Compound for organic electric element, organic electric element using the compound, and electronic device including the organic electric element

Abstract

The present invention provides an organic electronic element and an electronic device including the organic electronic element. The organic electronic element includes an anode, a cathode, and an organic material layer and a covering layer formed between the anode and the cathode, wherein the covering layer contains the compound of the present invention represented by Chemical Formula 1, thereby reducing the driving voltage of the organic electronic element and improving the luminous efficiency and service life of the organic electronic element.

Description

Technical Field

[0001] The present invention relates to an organic electronic component including a cover layer and an electronic device including the organic electronic component. Background Art

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

[0003] Materials used as organic material layers in organic electronic elements can be divided into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. Moreover, light-emitting materials can be divided into high molecular weight type and low molecular weight type according to molecular weight, and can be divided into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to the light-emitting mechanism. In addition, light-emitting materials can be divided into blue light-emitting materials, green light-emitting materials, and red light-emitting materials according to the light-emitting color, as well as yellow light-emitting materials and orange light-emitting materials necessary to achieve more natural colors.

[0004] However, when only one material is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and there is a problem of reduced color purity or reduced device efficiency due to the emission attenuation effect. Therefore, in order to increase color purity and increase luminous efficiency through energy transfer, a host / dopant system can be used as a light-emitting material. The principle is that when a small amount of a dopant having a smaller band gap than the band gap of the host forming the light-emitting layer is mixed in the light-emitting layer, the excitons generated in the light-emitting layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light with a desired wavelength can be obtained according to the type of dopant used.

[0005] In organic light-emitting diodes, the biggest issues are lifespan and efficiency. As displays become larger, efficiency and lifespan issues must be addressed. Efficiency, lifespan, driving voltage, etc. are related to each other. As efficiency increases, driving voltage decreases relatively, and as driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases, so lifespan tends to increase.

[0006] However, simply improving the organic material layer cannot maximize efficiency. This is because long life and high efficiency can only be achieved when the optimal combination of energy levels and T1 values ​​between organic material layers and the inherent properties of the material (mobility, interface characteristics, etc.) is achieved.

[0007] Therefore, it is necessary to develop a light-emitting material that has high thermal stability and can effectively achieve charge balance in the light-emitting layer. In other words, in order to fully demonstrate the excellent characteristics of organic electronic components, the materials constituting the organic material layer in the component (such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc.) need to be stable and effective materials, however, stable and effective organic material layer materials for organic electronic components have not yet been fully developed, among which, it is urgent to develop materials for the light-emitting layer.

[0008] Recently, in addition to the research on improving the characteristics of the element by changing the performance of each material, in the top element with a resonant structure, the technology of improving color purity and increasing efficiency by optimizing the optical thickness between the anode and the cathode is one of the important factors for improving the performance of the element. Compared with the bottom element structure of the non-resonant structure, the top element structure has a large light energy loss due to surface plasmon (SPP), because the formed light is reflected by the anode as a reflective film and emitted toward the cathode. Therefore, one of the important methods for improving the shape and efficiency of the EL spectrum is the method of using a light efficiency enhancement layer for the top cathode. Generally, in SPP, these four metals (such as Al, Pt, Ag and Au) are mainly used for electron emission, and surface plasma is generated on the surface of the metal electrode. For example, when the cathode uses Ag, the light emitted by the Ag of the cathode is quenched by SPP (due to the light energy loss caused by Ag), and the efficiency is reduced.

[0009] In contrast, when a light efficiency enhancement layer is used, SPP occurs at the interface between the MgAg electrode and the high-refractive organic material, and in which TE (transverse electric) polarized light is extinguished in the vertical direction by the evanescent wave at the surface of the light efficiency enhancement layer, and in the TM (transverse magnetic) polarized light moving along the cathode and the light efficiency enhancement layer, the wavelength is amplified due to the surface plasmon resonance, which increases the intensity of the peak, and ultimately, high-efficiency and effective color purity control is feasible. Summary of the invention

[0010] The present invention uses MgAg having an Ag ratio of 80% or more as a cathode and a capping material having a loss tangent value of 0.001 or less at a wavelength of 450 nm to realize a high-efficiency, long-life element, which are characteristics required of an organic electronic element.

[0011] [Technical solution]

[0012] In one aspect, the present invention provides an organic electronic element, wherein the organic electronic element includes: an anode; a cathode; an organic material layer formed between the anode and the cathode; and a covering layer; wherein the organic material layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the electron transport region includes an electron transport layer and an electron injection layer, wherein the anode is a mixture of magnesium (Mg) and silver (Ag), wherein the ratio of the silver (Ag) is 80% or greater, and wherein the covering layer contains a compound satisfying Formula 1 at a wavelength of 450 nm.

[0013] [Equation 1]

[0014] tanδ(loss tangent)≤0.001

[0015] in,

[0016] 1)tanδ is ε 2 / ε 1 ,

[0017] 2)ε 2 is the imaginary part of the complex dielectric constant of the dielectric material, representing the dielectric loss, expressed as 2nk,

[0018] 3)ε 1 is the real part of the complex dielectric constant, representing the dielectric constant, given by n 2 -k 2 express,

[0019] 4) n is the refractive index and k is the absorption coefficient.

[0020] In addition, the cover layer satisfies Equation 1 and is represented by Equation 1.

[0021] [Formula 1]

[0022]

[0023] In another aspect, the present invention provides an electronic device comprising the organic electronic element.

[0024] [Effects of the invention]

[0025] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and the color purity and life of the element can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figures 1 to 3 Examples of the organic electronic element according to the present invention are illustrated.

[0027] 100, 200, 300: organic electronic element 110: first electrode

[0028] 120: hole injection layer 130: hole transport layer

[0029] 140: Light-emitting layer 150: Electron transport layer

[0030] 160: electron injection layer 170: second electrode

[0031] 180: Covering layer (light efficiency enhancement layer)

[0032] 210: Buffer layer

[0033] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0034] 330: first hole transport layer 340: first light emitting layer

[0035] 350: first electron transport layer 360: first charge generation layer

[0036] 361: second charge generation layer 420: second hole injection layer

[0037] 430: second hole transport layer 440: second light emitting layer

[0038] 450: Second electron transport layer CGL: Charge generation layer

[0039] ST1: first stack ST2: second stack DETAILED DESCRIPTION

[0040] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, when a detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0041] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to limit the substance, order or sequence of the corresponding component, but is only used to distinguish the corresponding component from other components. It should be noted that if a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected", "coupled" or "connected" between the components.

[0042] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0043] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0044] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms and means a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0045] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes a straight chain or branched chain group.

[0046] Unless otherwise specified, the term "cycloalkyl group" as used herein means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0047] Unless otherwise specified, the term "alkoxy," "alkoxy group," or "alkyloxy" as used herein means an oxy group attached to an alkyl group having 1 to 60 carbon atoms, but is not limited thereto.

[0048] Unless otherwise specified, the term “aryloxy group” or “aryloxy group” as used herein means that an oxy group is connected to an aryl group having 6 to 60 carbon atoms, but is not limited thereto.

[0049] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. Herein, aryl groups or arylene groups mean monocyclic and polycyclic aromatic groups, and may also be formed by combining with adjacent groups. Examples of "aryl groups" may include phenyl groups, biphenyl groups, fluorene groups, or spirofluorene groups.

[0050] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl can be an alkyl substituted by an aryl group, and arylalkenyl can be an alkenyl substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0051] In addition, when the prefixes are named sequentially, this means that the substituents are listed in the order first described. For example, arylalkoxy means an alkoxy group substituted by an aryl group, alkoxycarbonyl means a carbonyl group substituted by an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted by an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0052] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, has 2 to 60 carbon atoms, but is not limited thereto, includes any one of a monocyclic ring and a polycyclic ring, and may include a heteroaliphatic ring and / or a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0053] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0054] In addition, the term "heterocyclic group" may include a ring containing SO2 instead of carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0055]

[0056] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R' and R" in the following structure are all hydrogen, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0057]

[0058] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. At this time, the atom shared by the two rings is called a "spiro atom", and these compounds are respectively called "single spiro-", "double spiro-" and "triple spiro-" according to the number of atoms in the compound.

[0059] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0060] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

[0061] In addition to the above-mentioned hetero compounds, other hetero compounds or hetero groups contain one or more hetero atoms, but are not limited thereto.

[0062] Unless otherwise specified, the term "substituted or unsubstituted" as used herein means that the substitution is substituted by at least one substituent selected from deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 Alkylthiophene group, C6-C 20Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 Aryl groups, deuterated C6-C 20 Aryl group, C8-C 20 Arylene groups, silane groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but not less than these.

[0063] Unless expressly stated otherwise, the formulae for the present invention as used herein apply in the same manner as the definitions of substituents according to the definitions of the indices of the following formulae.

[0064]

[0065] When a is an integer equal to zero, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 When a is an integer of 2 or 3, each substituent R 1 may be the same or different, and when a is an integer of 4 to 6, is connected to the benzene ring in a similar manner, but indication of hydrogen bonded to carbon forming the benzene ring is omitted.

[0066]

[0067] In the following, reference will be made to Figures 1 to 3 Laminated structures of organic electronic components comprising the compounds according to the invention are described.

[0068] When adding reference numerals to the components of each drawing, it should be noted that even if the same components are shown on different drawings, the same components should be given the same reference numerals as much as possible. In addition, when describing the present invention, if it is determined that the detailed description of related known configurations or functions may confuse the main points of the present invention, the detailed description thereof will be omitted.

[0069] Figures 1 to 3 is an exemplary view of an organic electronic element according to an embodiment of the present invention.

[0070] refer to Figure 1 , an organic electronic element (100) according to an embodiment of the present invention includes a first electrode (110) formed on a substrate (not shown), a second electrode (170), and an organic material layer formed between the first electrode (110) and the second electrode (170).

[0071] The first electrode (110) may be an anode (positive electrode), and the second electrode (170) may be a cathode (negative electrode). In the case of an inverted organic electronic element, the first electrode may be a cathode, and the second electrode may be an anode.

[0072] 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 formed on the first electrode (110).

[0073] Preferably, the cover layer (light efficiency enhancement layer; 180) can be formed on one side of both surfaces of the first electrode (110) or the second electrode (170), which surface is not in contact with the organic material layer. When the cover layer (180) is formed, the light efficiency of the organic electronic element can be improved.

[0074] For example, a capping layer (180) may be formed on the second electrode (170), and in the case of a top-emitting organic light-emitting device, light energy loss due to surface plasmon polaritons (SPP) in the second electrode (170) may be reduced by forming the capping layer (180), and in the case of a bottom-emitting organic light-emitting device, the capping layer (180) may be used as a buffer for the second electrode (170).

[0075] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will be referred to in detail. Figure 2 Give a description.

[0076] refer to Figure 2 According to another embodiment of the present invention, an organic electronic element (200) includes a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160) and a second electrode (170) formed in sequence on a first electrode (110), and a covering layer can be formed on the second electrode (170).

[0077] although Figure 2 Although not shown, an electron transport auxiliary layer may be further formed between the light emitting layer (140) and the electron transport layer (150).

[0078] In addition, the organic material layer according to another embodiment of the present invention may have a form in which a plurality of stacked bodies including a hole transport layer, a light emitting layer, and an electron transport layer are formed. Figure 3 Give a description.

[0079] refer to Figure 3 According to another embodiment of the present invention, an organic electronic element (300) includes 2 or more groups of stacks of multi-layer organic material layers ST1 and ST2 between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stacks of organic material layers.

[0080] Specifically, the organic electronic element according to the embodiment of the present invention includes a first electrode (110), a first stack (ST1), a charge generation layer (CGL), a second stack (ST2), a second electrode (170), and a buffer layer (180).

[0081] The first stack (ST1) is an organic material layer formed on the first electrode (110), and includes 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). In this way, the first stack and the second stack may be organic material layers having the same stack structure, but may also be organic material layers having different stack structures.

[0082] 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 a first charge generation layer (360) and a second charge generation layer (361). The charge generation layer (CGL) is formed between the first light emitting layer (340) and the second light emitting layer (440) to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.

[0083] When through Figure 3 When a plurality of light-emitting layers are formed by the multilayer stack structure method shown in FIG. 1 , an organic electroluminescent device that emits white light by a mixing effect of light emitted from each light-emitting layer can be manufactured, and an organic electroluminescent device that emits light of various colors can be manufactured.

[0084] The compound represented by Formula 1 of the present invention may be used as a material of the capping layer (180).

[0085] Even with the same and similar cores, the band gap, electrical properties, interface properties, etc. can vary depending on the position of the substituent bonded, so it is necessary to study the selection of the core and the combination of the substituents bonded thereto. In particular, when the energy levels and T1 values ​​between the organic material layers and the inherent properties of the materials (mobility, interface properties, etc.) are optimally combined, long service life and high efficiency can be achieved simultaneously.

[0086] The organic electroluminescent device according to the embodiment of the present invention can be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, the anode (110) is formed by depositing a conductive metal or metal oxide or an alloy thereof on a substrate, and an organic material layer including a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150) and an electron injection layer (160) is formed thereon, and then a material that can be used as a cathode (170) is deposited thereon.

[0087] In addition, a light-emitting auxiliary layer (220) may be formed between the hole transport layer (130) and the light-emitting layer (140), and an electron transport auxiliary layer (not shown) may be formed between the light-emitting layer (140) and the electron transport layer (150), and a stacked structure as shown may also be formed.

[0088] In addition, the organic material layer can be manufactured with a small number of layers by using various polymer materials, not by a deposition method, but by a solution process or a solvent process, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a doctor blade process, a screen printing process or a thermal transfer method. Since the organic material 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.

[0089] Furthermore, the organic electronic element according to an embodiment of the present invention may be selected from an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.

[0090] Another embodiment of the present invention may include a display device comprising the organic electronic 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 / wireless communication terminal, and includes all electronic devices, such as mobile communication terminals such as portable phones, PDAs, electronic dictionaries, PMPs, remote controllers, navigation systems, game consoles, various TVs, and various computers.

[0091] Hereinafter, an organic electronic element according to aspects of the present invention will be described.

[0092] An organic electronic element according to an embodiment of the present invention includes: an anode; a cathode; an organic material layer formed between the anode and the cathode; and a covering layer; wherein the organic material layer includes a hole transport region, a light-emitting layer and an electron transport region, wherein the electron transport region includes an electron transport layer and an electron injection layer, wherein the cathode is a mixture of magnesium (Mg) and silver (Ag), wherein the ratio of silver (Ag) is 80% or greater, and wherein the covering layer contains a compound that satisfies Equation 1 at a wavelength of 450 nm.

[0093] [Equation 1]

[0094] tanδ(loss tangent)≤0.001

[0095] in,

[0096] 1)tanδ is ε 2 / ε 1 ,

[0097] 2)ε 2 is the imaginary part of the complex dielectric constant of the dielectric material, representing the dielectric loss, expressed as 2nk,

[0098] 3)ε 1 is the real part of the complex dielectric constant, representing the dielectric constant, expressed as n 2 -k 2 ,

[0099] 4) n is the refractive index and k is the absorption coefficient.

[0100] In the prior art, semi-transparent electrodes such as LiF / Al / Ag, Ca / Mg and LiF / MgAg are used as cathodes. However, most of them are technologies with Mg content greater than 80% and Ag content less than 20%, and there is no prior art report proving the relevant effects of anodes with Ag content of 80% or more as in the present invention.

[0101] Therefore, the present invention has experimentally confirmed that the higher the Ag content (80% or higher), the better the conductivity, and the reflectivity is similar to the reflectivity when the Ag content is less than 20%, but the absorbance is reduced and the transmittance is increased, so that the light loss of the cathode can be reduced and the critical angle is increased, thereby significantly improving the efficiency of the element.

[0102] In Equation 1, the loss tangent (tan δ) is an index indicating the loss characteristics of a dielectric and is expressed as the imaginary part (ε 2 ) / real part (ε 1 The imaginary part of the dielectric constant itself means dielectric loss, and since the degree of loss varies depending on the size of the real part of the dielectric constant, it is expressed in the same ratio as imaginary part / real part.

[0103] Tan δ does not mean taking the tangent of the δ value, but is an exponent derived because horizontal is real and vertical is imaginary in the complex dielectric constant coordinate system. In other words, the imaginary part / real part is ultimately the ratio of vertical / horizontal and is mathematically equivalent to tangent.

[0104] The loss tangent is an index that expresses the loss characteristics of a dielectric, so the smaller the value, the better, and it is mainly used as a characteristic index of a microstrip substrate or a dielectric resonator.

[0105] Furthermore, the present invention provides an organic electronic element necessarily containing ytterbium (Yb) as a lanthanoid element in an electron transport region.

[0106] The higher the Ag content, the higher the transmittance, and the higher the conductivity, and thus the efficiency is greatly improved, but the driving voltage of the element may be slightly reduced due to poor electron injection characteristics. Therefore, it was confirmed that by using Yb with good conductivity for the electron injection layer, the existing advantages can be utilized and these disadvantages can be fully overcome.

[0107] Furthermore, the present invention provides an organic electronic element including a capping layer compound having a refractive index of 2.1 or more at a wavelength of 450 nm, a refractive index of 1.95 or more at a wavelength of 530 nm, and a refractive index of 1.85 or more at a wavelength of 620 nm.

[0108] Furthermore, the capping layer compound has a refractive index difference of 0.08 or more at wavelengths of 430 nm and 460 nm.

[0109] Furthermore, the absorption coefficient of the covering layer compound is 0.3 or more at a wavelength of 410 nm.

[0110] Furthermore, the absorption coefficient of the covering layer compound is 0.1 or more at a wavelength of 410 nm to 430 nm.

[0111] In addition, the cover compound is -5 mol / l concentration, has an absorbance of 0.2 or more at a wavelength of 400 nm to 410 nm in the absorption spectrum.

[0112] In addition, the present invention provides a compound for a cover layer of an organic electronic element, the compound satisfying Formula 1 and represented by Formula 1.

[0113] [Equation 1]

[0114] tanδ(loss tangent)≤0.001

[0115] in,

[0116] 1)tanδ is ε2 / ε 1 ,

[0117] 2)ε 2 is the imaginary part of the complex dielectric constant of the dielectric material, representing the dielectric loss, expressed as 2nk,

[0118] 3)ε 1 is the real part of the complex dielectric constant, representing the dielectric constant, expressed as n 2 -k 2 ,

[0119] 4) n is the refractive index and k is the absorption coefficient.

[0120] [Formula 1]

[0121]

[0122] In Formula 1, each symbol can be defined as follows.

[0123] 1) Ar 1 ,Ar 2 and Ar 3 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 condensed group; C1-C 60 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; and -L'-N(R a )(R b );

[0124] When Ar 1 ,Ar 2 and Ar 3 When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 24 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.,

[0125] When Ar 1 ,Ar 2 and Ar 3 When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, triazine, quinoxaline, etc.,

[0126] When Ar 1 ,Ar 2 and Ar 3 When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring condensed ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0127] When Ar 1 ,Ar 2 and Ar 3 When it is an alkyl group, it is preferably C1-C 30 Alkyl groups, more preferably C1-C 24 Alkyl groups,

[0128] 2) wherein L' is selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Aliphatic ring; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and combinations thereof,

[0129] When L' is an arylene group, it is preferably C6-C 30 Arylene groups, more preferably C6-C 24 Arylene groups, such as phenylene, biphenylene, naphthalene, terphenylene, etc.,

[0130] When L' is an aliphatic ring, it may preferably be C3-C 30 Aliphatic cyclic group, more preferably C3-C 24 Aliphatic cyclic groups,

[0131] When L' is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.,

[0132] 3) Where R a Selected from C6-C60 Aryl group; Fluorenyl group; C3-C 60 Aliphatic ring; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; and -L 4 Ar 5 ;

[0133] 4) Where R b Selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Aliphatic ring; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; and -L 5 Ar 6 ;

[0134] When R a and R b When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 24 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.,

[0135] When R a and R b is an aliphatic ring, which may preferably be C3-C 30 Aliphatic cyclic group, more preferably C3-C 24 Aliphatic cyclic groups,

[0136] When R a and R b When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.,

[0137] 5)Ar 5 and Ar 6 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 condensed group; C1-C 60 Alkyl group; C2-C 20 Alkenyl group; C2-C 20Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy groups;

[0138] When Ar 5 and Ar 6 When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 24 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.,

[0139] When Ar 5 and Ar 6 When it is an aliphatic ring, it may preferably be C3-C 30 Aliphatic cyclic group, more preferably C3-C 24 Aliphatic cyclic groups,

[0140] When Ar 5 and Ar 6 When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.,

[0141] When Ar 5 and Ar 6 When it is an alkyl group, it is preferably C1-C 30 Alkyl groups, more preferably C1-C 24 Alkyl groups,

[0142] 6) L 1 , L 2 , L 3 , L 4 and L 5 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C2-C 60 Heterocyclic groups;

[0143] When L 1 , L 2 , L 3 , L 4 and L 5 When it is an arylene group, it is preferably C6-C 30 Arylene groups, more preferably C6-C24 Arylene groups, such as phenylene, biphenylene, naphthalene, terphenylene, etc.,

[0144] When L 1 , L 2 , L 3 , L 4 and L 5 When it is a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring condensed ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused group.

[0145] When L 1 , L 2 , L 3 , L 4 and L 5 When it is a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.,

[0146] The aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, condensed ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl group; and -L'-N(R a )(R b ); wherein the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 Aliphatic ring, C6-C60 Aromatic ring or C2-C 60 A heterocyclic group, or a condensed ring formed by a combination thereof.

[0147] In addition, the compound represented by Formula 1 is represented by Formula 1-1.

[0148] [Formula 1-1]

[0149]

[0150] In formula 1-1, each symbol can be defined as follows.

[0151] 1) Ar 2 ,Ar 3 , L 1 , L 2 and L 3 Same as defined in Equation 1,

[0152] 2) X is O or S;

[0153] 3) Z is N or CR e ,

[0154] 4) R 1 and R e are each independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; and -L'-N(R a )(R b ); and R 1 The same as or different from each other.

[0155] When R 1 and R e When it is an aryl group, it is preferably C6-C 30 Aryl groups, more preferably C6-C 24 Aryl groups, such as phenyl, biphenyl, naphthalene, terphenyl, etc.,

[0156] When R 1 and R e is a heterocyclic group, which is preferably C2-C 30Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, triazine, quinoxaline, etc.,

[0157] When R 1 and R e is a fused ring group, which is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring condensed ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0158] When R 1 and R e When it is an alkyl group, it is preferably C1-C 30 Alkyl groups, more preferably C1-C 24 Alkyl groups,

[0159] 5) Where L', R a and R b Same as defined in Equation 1,

[0160] 6) a is i) when L 1 when bonded to *, an integer from 0 to 4, and ii) when L 1 When not bonded to *, an integer from 0 to 3.

[0161] In addition, the compound represented by Formula 1 is represented by Formula 1-2 or Formula 1-3.

[0162]

[0163]

[0164] in:

[0165] 1) Ar 2 ,Ar 3 , L 1 , L 2 and L 3 Same as defined in Equation 1,

[0166] 2) X, R 1 and a are the same as defined in Formula 1-1.

[0167] In addition, the compound represented by Formula 1 is represented by Formula 1-4.

[0168] [Formula 1-4]

[0169]

[0170] In formula 1-4, each symbol can be defined as follows.

[0171] 1) Ar 2 ,Ar 3 , L 1 , L 2 and L 3 Same as defined in Equation 1,

[0172] 2) Y is NR, CR'R", O or S,

[0173] 3) R, R' and R" are each independently selected from C1-C 50 Alkyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; or R' and R" are bonded to each other to form a C6-C 60 Aromatic hydrocarbon; fluorenyl group; C2-C3 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring; or C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups;

[0174] When R, R' and R" are alkyl groups, they are preferably C1-C 30 Alkyl groups, more preferably C1-C 24 Alkyl groups,

[0175] When R, R' and R" are aryl groups, they are preferably C6-C 30 Aryl groups, more preferably C6-C 24 Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.,

[0176] When R, R' and R" are heterocyclic groups, they are preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, triazine, quinoxaline, etc.,

[0177] When R' and R" are bonded to each other to form an aromatic hydrocarbon, it is preferably C6-C 30 Aromatic hydrocarbons, more preferably, may form C6-C24 Aromatic hydrocarbons,

[0178] When R' and R" are bonded to each other to form a heterocyclic group, it is preferably C2-C 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups,

[0179] When R' and R" are bonded to each other to form an aliphatic ring, it is preferably C3-C 30 Aliphatic ring, more preferably C3-C 24 Aliphatic ring,

[0180] When R' and R" are bonded to each other to form a fused ring group, it is preferably C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring condensed ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group,

[0181] 4) R 1 ' and R 2 ' and R in formula 1-1 1 have the same definition and are the same or different from each other,

[0182] 5) a′ is an integer from 0 to 4, and b′ is an integer from 0 to 3.

[0183] In addition, the compound represented by Formula 1 is represented by any one of Formula 2-1 to Formula 2-5.

[0184]

[0185]

[0186] in:

[0187] 1) Ar 3 , L 1 , L 2 and L 3 Same as defined in Equation 1,

[0188] 2) X, Z, R 1 and a are the same as those defined in Formula 1-1,

[0189] 3)X 1 and X 2 The definition of X is the same as that of formula 1-1,

[0190] 4) Y 1 and Y 2 Same as the definition of Y in formula 1-4,

[0191] 5) Z1 and Z 2 The definition of Z is the same as that of formula 1-1,

[0192] 6) R 2 , R 3 , R 4 , R 5 , R 6 and R 7 R of formula 1-1 1 The definition is the same as

[0193] 7) b is i) when L 2 when bonded to *, an integer from 0 to 4, ii) when L 2 When not bonded to *, an integer from 0 to 3;

[0194] 8)c is i) when L 3 when bonded to *, an integer from 0 to 4, ii) when L 3 When not bonded to *, an integer from 0 to 3,

[0195] 9) d and f are each independently an integer from 0 to 3, and e and g are each independently an integer from 0 to 4.

[0196] In addition, the compound represented by Formula 1 is represented by Formula 2-6 or Formula 2-7.

[0197]

[0198] in:

[0199] 1) Ar 3 , L 1 , L 2 and L 3 Same as defined in Equation 1,

[0200] 2) Y, R 1 '、R 2 ', a' and b' are the same as those defined in Formula 1-4,

[0201] 3) Y 1 and Y 2 Same as the definition of Y in formula 1-4,

[0202] 4) R 4 , R 5 , R 6 and R 7 R of formula 1-1 1 The definition is the same as

[0203] 5) d and f are each independently an integer from 0 to 3, and e and g are each independently an integer from 0 to 4.

[0204] In addition, the compound represented by Formula 1 is represented by Formula 3.

[0205] [Formula 3]

[0206]

[0207] in:

[0208] 1) Ar 2 ,Ar 3 , L 1 , L 2 and L 3 Same as defined in Equation 1,

[0209] 2) L 4 and L 5 With L in formula 1 1 The definition is the same as

[0210] 3) Ar 5 and Ar 6 With Ar in formula 1 1 The definition is the same as

[0211] In addition, the compound represented by Formula 1 is represented by any one of Formula 3-1 to Formula 3-4.

[0212]

[0213]

[0214] 1) Ar 2 ,Ar 3 , L', L 1 , L 2 and L 3 Same as defined in Equation 1,

[0215] 2) L 4 and L 5 With L in formula 1 1 The definition is the same as

[0216] 3) Ar 5 and Ar 6 With Ar in formula 1 1 The definition is the same as

[0217] 4) X, Z, R 1 and a are the same as those defined in Formula 1-1,

[0218] 5) Y, R 1 '、R 2 ', a' and b' are the same as those defined in Formula 1-4,

[0219] 6)X aThe definition of X is the same as that of formula 1-1,

[0220] 7) Y a The same definition as Y in formula 1-1,

[0221] 8) Z a The definition of Z is the same as that of formula 1-1,

[0222] 9) R 1 "、R 2 " and R 3 " and R of formula 1-1 1 The definition is the same as

[0223] 10) a is i) when L 2 when bonded to *, an integer from 0 to 4, ii) when L 2 When not bonded to *, an integer from 0 to 3,

[0224] 11) a", b" and c" are each independently an integer from 0 to 3.

[0225] Specifically, the compound represented by Formula 1 may be any one of the following Compound P-1 to Compound P-175.

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234] In addition, in the organic electronic element of the present invention, the organic material layer may include two or more stacks, wherein the stack includes a hole transport region, a light-emitting layer and an electron transport region sequentially formed on the anode, and the organic material layer may also include a charge generation layer formed between the two or more stacks.

[0235] In another aspect, the present invention provides an electronic device comprising a display device including an organic electronic element; and a control unit for driving the display device. In this case, the organic electroluminescent device may be at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochrome or white lighting.

[0236] Hereinafter, a synthesis example of the compound represented by the formula and a preparation example of the organic electronic element according to the present invention will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

[0237] [Synthesis example]

[0238] The compound (final product) represented by Formula 1 according to the present invention can be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1, but is not limited thereto. (Hal 1 =Br or Cl)

[0239] <Reaction Scheme 1>

[0240]

[0241] I. Synthesis of Sub 1

[0242] Sub 1 of Reaction Scheme 1 can be synthesized through the reaction path of Reaction Scheme 2, but is not limited thereto. (Hal 1 is Br or Cl, Hal 2 is I, Br or Cl. )

[0243] <Reaction Scheme 2>

[0244]

[0245] However, when Sub 1's Ar 1 yes When it can be synthesized via the reaction path of Reaction Scheme 2-1, or when Ar of Sub 1 1 Yes-L'-N(R a )(R b ), it can be synthesized by the reaction path of reaction scheme 2-2, but is not limited thereto. (Hal 1 is Br or Cl, Hal 2 is I, Br or Cl, R c and R d R 1 The same as defined above, l and m are each independently an integer from 0 to 3, and L', R a and R b Same as the definition above.)

[0246] <Reaction Scheme 2-1>

[0247]

[0248] <Reaction Scheme 2-2>

[0249]

[0250] 1. Synthesis example of Sub 1-3

[0251]

[0252] Sub a-1 (4.6 g, 28.2 mmol) was placed in a round-bottom flask and dissolved in THF (70 mL) and water (23 mL), Sub b-1 (5.9 g, 30.8 mmol), Pd(PPh3)4 (0.98 g, 0.9 mmol), NaOH (51.7 g, 56.4 mmol) were added and stirred at 75° C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 3.8 g (yield: 72%) of the product.

[0253] 2. Synthesis example of Sub 1-83

[0254]

[0255] In a round-bottom flask, Sub a'-83 (13.4 g, 80.1 mmol), Sub b'-83 (21.4 g, 80.1 mmol), NaOt-Bu (23.1 g, 240.4 mmol), P(t-Bu)3 (50 wt% Sol.) (1.6 mL, 4.0 mmol) were dissolved in toluene (270 mL), Pd2(dba)3 (0.73 g, 0.8 mmol) was added thereto, followed by stirring at 80° C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 20.7 g (yield: 73%) of the product.

[0256] 3. Synthesis example of Sub 1-118

[0257]

[0258] Sub a"-118 (10.8 g, 34.4 mmol), Sub b"-118 (5.8 g, 34.4 mmol), NaOt-Bu (9.9 g, 103.3 mmol), P(t-Bu)3(50wt%Sol.) (0.7 mL, 1.7 mmol), Pd2(dba)3(0.32 g, 0.3 mmol), toluene (220 mL) were added into a round-bottom flask, and 8.6 g (yield: 65%) of the product was obtained by using Sub 1-83 synthesis method.

[0259] 4. Synthesis example of Sub 1-138

[0260]

[0261] Sub a-138 (8.3 g, 46.6 mmol) was placed in a round bottom flask and dissolved in THF (125 mL) and water (41 mL). Sub b-1 (9.7 g, 50.8 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol) and NaOH (85.4 g, 93.3 mmol) were added, and 7.08 g (yield: 62%) of the product was obtained by using the Sub 1-3 synthesis method.

[0262] In addition, the compound belonging to Sub 1 may be the following compounds, but is not limited thereto, and the following Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compound belonging to Sub 1.

[0263]

[0264]

[0265]

[0266]

[0267]

[0268] [Table 1]

[0269]

[0270]

[0271]

[0272]

[0273] II. Synthesis of Sub 2

[0274] Sub 2 of Reaction Scheme 1 can be synthesized via the reaction path of Reaction Scheme 3, but is not limited thereto. 3 is Br or Cl)

[0275] <Reaction Scheme 3>

[0276]

[0277] 1. Synthesis example of Sub 2-11

[0278]

[0279] Sub d-1 (10.39 g, 111.60 mmol), Pd2(dba)3 (2.79 g, 3.04 mmol), 50% P(t-Bu)3 (2.5 mL, 6.09 mmol), NaOt-Bu (29.25 g, 304.38 mmol), toluene (710 mL) were added to the starting material Sub c-1 (23.65 g, 101.46 mmol), and the mixture was stirred at 80° C. When the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 20.66 g (yield: 83%) of the product.

[0280] 2. Synthesis example of Sub 2-23

[0281]

[0282] Sub d-2 (7.8 g, 54.1 mmol), Pd2(dba)3 (1.5 g, 1.62 mmol), 50% P(t-Bu)3 (1.3 mL, 3.25 mmol), NaOt-Bu (15.6 g, 162.31 mmol), toluene (200 mL) were added to the starting material Sub c-2 (15.7 g, 54.1 mmol), and 15.26 g (yield: 80%) of the product was obtained by using the Sub 2-11 synthesis method.

[0283] 3. Synthesis example of Sub 2-91

[0284]

[0285] Sub d-3 (10.6 g, 50.6 mmol), Pd2(dba)3 (1.4 g, 1.52 mmol), 50% P(t-Bu)3 (1.2 mL, 3.04 mmol), NaOt-Bu (14.6 g, 151.8 mmol), and toluene (200 mL) were added to the starting material Sub c-3 (12.5 g, 50.6 mmol), and 14.85 g (yield: 78%) of the product was obtained by using the Sub2-11 synthesis method.

[0286] 4. Synthesis example of Sub 2-196

[0287]

[0288] Sub d-4 (12.2 g, 54.3 mmol), Pd2(dba)3 (1.5 g, 1.63 mmol), 50% P(t-Bu)3 (1.3 mL, 3.26 mmol), NaOt-Bu (15.7 g, 163.0 mmol), and toluene (280 mL) were added to the starting material Sub c-4 (14.3 g, 54.3 mmol), and 14.85 g (yield: 78%) of the product was obtained by using the Sub2-11 synthesis method.

[0289] In addition, the compound belonging to Sub 2 may be the following compounds, but is not limited thereto, and Table 2 shows the FD-MS values ​​of the compounds belonging to Sub 2.

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298] [Table 2]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305] III. Synthesis of the final product

[0306] 1. Synthesis Example of P-2

[0307]

[0308] In a round-bottom flask, Sub 1-1 (8.8 g, 57.3 mmol) was dissolved in toluene (170 mL), Sub 2-2 (18.4 g, 57.3 mmol), Pd2(dba)3 (1.57 g, 1.7 mmol), P(t-Bu)3 (50 wt% Sol.) (1.4 mL, 3.4 mmol), NaOt-Bu (16.5 g, 171.9 mmol) were added thereto, and the mixture was stirred at 110° C. After extraction with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was purified by silica gel column and sublimation to obtain 19.1 g (yield: 76%) of the product.

[0309] 2. Synthesis Example of P-38

[0310]

[0311] Sub 1-8 (8.0 g, 28.8 mmol), Sub 2-30 (12.1 g, 28.8 mmol), Pd2(dba)3 (0.8 g, 0.86 mmol), NaOt-Bu (8.3 g, 86.4 mmol), P(t-Bu)3 (50 wt% Sol.) (0.7 mL, 1.7 mmol), and toluene (160 mL) were used to synthesize P-2, and 13.04 g (yield: 72%) of the product was obtained.

[0312] 3. Synthesis Example of P-154

[0313]

[0314] Sub 1-118 (10.2 g, 26.4 mmol), Sub 2-190 (10.4 g, 26.4 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), NaOt-Bu (7.6 g, 79.3 mmol), P(t-Bu)3 (50 wt% Sol.) (0.6 mL, 1.6 mmol), and toluene (200 mL) were used to synthesize P-2, and 14.7 g (yield: 75%) of the product was obtained.

[0315] 4. Synthesis Example of P-174

[0316]

[0317] Sub 1-138 (9.5 g, 38.8 mmol), Sub 2-202 (162 g, 38.8 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), NaOt-Bu (11.2 g, 116.5 mmol), P(t-Bu)3 (50 wt% Sol.) (0.9 mL, 2.3 mmol), and toluene (200 mL) were used to synthesize P-2, and 19.4 g (yield: 80%) of the product was obtained.

[0318] In addition, the FD-MS values ​​of Compound P-1 to Compound P-175 of the present invention prepared according to the above Synthesis Examples are shown in Table 3.

[0319] [Table 3]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325] [Example of measurement test]

[0326] For the compounds of the present invention, all thin films were deposited on Si wafers up to The thickness of the film was 0.50 mm and the n (refractive index) and k (absorption coefficient) were measured using JA Woollam's Focused Beam SpectroscopyEllipsometer RC2 XF instrument. After the measurement, the final results were analyzed using the Tawker-Lorentz model and the Gaussian model.

[0327] [Table 4]

[0328] Compound n(450nm) k(450nm) tanδ Comparative Example 1 <![CDATA[SiO2]]> 1.47 0.0023 0.0031293 Comparative Example 2 Comparative Compound A 2.413915 0.053885 0.0446676 Test Example 1 P-92 2.234374 0.000261 0.0002336 Test Example 2 P-95 2.302051 0.000118 0.0001025 Test Example 3 P-120 2.005773 0.000075 0.0000748 Test Example 4 P-151 2.153759 0.000005 0.0000046 Test Example 5 P-153 2.324989 0.00008 0.0000688 Test Example 6 P-154 2.119847 0.000053 0.0000500 Test Example 7 P-158 2.285066 0.000802 0.0007019 Test Case 8 P-159 2.166349 0.000033 0.0000305 Test Example 9 P-160 2.040186 0.000044 0.0000431

[0329] [Comparative Compound A]

[0330]

[0331] [Equipment Example]

[0332] (Comparative Example 1) Fabrication and Testing of Blue Organic Light Emitting Device

[0333] A N1-(naphthalene-2-yl)-N4,N4-bis(4-(naphthalene-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter, 2-TNATA) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a 60nm hole injection layer, and then a N,N'-bis(1-naphthalene)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter, NPB) film was vacuum deposited to a thickness of 60nm to form a hole transport layer. Then, on the hole transport layer, 9,10-di(naphthalene-2-yl)anthracene as a host and BD-052X (Idemitsu Kosan Co., Ltd.) as a dopant were doped with a dopant so that the weight ratio was 93:7 to form a light-emitting layer having a thickness of 30nm. Then, a hole blocking layer was formed by vacuum depositing (1,1'-biphenyl-4-radical)bis(2-methyl-8-quinolinolato)aluminum (hereinafter, BAlq) to a thickness of 10 nm on the light emitting layer, tris(8-hydroxyquinoline)aluminum (hereinafter, Alq3) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Then, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and a cathode was formed by depositing Mg:Ag at a ratio of 9:1 on the electron injection layer to a thickness of 150 nm, and then SiO2 was formed to a thickness of 60 nm to form a capping layer.

[0334] [Comparative Example 2]

[0335] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compound A was used instead of SiO 2 as the cover layer material.

[0336] [Comparative Example 3] to [Comparative Example 11]

[0337] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound of the present invention shown in Table 5 was used instead of SiO 2 as the cover layer material.

[0338] [Example 1] to [Example 9]

[0339] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compounds of the present invention shown in Table 5 were used instead of SiO 2 as the capping layer material, and the Mg:Ag ratio was changed to 2:8.

[0340] [Example 10] to [Example 18]

[0341] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compounds of the present invention shown in Table 5 were used instead of SiO 2 as the capping layer material, and the Mg:Ag ratio was changed to 1:9.

[0342] [Example 19] to [Example 27]

[0343] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that ytterbium (Yb) was used instead of LiF for the electron injection layer, and the compound of the present invention described in Table 5 was used instead of SiO2 as the capping layer material, and the Mg:Ag ratio was changed to 1:9.

[0344] By applying a forward bias DC voltage to the organic light emitting diodes prepared according to Examples 1 to 27 of the present invention and Comparative Examples 1 to 11, the electroluminescence (EL) characteristics were measured by PR-650 of Photoresearch, and the lifetime measurement equipment manufactured by McScience at 500 cd / m 2 The T95 lifetime was measured at a brightness of , and the measurement results are shown in Table 5.

[0345] [Table 5]

[0346]

[0347]

[0348]

[0349] As can be seen from the results of Table 5, it can be confirmed that the organic electrical device using the compound of the present invention exhibits superior characteristics to the comparative example device without the compound of the present invention.

[0350] It can be seen that the element using the compound of the present invention satisfying Formula 1 has slightly improved driving and service life, but has significantly better efficiency (Comparative Examples 3 to 11) compared to Comparative Examples 1 and 2 using compounds that do not satisfy Formula 1. This shows that when a compound satisfying the value of Formula 1 representing the dielectric loss characteristic is used as a covering layer, the overall characteristics of the element can be improved.

[0351] In addition, it was confirmed that the element in which the Ag ratio was changed to 80% showed significantly better efficiency than the comparative example element without this Ag ratio (Examples 1 to 9), and further, it was confirmed that the efficiency of the element with an Ag ratio of 90% was much improved (Examples 10 to 18). As described in the detailed description of the present invention, when the Ag content is 80% or more, the reflectivity is similar to that when the Ag content is less than 20%, but the absorbance is reduced and the transmittance is increased, thereby maximizing the efficiency by reducing the light loss of the cathode.

[0352] Among them, it was confirmed that in the embodiments, the results of the elements in which the electron injection layer was changed to Yb (Examples 19 to 27) showed the most excellent element characteristics in terms of driving, efficiency and service life. This is because, when the Ag content is increased, by using Yb with good conductivity, the disadvantage of slightly pushing the driving voltage due to low electron injection characteristics can be overcome.

[0353] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be understood by those skilled in the art that various modifications, additions and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be interpreted based on the appended claims, and should be interpreted as all technical concepts included in the scope equivalent to the claims belong to the present invention.

[0354] [Industrial Applicability]

[0355] According to the present invention, an organic device having excellent device characteristics of high brightness, high luminescence, and long lifespan can be manufactured, and thus has industrial applicability.

Claims

1. Organic electronic components, including: anode; cathode; forming an organic material layer between the anode and the cathode; and coverings; wherein the organic material layer includes a hole transport region, a light emitting layer, and an electron transport region, wherein the electron transport region includes an electron transport layer and an electron injection layer, wherein the cathode is a mixture of magnesium and silver, wherein the ratio of the silver is 80% or more, wherein the capping layer comprises a compound satisfying Formula 1 at a wavelength of 450 nm and represented by Formula 2-6, Formula 2-7, or Formula 3: [Equation 1] tanδ(loss tangent)≤0.001 in: 1) tanδ is ε 2 / ε 1 , 2)ε 2 is the imaginary part of the complex dielectric constant of the dielectric material, representing the dielectric loss, expressed as 2nk, 3)ε 1 is the real part of the complex dielectric constant, representing the dielectric constant, expressed as n 2 -k 2 , 4) n is the refractive index, k is the absorption coefficient, [Formula 3] in: 1) Ar 2 ,Ar 3 ,Ar 5 and Ar 6 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 condensed group; C1-C 60 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; and -L'-N(R a )(R b ); 2) R 4 , R 5 , R 6 , R 7 , R 1 ' and R 2 ' are each independently selected from hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; and -L'-N(R a )(R b ); and R 4 , R 5 , R 6 , R 7 , R 1 ' and R 2 'same or different from each other, 3) L' is selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Aliphatic ring; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups; and combinations thereof, 4) R a Selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Aliphatic ring; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; and -L 4 Ar 5’ ; 5) R b Selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Aliphatic ring; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; and -L 5 Ar 6’ ; 6) Ar 5’ and Ar 6’ 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 condensed group; C1-C 60 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy groups; 7) L 1 , L 2 , L 3 , L 4 and L 5 Each is independently selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C2-C 60 Heterocyclic groups; 8) Y, Y 1 and Y 2 are each independently NR, CR'R", O or S, 9) R, R' and R" are each independently selected from C1-C 50 Alkyl group; C6-C 60 Aryl group; fluorenyl group; C2-C 60 Heterocyclic group; or R' and R" are bonded to each other to form a C6-C 60 Aromatic hydrocarbon; fluorenyl group; C2-C3 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring; or C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, 10) a' is an integer from 0 to 4, b' is an integer from 0 to 3, d and f are each independently an integer from 0 to 3, and e and g are each independently an integer from 0 to 4, The aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the condensed ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 Arylalkenyl group; and -L'-N(R a )(R b ); wherein the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means C3-C 60 Aliphatic ring, C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group, or a condensed ring formed by a combination thereof. 2 . The organic electronic device according to claim 1 , wherein the electron transport region necessarily contains ytterbium as a lanthanoid element. 3 . The organic electronic element according to claim 1 , wherein the capping layer compound has a refractive index of 2.1 or more at a wavelength of 450 nm, a refractive index of 1.95 or more at a wavelength of 530 nm, and a refractive index of 1.85 or more at a wavelength of 620 nm. 4 . The organic electronic element according to claim 1 , wherein the capping layer compound has a refractive index difference of 0.08 or more at wavelengths of 430 nm and 460 nm. 5 . The organic electronic element as claimed in claim 1 , wherein the absorption coefficient of the capping layer compound is 0.3 or more at a wavelength of 410 nm. 6 . The organic electronic element as claimed in claim 1 , wherein the absorption coefficient of the capping layer compound is 0.1 or more at a wavelength of 410 nm to 430 nm.

7. The organic electronic device according to claim 1, wherein the covering layer compound is -5 The absorbance at a wavelength of 400 nm to 410 nm in the absorption spectrum at a concentration of 1.5 mol / l is 0.2 or more.

8. The organic electronic device according to claim 1, wherein Formula 3 is represented by any one of Formula 3-1 to Formula 3-4: in: 1) Ar 2 ,Ar 3 ,Ar 5 ,Ar 6 , L', L 1 , L 2 , L 3 , L 4 , L 5 , Y, R 1 '、R 2 ', a' and b' are the same as defined in claim 1, 2) X and X a are each independently O or S, 3) Z and Z a Each independently is N or CR e , 4) R 1 , R e , R 1 "、R 2 " and R 3 " and R in claim 1 4 The definition is the same as 5) Y a Same as the definition of Y in claim 1, 6) a is i) when L 2 when bonded to *, an integer from 0 to 4, ii) when L 2 When not bonded to *, an integer from 0 to 3, 7) a", b" and c" are each independently an integer from 0 to 3.

9. The organic electronic element according to claim 1, wherein the compound represented by Formula 2-6, Formula 2-7 or Formula 3 is any one of the following compounds: 10 . The organic electronic element according to claim 1 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport region, a light emitting layer, and an electron transport region sequentially formed on the anode. 11 . The organic electronic element according to claim 10 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies.

12. An electronic device comprising a display device including the organic electronic element according to claim 1; and a control unit for driving the display device. 13 . The electronic device of claim 12 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white lighting.

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