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

Abstract

The present invention relates to a compound for an organic electrical element, an organic electrical element using the compound, and an electronic device comprising the organic electrical element. The present invention can provide an organic electrical element with high luminous efficiency, low driving voltage, and high heat resistance, and can also improve the color purity and extend the life of the organic electrical element.

Description

Technical Field

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

[0002] Generally, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electrical components use organic light emitting phenomenon, and they usually have a structure including a positive electrode, a negative electrode and an organic layer therebetween. Among them, in order to improve the efficacy and stability of organic electrical components, the organic layer is often a multilayer structure composed of different substances, for example, it can be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

[0003] In organic electrical elements, the materials used as organic layers can be divided into luminescent materials and charge transport materials according to their functions, for example, they can be divided into hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. In addition, the luminescent materials can be divided into high molecular weight and low molecular weight according to their molecular weight, and can be divided into fluorescent materials derived from singlet electron excitation and phosphorescent materials derived from triplet electron excitation according to their luminescent mechanism. In addition, luminescent materials can be divided into blue, green, and red luminescent materials according to their luminescent colors, as well as yellow and orange luminescent materials required for presenting better natural colors.

[0004] In addition, when only one substance is used as a luminescent material, the following problems may occur: due to the interaction of molecules, the maximum luminescent wavelength moves to a long wavelength, resulting in a decrease in color purity, or, due to the luminescent attenuation effect, the efficiency of the element is low. Therefore, in order to enhance the luminous efficiency by improving color purity and energy transfer, the main body / dopant class can be used as a luminescent material. The principle is that when a small amount of dopants with a narrow energy band gap is mixed into the luminescent layer compared to the main body forming the luminescent layer, the excitons generated by the luminescent layer are transferred to the dopants, thereby emitting efficient light. At this time, the wavelength of the main body moves to the wavelength band of the dopant, so that light of the desired wavelength can be obtained according to the type of dopant used.

[0005] Currently, in the portable display market, large-area displays with increasing size have become a trend, and the power consumption required is greater than that of previous portable displays. Portable displays are equipped with batteries, and their power sources are limited. Therefore, from their perspective, power consumption has become an important factor, and efficiency and life issues are also important factors that must be solved.

[0006] Efficiency is related to lifespan, driving voltage, etc. When efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, the Joule heating generated during driving will reduce the crystallization of organic substances, resulting in a trend of longer lifespan. However, the efficiency cannot be maximized by simply improving the organic layer. This is because when the energy level and T1 value between each organic layer and the inherent properties of the substance (mobility, interface properties, etc.) form the best combination, long lifespan and high efficiency can be achieved at the same time.

[0007] In addition, the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer is one of the reasons for the shortened life of organic electrical components. Therefore, it is necessary to develop hole injection layer materials with high glass transition temperature that have stable characteristics for Joule heating generated when driving the components while delaying this process. In addition, the low glass transition temperature of hole transport layer materials will reduce the uniformity of the film surface when driving the components, which, according to the report data, has a significant impact on the life of the components.

[0008] However, this cannot be achieved by relying solely on the structural characteristics of the materials in the organic layer. Only by forming an appropriate combination of the core and substituent characteristics of the various materials and the organic layers can a component with high efficiency and long life be realized.

[0009] Because, in order to give full play to the excellent characteristics of organic electrical components, the substances that make up the organic layers within the components, such as hole injection substances, hole transport substances, luminescent substances, electron transport substances, electron injection substances, luminescent auxiliary layer substances, etc., must first be supported by stable and effective materials. It is particularly urgent to develop materials for hole transport layers and luminescent auxiliary layers. Summary of the invention

[0010] Issues to be solved

[0011] The object of the present invention is to provide a compound that can reduce the driving voltage of a component, improve the luminous efficiency of the component, increase the color purity and prolong the life, an organic electrical component using the compound and an electronic device including the organic electrical component.

[0012] Problem Solution

[0013] In one aspect, the present invention provides a compound represented by the following chemical formula.

[0014] <Chemical Formula 1>

[0015]

[0016] In another aspect, the present invention provides an organic electrical element and an electronic device using the compound represented by the chemical formula.

[0017] Effects of the Invention

[0018] When the compound of the present invention is used, the luminous efficiency of the element can be increased, the driving voltage can be reduced, and the color purity of the element can be improved and the life span can be prolonged. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figures 1 to 3 is a schematic diagram of an organic electrical element in an embodiment of the present invention.

[0020] Figure 4 The chemical formula of one aspect of the invention is shown.

[0021] * Reference Numbers *

[0022] 100, 200, 300: organic electrical element 110: first electrode 120: hole injection layer

[0023] 130: hole transport layer 140: light emitting layer 150: electron transport layer

[0024] 160: electron injection layer 170: second electrode 180: capping layer

[0025] 210: buffer layer 220: light-emitting auxiliary layer

[0026] 320: first hole injection layer 330: first hole transport layer 340: first light emitting layer

[0027] 350: first electron transport layer 360: first charge generation layer 361: second charge generation layer

[0028] 420: second hole injection layer 430: second hole transport layer 440: second light emitting layer

[0029] 450: Second electron transport layer

[0030] CGL: Second charge generation layer ST1: First stack ST2: Second stack DETAILED DESCRIPTION

[0031] The present invention provides a compound represented by the following chemical formula.

[0032] <Chemical Formula 1>

[0033]

[0034] In another aspect, the present invention provides an organic electrical element and an electronic device using the compound represented by the chemical formula.

[0035] Mode for carrying out the invention

[0036] Hereinafter, preferred embodiments of the present invention are described with reference to the accompanying drawings.

[0037] It should be noted that, for the purpose of describing the present embodiment, when reference symbols are given to the constituent elements shown in the drawings, even if the same constituent elements are shown in different drawings, the same symbols are used as much as possible. In addition, when describing the present invention, if it is considered that a detailed description of the relevant known structure or function will confuse the main points of the present invention, the detailed description thereof will be omitted. The drawings referenced below will not be scaled.

[0038] When describing the constituent elements of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. Such terms are only used to distinguish the constituent elements from other constituent elements, and the nature, order or sequence of the constituent elements are not limited by such terms.

[0039] When it is recorded that a certain constituent element is “connected”, “combined” or “accessed” to another constituent element, the constituent element may be directly connected or accessed to the other constituent element, but it should be understood that the respective constituent elements may also be “connected”, “combined” or “accessed” to other constituent elements.

[0040] Furthermore, when a component such as a layer, film, region, or plate is located "on" or "over" another component, it should be understood that it includes not only the case where it is located "directly above" another component, but also the case where there is another component in between. On the contrary, when a component is located "directly above" another part, it should be understood that there is no other part in between.

[0041] Unless otherwise described, the terms used in this specification and the appended claims are as follows within the scope that does not depart from the spirit of the present invention.

[0042] Unless otherwise described, the term "halo" or "halogen" used in the present application includes fluorine (F), fluorine (Cl), bromine (Br) and iodine (I).

[0043] Unless otherwise described, the term "alkyl" or "alkyl group" used in this application contains 1 to 60 carbon atoms connected by single bonds, and refers to a free radical of a saturated aliphatic functional group represented by a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and a cycloalkyl-substituted alkyl group.

[0044] Unless otherwise described, the term "haloalkyl group" or "halogenalkyl group" used in the present application refers to an alkyl group substituted with halogen.

[0045] Unless otherwise described, the term "alkenyl" or "alkynyl" used in the present application respectively has a double bond or a triple bond, contains a straight chain or a side chain, and has 2 to 60 carbon atoms, but is not limited thereto.

[0046] Unless otherwise described, the term "cycloalkyl" used in the present application means a cyclic alkane having 3 to 60 carbon atoms, but is not limited thereto.

[0047] The term "alkoxy group" or "alkyloxy group" used in the present application refers to an alkyl group (Alkyl) bonded to an oxygen radical, and unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

[0048] The term "alkenoxyl group", "alkenoxygroup", "alkenyloxyl group" or "alkenyloxy group" used herein means an alkenyl group to which an oxygen radical is bonded, and unless otherwise specified, has 2 to 60 carbon atoms, but is not limited thereto.

[0049] Unless otherwise described, the terms "aryl group" and "arylenel group" used in the present application have 6 to 60 carbons, respectively, but are not limited thereto. In the present application, aryl group or arylenel group include monocyclic type, cyclopolymer, condensed polycyclic compounds, etc. For example, the aryl group may include phenyl group, the monovalent functional group of biphenyl, the monovalent functional group of naphthalene, fluorenyl group and substituted fluorenyl group. Arylene group may include fluorenyl group and substituted fluorenyl group.

[0050] The term "ring assemblies" as used in the present application refers to two or more ring systems (monocyclic or fused ring systems) directly connected by a single bond or a double bond, indicating that the number of directly connected rings is less than the total number of ring systems contained in the compound. The ring assemblies may be directly connected by the same or different ring systems via a single bond or a double bond.

[0051] In the present application, the aryl group includes a cyclopolymer, and thus, the aryl group includes biphenyl and terphenyl connected by a single bond to a benzene ring as a monocyclic aromatic. In addition, the aryl group also includes a compound in which an aromatic ring system fused to an aromatic monocyclic ring is connected by a single bond, and thus, for example, a compound in which an aromatic ring system fused to a benzene ring as an aromatic monocyclic ring, i.e., fluorene, is connected by a single bond.

[0052] The term "fused polycyclic ring system" used in this application refers to a ring that shares at least two atoms and is fused, including: a form in which two or more hydrocarbon ring systems are fused and a form in which at least one heterocyclic ring system is fused and the heterocyclic ring system contains at least one heteroatom. The fused polycyclic ring system can be an aromatic ring, an aromatic heterocyclic ring, an aliphatic ring, or a combination of such rings. For example, an aryl group can be a naphthyl group, a phenanthrenyl group, a fluorenyl group, etc., but it is not limited thereto.

[0053] The term "spiro compound" used in the present application has a 'spiro union', which means that two rings share only one atom to form a connection. In this case, the atom shared by the two rings is called a 'spiro atom', and according to the number of spiro atoms contained in one compound, it is called a 'monospiro-', 'dispiro-', 'trispiro-' compound, respectively.

[0054] Unless otherwise described, the terms "fluorenyl group", "fluorenylene group" and "fluorene-triyl group" used in this application respectively represent monovalent, divalent or trivalent functional groups in which R, R', R" and R'" are all hydrogen in the following structures, and "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorene-triyl group" means that at least one of the substituents R, R', R", R'" is a substituent other than hydrogen, including the case where R and R' are bonded to each other and form a spiro compound together with the carbon to which they are bonded. In this specification, the fluorenyl group, fluorenylene group and fluorene-triyl group may be named as fluorenyl group without considering the equivalent number of monovalent, divalent and trivalent.

[0055]

[0056] Furthermore, the R, R', R" and R'" may independently represent an alkyl group having 1 to 20 carbon atoms, an olefin group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclyl group having 3 to 30 carbon atoms. For example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, and the heterocyclyl group may be 1 to 20 carbon atoms. The substituted fluorenyl group and fluorenyl group may be pyrrole, furan, thiophene, pyrazole, imidazole, triazole, pyridine, pyrimidone, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline. For example, the substituted fluorenyl group and fluorenyl group may be monovalent or divalent functional groups of 9,9-dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spirobi [9H-fluorene], respectively.

[0057] The term "heterocyclyl group" used in this application includes not only aromatic rings such as "heteroaryl group" or "heteroarylenel group", but also non-aromatic rings. Unless otherwise described, they respectively represent rings containing one or more heteroatoms and having a carbon number of 2 to 60, but are not limited thereto. Unless otherwise described, the term "heteroatom" used in this application represents N, O, S, P or Si, and a heterocyclyl group represents a monocyclic type, a cyclopolymer, a fused polycyclic system, a spiro compound, etc. containing a heteroatom.

[0058] For example, "heterocyclyl group" can also replace the cyclic carbon, including: such as the following compounds, containing SO 2, P=O and other heteroatom terminal groups.

[0059]

[0060] The term "ring" used in the present application includes monocyclic and polycyclic rings, and of course, hydrocarbon rings include heterocyclic rings, the heterocyclic rings contain at least one heteroatom, and include aromatic and non-aromatic rings.

[0061] The term "polycyclic" as used in this application includes ring assemblies such as biphenyl and terphenyl and fused polycyclic systems and spiro compounds, including not only aromatic but also non-aromatic rings. Of course, hydrocarbon rings include heterocyclic rings that contain at least one heteroatom.

[0062] The term "aliphatic cyclo group" used in this application refers to cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclic types, cyclopolymers, fused polycyclic systems, spiro compounds, etc., and unless otherwise specified, refers to a ring with a carbon number of 3 to 60, but is not limited thereto. For example, when an aromatic cyclobenzene and a non-aromatic cyclohexane are fused, they are also equivalent to an aliphatic ring.

[0063] Furthermore, when prefixes are used consecutively, it means that the substituents are arranged in the order of the description. For example, aryl alkoxy group means an alkoxy group substituted by an aryl group, alkoxy carbonyl group means a carbonyl group substituted by an alkoxy group, and aryl carbonyl alkenyl group means an alkenyl group substituted by an arylcarbonyl group, wherein aryl carbonyl group is a carbonyl group substituted by an aryl group.

[0064] Furthermore, unless otherwise specified, in the term “substituted” or “unsubstituted” used in the present application, “substituted” means substituted by one or more substituents selected from C 2 -C 20A group consisting of a heterocyclic group (heterocyclylgroup), which is composed of C 2 -C 20 The group consisting of the heterocyclic group contains at least one heteroatom selected from the group consisting of deutrium, halogen, amino group, nitrile group, nitro group, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy group, C 1 -C 20 Alkyl amine group, C 1 -C 20 Alkyl thiophene group, C 6 -C 20 aryl thiophene group, C 2 -C 20 The alkenyl group, C 2 -C 20 Alkinyl group, C 3 -C 20 Cycloalkyl group, C 6 -C 20 The aryl group, the C 6 -C 20 The aryl group, C 8 -C 20 aryl alkenyl group, silane group, boron group, germanium group and O, N, S, Si and P.

[0065] In the present application, the 'functional group name' corresponding to the aryl group, arylenel group, heterocyclyl group, etc. described in each label and its substituent examples may be recorded as 'functional group name reflecting valence' or 'name of the parent compound'. For example, 'phenanthrene' as an aryl group' can record the name of the 'group' according to the valence, such as recording the monovalent 'group' as 'phenanthryl (group)', and for the divalent 'group', the name of the 'group' can be recorded according to the valence, such as 'phenanthryl (group)', etc., but the name of the parent compound can also be recorded as 'phenanthrene' regardless of the valence.

[0066] Similarly, pyrimidine can be recorded as 'pyrimidine' regardless of the valence, or recorded as pyrimidinyl (base) when it is monovalent, and can be recorded as the 'name of the base' of the corresponding valence when it is divalent, such as pyrimidinylene (base), etc. Therefore, in the present application, when the type of substituent is recorded as the name of the parent compound, it can represent: a 'base' with an n-valence formed by the desorption of hydrogen atoms bonded to carbon atoms and / or heteroatoms of the parent compound.

[0067] In addition, in this specification, when recording the name of a compound or a substituent, the numerals or alphabets indicating the position may be omitted. For example, pyrido[4,3-d]pyrimidone may be recorded as pyrido pyrimidone, benzofuran[2,3-d]pyrimidone may be recorded as benzofuran pyrimidone, 9,9-dimethyl-9H-fluorene may be recorded as dimethylfluorene, etc. Therefore, benzo[g]quinoxaline or benzo[f]quinoxaline may be recorded as benzoquinoxaline.

[0068] Furthermore, unless otherwise explicitly stated, the chemical formulae used in this application are also subject to the definitions of substituents according to the index definitions of the following chemical formulae.

[0069]

[0070] Wherein, when a is an integer of 0, it indicates that the substituent R 1 does not exist, that is, when a is 0, the carbon atoms forming the benzene ring are all bonded to hydrogen atoms. In this case, the symbol of the hydrogen atoms bonded to the carbon atoms can be omitted and the chemical formula or compound can be recorded. 1 When a is an integer of 2 or 3, the bonding can be as follows. When a is an integer of 4 to 6, it can be bonded to the carbon of the benzene ring by a similar method. When a is an integer of 2 or more, R1 can be the same or different.

[0071]

[0072] In the present application, unless otherwise described, forming a ring means that adjacent groups are bonded to each other to form a monocyclic ring or a fused polycyclic ring, and the monocyclic ring and the formed fused polycyclic ring include not only hydrocarbon rings but also heterocyclic rings, which contain at least one heteroatom and may include aromatic and non-aromatic rings.

[0073] In addition, in this specification, unless otherwise described, when a condensed ring is represented, in the term "number-condensed ring", the number represents the number of condensed rings. For example, a condensed form of three rings can be represented as a 3-condensed ring, such as anthracene, phenanthrene, benzo quinoxaline, etc.

[0074] Below, reference Figures 1 to 3 The layered structure of an organic electric device including the compound of the present invention is described.

[0075] like Figure 1 As shown, an organic electrical device 100 according to an embodiment of the present invention includes a first electrode 110 and a second electrode 170 formed on a substrate (not shown), and an organic layer located between the first electrode 110 and the second electrode 170 and containing the compound of the present invention.

[0076] The first electrode 110 is an anode, and the second electrode 170 is a cathode. If it is an inverted type, the first electrode can be a cathode, and the second electrode can be an anode.

[0077] The organic 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.

[0078] Preferably, a capping layer 180 may be formed on the side of the first electrode 110 or the second electrode 170 that is not connected to the organic layer. The formation of the capping layer 180 may improve the light efficiency of the organic electrical element.

[0079] For example, a capping layer 180 may be formed on the second electrode 170. When a top emission type organic light emitting element forms the capping layer 180, the surface plasmonpolaritons (SPPs) of the second electrode 170 may reduce light energy loss. When a bottom emission type organic light emitting element forms the capping layer 180, it may serve as a buffer for the second electrode 170.

[0080] In addition, refer to Figure 2 A case where the buffer layer 210 or the light emitting auxiliary layer 220 is further formed between the hole transport layer 130 and the light emitting layer 140 is described.

[0081] like Figure 2 As shown, the organic electrical element 200 of another embodiment of the present invention may include 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 capping layer 180 may be formed on the second electrode.

[0082] 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 .

[0083] Furthermore, according to another embodiment of the present invention, the organic layer may be in the form of a plurality of stacks, the stacks including a hole transport layer, a light emitting layer and an electron transport layer. Figure 3 Give a description.

[0084] like Figure 3 As shown, according to another embodiment of the present invention, the organic electrical element 300 may be formed with two or more stacks of organic layers ST1 and ST2, which are located between the first electrode 110 and the second electrode 170. A charge generation layer CGL may also be formed between the stacks of organic layers.

[0085] Specifically, according to an embodiment of the present invention, the organic electrical element may include a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , a second electrode 170 and a capping layer 180 .

[0086] The first stack ST1 is an organic layer formed on the first electrode 110 , which may include a first hole injection layer 320 , a first hole transport layer 330 , a first light emitting layer 340 , and a first electron transport layer 350 .

[0087] 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 .

[0088] Thus, the first stack and the second stack may be organic layers having the same stacking structure, or may be organic layers having different stacking structures.

[0089] 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 enhance the current efficiency of each light emitting layer and smoothly distribute the charge.

[0090] The first light-emitting layer 340 may include a light-emitting material containing a blue fluorescent dopant on a blue main body, and the second light-emitting layer 440 may include: a material containing a greenish yellow dopant and a red dopant co-doped on a green main body, but the materials of the first light-emitting layer 340 and the second light-emitting layer 440 according to the embodiment of the present invention are not limited thereto.

[0091] At this time, the second hole transport layer 430 includes a second stack ST2 , and the set energy level of the second stack ST2 is higher than the triplet excited state energy level of the second light emitting layer 440 .

[0092] Since the energy level of the second hole transport layer 430 is higher than that of the second light emitting layer 440, it is possible to prevent the triplet excitons of the second light emitting layer 440 from transferring to the second hole transport layer 430 to reduce the light emitting efficiency. That is, the second hole transport layer 430 functions as an exciton blocking layer that transfers holes from the inherent second light emitting layer 440 and prevents the transfer of triplet excitons.

[0093] Furthermore, in order to function as an exciton blocking layer, the energy level of the first hole transport layer 330 may also be set to be higher than the energy level of triplet excitons in the first light-emitting layer 340. Furthermore, preferably, the energy level of the first electron transport layer 350 is also set to be higher than the energy level of triplet excitons in the first light-emitting layer 340, and the energy level of the second electron transport layer 450 is also set to be higher than the energy level of triplet excitons in the second light-emitting layer 440.

[0094] like Figure 3 As shown, n may be an integer from 1 to 5. When n is 2, a charge generation layer CGL and a third stack may be further stacked on the second stack ST2.

[0095] like Figure 3 As shown, when multiple light-emitting layers are formed in a multi-layer stacked structure, the mixing effect of the light emitted by each light-emitting layer can not only produce an organic electroluminescent element that emits white light, but also produce an organic electroluminescent element that emits light of multiple colors.

[0096] The compound represented by Chemical Formula 1 in the present invention can be used as a material for a hole injection layer 120, 320, 420, a hole transport layer 130, 330, 430, a buffer layer 210, a light-emitting auxiliary layer 220, an electron transport layer 150, 350, 450, an electron injection layer 160, a light-emitting layer 140, 340, 440 or a capping layer 180, but preferably, it can be used as a material for a hole transport layer 130, 330, 430, a light-emitting auxiliary layer 220, a light-emitting layer 140, 340, 440 and / or a capping layer 180.

[0097] like Figures 1 to 3 As shown, the organic electrical element may further include a protective layer (not shown) and an encapsulation layer (not shown). The protective layer may be located on the capping layer, and the encapsulation layer may be located on the capping layer. In order to protect the first electrode, the second electrode and the organic layer, the first electrode, the second electrode and the organic layer may be covered with a side view of at least one of the first electrode, the second electrode and the organic layer.

[0098] The protective layer can provide a flat surface to facilitate uniform formation of the encapsulation layer. During the preparation of the encapsulation layer, the protective layer can protect the first electrode, the second electrode and the organic layer.

[0099] The encapsulation layer can prevent external oxygen and moisture from penetrating into the interior of the organic electrical component.

[0100] In addition, even for the same or similar cores, the band gap, electrical properties, interface properties, etc. will be different depending on which substituent is bonded at which position. Therefore, it is necessary to study how to select the core and how to combine the (sub)-substituted bodies bonded to it. In particular, when the energy levels and T1 values ​​between each organic layer, the inherent properties of the material (mobility, interface properties, etc.) are optimally combined, both life extension and efficiency improvement can be achieved.

[0101] Therefore, the present invention uses the compound shown in Chemical Formula 1 as the material of the light-emitting auxiliary layer 220, the light-emitting layer 140, 340, 440 and / or the capping layer 180, so as to optimize the energy levels and T1 values ​​between the organic layers, the inherent properties of the material (mobility, interface properties, etc.), etc., while achieving the extension of the life of the organic electrical components and the improvement of their efficiency.

[0102] The organic electroluminescent element of one embodiment of the present invention can be prepared by a variety of evaporation methods (deposition). It can be prepared by evaporation methods such as PVD or CVD. For example, a metal or conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode 110, and an organic layer including a hole injection layer 120, 320, 420, a hole transport layer 130, 330, 430, a light-emitting layer 140, 340, 440, an electron transport layer 150, 350, 450 and an electron injection layer 160 is formed thereon, and then, a substance that can be used as a cathode 170 is evaporated thereon. In addition, a light-emitting auxiliary layer 220 can be further formed between the hole transport layer 130, 330, 430 and the light-emitting layer 140, 340, 440, and an electron transport auxiliary layer (not shown) can be further formed between the light-emitting layer 140 and the electron transport layer 150, and a stack structure can also be formed as described above.

[0103] Furthermore, a variety of polymer materials can be used to prepare an organic layer with fewer layers by a solution process or solvent process other than the evaporation method, such as a spin coating process, a spray printing process, an inkjet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a doctor blade forming process, a screen printing process or a thermal transfer method, etc. The present invention can adopt a variety of methods to form the organic layer, and its formation is not limited by the claims of the present invention.

[0104] The organic electrical device according to an embodiment of the present invention can be a top emission type, a bottom emission type or a double emission type according to the materials used.

[0105] The organic electrical element according to an embodiment of the present invention may include an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting element, a quantum dot display element, and the like.

[0106] Another embodiment of the present invention may include an electronic device, the electronic device including: a display device including the organic electrical element of the present invention; a control unit for controlling the display device. In this case, the electronic device may be all electronic devices including current or future wireless communication terminals, including mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controllers, navigators, game consoles, various TVs, various computers, etc.

[0107] Hereinafter, compounds according to one aspect of the present invention are described.

[0108] The compound according to one aspect of the present invention is expressed as the following Chemical Formula 1.

[0109] <Chemical Formula 1>

[0110]

[0111] In the chemical formula 1,

[0112] 1) Ar 1 To Ar 2 Independently of each other: C 6 ~C 60 an aryl group; a fluorenyl group; a C 2 ~C 60 heterocyclic group; or C 3 ~C 60 The aliphatic ring and C 6 ~C 60 A condensed aromatic ring (cyclo group); C 1 ~C 30 Alkyl; C 2 ~C 30 Alkenyl group; C 2 ~C 30 Alkinyl group; C 1 ~C 30 Alkoxyl group; C 6 ~C 30 Aryloxy group; -L a -N(R a )(R b ); or a combination thereof,

[0113] or,

[0114] 2) Ar 1 and Ar 2 At least one of them can be represented by the following chemical formula 1-a or chemical formula 1-b:

[0115]

[0116] 3) R 1 ~R 6 , R' and R" are independently: hydrogen; deuterium; halogen; cyano

[0117] (cyano group); nitro group; C 6 ~C 60an aryl group; a fluorenyl group; a C 2 ~C 60 Heterocyclyl group; C 3 ~C 60 The aliphatic ring and C 6 ~C 60 A condensed aromatic ring (cyclogroup); C 1 ~C 50 Alkyl; C 2 ~C 20 Alkenyl group; C 2 ~C 20 Alkinyl group; C 1 ~C 30 Alkoxyl group; C 6 ~C 30 Aryloxy group; -L a -N(R a )(R b ), or, adjacent groups may be bonded to form a ring,

[0118] 4) R a To R b Independently of each other: C 6 ~C 60 an aryl group; a fluorenyl group; a C 2 ~C 60 heterocyclic group; or C 3 ~C 60 The aliphatic ring and C 6 ~C 60 A condensed aromatic ring (cyclo group); or a combination thereof,

[0119] 5) L a is a single bond; C 6 ~C 60 an arylenel group; a fluorenylene group; a C 2 ~C60 Heterocyclyl group; C 3 ~C 60 The aliphatic ring and C 6 ~C 60 A condensed aromatic ring (cyclo group); or a combination thereof,

[0120] 6) R 7 It is hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ~C 60 an aryl group; a fluorenyl group; a C 2 ~C 60 Heterocyclyl group; C 3 ~C 60 The aliphatic ring and C 6 ~C 60 A condensed aromatic ring (cyclo group); C 1 ~C 50 Alkyl; C 2 ~C 20 Alkenyl group; C 2 ~C 20 Alkinyl group; C 1 ~C 30 Alkoxyl group; C 6 ~C 30 Alternatively, adjacent groups may be bonded to form a ring.

[0121] 7)X 1 is CR'R", NR', O, S, Se or SiR'R",

[0122] 8)X 2 is CR'R", NR', O, S, Se, SiR'R" or a single bond,

[0123] 9) n, p, q and r are independently integers from 0 to 4,

[0124] 10) m and o are independently integers from 0 to 3,

[0125] 11) Ar 1 To Ar2 , R 1 To R 7 , R', R", R a To R b , L a The rings formed by bonding adjacent groups to each other may be further substituted by one or more substituents selected from the group consisting of: deuterium; halogen; 1 -C 20 Alkyl or C 6 -C 20 aryl group substituted or unsubstituted silane group; siloxane group; boryl group; germanium group; cyano group; amino group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryl alkoxy group; C 1 -C 20 Alkyl; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkinyl group; C 6 -C 20 Aryl group; C substituted by deuterium 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 20 Aliphatic cyclo group; C 7 -C 20 Aryl alkyl group; C 8 -C 20aryl alkenyl group; and combinations thereof.

[0126] The Ar 1 To Ar 2 , R 1 To R 7 , R', R" and R a To R b When it is an aryl group, preferably, it can be C 6 ~C 30 The aryl group may be C 6 ~C 18 The aryl group may be, for example, phenyl, biphenyl, naphthyl, terphenyl, etc.

[0127] The Ar 1 To Ar 2 , R 1 To R 7 , R', R" and R a To R b When it is a heterocyclic group, preferably, it can be C 2 ~C 30 The heterocyclic group (heterocyclyl group), further preferably, can be C 2 ~C 18 The heterocyclic group may include dibenzo furan, dibenzothiophene, naphtho benzo thiophene, naphtho benzo furan and the like.

[0128] The Ar 1 To Ar 2 , R 1 To R 7 , R', R" and R a To R b When it is a fluorenyl group, preferably, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorene, or the like.

[0129] The La When it is an arylenel group, preferably, it can be C 6 ~C 30 The arylene group, further preferably, may be C 6 ~C 18 The arylene group may be, for example, phenyl, biphenyl, naphthyl, terphenyl, or the like.

[0130] The R 1 To R 7 When R' and R" are alkyl, preferably, they can be C 1 ~C 10 The alkyl group (Alkyl) may be, for example, a methyl group, a t-butyl group, or the like.

[0131] The R 1 To R 7 When R' and R" are alkoxy groups, preferably, they can be C 1 ~C 20 The alkoxyl group, further preferably, may be C 1 ~C 10 The alkoxyl group may be, for example, methoxy, t-butoxy, or the like.

[0132] The Ar 1 To Ar 2 , R 1 To R 7 , R', R", R a To R b And in L a The ring formed by bonding adjacent groups of 6 ~C 60 an aromatic cyclo group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si and P; 2 ~C 60 or C 3 ~C 60 For example, when adjacent groups are bonded to each other to form an aromatic ring, preferably, C 6 ~C20 The aromatic ring may preferably form a C 6 ~C 14 The aromatic ring can form, for example, benzene, naphthalene, phenanthrene, etc.

[0133] The chemical formula 1 can be expressed as any one of the following chemical formulas 2 to 4, but is not limited thereto.

[0134]

[0135] In the chemical formula 2 to the chemical formula 4,

[0136] 1) Z is CR'R", NR', O, S, Se, SiR'R" or a single bond.

[0137] 2) For the Ar 1 To Ar 2 , R', R" and R 1 To R 2 The same definitions as in Chemical Formula 1 apply.

[0138] The chemical formula 1 can be expressed as the following chemical formula 5 or chemical formula 6, but is not limited thereto.

[0139]

[0140] In the chemical formula 5 and the chemical formula 6,

[0141] For the X 1 , X 2 ,Ar 1 , R 1 To R 4 , R 7 , m to p and r are defined the same as in Chemical Formula 1.

[0142] The chemical formula 1 can be expressed as the following chemical formula 7 or chemical formula 8, but is not limited thereto.

[0143]

[0144] In the chemical formula 7 and the chemical formula 8,

[0145] For the Ar 1 , R 1 To R 7 R', R", and m to r are defined the same as in Chemical Formula 1.

[0146] The chemical formula 1-a can be expressed as any one of the following chemical formulas 1-a-1 to 1-a-5, but is not limited thereto.

[0147]

[0148] In the chemical formula 1-a-1 to chemical formula 1-a-5,

[0149] For the X 1 , R 3 To R 4 , R', R", o and p are defined the same as in Chemical Formula 1.

[0150] Furthermore, the compound represented by the chemical formula 1 may be any one of the following P-1 to P-90, but is not limited thereto.

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] In another specific example of the present invention, the present invention provides an organic electrical element, comprising: a first electrode; a second electrode; and an organic layer formed between the first electrode and the second electrode. The organic layer contains the compound represented by Chemical Formula 1 alone or in combination.

[0157] In another specific example of the present invention, the present invention provides an organic electrical element, comprising: a first electrode; a second electrode; an organic layer formed between the first electrode and the second electrode; and a capping layer. The capping layer is formed on one side of the first electrode and the second electrode that is not connected to the organic layer, and the organic layer or the capping layer contains the compound represented by Chemical Formula 1 alone or in combination.

[0158] The organic layer includes at least one of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. That is, at least one layer of the hole injection layer, the hole transport layer, the luminescence auxiliary layer, the luminescent layer, the electron transport auxiliary layer, the electron transport layer, and the electron injection layer included in the organic layer may contain the compound represented by chemical formula (1).

[0159] Preferably, the organic layer includes at least one of the hole transport layer, the luminescence auxiliary layer and the luminescent layer. That is, the compound may be contained in at least one of the hole transport layer, the luminescence auxiliary layer and the luminescent layer.

[0160] The organic layer may include two or more stacks, wherein the stack includes a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode.

[0161] Preferably, the organic layer further includes a charge generation layer formed between the two or more stacks.

[0162] In yet another specific example of the present invention, the present invention provides an electronic device, which includes: a display device, which includes an organic electrical element, and the organic electrical element contains the compound represented by Chemical Formula 1; and a control unit, which is used to drive the display device.

[0163] In a specific example of the present invention, the compound of Chemical Formula 1 may be contained alone, or may be contained in two or more different combinations, or may be contained in two or more combinations with other compounds.

[0164] Hereinafter, examples are given to specifically describe the synthesis example of the compound represented by Chemical Formula 1 and the preparation example of the organic electrical element in the present invention. However, the present invention is not limited to the following examples.

[0165] <Synthesis example>

[0166] According to the present invention, the final product represented by the chemical formula 1 can be synthesized by reacting Sub1 and Sub2 according to the following reaction formula 1, but the present invention is not limited thereto.

[0167] <Reaction formula 1>

[0168]

[0169] In the reaction formula 1,

[0170] For the R 1 , R 2 , R 7 ,Ar 1 ,Ar 2 , n, m and r are defined the same as in Chemical Formula 1.

[0171] I. Synthesis example of Sub1

[0172] Sub1 of the reaction formula 1 can be synthesized according to the following reaction formula 2, but is not limited thereto.

[0173] <Reaction 2>

[0174]

[0175] Synthesis example of Sub1-A-1

[0176]

[0177] Prepare a dry 2000ml round-bottom flask, add 535ml of THF and 2,2'-dibromo-1,1'-biphenyl (50.00g, 160.25mmol) under nitrogen atmosphere, and cool to -78°C. Then, slowly drip 64.1ml of n-BuLi into the reaction container. After melting adamantane-2-one (24.07g, 160.25mmol) with 150ml of THF, slowly drip it into the cooled reaction solution. After slowly warming the reaction solution to room temperature, let it react at room temperature for 3 hours. After the reaction is completed, quench the reaction solution with 1N HCl aqueous solution and extract it with ethyl acetate. Use MgSO 4 The extracted organic layer was dried, filtered and concentrated. 500 ml of acetic acid and 100 ml of HCl aqueous solution (35%) were added to the concentrated mixture, and the mixture was stirred for 6 hours in a circular flow. After the reaction was completed, the reaction solution was cooled at room temperature and the solid was filtered out. 47.47 g of the product (yield: 81.1%) was obtained from the filtered solid by silica gel column chromatography.

[0178] Synthesis example of Sub1-1

[0179]

[0180] Sub1-A-1 (20.21 g, 55.32 mmol), (2-chlorophenyl)boronic acid (9.08 g, 58.09 mmol), Pd(PPh 3 ) 4 (1.92g 1.66mmol) and THF 185ml were added into a 500ml round bottom flask, and K was dissolved with water 45ml. 2 CO 3 (22.94 g, 165.97 mmol) was added, and then the mixture was stirred for 10 hours in a circular flow. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and then MgSO 4 The organic layer was dried, filtered, and then concentrated. From the generated compound, 20.13 g of a product was obtained by silica gel column chromatography (yield: 91.7%).

[0181] Synthesis example of Sub1-19

[0182]

[0183] Sub1-A-2 (16.74 g, 45.82 mmol), (3-chloropyridin-4-yl)boronic acid (7.57 g, 48.12 mmol), Pd(PPh 3 ) 4 (1.59 g, 1.37 mmol) and 155 ml of THF were added to a 500 ml round-bottom flask, and K was dissolved in 40 ml of water. 2 CO 3 (19.00 g, 137.47 mmol) was added, and then the mixture was stirred for 10 hours in a circular flow. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and then MgSO 4 The organic layer was dried, filtered, and then concentrated. From the generated compound, 14.88 g of a product was obtained by silica gel column chromatography (yield: 81.6%).

[0184] Synthesis example of Sub1-20

[0185]

[0186] Sub 1-A-3 (21.40 g, 40.19 mmol), (2-chlorophenyl)boronic acid (6.60 g, 42.19 mmol), Pd(PPh 3 ) 4 (1.39 g 1.12 mmol) and 135 ml of THF were added to a 500 ml round-bottom flask, and K was dissolved in 40 ml of water. 2 CO 3 (16.66 g, 120.56 mmol) was added, and then the mixture was stirred for 10 hours in a circular flow. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and then MgSO 4 The organic layer was dried, filtered, and then concentrated. From the generated compound, 18.00 g of a product was obtained by silica gel column chromatography (yield: 79.4%).

[0187] Synthesis example of Sub1-25

[0188]

[0189] Sub 1-A-4 (23.98 g, 57.73 mmol), (2-chlorophenyl)boronic acid (9.48 g, 60.62 mmol), Pd(PPh 3 ) 4 (2.00 g 1.73 mmol) and THF 195 ml were added to a 500 ml round bottom flask, and K was dissolved in 50 ml water. 2 CO 3 (23.94 g, 173.19 mmol) was added, and then the mixture was stirred for 10 hours in a circular flow. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and then MgSO 4 The organic layer was dried, filtered, and then concentrated. From the generated compound, 22.53 g of a product was obtained by silica gel column chromatography (yield: 87.3%).

[0190] Synthesis example of Sub1-40

[0191]

[0192] Sub 1-A-5 (19.76 g, 54.09 mmol), (1-chlorodibenzo[b,d]furan-4-yl)boronic acid (14.00 g, 56.80 mmol), Pd(PPh 3 ) 4 (1.88 g 1.62 mmol) and 180 ml of THF were added to a 500 ml round bottom flask, and K was dissolved in 50 ml of water. 2 CO 3 (22.43 g, 162.27 mmol) was added, and then the mixture was stirred for 10 hours in a circular flow. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and then MgSO 4 The organic layer was dried, filtered, and then concentrated. From the generated compound, 22.70 g of a product was obtained by silica gel column chromatography (yield: 86.2%).

[0193] The compounds belonging to Sub1 may be the following compounds, but are not limited thereto.

[0194]

[0195] Table 1 below lists the FD-MS values ​​of the compounds belonging to Sub1.

[0196]

Table 1

[0197] Compound FD-MS Compound FD-MS Sub 1-1 <![CDATA[m / z=396.16(C 28 H 25 Cl=396.96)]]> Sub 1-2 <![CDATA[m / z=396.16(C 28 H 25 Cl=396.96)]]> Sub 1-3 <![CDATA[m / z=446.18(C 32 H 27 Cl=447.02)]]> Sub 1-4 <![CDATA[m / z=396.16(C 28 H 25 Cl=396.96)]]> Sub 1-5 <![CDATA[m / z=396.16(C 28 H 25 Cl=396.96)]]> Sub 1-6 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-7 <![CDATA[m / z=396.16(C 28 H 25 Cl=396.96)]]> Sub 1-8 <![CDATA[m / z=421.16(C 29 H 24 ClN=421.97)]]> Sub 1-9 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-10 <![CDATA[m / z=636.26(C 47 H 37 Cl=637.26)]]> Sub 1-11 <![CDATA[m / z=446.18(C 32 H 27 Cl=447.02)]]> Sub 1-12 <![CDATA[m / z=522.21(C 38 H 31 Cl=523.12)]]> Sub 1-13 <![CDATA[m / z=518.15(C 34 H 27 ClOS=519.10)]]> Sub 1-14 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-15 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-16 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-17 <![CDATA[m / z=486.18(C 34 H 27 ClO=487.04)]]> Sub 1-18 <![CDATA[m / z=486.18(C 34 H 27 ClO=487.04)]]> Sub 1-19 <![CDATA[m / z=397.16(C 27 H 24 ClN=397.95)]]> Sub 1-20 <![CDATA[m / z=563.24(C 40 H 34 ClN=564.17)]]> Sub 1-21 <![CDATA[m / z=563.24(C 40 H 34 ClN=564.17)]]> Sub 1-22 <![CDATA[m / z=522.21(C 38 H 31 Cl=523.12)]]> Sub 1-23 <![CDATA[m / z=654.25(C 46 H 36 ClNO=653.25)]]> Sub 1-24 <![CDATA[m / z=498.21(C 36 H 31 Cl=499.09)]]> Sub 1-25 <![CDATA[m / z=446.18(C 32 H 27 Cl=447.02)]]> Sub 1-26 <![CDATA[m / z=447.18(C 31 H 26 ClN=448.01)]]> Sub 1-27 <![CDATA[m / z=564.22(C 40 H 33 ClO=565.15)]]> Sub 1-28 <![CDATA[m / z=502.17(C 34 H 27 ClO 2 =503.04)]]> Sub 1-29 <![CDATA[m / z=446.18(C 32 H 27 Cl=447.02)]]> Sub 1-30 <![CDATA[m / z=679.30(C 49 H 42 ClN=680.33)]]> Sub 1-31 <![CDATA[m / z=421.16(C 29 H 24 ClN=421.97)]]> Sub 1-32 <![CDATA[m / z=452.23(C 32 H 33 Cl=453.07)]]> Sub 1-33 <![CDATA[m / z=650.24(C 47 H 35 ClO=651.25)]]> Sub 1-34 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-35 <![CDATA[m / z=695.33(C 50 H 46 ClN=696.38)]]> Sub 1-36 <![CDATA[m / z=414.16(C 28 H 24 ClF=414.95)]]> Sub 1-37 <![CDATA[m / z=502.17(C 34 H 27 ClO 2 =503.04)]]> Sub 1-38 <![CDATA[m / z=432.15(C 28 H 23 ClF 2 =432.94)]]> Sub 1-39 <![CDATA[m / z=472.20(C 34 H 29 Cl=473.06)]]> Sub 1-40 <![CDATA[m / z=584.32(C 42 H 45 Cl=585.27)]]>

[0198] II. Sub2 synthesis example

[0199] Sub2 of the reaction formula 1 can be synthesized through the reaction path of the following reaction formula 3, but is not limited thereto.

[0200] <Reaction 3>

[0201]

[0202] Furthermore, the compounds belonging to Sub2 may be the following compounds, but are not limited thereto.

[0203]

[0204]

[0205] Table 2 below lists the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub2.

[0206]

Table 2

[0207]

[0208]

[0209] III. Synthesis Examples of Final Compounds

[0210] P-4 Synthesis Example

[0211]

[0212] Sub1-1 (16.50 g, 41.57 mmol) and Sub2-1 (15.03 g, 41.57 mmol) in a round-bottom flask were melted with 140 ml of toluene, and then Pd 2 (dba) 3 (1.14 g, 1.25 mmol), P(t-Bu) 350% toluene solution (1.01 ml, 2.49 mmol) and NaOt-Bu (11.98 g, 124.70 mmol) were added, and then stirred at 110°C for 3 hours. After the reaction, the organic layer was extracted with toluene and water, and then MgSO 4 The organic layer was dried and concentrated, and 22.08 g (yield: 73.6%) of a product was obtained from the generated compound through separation and recrystallization by silica gel column chromatography.

[0213] Synthesis example of P-8

[0214]

[0215] Sub2-7 (18.84 g, 38.79 mmol), Pd 2 (dba) 3 (1.07 g, 1.16 mmol), P(t-Bu) 3 50% toluene solution (0.94 ml, 2.33 mmol), NaOt-Bu (11.19 g, 116.38 mmol) and toluene 130 ml were used to obtain 27.34 g (yield: 83.3%) of product P-8 using the P-4 synthesis method.

[0216] Synthesis example of P-24

[0217]

[0218] Sub2-3 (6.57 g, 23.04 mmol), Pd 2 (dba) 3 (0.63 g, 0.69 mmol), P(t-Bu) 3 50% toluene solution (0.56 ml, 1.38 mmol), NaOt-Bu (6.64 g, 69.11 mmol) and toluene (80 ml), the P-4 synthesis method was used to obtain the product P-24 10.4 g (yield: 61.5%).

[0219] Synthesis example of P-32

[0220]

[0221] Sub2-24 (15.99 g, 42.57 mmol), Pd 2 (dba) 3 (1.17 g, 1.28 mmol), P(t-Bu) 3 50% toluene solution (1.03 ml, 2.55 mmol), NaOt-Bu (12.28 g, 127.72 mmol) and toluene 145 ml were used to obtain the product P-3622.84 g (yield: 72.9%) using the P-4 synthesis method.

[0222] Synthesis example of P-44

[0223]

[0224] Sub2-1 (8.92 g, 24.69 mmol), Pd 2 (dba) 3 (0.68 g, 0.74 mmol), P(t-Bu) 3 50% toluene solution (0.60 ml, 1.48 mmol), NaOt-Bu (7.12 g, 74.06 mmol) and toluene 85 ml were used to obtain the product P-44 11.08 g (yield: 58.1%) using the P-4 synthesis method.

[0225] Synthesis example of P-60

[0226]

[0227] Sub1-30 (13.20 g, 19.40 mmol) was added to a round-bottom flask with Sub2-3 (5.54 g, 19.40 mmol), Pd 2 (dba) 3 (0.53 g, 0.58 mmol), P(t-Bu) 3 50% toluene solution (0.47 ml, 1.16 mmol), NaOt-Bu (5.59 g, 58.21 mmol) and toluene 65 ml were used to obtain the product P-60 12.31 g (yield: 68.3%) using the P-4 synthesis method.

[0228] Synthesis example of P-80

[0229]

[0230] Sub1-14 (11.23 g, 23.74 mmol) was added to a round-bottom flask with Sub2-57 (6.94 g, 23.74 mmol), Pd 2 (dba) 3 (0.65 g, 0.71 mmol), P(t-Bu) 3 50% toluene solution (0.58 ml, 1.42 mmol), NaOt-Bu (4.56 g, 47.48 mmol) and toluene 80 ml were used to obtain the product P-80 12.37 g (yield: 71.5%) using the P-4 synthesis method.

[0231] Synthesis example of P-86

[0232]

[0233] Sub1-37 (8.09 g, 16.08 mmol) was added to a round-bottom flask. Sub2-2 (4.59 g, 16.08 mmol), Pd 2 (dba) 3 (0.44 g, 0.48 mmol), P(t-Bu) 3 50% toluene solution (0.39 ml, 0.96 mmol), NaOt-Bu (3.09 g, 32.16 mmol) and toluene 55 ml were used to obtain 8.23 ​​g (yield: 68.1%) of product P-86 using the P-4 synthesis method.

[0234] Synthesis example of P-89

[0235]

[0236] Sub2-64 (10.10 g, 29.07 mmol), Pd 2 (dba) 3 (0.80 g, 0.87 mmol), P(t-Bu) 3 50% toluene solution (0.71 ml, 1.74 mmol), NaOt-Bu (5.59 g, 58.14 mmol) and toluene 100 ml were used to obtain the product P-89 11.81 g (yield: 57.4%) using the P-4 synthesis method.

[0237] In addition, the FD-MS values ​​of the compounds P-1 to P-69 of the present invention prepared according to the synthesis example are shown in Table 3 below.

[0238]

Table 3

[0239]

[0240]

[0241] Evaluation of organic electrical component preparation

[0242] (Example 1) Green organic light emitting element (hole transport layer)

[0243] An organic electroluminescent device was prepared according to a conventional method using the compound of the present invention as a hole transport layer substance.

[0244] First, N was vacuum-deposited on the ITO layer (anode) formed on the glass substrate. 1 -(Naphthalen-2-yl)-N 4 ,N 4 -Bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter referred to as 2-TNATA) was deposited to a thickness of 60 nm to form a hole injection layer.

[0245] On the hole injection layer, the compound P-2 of the present invention was vacuum-deposited as a hole transport compound with a deposition thickness of 60 nm to form a hole transport layer.

[0246] On the upper part of the hole transport layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as CBP) is used as a host, tris(2-phenylpyridine)-iridium (hereinafter referred to as Ir(ppy) 3 ) is used as an impurity doping agent and doping is carried out with a weight ratio of 90:10 to evaporate a light-emitting layer with a thickness of 30nm.

[0247] On the light-emitting layer, (1,1'-biphenyl-4-yl)bis(2-methyl-8-quinolinolato)aluminum (hereinafter referred to as BAlq) was vacuum-deposited to a thickness of 5 nm to form a hole blocking layer.

[0248] On the hole blocking layer, tris(8-quinolinol)aluminum (hereinafter referred to as Alq3) was vacuum-deposited to a thickness of 40 nm to form an electron transport layer.

[0249] Then, alkali metal halide LiF was evaporated to a thickness of 0.2 nm to form an electron injection layer, and then Al was evaporated to a thickness of 150 nm to form a cathode, thereby preparing an organic electroluminescent element.

[0250] (Example 2) to (Example 14)

[0251] An organic electroluminescent element was prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 4 below was used instead of the compound P-2 as the hole transport layer material.

[0252] (Comparative Example 1)

[0253] An organic electroluminescent element was prepared in the same manner as in Example 1 except that N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as NPB) was used as the hole transport layer material.

[0254] (Comparative Example 2) to (Comparative Example 4)

[0255] An organic electroluminescent element was prepared by the same method as in Example 1, except that the following comparative compounds 1 to 3 were used as the hole transport layer.

[0256]

[0257] The organic electroluminescent elements prepared according to Examples 1 to 20 and Comparative Examples 1 to 4 were input with a forward bias DC voltage, and the electroluminescent (EL) characteristics were tested using a PR-650 from Photo Research. 2 At a brightness of 1.5 Å, the life of T95 was tested using a life testing device manufactured by Mcscience Inc. The prepared components and the test results are shown in Table 4 below.

[0258]

Table 4

[0259]

[0260] As shown in Table 4, the electrical characteristics of the device using the compound represented by Chemical Formula 1 of the present invention as the hole transport layer material are significantly improved compared with the device using the comparative compound as the hole transport layer material.

[0261] That is, the element described in Comparative Example 1 is prepared using NPB mainly used as a hole transport layer material, but in Comparative Examples 2 to 4, when preparing the element, Comparative Compounds 1 to 3 containing a fluorenyl group in the amine group are used, and their electrical properties (driving voltage, efficiency and life) are improved compared with the former. Compared with Comparative Examples 2 to 4, when the compound represented by Chemical Formula 1 of the present invention is used as a hole transport layer material, the luminous efficiency of the organic electroluminescent element is improved, the life is extended, the driving voltage is slightly reduced, and the electrical properties of the element are improved.

[0262] First, from the perspective of the overall framework, the basic structures of comparative compounds 1 to 3 are similar to the compound shown in Chemical Formula 1 of the present invention, and both contain an amine group and a fluorenyl group in their structures. However, based on the evaluation of the compound of the present invention, it can be seen that the difference between the comparative compound 1 and the compound of the present invention is that the spiro-adamantane fluorene The amine group is directly bonded, and in comparative compound 2, a para-phenyl linking group is introduced between spiro-adamantyl-fluorene and the amine group, and in comparative compound 3, an ortho-phenyl linking group is introduced between diphenylfluorene and the amine group, but the spiro-adamantyl-fluorene skeleton is not included in the structure.

[0263] First, by studying Comparative Examples 2 and 3 to 4, it can be seen that Comparative Examples 3 and 4 have a linking group between the amine group and the fluorenyl group (spiro-adamantyl-fluorene / diphenyl fluorene), and the characteristics of the device are improved compared with Comparative Example 2. It can be seen that whether a linking group is introduced between the amine group and the fluorenyl group will affect the electrical characteristics of the device.

[0264] Furthermore, from studying Comparative Examples 3 and 4, it can be seen that the two are similar in that a linking group is introduced between the amine group and the fluorenyl group. However, since Comparative Example 3 contains a spiro-adamantyl-fluorene skeleton, the device characteristics are improved in terms of life; and since Comparative Example 4 contains an ortho-phenyl linking group, the device characteristics are improved in terms of efficiency. It can be seen that the bending degree of the linking group or the structural morphology of the fluorenyl group will affect the electrical characteristics of the device.

[0265] From the results of these comparative examples, it can be seen that the compound of the present invention represented by Chemical Formula 1 of the present invention contains an amine group and a spiro-adamantyl-fluorene skeleton, and there must be an ortho-bent linking group therebetween. Therefore, compared with Comparative Examples 2 to 4, the device characteristics of Examples 1 to 14 are significantly improved.

[0266] By comparing the components made of the compound of the present invention and the comparative compound, it can be seen that the energy levels (HOMO, LUMO and T1, etc.) of the compounds will be significantly different depending on whether there is a linking group between the amine group and the fluorenyl group, the substitution form of the linking group, and the structural form of the fluorenyl group. When evaporating the components, the difference in the physical properties of the chemicals will become the main factor in improving the performance of the components. Therefore, as mentioned above, different results will appear in the components.

[0267] Furthermore, it can be seen that, as in the chemical formula of the present invention, when the structure is as follows: the fluorenyl group is spiro-adamantyl-fluorene and is connected to the amine group via an ortho-linking group, it is suitable for improving the performance of the device.

[0268] In addition, the above-mentioned device preparation and evaluation results describe the characteristics expressed by the device when the compound of the present invention is applied to the hole transport layer, but the compound of the present invention can be applied to more than one layer among the light-emitting layer, the hole transport layer and the light-emitting auxiliary layer.

[0269] The above contents are merely examples of the present invention. However, anyone skilled in the art can make various modifications to the performance improvement methods, including other compounds, without departing from the essential characteristics of the present invention.

[0270] Therefore, the embodiments described in this specification are not used to limit the present invention, but to describe the present invention, and the scope of the present invention is not limited by such embodiments. It should be interpreted that the protection scope of the present invention should be interpreted according to the following claims, and all technologies within the same scope should fall within the scope of the claims of the present invention.

Claims

1. A compound represented by the following Chemical Formula 5 or Chemical Formula 6, characterized in that: In the chemical formula 5 and the chemical formula 6, 1) Ar 1 C6~C 18 Aryl; Chemical Formula 1-a; or Chemical Formula 1-b: Among them, Ar 1 Optionally further substituted by one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1-C 20 Alkyl; C6-C 20 Aryl; C6-C substituted by deuterium 20 and a C2-C 20 A heterocyclic group, and 2) R 1 ~R 6 Independently of each other: hydrogen; deuterium; halogen; cyano; C6~C 18 aryl; fluorenyl; C2~C 18 Heterocyclic group; C1~C 10 Alkyl; or C2~C 20 The alkenyl group, and 3) R' and R" are independently: C6~C 18 or C1~C 10 of an alkyl group, and 4) R 7 It is hydrogen; deuterium; or C6~C 18 of an aromatic group, and 5)X 1 is CR'R", NR', O, S, Se or SiR'R", and 6)X 2 is a single bond, and 7) n, p, q and r are independently integers from 0 to 4, and 8) m and o are independently integers from 0 to 3.

2. A compound, characterized in that: The compound is any one of the following compounds:

3. An organic electrical component, characterized in that: include: a first electrode; a second electrode; as well as An organic layer is formed between the first electrode and the second electrode, wherein the organic layer comprises the compound according to claim 1 or 2.

4. An organic electrical component, characterized in that: The organic electrical element comprises a first electrode; a second electrode; an organic layer formed between the first electrode and the second electrode; and the capping layer, The capping layer is formed on one side of the first electrode and the second electrode that does not contact the organic layer. The organic layer or the capping layer comprises the compound according to claim 1 or 2.

5. The organic electrical device according to claim 3 or 4, characterized in that: The organic layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

6. The organic electrical device according to claim 5, characterized in that: The organic layer includes at least one of the hole transport layer, the light-emitting auxiliary layer and the light-emitting layer.

7. The organic electrical device according to claim 3 or 4, characterized in that: The organic layer includes more than two stacks, and the stack includes a hole transport layer, a light emitting layer and an electron transport layer which are sequentially formed on the anode.

8. The organic electrical device according to claim 7, characterized in that: The organic layer further includes a charge generation layer formed between the two or more stacks.

9. An electronic device comprising: A display device comprising the organic electric element according to claim 3 or 4; as well as A control unit is used to drive the display device.

10. The electronic device according to claim 9, characterized in that: The organic electrical element is selected from the group consisting of an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, an element for monochromatic lighting, and an element for quantum dot display.

Images