type charge generation layer is stacked so as to face the first electrode, and the p-type charge generation layer is stacked so as to face the second electrode. The above n-type charge generation layer is doped with ytterbium (Yb). An organic electric device characterized in that the p-type charge generation layer comprises a tertiary amine compound, and the tertiary amine compound comprises at least one diphenylfluorene substituent and at least one fluorene substituent.

2. An organic electric device according to claim 1, wherein the n-type charge generation layer is doped with ytterbium (Yb), and the ytterbium (Yb) is doped at 0.5 w% to 5 w%.

3. An organic electric device according to claim 1, characterized in that the p-type charge generation layer is doped with a doping material of 5 w% to 10 w%.

4. In the first paragraph, the organic electric device characterized in that the tertiary amine compound is represented by the following chemical formula 1. <Chemical Formula 1> {In the above chemical formula 1, A is C6~C 60 is an aryl group, R 1 and R 2 are independently of each other, identical or different, and independently of each other, hydrogen; deuterium; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; and C1~C 30 is selected from the group consisting of an alkoxyl group; R 3 , R 4 , R 5 and R 6 are independently of each other, the same or different, and independently of each other, hydrogen; deuterium; C6~C 60 Aryl group of; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group; Fluorenyl group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; or adjacent multiple R 3 R's or multiple R's 4 R's or multiple R's 5 R's or multiple R's 6 They can combine with each other to form rings, R 7 and R 8 are independently C1~C 50 alkyl group of; and, a, c and f are each independently an integer from 0 to 4, b is an integer from 0 to 5, d and e are each independently an integer from 0 to 3, L 1 , L 2 and L 3 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of; Ar 1 Silver C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C3~C 60 Cycloalkyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; Here, the aryl group, arylene group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents is C6~C substituted or unsubstituted with one or more deuterium, cyano group, or deuterium. 20 It can be further substituted with an aryl group, and these substituents can also combine with each other to form a ring, where the 'ring' refers to C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

5. In the fourth paragraph, the organic electric element characterized in that the chemical formula 1 is represented by any one of the following chemical formulas 1-A1 to 1-A4. <Chemical Formula 1-A1> <Chemical Formula 1-A2> <Chemical Formula 1-A3> <Chemical Formula 1-A4> {In the above chemical formulas 1-A1 to 1-A4, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1 is the same as defined in claim 4 above.} 6. In the fourth paragraph, the organic electric element characterized in that the chemical formula 1 is represented by any one of the following chemical formulas 1-B1 to 1-B3. <Chemical Formula 1-B1> <Chemical Formula 1-B2> <Chemical Formula 1-B3> {In the above chemical formulas 1-B1 to 1-B3, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1 is the same as defined in claim 4 above.} 7. In the fourth paragraph, the organic electric element characterized in that the chemical formula 1 is represented by any one of the following chemical formulas 1-C1 to 1-C4. <Chemical Formula 1-C1> <Chemical Formula 1-C2> <Chemical Formula 1-C3> <Chemical Formula 1-C4> {In the above chemical formulas 1-C1 to 1-C4, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, L 1 , L 2 , L 3 and Ar 1 is the same as defined in claim 4 above.} 8. First electrode; a second electrode; and An organic layer disposed between the first electrode and the second electrode; The organic layer comprises a first stack and a second stack, A charge generation region is further included between the first stack and the second stack, The above charge generation region includes an n-type charge generation layer and a p-type charge generation layer, The n-type charge generation layer is stacked so as to face the first electrode, and the p-type charge generation layer is stacked so as to face the second electrode. The above n-type charge generation layer is doped with ytterbium (Yb). An organic electric device characterized in that the p-type charge generation layer has a lateral resistance of 10Ω / sq to 50Ω / sq.

9. An organic electric device according to claim 8, wherein the p-type charge generation layer having a lateral resistance of 10Ω / sq to 50Ω / sq comprises a compound represented by the following chemical formula 1. <Chemical Formula 1> {In the above chemical formula 1, A is C6~C 60 is an aryl group, R 1 and R 2 are independently of each other, identical or different, and independently of each other, hydrogen; deuterium; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; and C1~C 30 is selected from the group consisting of an alkoxyl group; R 3 , R 4 , R 5 and R 6 are independently of each other, the same or different, and independently of each other, hydrogen; deuterium; C6~C 60 Aryl group of; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group; Fluorenyl group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; or adjacent multiple R 3 R's or multiple R's 4 R's or multiple R's 5 R's or multiple R's 6 They can combine with each other to form rings, R 7 and R 8 are independently C1~C 50 alkyl group of; and, a, c and f are each independently an integer from 0 to 4, b is an integer from 0 to 5, d and e are each independently an integer from 0 to 3, L 1 , L 2 and L 3 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of; Ar 1 Silver C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C3~C 60 Cycloalkyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; Here, the aryl group, arylene group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

10. An organic electric device according to claim 1 or claim 8, further comprising a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic layer.

11. An organic electric device according to claim 1 or claim 8, wherein the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on a first electrode.

12. An organic electric device according to claim 11, characterized in that the organic layer further includes a charge generation layer formed between the two or more stacks.

13. An electronic device comprising a display device including an organic electric element of claim 1 or claim 8; and a control unit for driving the display device.

14. An electronic device according to claim 13, wherein the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element.

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