Organic electrical components

Abstract

The present disclosure relates to an organic electrical element for achieving high luminous efficiency and high heat resistance of the element, improving the color purity of the element, and extending the life of the element.

Description

Technical Field

[0001] The present disclosure relates to an organic electric component. Background Art

[0002] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic electrical element utilizing the organic light-emitting phenomenon has a structure including an anode, a cathode, and an organic material layer disposed between the cathode and the anode. Here, in many cases, the organic material layer has a multilayer structure made of different materials to improve the efficiency and stability of the organic electrical element. For example, the organic material layer may include 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 material used for the organic material layer may be divided into a light emitting material and a charge transporting material according to functions, such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material.

[0004] In addition, luminescent materials can be divided into high molecular weight type and low molecular weight type according to molecular weight, and can also be divided into fluorescent materials based on electron singlet excitation and phosphorescent materials based on electron triplet excitation according to the luminescence mechanism. In addition, luminescent materials can be divided into blue, green and red luminescent materials according to the color of light emission, as well as yellow and orange luminescent materials required to achieve more natural colors.

[0005] When a single material is used as a light-emitting material, the maximum emission wavelength may shift to a long wavelength and the color purity may decrease due to the interaction between molecules, or the device efficiency may decrease due to the emission quenching effect. Therefore, the host-dopant system can be used as a light-emitting material to improve the color purity and improve the luminous efficiency through energy transfer. According to this principle, when a small amount of dopant with a smaller energy band gap than the host of the light-emitting layer is added to the light-emitting layer, the excitons generated in the light-emitting layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host is shifted toward the wavelength band of the dopant, light with the expected wavelength can be obtained according to the type of dopant used.

[0006] Currently, in the portable display market, the size of the display is increasing to a large-area display. Since the portable display is equipped with a battery used as a power source, the portable display requires more efficient power consumption than the existing power consumption. In addition, in this case, not only the challenge of efficient power consumption but also the challenge of luminous efficiency and lifespan must be met.

[0007] Efficiency, lifespan, driving voltage, etc. are interrelated. The improvement of efficiency leads to a relatively reduced driving voltage, thereby reducing the crystallization of organic materials caused by Joule heat during the driving process, thereby extending the lifespan. However, simply improving the organic material layer may not maximize the efficiency. This is because when the energy level and T1 value between each organic material layer are optimally combined with the inherent properties of the material (mobility, interface properties, etc.), extended lifespan and high efficiency can be achieved simultaneously. Therefore, it is necessary to develop a light-emitting material that can effectively achieve charge balance in the light-emitting layer while having high thermal stability.

[0008] That is to say, in order to give full play to the excellent characteristics of organic electrical components, the materials forming the organic material layer in the component, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials and emission auxiliary layer materials, should be supported by stable and efficient materials. However, such stable and efficient organic material layer materials for organic electronic components have not been fully developed.

[0009] Recently, one of the important factors for improving device performance may be a technique for improving color purity and improving efficiency by optimizing the optical thickness between the anode and the cathode in the top device having a resonant structure and a study on improving device characteristics by changing the properties of each material. Compared with the bottom device structure having a non-resonant structure, the top device structure has a larger light energy loss due to surface plasmon polariton (SPP) because the formed light is reflected by the anode (the anode is a reflective film) and emitted toward the cathode.

[0010] Therefore, one of the important methods to improve the spectral shape and efficiency of organic electronic components is to use a capping layer for the top cathode. Generally speaking, four metals, such as Al, Pt, Ag, and Au, are mainly used for electron emission in SPP and surface plasma is generated on the surface of the metal electrode. For example, when Ag is used as the cathode, the light emitted by Ag of the cathode is quenched by SPP and the efficiency is reduced due to the loss of light energy of Ag.

[0011] On the other hand, when a capping layer is used, SPP is generated at the interface between the MgAg electrode and the high-refractive organic material. In this case, its TM (transverse magnetic) polarized light is annihilated by the evanescent wave in the vertical direction on the capping layer surface and the TM polarized light moves along the cathode, and the capping layer is amplified by the surface plasmon resonance, thereby increasing the intensity peak and ultimately achieving efficient and effective color purity control. Summary of the invention

[0012] Technical issues

[0013] The present disclosure aims to provide an organic electric element capable of providing excellent luminous efficiency, high heat resistance, high color purity, and extended lifespan.

[0014] Technical Solution

[0015] According to one aspect, the present disclosure provides an organic electrical element, comprising: a first electrode; a second electrode; an organic material layer, the organic material layer being located between the first electrode and the second electrode; and a covering layer, the covering layer being disposed on at least one of a surface of the first electrode opposite to the organic material layer and a surface of the second electrode opposite to the organic material layer; wherein the covering layer comprises a compound represented by the following Formula 1.

[0016] Formula 1

[0017]

[0018] Beneficial Effects

[0019] As described above, by including a capping layer using the disclosed compound, excellent luminous efficiency, high heat resistance, high color purity, and extended lifespan can be achieved. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figures 1 to 3 A cross-sectional view showing an organic light emitting element according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0021] Hereinafter, embodiments of the present disclosure will be described in detail with reference to the accompanying drawings.

[0022] When the components of the drawings are represented by reference numerals, the same components will be represented by the same reference numerals if possible, even though the components are shown in different drawings. In addition, in the following description of the present disclosure, detailed descriptions of known functions and configurations incorporated herein will be omitted, which will apply to situations where the subject matter of the present disclosure may become unclear. When "including", "having", "consisting of...", etc. mentioned in this specification are used, other parts may be added unless "only" is used. When a component is represented in the singular, it may include plural cases unless otherwise explicitly stated.

[0023] In addition, when describing the components of the present disclosure, terms such as first, second, A, B, (a) or (b) may be used herein. Each of these terms is not used to define the elements, order or sequence of the corresponding components, but is only used to distinguish the corresponding components from other components.

[0024] When describing that a certain component is “connected”, “coupled” or “joined” to another component, it should be understood that the other component may be “connected”, “coupled” or “joined” to the component not only directly but also indirectly through a connecting component. Herein, other components may be included in one or more of the two or more components that are “connected”, “coupled” or “joined” to each other.

[0025] In addition, when describing that a component, such as a layer, film, region, or plate, is "on" or "over" another component, it should be understood that the component can be not only "directly" but also indirectly on the other component through an intermediate component. In contrast, when describing that a component is "directly above" another component, it should be understood that there are no intermediate elements.

[0026] When using words such as "after", "next", "before", etc. to describe time priority or process priority relationships, discontinuities may be included in the description of time process relationships related to components, operating methods, manufacturing methods, etc., unless "immediately" or "directly" is used.

[0027] On the other hand, when referring to the numerical value or corresponding information of a component, even if not explicitly described separately, the numerical value or corresponding information can be construed as including an error range that may be caused by various factors (e.g., method factors, internal or external impact, noise, etc.).

[0028] As used herein, unless otherwise indicated, the term "halo" or "halogen" includes fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0029] Unless otherwise specified, the term "alkyl" or "alkyl group" used herein has a single bond, has 1 to 60 carbon atoms, and refers to a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0030] Unless otherwise stated, the term "haloalkyl" or "halogen alkyl" as used herein includes alkyl groups substituted with halogen.

[0031] Unless otherwise specified, the term "alkenyl group" or "alkynyl group" used herein has a double bond or a triple bond and has 2 to 60 carbon atoms, and includes a linear group or a branched group, but is not limited thereto.

[0032] As used herein, unless otherwise specified, the term "cycloalkyl" refers to, but is not limited to, an alkyl group forming a ring having from 3 to 60 carbon atoms.

[0033] As used herein, the term "alkoxy group" or "alkyloxy group" refers to an alkyl group to which is attached an oxygen group, and unless otherwise specified, has, but is not limited to, 1 to 60 carbon atoms.

[0034] The term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group" or "alkenyloxy group" refers to an alkenyl group to which is attached an oxygen group, unless otherwise specified, having but not limited to 2 to 60 carbon atoms.

[0035] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has, but is not limited to, 6 to 60 carbon atoms. In this specification, aryl groups or arylene groups include monocyclic compounds, ring assemblies, fused polycyclic systems, spirocyclic compounds, etc. For example, aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, indenyl, phenanthrenyl, triphenylenyl, pyrenyl, perylene, The naphthyl group may include 1-naphthyl and 2-naphthyl, and the anthracenyl group may include 1-anthracenyl, 2-anthracenyl and 9-anthracenyl.

[0036] Unless otherwise indicated, the term "fluorenyl group" or "fluorenylene group" as used herein may refer to a monovalent or divalent functional group of fluorene. In addition, a "fluorenyl group" or "fluorenylene group" may refer to a substituted fluorenyl group or a substituted fluorenylene group. As used herein, the term "substituted fluorenyl group" or "substituted fluorenylene group" may refer to a monovalent or divalent functional group of substituted fluorene. The term "substituted fluorene" may refer to a compound in which at least one of the substituent groups R, R', R" or R'" is a functional group other than hydrogen, and includes the case where R and R' are bonded to form a spirocyclic compound together with the carbon atom attached thereto.

[0037]

[0038] As used herein, the term "spiro compound" may have a "spiro union", and the spiro union may refer to a connection formed by two rings that share only one atom. In this case, the atom shared by the two rings may be referred to as a "spiro atom", which may refer to a "single spiro" compound, a "double spiro" compound, or a "triple spiro" compound, depending on the number of spiro atoms in the compound.

[0039] As used herein, the term "heterocyclic group" includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group", but also non-aromatic rings, unless otherwise specified, and may refer to a ring having 2 to 60 carbon atoms, including 1 or more heteroatoms, but is not limited thereto. Unless otherwise specified, as used herein, the term "heteroatom" refers to N, O, S, P or Si, and the heterocyclic group may refer to a monocyclic group including a heteroatom, a ring aggregate, a fused polycyclic system, a spy compound, etc.

[0040] In addition, as used herein, a "heterocyclic group" or "hetero ring group" may include a ring having SO2 replacing a ring-forming carbon atom. For example, a "heterocyclic group" includes the following compounds:

[0041]

[0042] As used herein, the term "ring" refers to a monocyclic ring and a polycyclic ring, includes not only a hydrocarbon ring but also a heterocyclic ring containing at least one heteroatom, and includes an aromatic ring and a non-aromatic ring.

[0043] As used herein, the term "polycyclic" includes ring assemblies such as biphenyl ring systems or terphenyl ring systems, fused polycyclic ring systems, and spirocyclic compounds. Polycyclic includes not only aromatic compounds but also non-aromatic compounds, not only hydrocarbon rings but also heterocyclic rings containing at least one heteroatom.

[0044] As used herein, the term "aliphatic ring group" may refer to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring assembly, a condensed polycyclic system, a spirocyclic compound, etc. Unless otherwise specified, it may refer to a ring having 3 to 60 carbon atoms. For example, even when benzene, an aromatic ring, and cyclohexane, a non-aromatic ring, are condensed, it is equivalent to an aliphatic ring.

[0045] As used herein, the term "ring assembly" may refer to a compound in which two or more rings (monocyclic or condensed ring systems) are directly connected by a single bond or a double bond, and the number of such direct ring connections is less than the total number of ring systems in the compound by 1. In the ring assembly, the same or different ring systems may be directly connected by a single bond or a double bond. For example, in the case of an aryl group, it may be a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0046] As used herein, the term "fused polycyclic ring system" may refer to a form of fused rings that share at least two atoms. For example, in the case of an aryl group, it may be a naphthyl group, a phenanthrenyl group, a fluorenyl group, etc., but is not limited thereto.

[0047] In addition, in the case of consecutive prefixes, it means that the substituents are listed in the order of the prefixes. For example, an arylalkoxy group refers to an alkoxy group substituted by an aryl group, an alkoxycarbonyl group refers to a carbonyl group substituted by an alkoxy group, and an arylcarbonylalkenyl group refers to an alkenyl group substituted by an arylcarbonyl group, wherein an arylcarbonyl group is a carbonyl group substituted by an aryl group.

[0048] Unless otherwise expressly stated, the term "substituted" in the term "substituted or unsubstituted" as used herein may refer to substitution with one or more substituents selected from, but not limited to, deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 Alkylthiophene group, C6-C 20 Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 Aryl groups, deuterium-substituted C6-C 20 Aryl group, C8-C 20 an arylalkenyl group, a silane group, a boron group, a germanium group, and a C2-C4-H2O group containing at least one heteroatom selected from O, N, S, Si and P. 20 Heterocyclic group.

[0049] Herein, the "name of the functional group" corresponding to the aryl group, arylene group, heterocyclic group, etc. and their substituents shown with their respective symbols can be written in the "name of the functional group reflecting the valence state of the functional group" or can be written in the "name of the parent compound of the functional group". For example, phenanthrene, a kind of aryl group, can be written in the group name by distinguishing the valence state. That is, a monovalent phenanthrene "group" can be written as "phenanthrene (group)", and a divalent phenanthrene "group" can be written as "sub-phenanthrene (group)". In contrast, the phenanthrene group can be written as "phenanthrene", the name of the parent compound, regardless of the valence state. Similarly, pyrimidine can be written as "pyrimidine" regardless of the valence state, or it can be written as the group name corresponding to the valence state, wherein a monovalent pyrimidine group is written as pyrimidinyl (group) and a divalent pyrimidine group is written as pyrimidinylen (group). Therefore, in this specification, when the type of substituent group is written in the name of the parent compound, the written name may refer to an n-valent "group" formed by removing carbon atom and / or heteroatom-bonded hydrogen from the parent compound.

[0050] Furthermore, unless otherwise specifically stated, the formulae used herein apply in the same manner as the definitions of substituents defined based on the subscripts of the following formulae:

[0051]

[0052] Herein, when a is 0, there is no substituent R 1 When a is 1, a single substituent R 1 When a is 2 or 3, the substituent R 1 Connect in the following manner, where R 1 can have the same or different values. When a is an integer between 4 and 6, the substituent R 1 In a similar manner, the hydrogen atoms connected to the carbon atoms of the benzene ring are omitted herein.

[0053]

[0054] Herein, the expression "substituents bonded to form a ring / substituents bonded to form a ring" may refer to the case where adjacent groups bond to each other to form a monocyclic ring or a condensed polycyclic ring, and the monocyclic ring and the formed condensed polycyclic ring may include not only hydrocarbon rings but also heterocyclic rings containing at least one heteroatom, and may include aromatic rings and non-aromatic rings.

[0055] As used herein, the organic electrical element may refer to an organic light emitting diode including one or more components between an anode and a cathode, or including an anode, a cathode, and one or more components between the anode and the cathode.

[0056] In addition, in some cases, as used herein, an organic electrical element may refer to an organic light emitting diode and a panel including the organic light emitting diode, or may refer to an electronic device including the panel and a circuit. Herein, for example, electronic devices include display devices, lighting devices, solar cells, portable or mobile terminals (such as smart phones, tablet computers, PDAs, electronic dictionaries, PMPs, etc.), navigation terminals, game consoles, various televisions, and various computers. Electronic devices may include all monitors, etc., but are not limited thereto, and may include any type of device, provided that one or more components are included.

[0057] Figures 1 to 3 A cross-sectional view showing an organic light emitting element according to an embodiment of the present disclosure is shown.

[0058] The organic electrical element of the disclosed embodiment may include: a first electrode; a second electrode; an organic material layer located between the first electrode and the second electrode; and a covering layer disposed on at least one surface of a surface of the first electrode opposite to the organic material layer and a surface of the second electrode opposite to the organic material layer.

[0059] Reference Figure 1 , showing an organic electrical element according to an embodiment of the present disclosure, a first electrode 110, a second electrode 170, and organic material layers 120, 130, 140, 150, and 160 located between the first electrode 110 and the second electrode 120, and showing a cover layer 180, which may be located on a surface of the second electrode 170 opposite to the organic material layer. Figure 1 In the illustrated embodiment, the capping layer 180 is located on one surface of the second electrode 170, but in the embodiment of the present disclosure, the capping layer 180 may also be located on one surface of the first electrode 110. When the capping layer 180 is located on one surface of the first electrode 110, the surface is one of the surfaces of the first electrode 110 that is opposite to the organic material layer, so that the capping layer 180 may be located at the lower portion of the first electrode 110.

[0060] The thickness of the cover layer 180 may be 30 nm to 120 nm. The lower limit of the thickness of the cover layer 180 may be, for example, 40 nm or more, 50 nm or more, or 55 nm or more. The upper limit of the thickness of the cover layer 180 may be, for example, 100 nm or less, 80 nm or less, or 65 nm or less. When the thickness of the cover layer is adjusted within the above range, an organic electrical element having high luminous efficiency and color purity due to surface plasmon resonance may be provided.

[0061] The cover layer 180 may have a refractive index of 1.85 or more for light having a wavelength of 450 nm to 750 nm. The upper limit of the refractive index of the cover layer for light having a wavelength of 450 nm to 750 nm is not particularly limited, but may be, for example, 3.0 or less or 2.5 or less. When the refractive index of the cover layer is adjusted within the above range, an organic electrical element having high luminous efficiency and color purity due to surface plasmon resonance may be provided.

[0062] Figure 1 The first electrode 110 shown in the figure may be an anode, and the second electrode 170 may be a cathode. In the case of a reverse type, the first electrode is a cathode, and the second electrode may be an anode.

[0063] The organic material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially disposed on the first electrode 110.

[0064] In addition, reference Figure 2 In an organic electrical element 200 according to another embodiment of the present disclosure, a hole injection layer 220 and a hole transport layer 230, a buffer layer 243, a light-emitting auxiliary layer 253, a light-emitting layer 240, an electron transport layer 250, an electron injection layer 260, a second electrode 270 and a covering layer 280 are sequentially arranged on a first electrode 210. Figure 2 In the embodiment of the present disclosure, the capping layer 280 is located on one surface of the second electrode 270, but in the embodiment of the present disclosure, the capping layer 280 is located on one surface of the first electrode 210. When the capping layer 280 is located on one surface of the first electrode 210, the one surface is one surface of the first electrode 210 that is opposite to the organic material layer, so that the capping layer 280 can be located at the lower part of the first electrode 210.

[0065] At the same time, although Figure 2 Although not shown, an electron transport auxiliary layer may be further disposed between the light emitting layer 240 and the electron transport layer 250 .

[0066] In addition, reference Figure 3, the organic electrical element 300 of another embodiment of the present disclosure may be that two or more stacks ST1 and ST2 of the multi-layer organic material layer may be disposed between the first electrode 310 and the second electrode 370. For example, the first stack ST1 is disposed on the first electrode 310, the second stack ST2 is disposed on the first stack ST1, the second electrode 370 is disposed on the second stack ST2, and the covering layer 380 may be disposed on the second electrode 370. The charge generating layer CGL (charge generating layer) may be disposed between the first stack ST1 and the second stack ST2. Figure 3 In the illustrated embodiment, the capping layer 380 is located on one surface of the second electrode 370, but in the embodiment of the present disclosure, the capping layer 380 is located on one surface of the first electrode 310. When the capping layer 380 is located on one surface of the first electrode 310, the one surface is one surface of the first electrode 310 opposite to the organic material layer, so that the capping layer 380 can be located at the lower portion of the first electrode 310.

[0067] Specifically, the organic electric element 300 includes a first electrode 310 , a first stack ST1 , a charge generation layer CGL, a second stack ST2 , and a second electrode 370 and a capping layer 380 .

[0068] The first stack ST1 is an organic material layer formed on the first electrode 310, which includes a first hole injection layer 321, a first hole transport layer 331, a first light emitting layer 341, and a first electron transport layer 351. The second stack ST2 may include a second hole transport layer 332, a second light emitting layer 342, and a second electron transport layer 352. In addition, an electron injection layer 360 may be included between the second electrode and the second electron transport layer. In this way, the first stack and the second stack may be organic material layers having the same stack structure.

[0069] The charge generation layer CGL may include a first charge generation layer 390 and a second charge generation layer 391. The charge generation layer CGL is disposed between the first and second light emitting layers 341 and 342 to increase efficiency of current generated in each light emitting layer and may function to smoothly distribute charges.

[0070] For example, the first light-emitting layer 341 may include: a light-emitting material, the light-emitting material including a blue fluorescent dopant doped in a blue host; and a second light-emitting layer 342, the second light-emitting layer 342 including a material of a yellow-green dopant and a red dopant doped in a green host, but the materials of the first light-emitting layer 341 and the second light-emitting layer 342 of the embodiment of the present disclosure are not limited thereto.

[0071] The charge generation layer CGL and the second stack ST2 may be repeatedly placed n times, where n is a positive integer. For example, n may be an integer from 1 to 5. For example, when n is 2, the charge generation layer CGL and the third stack may be further stacked on the second stack ST2.

[0072] like Figure 1-3 As shown, the cover layer 180, 280 and 380 can be disposed on one surface of the first electrode 110, 210, 310 opposite to the organic material layer and on one surface of the second electrode 170, 270, 370 opposite to the organic material layer. When the cover layer is disposed thereon, the light efficiency of the organic electrical element can be improved. For example, when the cover layer is located below the first electrode 110, 210 and 310 or above the second electrode 170, 270, 370, the light emitted through the electrode is emitted from the cover layer having a relatively high refractive index. When light passes through, the wavelength of the light is amplified and the luminous efficiency can be improved.

[0073] In the case of a top-emitting organic light-emitting element, the capping layer 180, 280, 380 can play a role in reducing light energy loss due to surface plasmon polaritons (SPP) in the second electrode 170, 270, 370. In the case of a bottom-emitting organic light-emitting element, the capping layer 180, 280, 380 can serve as a buffer layer for the second electrode 170, 270, 370.

[0074] On the other hand, Figure 3 As shown, when a plurality of light-emitting layers are formed by a multi-layer stacking structure method, an organic electrical element that emits white light by a mixing effect of light emitted from each light-emitting layer can be manufactured.

[0075] The organic light-emitting element of the embodiment of the present disclosure can be manufactured using a variety of deposition methods. The organic light-emitting element can be manufactured using a deposition method such as physical vapor deposition (PVD) or chemical vapor deposition (CVD). For example, the organic light-emitting element can be manufactured in the following manner: forming anodes 110, 210 and 310 by depositing metal, conductive metal oxide or alloy thereof on a substrate; forming an organic material layer thereon, the organic material layer including hole injection layers 120, 220 and 321, hole transport layers 130, 230, 331 and 332, light-emitting layers 140, 240, 341 and 342, electron transport layers 150, 250, 351 and 352, and electron injection layers 160, 260 and 360; and depositing materials used as cathodes 170, 270 and 370 thereon.

[0076] In addition, the organic material layer can be made into a smaller number of layers using various polymer materials by a solution method or a solvent method, such as a spin coating method, a nozzle printing method, an inkjet printing method, a slit coating method, a dip coating method, a roll-to-roll method, a doctor blade method, a screen printing method, or a thermal transfer method. Since the organic material layer of the present disclosure can be formed by a variety of methods, the scope of the present disclosure is not limited by the method for forming the organic material layer.

[0077] The organic electrical element of the present disclosure may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0078] White organic light-emitting devices (WOLEDs) have many advantages, such as easy realization of high resolution, excellent processing capabilities, and the ability to be manufactured using existing liquid crystal display (LCD) color filter technology. For WOLEDs, which are mainly used in backlight units, a variety of structures have been proposed and patented. Representative are planar side-by-side red (R), green (G), and blue (B) light-emitting structures, vertical stacking arrangements of RGB light-emitting structures, and color conversion material (CCM) structures, in which electroluminescence from a blue (B) organic light-emitting layer and photoluminescence from an inorganic light-emitting material using electroluminescence are used. The present disclosure can be applied to WOLEDs.

[0079] In the embodiment of the present disclosure, the hole injection layer 120, 220 and 321, the hole transport layer 130, 230, 331 and 332, the buffer layer 243, the light-emitting auxiliary layer 253, the electron transport layer 150, 250, 351 and 352, the electron injection layer 160, 260 and 360, the light-emitting layer 140, 240, 341 and 342, or the capping layer 180, 280 and 380 may include a compound represented by Formula 1. For example, the capping layers 180, 280 and 380 may include a compound represented by Formula 1.

[0080] Hereinafter, the compound of aspects of the present disclosure is represented by Formula 1 below.

[0081] Formula 1

[0082]

[0083] Formula 1-1

[0084]

[0085] The substituents and linking groups described in Formula 1 are described below.

[0086] Ar 1 To Ar 4 Can be independently selected from: C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group.

[0087] For example, Ar 1 To Ar 4 Can be independently selected from: C6-C 60 An aryl group; a fluorenyl group; and a C2-C 60 Heterocyclic group.

[0088] When Ar 1 To Ar 4 When they are aryl groups, Ar 1 To Ar 4 Each of which can be independently C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10 In this case, Ar 1 To Ar 4 May be the same as or different from each other.

[0089] When Ar 1 To Ar 4 When they are heterocyclic groups, Ar 1 To Ar 4 Each of them can be C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 In this case, Ar 1 To Ar 4 May be the same as or different from each other.

[0090] Ar 1 To Ar 4 At least one of is represented by Formula 1-1.

[0091] L 1 and L 2 Can be independently selected from: single bond; C1-C 50 Alkylene group; C2-C 20Alkenylene group; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group.

[0092] When L 1 and L 2 When L is an arylene group, 1 and L 2 Each of them can be independently C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25 Arylene group or C6-C 10 In this case, L 1 and L 2 May be the same as or different from each other.

[0093] When L 1 and L 2 When they are heterocyclic groups, L 1 and L 2 Each of these can be C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 In this case, L 1 and L 2 May be the same as or different from each other.

[0094] L 3 To L 6 Can be independently selected from: single bond; C1-C 50 Alkylene group; C2-C 20 Alkenylene group; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group.

[0095] When L 3 To L 6 When L is an arylene group, 3 To L 6 Each of which can be independently C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25Arylene group or C6-C 10 In this case, L 3 To L 6 May be the same as or different from each other.

[0096] When L 3 To L 6 When they are heterocyclic groups, L 3 To L 6 Each of them can be C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 In this case, L 3 To L 6 May be the same as or different from each other.

[0097] R 1 and R 2 can be independently selected from: deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-N(R a )(R b ); and one or more adjacent R 1 are the same or different and multiple R 1 bonded to form a ring, and one or more adjacent R 2 are the same or different and multiple R 2 The bonds form a ring.

[0098] For example, R 1 and R 2 can be independently selected from: deuterium; C6-C 60 An aryl group; a fluorenyl group; and a C2-C 60 Heterocyclic group.

[0099] When R 1 and R 2 When they are aryl groups, R 1 and R 2 Each of them can be independently C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10In this case, R 1 and R 2 May be the same as or different from each other.

[0100] When R 1 and R 2 When they are heterocyclic groups, R 1 and R 2 Each of these can be C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 In this case, R 1 and R 2 May be the same as or different from each other.

[0101] R 3 Can be selected from: Deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-N(R a )(R b ); and one or more adjacent R 3 are the same or different, multiple R 3 The bonds form a ring.

[0102] For example, R 3 can be independently selected from: deuterium; C6-C 60 An aryl group; a fluorenyl group; and a C2-C 60 Heterocyclic group.

[0103] When R 3 When each R 3 Can be independently C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10 In this case, multiple R 3 , R 2 Can be the same or different.

[0104] When R 3 When they are heterocyclic groups, each R 3 Can be C2-C 60 Heterocyclic group, C2-C40 Heterocyclic group or C2-C 20 In this case, multiple R 3 , R 2 Can be the same or different.

[0105] a and b may each independently be an integer from 0 to 3.

[0106] c can be an integer from 0 to 4, and when Ar 1 To Ar 4 When two or more of c can be represented by Formula 1-1, the plurality of c may be the same or different.

[0107] L' can be independently selected from: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group.

[0108] R a and R b Can be independently selected from: C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group.

[0109] X can be O or S.

[0110] Ring A can be independently C6-C 30 Aryl group, C6-C 25 Aryl group or C6-C 10 Aryl group. Ring A is an aryl group satisfying the above-mentioned carbon number range, and may be an aryl group fused to the substituent represented by Formula 1-1. For example, ring A may be each independently selected from benzene, naphthalene, phenanthrene, and anthracene.

[0111] Y can be independently CR a R b or NR c , and when Y is bonded to Formula 1, Y may be N or C. When Y may be plural, a plurality of Ys may be the same or different.

[0112] Y' may each independently be N, O or S.

[0113] R a , R b and Rc can be independently: hydrogen; deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 A fused group of aromatic rings; or combinations thereof.

[0114] When R a , R b and R c When they are aryl groups, R a , R b and R c Each of them can be independently C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10 In this case, R a , R b and R c May be the same as or different from each other.

[0115] When R a , R b and R c When they are heterocyclic groups, R a , R b and R c Each of these can be C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 In this case, R a , R b and R c May be the same as or different from each other.

[0116] Adjacent L 1 and R 1 They may be bonded to form a ring.

[0117] Adjacent L 1 and Ar 1 They may be bonded to form a ring.

[0118] Adjacent L 1 and Ar 2 They may be bonded to form a ring.

[0119] Adjacent L 1 and L 3 They may be bonded to form a ring.

[0120] Adjacent L 1 and L 4 They may be bonded to form a ring.

[0121] Adjacent L 2 and R 2 They may be bonded to form a ring.

[0122] Adjacent L 2 and Ar 3 They may be bonded to form a ring.

[0123] Adjacent L 2 and Ar 4 They may be bonded to form a ring.

[0124] Adjacent L 2 and L 5 They may be bonded to form a ring.

[0125] Adjacent L 2 and L 6 They may be bonded to form a ring.

[0126] In Ar 1 To Ar 4 , L 1 To L 6 , R 1 To R 3 , R a and R b In the above, each of the aryl group, fluorenyl group, heterocyclic group, condensed ring group, alkyl group, alkenyl group, alkylene group, arylene group and fluorenyl group may be further substituted by one or more substituents selected from the group consisting of: deuterium; nitro group; nitrile group; halogen group; amino 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; deuterium substituted C6-C 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. Therefore, when Ar 1 To Ar 4 , L 1 To L 6 , R 1 To R 3, R a and R b When understood as a primary substituent, additionally substituted substituents may be understood as secondary substituents.

[0127] The additional substituents as secondary substituents may be bonded to form a ring, and each substituent is further substituted by one or more substituents selected from: deuterium; nitro group; nitrile group; halogen group; amino 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; deuterium substituted C6-C 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 allow substituents to bond to form a ring. Additional substituents from secondary substituents can be understood as tertiary substituents.

[0128] L 1 To L 6 Any of the following formulas a-1 to a-13 may be used.

[0129]

[0130] The substituent groups of formulae a-1 to a-13 are as follows.

[0131] Z is O, S, CR d R e or NR f , and when Z is bonded to Formula 1, Z may be N or C.

[0132] R d , R e and R f Each independently selected from: hydrogen; deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic groups and C3-C 60 Aliphatic ring and C6-C 60 The aromatic fused ring group contains at least one heteroatom selected from O, N, S, Si and P.

[0133] When R d, R e and R f When it is an aryl group, for example, the aryl group is C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10 An aryl group, and R d , R e and R f Can be the same or different.

[0134] When R d , R e and R f When it is a heterocyclic group, for example, the heterocyclic group is C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 A heterocyclic group, and R d , R e and R f May be the same as or different from each other.

[0135] a″, c″, d″, and e″ may each independently be an integer of 0 to 4, and b″ may be an integer of 0 to 6.

[0136] f" and g" may each independently be an integer of 0 to 3, h" may be an integer of 0 to 2, and i" may be an integer of 0 or 1.

[0137] R 7 To R 9 Each independently selected from: deuterium; C6-C 60 Aryl group; fluorenyl group; C2-C 60 heterocyclic group, and may be bonded to form a ring.

[0138] When R 7 To R 9 When it is an aryl group, for example, the aryl group is C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10 An aryl group, and R 7 To R 9 Can be the same or different.

[0139] When R 7 To R 9 When it is a heterocyclic group, for example, the heterocyclic group is C2-C 60 Heterocyclic group, C2-C 40Heterocyclic group or C2-C 20 A heterocyclic group, and R 7 To R 9 They may be the same as or different from each other.

[0140] Z 49 , Z 50 and Z 51 can be independently CR' or N, and Z 49 , Z 50 and Z 51 At least one of can be N.

[0141] R' is independently selected from: hydrogen; deuterium; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; and may be bonded to form a ring.

[0142] When R' is an aryl group, for example, R' can be C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group or C6-C 10 aryl group, and R' may be the same as or different from each other.

[0143] When R' is a heterocyclic group, for example, R' can be C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group or C2-C 20 A heterocyclic group, and R' may be the same as or different from each other.

[0144] The compound represented by Formula 1 is represented by one of the following Formulas 1-A to 1-T.

[0145]

[0146]

[0147]

[0148] Among them, Ar in Formulas 1-A to 1-T 1 To Ar 4 , R 1 To R 3 , L 1 To L 6 , a, b, c, X, Y and Y' are the same as those in Formula 1, and R 4 To R 6 With R defined in the formula 1The same, d is an integer from 0 to 5, e is an integer from 0 to 2, f is an integer from 0 to 3, and multiple d, e, and f are the same as or different from each other.

[0149] Ar 1 To Ar 4 At least one of may be represented by the following formulae 1-1a to 1-e.

[0150]

[0151] In Formulas 1-1a to 1-1e, R 3 and c are the same as defined in Formula 1.

[0152] The compound represented by Formula 1 includes one of the following compounds, but is not limited thereto.

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] The compound contained in each of the capping layer and the organic material layer may be a single compound or two or more types of compounds having different structures.

[0159] For example, in the organic material layer, two types of compounds having different structures among the above compounds may be mixed at a molar ratio of 99:1 to 1:99.

[0160] Hereinafter, a synthesis example of the compound represented by Formula 1 and a manufacturing example of the organic electric element according to an embodiment of the present disclosure will be described in detail, but the present disclosure is not limited thereto.

[0161] [Synthesis Example]

[0162] The compound (or final product) represented by Formula 1 of the present disclosure is synthesized by reacting Sub 1 and Sub 2 as shown in the following reaction scheme 1, but is not limited thereto. 1 To L 6 ,Ar 1 To Ar 4 , R 1 , R 2 , a and b are the same as those described above with respect to Formula 1, and Hal 1 is Br, Cl or I.

[0163] <Reaction Scheme 1>

[0164]

[0165] However, if the amino group of Sub 1 is the same as that of Sub 2, the final product can be directly synthesized via Sub 1a and Sub 2.

[0166] Sub 1 of Synthesis Example

[0167] Sub 1 of Reaction Scheme 1 can be synthesized through the reaction path of the following Reaction Scheme 2, but is not limited thereto.

[0168] Hal 2 is Br, Cl or I.

[0169] <Reaction Scheme 2>

[0170]

[0171] 1. Synthesis Example of Sub 1-2

[0172]

[0173] Sub 1-2a (50 g, 111.3 mmol), Sub 1-2b (25.2 g, 111.3 mmol), Pd2(dba)3 (3.1 g, 3.3 mmol), P(t-Bu)3 (1.4 g, 6.7 mmol), NaOt-Bu (21.4 g, 222.7 mmol) and toluene (557 mL) were added to a round-bottom flask and then reacted at 50°C. Once the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic material layer was dried with MgSO4, concentrated, and the obtained organic material layer was recrystallized by silica gel column to obtain 45.1 g of product. (Yield: 74%)

[0174] 2. Synthesis Examples of Sub 1-12

[0175]

[0176] Sub 1-12a (50 g, 134.1 mmol), Sub 1-12b (52.6 g, 134.1 mmol), Pd2(dba)3 (3.7 g, 4.0 mmol), P(t-Bu)3 (1.6 g, 8.0 mmol), NaOt-Bu (25.8 g, 268.1 mmol) and toluene (670 mL) placed in a round-bottom flask were used to obtain 52.8 g of the product in the same manner as in Sub 1-2. (Yield: 72%)

[0177] In addition, the compounds belonging to Sub 1 may be, but are not limited to, the following compounds. Table 1 shows field desorption-mass spectrometry (FD-MS) values ​​of the compounds belonging to Sub 1.

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] Table 1

[0184]

[0185]

[0186] II. Synthesis of Sub 2

[0187] Substituent 2 of Reaction Scheme 1 can be synthesized according to the following Reaction Scheme 3, but is not limited to the following Reaction Scheme 3.

[0188] <Reaction Scheme 3>

[0189]

[0190] 1. Synthesis Example of Sub 2-2

[0191]

[0192] Sub 2-2a (50 g, 253.8 mmol), Sub 2-1b (23.6 g, 253.8 mmol), Pd2(dba)3 (7.0 g, 7.6 mmol), P(t-Bu)3 (3.1 g, 15.2 mmol), NaOt-Bu (48.8 g, 507.5 mmol) and toluene (1269 mL) were added to a round-bottom flask and then reacted at 80°C. After the reaction was completed, the reaction solution was extracted with CH2Cl2 and water, the organic material layer was dried with MgSO4, concentrated, and the obtained organic material was recrystallized with a silica gel column to obtain 29.0 g of the product. (Yield: 76%)

[0193] 2. Synthesis Example of Sub 2-8

[0194]

[0195] Sub 2-8a (50 g, 182.4 mmol), Sub 2-1b (17.0 g, 182.4 mmol), Pd2(dba)3 (5.0 g, 5.5 mmol), P(t-Bu)3 (2.2 g, 10.9 mmol), NaOt-Bu (35.1 g, 364.8 mmol) and toluene (912 mL) placed in a round-bottom flask were used to obtain 38.6 g of the product in the same manner as Sub 2-2. (Yield: 74%)

[0196] 3. Synthesis Example of Sub 2-44

[0197]

[0198] Sub 2-8a (50 g, 182.4 mmol), Sub 2-2b (33.4 g, 182.4 mmol), Pd2(dba)3 (5.0 g, 5.5 mmol), P(t-Bu)3 (2.2 g, 10.9 mmol), NaOt-Bu (35.1 g, 346.8 mmol) and toluene (912 mL) placed in a round-bottom flask were used to obtain 48.1 g of the product in the same manner as Sub 2-2. (Yield: 70%)

[0199] The compounds belonging to Sub 2 may be, but are not limited to, the following compounds. Table 2 shows the FD-MS values ​​of the compounds belonging to Sub 2.

[0200]

[0201]

[0202] Table 2

[0203] Compound FD-MS Compound FD-MS Sub 2-1 <![CDATA[m / z=210.08(C 13 H 10 N2O=210.24)]]> Sub 2-2 <![CDATA[m / z=169.09(C 12 H 11 N=169.23)]]> Sub 2-3 <![CDATA[m / z=275.08(C 18 H 13 NS=275.37)]]> Sub 2-4 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=403.13(C <h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> N3O2 = 403.44<h2 style=";text-align:left;direction:ltr"> Sub 2-5 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=251.07(C <h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> H9N3O2 = 251.25<h2 style=";text-align:left;direction:ltr"> Sub 2-6 <![CDATA[m / z=285.13(C 19 H 15 N3=285.35)]]> Sub 2-7 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=403.13(C <h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> N3O2 = 403.44<h2 style=";text-align:left;direction:ltr"> Sub 2-8 <![CDATA[m / z=286.11(C 19 H 14 N2O=286.33)]]> Sub 2-9 <![CDATA[m / z=286.11(C 19 H 14 N2O=286.33)]]> Sub 2-10 <![CDATA[m / z=226.06(C 13 H 10 N2S=226.3) <!-- 29 -->]]> Sub 2-11 <![CDATA[m / z=335.14(C 23 H 17 N3=335.41)]]> Sub 2-12 <![CDATA[m / z=526.2(C 38 H 26 N2O=526.64)]]> Sub 2-13 <![CDATA[m / z=260.09(C 17 H 12 N2O=260.3)]]> Sub 2-14 <![CDATA[m / z=286.12(C 18 H 14 N4=286.34)]]> Sub 2-15 <![CDATA[m / z=392.1(C 25 H 16 N2OS=392.48)]]> Sub 2-16 <![CDATA[m / z=219.1(C 16 H 13 N=219.29)]]> Sub 2-17 <![CDATA[m / z=362.14(C 25 H 18 N2O=362.43)]]> Sub 2-18 <![CDATA[m / z=416.13(C 26 H 16 N4O2=416.44)]]> Sub 2-19 <![CDATA[m / z=284.09(C 19 H 12 N2O=284.32)]]> Sub 2-20 <![CDATA[m / z=285.13(C 19 H 15 N3=285.35)]]> Sub 2-21 <![CDATA[m / z=284.09(C 19 H 12 N2O=284.32)]]> Sub 2-22 <![CDATA[m / z=286.12(C 18 H 14 N4=286.34)]]> Sub 2-23 <![CDATA[m / z=209.1(C 13 H 11 N3=209.25)]]> Sub 2-24 <![CDATA[m / z=362.15(C 24 H 18 N4=362.44)]]> Sub 2-25 <![CDATA[m / z=302.09(C 19 H 14 N2S=302.4)]]> Sub 2-26 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=211.07(C <h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> H9N3O=211.22)]]><h2 style=";text-align:left;direction:ltr"> Sub 2-27 <![CDATA[m / z=361.16(C 25 H 19 N3=361.45)]]> Sub 2-28 <![CDATA[m / z=286.11(C 19 H 14 N2O=286.33)]]> Sub 2-29 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=403.13(C <h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> N3O2 = 403.44<h2 style=";text-align:left;direction:ltr"> Sub 2-30 <![CDATA[m / z=620.2(C 42 H 28 N4S=620.77)]]> Sub 2-31 <![CDATA[m / z=250.09(C 14 H 10 N4O=250.26)]]> Sub 2-32 <![CDATA[m / z=412.16(C 29 H 20 N2O=412.49)]]> Sub 2-33 <![CDATA[m / z=285.13(C 19 H 15 N3=285.35)]]> Sub 2-34 <![CDATA[m / z=167.07(C 12 H9N=167.21)]]> Sub 2-35 <![CDATA[m / z=437.19(C 31 H 23 N3=437.55)]]> Sub 2-36 <![CDATA[m / z=302.09(C 19 H 14 N2S=302.4)]]> Sub 2-37 <![CDATA[m / z=392.1(C 25 H 16 N2OS=392.48)]]> Sub 2-38 <![CDATA[m / z=286.11(C 19 H 14 N2O=286.33)]]> Sub 2-39 <![CDATA[m / z=286.12(C 18 H 14 N4=286.34)]]> Sub 2-40 <![CDATA[m / z=362.15(C 24 H 18 N4=362.44)]]> Sub 2-41 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=403.13(C <h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> N3O2 = 403.44<h2 style=";text-align:left;direction:ltr"> Sub 2-42 <![CDATA[m / z=401.16(C 26 H 19 N5=401.47)]]> Sub 2-43 <![CDATA[m / z=284.09(C 19 H 12 N2O=284.32)]]> Sub 2-44 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=376.12(C <h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 16 <h2 style=";text-align:left;direction:ltr"> N2O2 = 376.42<h2 style=";text-align:left;direction:ltr">

[0204] III. Synthesis Example of Final Product

[0205] 1. Synthesis Example of P-2

[0206]

[0207] Sub 1-2 (45.1 g, 82.4 mmol), Sub 2-2 (13.9 g, 82.4 mmol), Pd2(dba)3 (2.3 g, 2.5 mmol), P(t-Bu)3 (1.0 g, 4.9 mmol), NaOt-Bu (15.8 g, 164.8 mmol) and toluene (412 mL) placed in a round-bottom flask were used to obtain 35.6 g of the product in the same manner as Sub 2-2. (Yield: 68%)

[0208] 2. Synthesis Example of P-12

[0209]

[0210] Sub 1-12 (52.8 g, 84.7 mmol), Sub 2-2 (14.3 g, 84.7 mmol), Pd2(dba)3 (2.3 g, 2.5 mmol), P(t-Bu)3 (1.0 g, 5.1 mmol), NaOt-Bu (16.3 g, 169.3 mmol) and toluene (423 mL) placed in a round-bottom flask were used to obtain 47.3 g of the product in the same manner as in Sub 2-2. (Yield: 77%)

[0211] 3. Synthesis Example of P-41

[0212]

[0213] Sub 1-41 (50.0 g, 101.2 mmol), Sub 2-23 (42.3 g, 202.3 mmol), Pd2(dba)3 (2.8 g, 3.0 mmol), P(t-Bu)3 (1.2 g, 6.1 mmol), NaOt-Bu (19.4 g, 202.3 mmol) and toluene (506 mL) placed in a round-bottom flask were used to obtain 53.9 g of the product in the same manner as Sub 2-2. (Yield: 71%)

[0214] 4. Synthesis Example of P-63

[0215]

[0216] Sub 1-63a (50.0 g, 146.2 mmol), Sub 2-8 (83.7 g, 292.4 mmol), Pd2(dba)3 (4.0 g, 4.4 mmol), P(t-Bu)3 (1.8 g, 8.8 mmol), NaOt-Bu (28.1 g, 292.4 mmol) and toluene (731 mL) placed in a round-bottom flask were used to obtain 86.9 g of the product in the same manner as Sub 2-2. (Yield: 79%)

[0217] 5. Synthesis Example of P-67

[0218]

[0219] Sub 1-67a (50.0 g, 46.2 mmol), Sub 2-8 (83.7 g, 292.4 mmol), Pd2(dba)3 (4.0 g, 4.4 mmol), P(t-Bu)3 (1.8 g, 8.8 mmol), NaOt-Bu (28.1 g, 292.4 mmol) and toluene (731 mL) placed in a round-bottom flask were used to obtain 88.0 g of the product in the same manner as in Sub 2-2. (Yield: 80%)

[0220] In addition, the FD-MS values ​​of the compounds P-1 to P-88 of the present disclosure prepared according to the above-mentioned synthesis examples are shown in Table 3.

[0221] Table 3

[0222]

[0223]

[0224] Evaluation of organic electrical component manufacturing

[0225] Embodiment 1) Evaluation of blue organic electrical element manufacturing

[0226] [Example 1] to [Example 20] Blue organic light emitting element (covering layer)

[0227] An organic light-emitting element is manufactured by conventional methods using the compounds disclosed in the present invention as an auxiliary light-emitting layer. First, an indium tin oxide (ITO) layer (i.e., a positively charged electrode) is formed on a glass substrate, and a hole injection layer is formed on the indium tin oxide layer by vacuum depositing 60 nm thick 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as "2-TNATA"), and then a hole transport layer is formed on the hole injection layer by vacuum depositing 60 nm thick N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as "NPB") . Next, a light-emitting layer is formed on the hole transport layer by vacuum depositing a main material with a thickness of 30 nm. The main material is a dopant material BD-052X (Idemitsu Then, a hole blocking layer was formed on the light-emitting layer by vacuum depositing (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter referred to as "BAlq") with a thickness of 10 nm, and then a hole blocking layer was formed on the hole blocking layer by vacuum depositing 45 nm thick Tris(8-hydroxyquinoline)aluminum (hereinafter referred to as "Alq3") and bis(10-hydroxybenzo[h]hydroxyquinoline)beryllium (hereinafter referred to as "BeBq2") mixed in a ratio of 1:1 form an electron transport layer. Thereafter, an electron injection layer is formed by depositing an alkali metal halide LiF with a thickness of 0.2nm, and then a negatively charged electrode is formed by depositing Al with a thickness of 150nm. In this way, an organic light-emitting element is manufactured by forming a capping layer with a thickness of 60nm on the compound of the present disclosure represented by Formula 1 as shown in Table 4.

[0228] [Comparative Example 1]

[0229] An organic light emitting element was manufactured in the same manner as in Example 1, except that no capping layer was used.

[0230] [Comparative Examples 2 to 5]

[0231] An organic light emitting element was manufactured in the same manner as in Example 1, except that the following Comparative Compounds 1 to 4 were used as a covering layer material instead of the compound represented by Formula 1 of the present disclosure.

[0232]

[0233] The electroluminescence (EL) performance of the organic light emitting elements manufactured according to Examples 1 to 20 and Comparative Examples 1 to 5 of the present disclosure was measured by applying a forward bias DC voltage to the organic light emitting elements using a PR-650 purchased from Photo Research. The T95 lifetime of the manufactured organic light emitting elements was measured using a lifetime measurement device manufactured by McScience at 500 cd / m 2 The measurement results are shown in Table 4 below.

[0234] [Table 4]

[0235]

[0236] Implementation 2) Evaluation of green organic electrical device production

[0237] [Example 21] to [Example 40] Green organic light emitting element (covering layer)

[0238] An organic light-emitting element was manufactured in the same manner as in Example 1, except that CBP [4,4'-N,N'-dicarbazole-biphenyl] was used instead of 9,10-di(naphthalene-2-yl)anthracene as the host, and tri(2-phenylpyridine)-iridium was used instead of BD-052X (Idemitsu kosan) as the dopant, and the host and the dopant were used in a weight ratio of 95:5.

[0239] [Comparative Example 6]

[0240] An organic light emitting element was manufactured in the same manner as in Example 21, except that no capping layer was used.

[0241] [Comparative Examples 7 to 10]

[0242] An organic light emitting element was manufactured in the same manner as in Example 21, except that Comparative Compounds 1 to 4 were used as a capping layer material instead of the compound represented by Formula 1 of the present disclosure.

[0243] The electroluminescent (EL) characteristics of the organic light emitting elements manufactured according to Examples 21 to 40 and Comparative Examples 6 to 10 of the present disclosure were measured by applying a forward bias DC voltage to the organic light emitting elements using a PR-650 available from Photo Research. The T95 lifetime of the manufactured organic light emitting elements was measured using a lifetime measurement device manufactured by McScience at 5000 cd / m 2 The measurement results are shown in Table 5 below.

[0244] Table 5

[0245]

[0246]

[0247] Embodiment 3) Evaluation of the production of red organic electrical components

[0248] [Example 41] to [Example 60] Red organic light emitting element (covering layer)

[0249] An organic light-emitting element was manufactured in the same manner as in Example 1, except that CBP [4,4'-N,N'-dicarbazole-biphenyl] was used instead of 9,10-di(naphthalene-2-yl)anthracene as the host, and (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate] was used instead of BD-052X (Idemitsu Kosan) as the dopant, and the host and the dopant were used in a weight ratio of 95:5.

[0250] [Comparative Example 11]

[0251] An organic light emitting element was manufactured in the same manner as in Example 41, except that no cover layer was used.

[0252] [Comparative Examples 12 to 15]

[0253] An organic light emitting element was manufactured in the same manner as in Example 41, except that Comparative Compounds 1 to 4 were used instead of the compound represented by Formula 1 of the present disclosure as a capping layer material.

[0254] The electroluminescent (EL) characteristics of the organic light emitting elements manufactured in Examples 41 to 60 and Comparative Examples 11 to 15 of the present disclosure were measured by applying a forward bias DC voltage to the organic light emitting elements using a PR-650 available from Photo Research. The T95 lifetime of the manufactured organic light emitting elements was measured using a lifetime measurement device manufactured by McScience at 2500 cd / m 2 The measurement results are shown in Table 6 below.

[0255] [Table 6]

[0256]

[0257]

[0258] As can be seen from the results of Tables 4 to 6, when the organic light-emitting element material of the present disclosure is used as the covering layer material represented by Formula 1 to manufacture the organic light-emitting element, the organic light-emitting element can have high purity and improved luminous efficiency compared to the comparative example. Comparing the results with and without the covering layer, it can be seen that the color purity and luminous efficiency are improved by introducing the covering layer. It can be seen that when the compound of the present invention is used as the covering layer instead of the comparative compounds 1 to 4, the luminous efficiency is significantly improved.

[0259] When the cover layer is introduced, SPP (surface plasmon polariton) is generated at the interface between the aluminum electrode and the high-refractive organic material. In this case, TE (transverse electric) polarized light is annihilated by the evanescent wave in the vertical direction on the surface of the cover layer, and TM polarized light moving along the cathode and the cover layer is amplified by the surface plasmon resonance, thereby achieving high efficiency and effective color purity control.

[0260] As described above, in the visible light band of 430 nm to 780 nm, the compound disclosed in the present invention includes a substituent as a core and dibenzothiophene or dibenzofuran containing a sulfur or oxygen atom (which is a heteroelement with a high refractive index), in which a benzene ring such as benzimidazole or benzoxazole and a 5-membered ring having at least one N are fused to increase the refractive index, and thus has a higher refractive index than that of the comparative compound B or the comparative compound C. Therefore, the light emitted in the organic material layer is extracted more efficiently to the outside of the organic light-emitting element due to the principle of constructive interference, thereby greatly contributing to improving the light efficiency of the light-emitting element.

[0261] The above description provides the embodiments of the present disclosure for illustrative purposes only. Persons with ordinary knowledge in the technical field to which the present disclosure belongs should understand that various modifications can be made without departing from the basic features of the present disclosure. Therefore, the embodiments disclosed in the present disclosure are intended to illustrate the technical ideas of the present disclosure, and the scope of the present disclosure is not limited by these embodiments.

[0262] The scope of the present disclosure should be interpreted based on the appended claims, and the interpretation method is that all technical ideas included in the equivalent scope of the claims belong to the present disclosure.

[0263] [Explanation of symbols]

[0264] 100, 200, 300: organic electrical components

[0265] 110, 110, 310: First electrode

[0266] 120, 220, 320: hole injection layer

[0267] 321: First hole injection layer

[0268] 130, 230: Hole transport layer

[0269] 331: First hole transport layer

[0270] 332: Second hole transport layer

[0271] 243: Buffer layer

[0272] 253: Luminous auxiliary layer

[0273] 140, 240: Luminous layer

[0274] 341: First light-emitting layer

[0275] 342: Second luminous layer

[0276] 150, 250: Electron transport layer

[0277] 351: First electron transport layer

[0278] 352: Second electron transport layer

[0279] 160, 260, 360: electron injection layer

[0280] 170, 270, 370: Second electrode

[0281] 180, 280, 380: Overlay

[0282] 390: First charge generation layer

[0283] 391: Second charge generation layer

[0284] ST1: First stack

[0285] ST2: Second stack

[0286] CGL: Charge Generation Layer

[0287] CROSS-REFERENCE TO RELATED APPLICATIONS

[0288] Pursuant to Section 119(a) of the United States Patent Act (35 USC §119(a)), the entire text of Patent Application No. 10-2019-0075219 filed in Korea on June 24, 2019 is incorporated herein by reference for all purposes as if fully described herein. In addition, if this patent application claims priority in a country other than the United States for the same reasons as above, the entire contents of the priority document are incorporated by reference into this patent application.

Claims

1. An organic electrical component, comprising: a first electrode; a second electrode; an organic material layer, the organic material layer being located between the first electrode and the second electrode, and a covering layer provided on at least one of a surface of the first electrode opposite to the organic material layer and a surface of the second electrode opposite to the organic material layer, Wherein, the covering layer includes a compound represented by the following formula 1: Formula 1 Formula 1-1 In formula 1, 1) Ar 1 To Ar 4 Each independently selected from: C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 2) Ar 1 To Ar 4 At least one of is represented by Formula 1-1, 3) L 1 and L 2 Each is independently selected from: a single bond; C1-C 50 Alkylene group; C2-C 20 Alkenylene group; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 4) L 3 To L 6 Each is independently selected from: a single bond; C1-C 50 Alkylene group; C2-C 20 Alkenylene group; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 5) R 1 and R 2 Each independently selected from: deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-N(R a )(R b ), and one or more adjacent R 1 are the same or different and multiple R 1 bonded to form a ring, and one or more adjacent R 2 are the same or different and multiple R 2 Combine to form a ring, 6) R 3 Selected from: Deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; and -L'-N(R a )(R b ), and one or more adjacent R 3 are the same or different and multiple R 3 Bonding to form a ring, 7) a and b are each independently an integer from 0 to 3, c is an integer from 0 to 4, and when Ar 1 To Ar 4 When two or more of are represented by Formula 1-1, the plurality of c are the same or may be different, 8) L' is independently selected from: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 9) R a and R b Each independently selected from: C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 10) X is O or S, 11) Ring A is each independently C6-C 30 Aryl groups, 12) Y is each independently CR a R b or NR c , when Y is bonded to Formula 1, Y may be N or C; 13) Y' is each independently N, O or S, 14) R a , R b and R c Each independently represents: hydrogen; deuterium; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 15) Adjacent L 1 With R 1 , L 1 with Ar 1 , L 1 with Ar 2 , L 1 With L 3 , L 1 With L 4 , adjacent L 2 With R 2 , L 2 with Ar 3 , L 2 with Ar 4 , L 2 With L 5 , L 2 With L 6 Bonding to form a ring, 16) In Ar 1 To Ar 4 , L 1 To L 6 , R 1 To R 3 , R a and R b In the formula (A), each of the aryl group, fluorenyl group, heterocyclic group, condensed ring group, alkyl group, alkenyl group, alkylene group, arylene group and fluorenylene group is further substituted by one or more substituents selected from the group consisting of deuterium, nitro group, nitrile group, halogen group, amino group, C1-C 20 Alkylthio groups, C1-C 20 Alkoxy groups, C1-C 20 Alkyl groups, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C6-C 20 Aryl groups, deuterium-substituted C6-C 20 Aryl group, fluorenyl group, C2-C 20 Heterocyclic group, C3-C 20 Cycloalkyl groups, C7-C 20 Arylalkyl groups and C8-C 20 Arylalkenyl groups, these substituents allow bonding to form a ring; and each substituent is further substituted by one or more substituents selected from: deuterium, nitro groups, nitrile groups, halogen groups, amino groups, C1-C 20 Alkylthio groups, C1-C 20 Alkoxy groups, C1-C 20 Alkyl groups, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C6-C 20 Aryl groups, deuterium substituted C6-C 20 Aryl group, fluorenyl group, C2-C 20 Heterocyclic group, C3-C 20 Cycloalkyl groups, C7-C 20 Arylalkyl groups and C8-C 20 The arylalkenyl group, and the substituents allow bonding to form a ring.

2. The organic electric element according to claim 1, wherein 1) Ar 1 To Ar 4 Each independently selected from: C6-C 25 An aryl group; a fluorenyl group; and a C2-C 20 Heterocyclic groups, 2) L 1 and L 2 Each is independently selected from: a single bond; C6-C 25 An arylene group; a fluorenyl group; and a C2-C 20 Heterocyclic groups, 3) L 3 To L 6 Each is independently selected from: a single bond; C6-C 25 An arylene group; a fluorenyl group; and a C2-C 20 Heterocyclic groups, 4) R 1 and R 2 Each independently selected from deuterium, C6-C 25 An aryl group, a fluorenyl group, and a C2-C4-C6 ... 20 A heterocyclic group, and adjacent R1s may be bonded to each other to form a ring, and adjacent R2s may be bonded to each other to form a ring, 6) R 3 Each independently selected from deuterium, C6-C 25 An aryl group, a fluorenyl group, a C2-C4- 20 A heterocyclic group, and adjacent R3 may be bonded to each other to form a ring, 7) Ring A is independently selected from benzene, naphthalene, phenanthrene and anthracene, 8) R a , R b and R c Each independently selected from: hydrogen; deuterium; C6-C 25 An aryl group; a fluorenyl group; and a C2-C 20 Heterocyclic group.

3. The organic electric element according to claim 1, wherein The compound represented by Formula 1 is represented by one of the following Formulas 1-A to 1-E: Wherein, Ar in Formulas 1-A to 1-E 1 To Ar 3 , R 1 To R 3 , L 1 To L 6 , a, b, c, X, Y and Y' are the same as defined in Formula 1 of Claim 1.

4. The organic electric element according to claim 1, wherein The compound represented by Formula 1 is represented by one of the following Formulas 1-F to 1-L: Among them, Ar in Formulas 1-F to 1-L 1 To Ar 4 , R 1 , L 1 To L 6 , a and X are the same as those defined in Formula 1 of claim 1, R 4 R defined in claim 1 1 The same, d is an integer from 0 to 5, and multiple d's are the same as or different from each other.

5. The organic electric element according to claim 1, wherein The compound represented by Formula 1 is represented by one of the following Formulas 1-M to 1-O, Among them, Ar in formula 1-M to 1-O 1 To Ar 4 , R 1 , L 1 To L 6 , a, b and X are the same as those defined in Formula 1 of claim 1, R 5 and R 6 R defined in claim 1 1 The same, e is an integer from 0 to 2, and the multiple e's are the same as or different from each other, f is an integer from 0 to 3, and the multiple f's are the same as or different from each other.

6. The organic electric element according to claim 1, wherein The compound represented by Formula 1 is represented by one of the following Formulas 1-P and 1-Q: Among them, Ar in formula 1-P to 1-Q 1 To Ar 4 , R 1 , R 2 , L 1 To L 6 , a and b are the same as defined in Formula 1 of claim 1.

7. The organic electric element according to claim 1, wherein The compound represented by Formula 1 is represented by one of the following Formulas 1-R to 1-T: Among them, Ar in formula 1-R to 1-T 1 To Ar 4 , R 1 , R 2 , L 1 To L 6 , a and b are the same as defined in Formula 1 of claim 1.

8. The organic electrical device according to claim 1, wherein Ar 1 To Ar 4 One is represented by one of the following formulae 1-1a to 1-1e: in, R in Formulas 1-1a to 1-1e 3 and c are the same as defined in Formula 1 of Claim 1.

9. The organic electric device according to claim 1, characterized in that: The compound represented by Formula 1 includes one of the following compounds: 。 10. The organic electrical element according to claim 1, wherein the organic material layer comprises 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, and 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 or an electron injection layer included in the organic material layer includes the compound represented by Formula 1.

11. The organic electric element according to claim 1, wherein The organic material layer includes: a first stack; a charge generation layer, the charge generation layer is located on the first stack; and a second stack, the second stack is located on the charge generation layer; and The first stack includes a first light-emitting layer, and the second stack includes a second light-emitting layer.

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