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

Abstract

The present application provides an organic electrical device including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including a compound represented by Chemical Formula 1, and an electronic device including the organic electrical device. The organic layer including the compound represented by Chemical Formula 1 can reduce the driving voltage of the organic electrical device, and can improve the light emitting efficiency and the lifespan.

Description

Technical Field

[0001] This invention relates to compounds for organic electrical components, organic electrical components utilizing the same, and electronic devices thereof. Background Technology

[0002] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical components utilizing organic light emission usually have an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of the organic electrical components, the organic layer is generally formed as a multilayer structure composed of various materials; for example, it can be formed as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] In organic light-emitting diodes (OLEDs), the most problematic aspects are lifespan and efficiency. As displays become increasingly larger, these efficiency or lifespan issues have become matters that must be addressed.

[0004] Efficiency, lifetime, and driving voltage are interrelated. Increased efficiency leads to a relative decrease in driving voltage. This, in turn, reduces the crystallization of organic materials during Joule heating, ultimately resulting in a longer lifetime. However, simply improving the organic layers alone cannot maximize efficiency. This is because only when the energy levels and T1 values ​​between the organic layers, along with the inherent properties of the materials (mobility, surface properties, etc.), are optimally combined can both long lifetime and high efficiency be achieved simultaneously.

[0005] Therefore, in order to fully utilize the excellent characteristics of organic electrical components, it is necessary to develop the materials that constitute the organic layer within the component, especially the hole transport layer and the light-emitting auxiliary layer. Summary of the Invention

[0006] Technical issues

[0007] The object of the present invention is to provide compounds that can reduce the driving voltage of components and improve luminous efficiency and lifespan, and organic electrical components and electronic devices utilizing the same.

[0008] Technical solution

[0009] In one aspect, the present invention provides compounds represented by the following chemical formula.

[0010]

[0011] In another aspect, the present invention provides an organic electrical component and electronic device thereof comprising a compound represented by the above chemical formula.

[0012] Technical effect

[0013] By utilizing the compounds of the present invention, not only can the driving voltage of the device be reduced, but the luminous efficiency and lifespan of the device can also be improved. Attached Figure Description

[0014] Figures 1 to 3 This is an example diagram of an organic electroluminescent element according to an embodiment of the present invention.

[0015] Explanation of reference numerals in the attached figures

[0016] 100, 200, 300: Organic electrical components; 110: First electrode

[0017] 120: Hole injection layer; 130: Hole transport layer

[0018] 140: Light-emitting layer; 150: Electron transport layer

[0019] 160: Electron injection layer; 170: Second electrode

[0020] 180: Light efficiency improvement layer; 210: Buffer layer

[0021] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0022] 330: First hole transport layer; 340: First luminescent layer

[0023] 350: First electron transport layer; 360: First charge generation layer

[0024] 361: Second charge generation layer; 420: Second hole injection layer

[0025] 430: Second hole transport layer; 440: Second luminescent layer

[0026] 450: Second electron transport layer; CGL: Charge generation layer

[0027] ST1: First stack ST2: Second stack Detailed Implementation

[0028] The terms "aryl" and "arylene" as used in this invention, unless otherwise specified, refer to compounds having a number of carbons from 6 to 60, but are not limited thereto. In this invention, aryl or arylene compounds include monocyclic, cyclic aggregates, fused polycyclic, and spirocyclic compounds, etc.

[0029] In this invention, the term "fluorenyl" means a substituted or unsubstituted fluorenyl group, and "fluorene-like" means a substituted or unsubstituted fluorene-like group. Fluorenyl or fluorene-like groups as used in this invention include spiro compounds formed by the interaction of R and R' in the following structures, and also include cyclic compounds formed by the interaction of adjacent R" groups. "Substituted fluorenyl" and "substituted fluorene-like" mean that in the following structures, at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R" in the following structures can be 1 to 8 valences. Regardless of valence, fluorenyl and fluorene-like groups may be referred to as fluorenylfluorene ring or fluorene in this specification.

[0030]

[0031] In this invention, the term "spirocyclic compound" means "spiro union," which implies a connection achieved by two spirocyclic rings sharing only one atom. The atom shared between the two rings is referred to as "spiro," and these are respectively called "monospirocyclic," "bispirral," and "trispirral" compounds, depending on the number of spirocyclic atoms contained in the compound.

[0032] The term "heterocyclic group" as used in this invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene," but also non-aromatic rings. Unless otherwise specified, it means a ring with 2 to 60 carbon atoms containing one or more heteroatoms, but the invention is not limited thereto. The term "heteroatom" as used in this invention, unless otherwise specified, refers to elements other than carbon, such as N, O, S, P, or Si, and may also include compounds containing heteroatomic groups such as SO2, P=O, etc., instead of the carbon forming the ring. Heterocyclic group means monocyclic, cyclic aggregates, fused polycyclic, and spirocyclic compounds containing heteroatoms.

[0033]

[0034] The term "aliphatic cyclic group" as used in this invention means cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclic, cyclic aggregates, fused polycyclic and spirocyclic compounds, etc. Unless otherwise specified, it means a ring with 3 to 60 carbon atoms, but is not limited thereto. For example, the fusion of benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, also corresponds to an aliphatic ring.

[0035] In this specification, the "group name" corresponding to aryl, arylene, heterocyclic, etc., shown by way of examples of various symbols and their substituents, may be written as "the name of the group reflecting the valence," but it may also be written as "the name of the parent compound." For example, in the case of "phenanthrene," which is an aryl group, the monovalent "group" is "phenanthryl," the divalent group is "phenanthrylene," etc. The name of the group may be written by distinguishing the valence, but it may also be written as "phenanthrene" as the name of the parent compound, regardless of the valence. Similarly, in the case of pyrimidine, it may be written as "pyrimidine," regardless of the valence, or it may be written as "the name of the group with that valence," for example, in the case of monovalent, it may be written as pyrimidinyl, and in the case of divalent, it may be written as pyrimidinyl, etc.

[0036] Furthermore, when describing the names of compounds or substituents in this invention, numbers or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofurano[2,3-d]pyrimidine as benzofuranopyrimidine, and 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzo[g]quinoxaline.

[0037] Furthermore, unless otherwise specified, the chemical formulas used in this specification are applicable in the same way as the definitions of substituents defined by the index of the following chemical formulas.

[0038]

[0039] Where, when a is an integer of 0, the substituent R 1 If a is 0, it means that all carbons forming the benzene ring are bonded to hydrogen. In this case, the representation of the hydrogens bonded to the carbons can be omitted, and the chemical formula or compound can be written. Furthermore, if a is an integer of 1, a substituent R... 1 It combines with one of the carbons used to form the benzene ring, in the following manner when a is an integer of 2 or 3, and in a similar manner with the carbons of the benzene ring when a is an integer of 4 to 6, and R when a is an integer of 2 or more. 1 They can be the same or different from each other.

[0040]

[0041] Furthermore, unless otherwise stated in this specification, when representing condensed rings, the number in 'numerical-condensed ring' indicates the number of condensed rings. For example, the condensed form of three rings such as anthracene, phenanthrene, and benzoquinazoline can be represented as a 3-condensed ring.

[0042] Furthermore, unless otherwise stated in this specification, when a ring is represented in the form of 'numerical atom' such as a five-membered ring or a six-membered ring, the number in 'numerical-atom' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a five-membered ring, and benzene or pyridine may correspond to a six-membered ring.

[0043] Furthermore, unless otherwise stated in this specification, the rings formed by the bonding of adjacent groups are selected from C6 to C6. 60 Aromatic cyclic groups; fluorene groups; C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic cyclic groups.

[0044] Unless otherwise stated in this specification, 'between adjacent groups' means, taking the following chemical formulas as examples, not only between R1 and R2, R2 and R3, R3 and R4, and R5 and R6, but also between R7 and R8 sharing a carbon atom, and may also include substituents bonded to non-directly adjacent ring-forming elements (carbon or nitrogen, etc.), such as between R1 and R7, R1 and R8, or R4 and R5. That is, when a ring-forming element such as directly adjacent carbon or nitrogen has a substituent, it can be an adjacent group; however, when no substituent is bonded to a ring-forming element in a directly adjacent position, it can be an adjacent group with a substituent bonded to the next ring-forming element. Furthermore, substituents bonded to the same carbon atom in the same ring can also be called adjacent groups. In the following chemical formulas, when rings are formed by the interaction of substituents bonded to the same carbon atom, such as R7 and R8, compounds containing spirocyclic moieties can be formed.

[0045]

[0046] Furthermore, the expression 'adjacent groups can combine to form a ring' in this specification is used to mean the same thing as 'adjacent groups can combine to selectively form a ring', and implies the situation where at least one pair of adjacent groups combine to form a ring.

[0047] Furthermore, unless otherwise stated in this specification, aryl, arylene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and rings formed by the combination of adjacent groups can be selected from deuterium, halogen, C1-C2, etc. 20 Alkyl or C6-C 20 Aryl-substituted or unsubstituted amino groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic groups, and C3~C 20 One or more substituents in the group consisting of aliphatic cyclic groups are further substituted.

[0048] Below, refer to Figures 1 to 3 The layered structure of organic electrical components containing the compounds of the present invention will be described.

[0049] When affixing reference numerals to the structural elements in the accompanying drawings, care should be taken to assign the same reference numerals to the same structural elements, even if they are shown in different drawings. Furthermore, in describing the invention, detailed descriptions will be omitted where it is determined that a detailed explanation of a known structure or function would obscure the essence of the invention.

[0050] In describing the structural elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are used only to distinguish the structural elements from each other, and the nature, order, or sequence of the related structural elements are not limited by these terms. When a structural element is "connected," "combined," or "linked" to another structural element, the structural element may be directly connected or linked to the other structural element, but it can also be understood that other structural elements are "connected," "combined," or "linked" between the structural elements.

[0051] Furthermore, when structural elements such as layers, membranes, regions, and plates are located "above" or "above" other structural elements, this can be understood not only as being "directly above" other structural elements, but also as having other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood as having no other part in between.

[0052] Figures 1 to 3 This is an example diagram of an organic electroluminescent element according to an embodiment of the present invention.

[0053] Reference Figure 1An organic electrical component 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 layer between the first electrode 110 and the second electrode 170.

[0054] The first electrode 110 can be an anode, and the second electrode 170 can be a cathode. In the case of the inverted type, the first electrode can be a cathode and the second electrode can be an anode.

[0055] The aforementioned 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 formed sequentially on the first electrode 110.

[0056] Preferably, a light efficiency improvement layer 180 can be formed on one of the two sides of the first electrode 110 or the second electrode 170 that does not contact the organic layer. When the light efficiency improvement layer 180 is formed, the light efficiency of the organic electrical component can be improved.

[0057] For example, a light efficiency improvement layer 180 can be formed on the second electrode 170. However, if it is a top-emission organic light-emitting element, the formation of the light efficiency improvement layer 180 can reduce the loss of optical energy caused by surface plasmon polarizations (SPPs) in the second electrode 170. If it is a bottom-emission organic light-emitting element, the light efficiency improvement layer 180 can perform a buffering effect on the second electrode 170.

[0058] A buffer layer 210 or a light-emitting auxiliary layer 220 may also be formed between the hole transport layer 130 and the light-emitting layer 140. For this purpose, refer to... Figure 2 Please provide an explanation.

[0059] Reference Figure 2 According to another embodiment of the present invention, the organic electrical component 200 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 sequentially on a first electrode 110, and a light efficiency improvement layer 180 may be formed on the second electrode.

[0060] Although not illustrated Figure 2 An electron transport auxiliary layer may also be formed between the light-emitting layer 140 and the electron transport layer 150.

[0061] Furthermore, according to another embodiment of the present invention, the organic layer may also be in the form of a stack comprising multiple hole transport layers, light-emitting layers, and electron transport layers. See also... Figure 3 Please provide an explanation.

[0062] Reference Figure 3 According to another embodiment of the present invention, the organic electrical element 300 may form two or more stacks (ST1, ST2) of organic layers arranged in multiple layers between the first electrode 110 and the second electrode 170, and a charge generation layer CGL is formed between the stacks of organic layers.

[0063] Specifically, an organic electrical component according to an embodiment of the present invention may include a first electrode 110, a first stack ST1, a charge generation layer CGL (charge generation layer), a second stack ST2, a second electrode 170, and a light efficiency improvement layer 180.

[0064] The first stack ST1, as an organic layer formed on the first electrode 110, 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. 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. Thus, the first and second stacks may be organic layers with the same stacked structure, or they may be organic layers with different stacked structures.

[0065] A charge generation layer CGL can 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. This charge generation layer CGL, formed between the first light-emitting layer 340 and the second light-emitting layer 440, increases the current efficiency generated in each light-emitting layer and plays a role in smoothly distributing charge.

[0066] Although the first light-emitting layer 340 may include a light-emitting material containing a blue fluorescent dopant in a blue body, and the second light-emitting layer 440 may include a material containing a green body doped with both greenish yellow and red dopant, the materials of the first light-emitting layer 340 and the second light-emitting layer 440 according to embodiments of the present invention are not limited thereto.

[0067] exist Figure 3 In this case, n can be an integer from 1 to 5, but when n is 2, a charge generation layer CGL and a third stack can be further stacked on the second stack ST2.

[0068] like Figure 3By forming multiple light-emitting layers through a multi-layer stacked structure, it is possible not only to fabricate organic electroluminescent elements that emit white light by means of the mixing effect of light emitted from each light-emitting layer, but also to fabricate organic electroluminescent elements that emit light of multiple colors.

[0069] While the compound represented by chemical formula 1 of the present invention can be used as a material for hole injection layers 120, 320, 420, hole transport layers 130, 330, 430, buffer layer 210, light-emitting auxiliary layer 220, electron transport layers 150, 350, 450, electron injection layer 160, light-emitting layer 140, 340, 440 or light efficiency improvement layer 180, it is preferred to use it as a material for hole transport layers 130, 330, 430, light-emitting auxiliary layer 220 and / or light efficiency improvement layer 180.

[0070] Even with the same or similar nuclei, the band gap, electrical properties, and surface properties may differ depending on which substituent is bonded at which position. Therefore, it is necessary to study the selection of the nucleus and the combination of its bonded substituents. In particular, when the energy levels and T1 values ​​between the organic layers, as well as the inherent properties of the material (mobility, surface properties, etc.) are optimally combined, long lifetime and high efficiency can be achieved simultaneously.

[0071] Therefore, the compound represented by chemical formula 1 in this invention is used as a material for hole transport layers 130, 330, 430, light-emitting auxiliary layer 220 and / or light efficiency improvement layer 180, thereby optimizing the energy level and T1 value, inherent characteristics (mobility, surface characteristics, etc.) between organic layers, while improving the lifespan and efficiency of organic electrical components.

[0072] An organic electroluminescent element according to an embodiment of the present invention can be fabricated using various vapor deposition methods. It can be fabricated using vapor deposition methods such as PVD or CVD. For example, it can be fabricated by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate to form an anode 110, and then forming an organic layer thereon 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, followed by depositing a material that can serve as a cathode 170 thereon. Furthermore, a light-emitting auxiliary layer 220 can be formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) can be formed between the light-emitting layer 140 and the electron transport layer 150. As described above, it can also be formed in a stacked structure.

[0073] Furthermore, the organic layer utilizes various polymer materials and is formed into a smaller number of layers through solvent treatment or solvent refining methods other than vapor deposition, such as spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll coating, doctor blade coating, screen printing, or thermal transfer. Since the organic layer of this invention can be formed by various methods, the scope of protection of this invention is not limited by the formation method.

[0074] According to one embodiment of the present invention, the organic electrical component can be classified into front-emitting type, rear-emitting type or double-sided-emitting type based on the material used.

[0075] Furthermore, according to an embodiment of the present invention, the organic electrical component is selected from the group consisting of organic light-emitting elements, organic solar cells, organic photosensitive elements, organic transistors, monochrome lighting elements, and quantum dot display elements.

[0076] Another embodiment of the present invention may include an electronic device, which includes: a display device comprising the organic electrical components of the present invention described above; and a control unit for controlling the display device. In this case, the electronic device can be a current or future wireless communication terminal, and includes mobile communication terminals such as mobile phones, navigators, game consoles, various TVs, various computers, and all other electronic devices.

[0077] Hereinafter, a compound of one aspect of the present invention will be described.

[0078] The compounds of one aspect of the present invention are represented by the following chemical formula 1.

[0079] <Chemical Formula 1>

[0080]

[0081] In the above chemical formula 1, each symbol can be defined in the following manner.

[0082] The nitrogen (N) of the amine group can be bound to the benzene ring of the fluorene moiety, or to R', or to R.

[0083] R1 to R4 are independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6 to C4. 60 aryl; fluorenyl; C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; C3~C 60 Aliphatic cyclic groups; C1~C 20 Alkyl groups; C2-C 20 alkenyl group; C2~C 20 alkynyl group; C1~C 20 alkoxy groups; C6~C20 aryloxy groups; and -L'-N(R a (R) b A group consisting of ) and adjacent groups can combine to form a ring.

[0084] a to c are integers from 0 to 4, and d is an integer from 0 to 7. When a and c are integers of 2 or higher, R1, R2, R3, and R4 are either the same or different.

[0085] When the nitrogen (N) of the amine group is bonded to the benzene ring of the fluorene moiety, a+b can be an integer of 7 or less.

[0086] When adjacent groups, for example, adjacent R1, adjacent R2, adjacent R3, or adjacent R4, combine to form a ring, the ring may be selected from C6 to C4. 60 Aromatic cyclic groups; fluorene cyclic groups; C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic cyclic groups.

[0087] When the ring formed by the interaction of adjacent groups is an aromatic ring, the aforementioned aromatic ring can be C6 to C6. 20 C6~C 18 C6~C 16 C6~C 14 C6~C 13 C6~C 12 C6~C 10 C6, C 10 C 12 C 14 C 15 C 16 C 18 Aromatic rings, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0088] R' and R” are independently selected from hydrogen; C6~C 60 aryl; fluorene; C2-C containing at least one heteroatom selected from O, N, S, Si and P 60 Heterocyclic groups; C3~C 60 Aliphatic cyclic groups; C1~C 20 Alkyl groups; C2-C 20 alkenyl group; C2~C 20 alkynyl group; C1~C 20 alkoxy groups; and C6~C 20The group consists of aryl groups, and R' and R" can combine with each other to form a ring. The nitrogen N of the amine group can be combined with the R' or R" of the fluorene moiety. For example, when R' or R" is an aryl group, the nitrogen N of the amine group can be combined with the aryl group.

[0089] When R' and R" can combine to form a ring, a spirocyclic compound can be formed. For example, when R' and R" can combine to form a ring, the ring can be selected from C6 to C6. 60 Aromatic cyclic group; fluorene cyclic group; C2-C2 group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic ring groups, especially R' and R" which can combine with each other to form rings of oxaline, fluorene, acridine, etc., for example, rings including the following structures can be formed.

[0090]

[0091] In the above structure, * corresponds to spirocyclic atoms, sharing fluorene and carbon atoms bonded by R' and R”. In the above structure, X can be a direct bond, O, S, N (Ar) 1 ) or C(R 1 (R) 2 When X is a direct bond, the above structure corresponds to fluorene (aryl); when X is O, the above structure corresponds to 9H-xanthene; when X is S, the above structure corresponds to 9H-thioxanthene; and when X is N (Ar)... 1 When X is a direct bond, the above structure corresponds to acridine or its derivatives. When X is a direct bond, R' and R" combine with each other to eventually form spirobisfluorene or its derivatives.

[0092] In C(R) 1 (R) 2 In ), R 1 and R 2 Independently selected from hydrogen, deuterium, halogens, and C1-C2 atoms. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C20 alkynyl group, C6~C 30 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 heterocyclic groups, and C3~C 30 The group composed of aliphatic ring groups, R 1 and R 2 They can combine with each other to form a ring.

[0093] R 1 and R 2 When the above-mentioned rings are formed by mutual combination, the rings can be freely selected from C6 to C6. 60 Aromatic cyclic groups; fluorene cyclic groups; C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; and C3~C 60 The group composed of aliphatic ring groups, for example, if R 1 and R 2 When they combine to form fluorene rings, they can form spirobic fluorene rings together with C atoms that contain these rings.

[0094] In N(Ar) 1 ), Ar 1 Choose freely from C6 to C 30 Aryl, fluorenyl, C2-C containing at least one heteroatom selected from O, N, S, Si, and P 30 heterocyclic group, C3~C 30 The group consisting of aliphatic cyclic groups and combinations thereof.

[0095] L is selected from C6 to C. 60 arylene; fluorene; C3~C 60 Aliphatic cyclic groups; C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; and groups composed of their combinations.

[0096] Ar1 is selected freely from C6 to C6. 60 aryl; fluorenyl; C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; C3~C 60 Aliphatic cyclic groups; and groups composed of their combinations. For example, Ar1 can be C 12 ~C 25 Aryl or fluorene.

[0097] The L' above is a single key; C6~C 60 arylene; fluorene; C3~C 60Aliphatic rings; and C2-C2 rings containing at least one heteroatom selected from O, N, S, Si, and P. 60 The group is composed of heterocyclic groups.

[0098] The above R a and R b Choose independently from C6 to C6. 60 aryl; fluorenyl; C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic cyclic groups.

[0099] In the above R1 to R4, Ar1, R', R”, R 1 R 2 R a R b When at least one of the components is an aryl group, the aforementioned aryl group may be, for example, C6 to C6. 30 C6~C 29 C6~C 28 C6~C 27 C6~C 26 C6~C 25 C6~C 24 C6~C 23 C6~C 22 C6~C 21 C6~C 20 C6~C 19 C6~C 18 C6~C 17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 The aryl group can be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

[0100] When at least one of L and L' is an aryl group, the aryl group can be, for example, C6 to C6. 30 C6~C 29 C6~C 28 C6~C 27 C6~C 26 C6~C 25 C6~C 24 C6~C 23 C6~C 22 C6~C 21 C6~C 20 C6~C 19 C6~C 18 C6~C 17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 The arylene group can be phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenylene, etc.

[0101] In the above R1 to R4, Ar1, R', R”, R 1 R 2 R a R b When at least one of L, L' is a heterocyclic group, the aforementioned heterocyclic group can be, for example, C2 to C3. 30 C2~C 29 C2~C 28 C2~C 27 C2~C 26 C2~C 25 C2~C 24 C2~C 23 C2~C 22 C2~C 21 C2~C 20 C2~C 19 C2~C 18C2~C 17 C2~C 16 C2~C 15 C2~C 14 C2~C 13 C2~C 12 C2~C 11 C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 C 19 C 20 C 21 C 22 C 23 C 24 C 25 C 26 C 27 C 28 C 29 Heterocyclic groups, specifically, can be pyridine, pyrazine, pyridazine, triazine, furan, pyrrole, thiorrole, indole, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazindoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, benzene-carbazole, benzocarbazole, benzene-benzocarbazole, naphthobenzocarbazole, naphthobenzocarbazole Dibenzocarbazole, indolocarbazole, benzofuranopyridine, benzothiophenepyridine, benzofuranopyridine, benzothiophenepyrimidine, benzofuranopyrimidine, benzothiophenepyrazine, benzofuranopyrazine, benzimidazole, benzothiazole, benzoxazole, benzothiol, phenanthrene, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenthiazine, dibenzodioxane, benzodibenzodioxane, thiaanthracene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thiaxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthrene], etc.

[0102] In the above R1 to R4, Ar1, Ar 1 、R'、R”、R 1 R2 R a R b When at least one of L and L' is fluorenyl or at least one of L and L' is fluoreneyl, the aforementioned fluorenyl or fluoreneyl group can be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirodifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphth-2-yl)9-phenyl-9H-fluorene, etc.

[0103] In the above R1 to R4, Ar1, Ar 1 、R'、R”、R 1 R 2 R a R b When at least one of L, L' is an aliphatic cyclic group, the aforementioned aliphatic cyclic group can be, for example, C3 to C4. 30 C3~C 29 C3~C 28 C3~C 27 C3~C 26 C3~C 25 C3~C 24 C3~C 23 C3~C 22 C3~C 21 C3~C 20 C3~C 19 C3~C 18 C3~C 17 C3~C 13 C3~C 15 C3~C 14 C3~C 13 C3~C 12 C3~C 11 C3~C 10 C3~C8, C3~C6, C6, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aliphatic cyclic groups, specifically cyclohexanyl group, adamantyl group, etc.

[0104] In the above R1 to R4, R', R”, R 1 R 2When at least one of them is an alkyl group, the alkyl group may be, for example, C1 to C2. 20 C1~C 10 Alkyl groups such as C1-C4, C1, C2, C3, and C4, for example, can be methyl, ethyl, tert-butyl, etc.

[0105] The above-mentioned aryl, arylene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, rings formed by the combination of adjacent groups, rings formed by the combination of R' and R" groups, and R 1 and R 2 The rings formed by their interlocking can be selected from deuterium, halogens, and C1-C2 atoms, respectively. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6-C 30 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 heterocyclic group, C3~C 30 The aliphatic cyclic group and combinations thereof are further substituted with one or more substituents.

[0106] Preferably, the above-mentioned aryl, arylene, fluorene, fluoreneyl, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, rings formed by the combination of adjacent groups, rings formed by the combination of R' and R" are preferred. 1 and R 2 The rings formed by their interlocking can be selected from deuterium, halogens, and C1-C2 atoms, respectively. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6~C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic group, C3~C 20 The aliphatic cyclic group and combinations thereof are further substituted with one or more substituents.

[0107] When the above-mentioned aryl, fluorene, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, fluorene, aryl, adjacent groups combine to form a ring, or R' and R" combine to form a ring, R 1 and R 2 When at least one of the rings formed by the interlocking elements is replaced by an aryl group, the aryl group can be, for example, C2 to C3. 30 C2~C 29 C2~C 28 C2~C 27 C2~C 26 C2~C 25 C2~C 24 C2~C 23 C2~C 22 C2~C 21 C2~C 20 C2~C 19 C2~C 18 C2~C 17 C2~C 16 C2~C 15 C2~C 14 C2~C 13 C2~C 12 C2~C 11 C2~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aryl groups, etc.

[0108] When the above-mentioned aryl, fluorene, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, fluorene, aryl, adjacent groups combine to form a ring, or R' and R" combine to form a ring, R 1 and R2 When at least one of the rings formed by the interlocking elements is replaced by a heterocyclic group, the heterocyclic group can be, for example, C2 to C3. 30 C2~C 29 C2~C 28 C2~C 27 C2~C 26 C2~C 25 C2~C 24 C2~C 23 C2~C 22 C2~C 21 C2~C 20 C2~C 19 C2~C 18 C2~C 17 C2~C 16 C2~C 15 C2~C 14 C2~C 13 C2~C 12 C2~C 11 C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 C 19 C 20 C 21 C 22 C 23 C 24 C 25 C 26 C 27 C 28 C 29 Heterocyclic groups such as...

[0109] When the above-mentioned aryl, fluorene, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, fluorene, aryl, adjacent groups combine to form a ring, or R' and R" combine to form a ring, R 1 and R 2When at least one of the rings formed by the interaction of the elements is substituted with a fluorene group, the fluorene group can be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirodifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphth-2-yl)9-phenyl-9H-fluorene, etc.

[0110] When the above-mentioned aryl, fluorene, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, fluorene, aryl, adjacent groups combine to form a ring, or R' and R" combine to form a ring, R 1 and R 2 When at least one of the rings formed by the interlocking elements is replaced by an alkyl group, the alkyl group can be, for example, C1 to C2. 20 C1~C 10 Alkyl groups, such as C1-C4, C1, C2, C3, and C4.

[0111] When the above-mentioned aryl, fluorene, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, fluorene, aryl, adjacent groups combine to form a ring, or R' and R" combine to form a ring, R 1 and R 2 When at least one of the rings formed by the interlocking elements is substituted with an alkoxy group, the alkoxy group can be, for example, C1 to C2. 20 C1~C 10 Alkoxy groups of C1 to C4, C1, C2, C3, C4, etc.

[0112] When the above-mentioned aryl, fluorene, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, fluorene, aryl, adjacent groups combine to form a ring, or R' and R" combine to form a ring, R 1 and R 2 When at least one of the rings formed by the interlocking elements is replaced by an aliphatic cyclic group, the aliphatic cyclic group can be, for example, C3 to C4. 30 C3~C 29 C3~C 28 C3~C 27 C3~C 26 C3~C 25 C3~C 24 C3~C 23 C3~C 22 C3~C 21 C3~C 20 C3~C 19 C3~C18 C3~C 17 C3~C 13 C3~C 15 C3~C 14 C3~C 13 C3~C 12 C3~C 11 C3~C 10 C3~C8, C3~C6, C6, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aliphatic cyclic groups, etc.

[0113] The compound represented by the above chemical formula 1 can be represented by one of the following chemical formulas 2 to 22, and chemical formulas 7-1 to 10-1.

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] In the above chemical formulas 2 to 22, and chemical formulas 7-1 to 10-1, each symbol can be defined in the following manner.

[0120] R1~R4, R', R”, Ar1, L, a, c, d are defined in the same way as in Formula 1, and * indicates the bonding position. For example, in Formulas 12, 17, and 18, the amine group can be bonded to the carbon represented by *, and in Formulas 14, 21, and 22, the fluorene substituent can be bonded to the carbon represented by *.

[0121] In chemical formulas 2 to 6, b is defined the same as in chemical formula 1. In chemical formulas 7, 8, 11, 12, 15 to 18, 7-1, and 8-1, b is an integer from 0 to 3. In chemical formulas 9, 10, 13, 14, 19 to 22, 9-1, and 10-1, b is an integer from 0 to 4. When b is an integer of 2 or higher, R2 is either the same or different.

[0122] X is the direct linker, O, S, N (Ar) 1 ) or C(R 1 (R) 2 ).

[0123] R5, R6, R 11 To R 15 R 1 and R 2 Independently selected from hydrogen, deuterium, halogens, and C1 to C2 atoms. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6~C 30 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 heterocyclic group, C3~C 30 A group consisting of aliphatic cyclic groups and combinations thereof, wherein adjacent groups can combine to form rings, R 1 and R 2 They can combine with each other to form a ring.

[0124] Between adjacent groups, for example, between adjacent R5s, between adjacent R6s, and between adjacent R... 11 Between, adjacent R 12 Between, adjacent R 13 Between, adjacent R 14 Between or adjacent R 15 When the elements combine to form a ring, the aforementioned rings can be freely selected from C6 to C6. 30 Aromatic cyclic groups; fluorene cyclic groups; C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 30 Heterocyclic groups; and C3~C 30 The group is composed of aliphatic cyclic groups.

[0125] When the ring formed by the interaction of adjacent groups is an aromatic ring, the aforementioned aromatic ring can be, for example, C6 to C6. 20 C6~C 18 C6~C 16C6~C 14 C6~C 13 C6~C 12 C6~C 10 C6, C 10 C 12 C 14 C 15 C 16 C 18 Aromatic rings, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0126] When R 1 and R 2 When these molecules can combine to form a ring, spirocyclic compounds can be formed. When R... 1 and R 2 When the elements can combine to form a ring, the aforementioned rings can be freely selected from C6 to C6. 30 Aromatic cyclic groups; fluorene cyclic groups; C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 30 Heterocyclic groups; and C3~C 30 The group is composed of aliphatic cyclic groups.

[0127] The above Ar 1 Choose freely from C6 to C6. 30 aryl, fluorenyl, C2-C containing at least one heteroatom selected from O, N, S, Si and P 30 heterocyclic group, C3~C 30 The group consisting of aliphatic cyclic groups and combinations thereof.

[0128] In chemical formulas 6, 7-1 to 10-1, e is an integer from 0 to 5. In chemical formulas 11 to 22, e is an integer from 0 to 4. When e is an integer of 2 or above, R5 is the same or different.

[0129] f is an integer from 0 to 5, m, n, o, and p are integers from 0 to 4, and q is an integer from 0 to 3. When these integers are 2 or higher, R6, R... 11 R respectively 12 R respectively 13 R respectively 14 R respectively 15 They are the same or different.

[0130] In chemical formulas 2 to 4, 7 to 14, and 7-1 to 10-1, d can be 0, or R4 can be hydrogen. Additionally, in chemical formula 8, R1 to R6, R... 11 and R 12 It can be all hydrogen, or a to f, m and n can all be 0.

[0131] In the above R5, R6, R 11 To R 15 R 1 R 2 Ar 1 When at least one of the components is an aryl group, the aforementioned aryl group may be, for example, C6 to C6. 30 C6~C 29 C6~C 28 C6~C 27 C6~C 26 C6~C 25 C6~C 24 C6~C 23 C6~C 22 C6~C 21 C6~C20, C6~C 19 C6~C 18 C6~C 17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 The aryl group can be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

[0132] In the above R5, R6, R 11 To R 15 R 1 R 2 Ar 1 When at least one of them is a heterocyclic group, the aforementioned heterocyclic group can be, for example, C2 to C3. 30 C2~C 29 C2~C 28 C2~C 27 C2~C 26 C2~C 25 C2~C 24 C2~C 23 C2~C 22C2~C 21 C2~C 20 C2~C 19 C2~C 18 C2~C 17 C2~C 16 C2~C 15 C2~C 14 C2~C 13 C2~C 12 C2~C 11 C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 C 19 C 20 C 21 C 22 C 23 C 24 C 25 C 26 C 27 C 28 C 29 Heterocyclic groups such as...

[0133] In the above R5, R6, R 11 To R 15 R 1 R 2 Ar 1 When at least one of them is fluorenyl, the fluorenyl group can be 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirodifluorenyl, spiro[benzo[b]fluoren-11,9'-fluorenyl], benzo[b]fluorenyl, 11,11-diphenyl-11H-benzo[b]fluorenyl, 9-(naphthyl-2-yl)9-phenyl-9H-fluorenyl, etc.

[0134] In the above R5, R6, R 11 To R 15 R 1 R 2 Ar 1 When at least one of them is an aliphatic cyclic group, the aforementioned aliphatic cyclic group can be, for example, C3 to C4. 30 C3~C 29 C3~C28 C3~C 27 C3~C 26 C3~C 25 C3~C 24 C3~C 23 C3~C 22 C3~C 21 C3~C 20 C3~C 19 C3~C 18 C3~C 17 C3~C 13 C3~C 15 C3~C 14 C3~C 13 C3~C 12 C3~C 11 C3~C 10 C3~C8, C3~C6, C6, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aliphatic cyclic groups, specifically cyclohexanyl group, adamantyl group, etc.

[0135] In the above R5, R6, R 11 To R 15 R 1 R 2 When at least one of them is an alkyl group, the alkyl group may be, for example, C1 to C2. 20 C1~C 10 Alkyl groups such as C1-C4, C1, C2, C3, and C4, for example, can be methyl, ethyl, tert-butyl, etc.

[0136] The above R5, R6, R 11 To R 15 R 1 R 2 Ar 1 A ring formed by the bonding of adjacent groups, R 1 and R 2 The rings formed by their interlocking can be selected from deuterium, halogens, and C1-C2 atoms, respectively. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6-C 30 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 heterocyclic group, C3~C 30 The aliphatic cyclic group is further substituted with one or more substituents.

[0137] Specifically, the compound represented by the above chemical formula 1 can be one of the following compounds, but is not limited to this.

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] According to another aspect of the invention, the invention provides an organic electrical element comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by chemical formula 1.

[0148] The aforementioned organic layer may include a light-emitting layer, a hole transport layer located between the light-emitting layer and the first electrode, and a light-emitting auxiliary layer located between the hole transport layer and the first electrode, wherein the aforementioned compound may be included in at least one of the hole transport layer and the light-emitting auxiliary layer.

[0149] The aforementioned organic electrical component also includes a light efficiency improvement layer, which contains a compound represented by chemical formula 1. In this case, the light efficiency improvement layer is formed on the side of the first electrode and the second electrode that is not in contact with the organic layer.

[0150] The aforementioned organic layer may include two or more stacks, which may include a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the aforementioned anode. The aforementioned organic layer may also include a charge generation layer formed between the aforementioned two or more stacks.

[0151] According to another aspect of the present invention, an electronic device is provided, comprising a display device and a control unit, wherein the display device comprises a compound represented by chemical formula 1, and the control unit is used to drive the display device.

[0152] The following examples illustrate the synthesis of compounds represented by chemical formula 1 and the preparation of organic electrical components according to the present invention, but the present invention is not limited to the following examples.

[0153] [Synthesis example]

[0154] The compound represented by chemical formula 1 according to the present invention can be prepared by reacting Sub1 with Sub2 as shown in the following reaction formula 1, but is not limited thereto.

[0155] <Reaction Formula 1> (Hal can be I, Br, or Cl.)

[0156]

[0157] Example of Sub1

[0158] Sub1 in reaction formula 1 can be, but is not limited to, the following compounds. The FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are shown in Table 1.

[0159]

[0160]

[0161] [Table 1]

[0162] compound FD-MS compound FD-MS Sub 1-1 CAS NO = 1225053-54-2 Sub 1-2 CAS NO = 28320-31-2 Sub 1-3 CAS NO = 1190360-23-6 Sub 1-4 CAS NO = 942615-32-9 Sub 1-5 <![CDATA[m / z=348.05(C 21 H 17 Br=349.27)]]> Sub 1-6 <![CDATA[m / z=348.05(C 21 H 17 Br=349.27)]]> Sub 1-7 <![CDATA[m / z=406.13(C 25 H 27 Br=407.4)]]> Sub 1-8 <![CDATA[m / z=328.08(C 19 H 21 Br=329.28)]]> Sub 1-9 CAS NO = 171408-76-7 Sub 1-10 CAS NO = 1161009-88-6 Sub 1-11 <![CDATA[m / z=394.04(C 25 H 15 Br=395.3)]]> Sub 1-12 <![CDATA[m / z=470.07(C 31 H 19 Br=471.4)]]> Sub 1-13 <![CDATA[m / z=528.15(C 35 H 29 Br=529.52)]]> Sub 1-14 <![CDATA[m / z=450.1(C 29 H 23 Br=451.41)]]> Sub 1-15 CAS NO = 1547491-70-2 Sub 1-16 <![CDATA[m / z=396.05(C 25 H 17 Br=397.32)]]> Sub 1-17 <![CDATA[m / z=530.16(C 35 H 31 Br=531.54)]]> Sub 1-18 <![CDATA[m / z=452.11(C 29 H 25 Br=453.42)]]> Sub 1-19 <![CDATA[m / z=472.08(C 31 H 21 Br=473.41)]]> Sub 1-20 <![CDATA[m / z=334.04(C 20 H 15 Br=335.24)]]> Sub 1-21 <![CDATA[m / z=334.04(C 20 H 15 Br=335.24)]]> Sub 1-22 <![CDATA[m / z=334.04(C 20 H 15 Br=335.24)]]> Sub 1-23 <![CDATA[m / z=390.1(C 24 H 23 Br=391.35)]]> Sub 1-24 <![CDATA[m / z=396.05(C 25 H 17 Br=397.32)]]> Sub 1-25 CAS NO = 1257251-75-4 Sub 1-26 CAS NO = 1998216-26-4 Sub 1-27 <![CDATA[m / z=562.09(C 37 H 23 Br0=563.49)]]> Sub 1-28 CAS NO = 1477458-14-2 Sub 1-29 CAS NO = 899422-06-1 Sub 1-30 CAS NO = 1643935-07-2 Sub 1-31 CAS NO = 1640344-19-9 Sub 1-32 CAS NO = 2086293-11-8 Sub 1-33 CAS NO = 2360947-56-2 Sub 1-34 <![CDATA[m / z=492.11(C 31 H 25 BrO=493.44)]]> Sub 1-35 <![CDATA[m / z=466.09(C 29 H 23 Br0=467.41)]]> Sub 1-36 <![CDATA[m / z=508.09(C 31 H 25 BrS=509.51)]]> Sub 1-37 <![CDATA[m / z=502.04(C 31 H 19 BrS=503.46)]]> Sub 1-38 <![CDATA[m / z=485.08(C 31 H 20 BrN=486.41)]]> Sub 1-39 <![CDATA[m / z=436.08(C 28 H 21 Br=437.38)]]> Sub 1-40 <![CDATA[m / z=394.04(C 25 H 15 Br=395.3)]]>

[0163] Synthesis example of Sub2

[0164] Sub2 of reaction 1 can be synthesized via the reaction pathway described in reaction 2 below, and Sub2-I below can be synthesized via reaction 3 below, but is not limited thereto.

[0165] <Reaction 2>

[0166]

[0167] <Reaction Formula 3>

[0168]

[0169] 1. Synthesis example of Sub2-3

[0170]

[0171] (1) Example of Sub2-3-c synthesis

[0172] Sub2-3-b (22.8 g, 91.9 mmol), Pd(PPh3)4 (0.05 equivalents), K2CO3 (3 equivalents), and THF / H2O (306 ml / 153 ml) were added to Sub2-3-a (26 g, 91.9 mmol), and the mixture was refluxed for 12 hours. After the reaction was complete, the reactants were cooled to room temperature, and THF was removed. The mixture was extracted with MC and wiped with water. The organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography to obtain 28.5 g (yield: 96.4%) of the product.

[0173] (2) Example of Sub2-I-3 synthesis

[0174] Sub2-3-d (12.4 g, 79.3 mmol), Pd(PPh3)4 (0.05 equivalents), K2CO3 (3 equivalents), and THF / H2O (264 ml / 132 ml) were added to Sub2-3-c (28.5 g, 79.3 mmol) and synthesized using the same method as in the above example of Sub2-3-c synthesis, to obtain 25.8 g of product (yield: 83.4%).

[0175] (3) Synthesis example of Sub2-3

[0176] Sub2-I-3 (25.8 g, 66 mmol) was dissolved in toluene (676 ml), and then Sub2-II-3 (11.7 g, 69.3 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), and NaOt-Bu (3 equivalents) were added. The mixture was stirred at 100 °C. After the reaction was complete, the product was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to obtain 28.4 g (yield: 82.3%) of the product.

[0177] 2. Synthesis example of Sub2-8

[0178]

[0179] Sub2-II-8 (18.8 g, 83.38 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (814 ml) were added to Sub2-I-8 (25 g, 79.4 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 32.2 g of product (yield: 80.7%).

[0180] 3. Synthesis example of Sub2-14

[0181]

[0182] Sub2-II-14 (15.4 g, 73.4 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (716 ml) were added to Sub2-I-14 (22 g, 69.9 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 27.6 g of product (yield: 81%).

[0183] 4. Synthesis example of Sub2-27

[0184]

[0185] Sub2-II-27 (12.9 g, 61.8 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (603 ml) were added to Sub2-I-27 (23 g, 58.8 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 26.7 g of product (yield: 80.5%).

[0186] 5. Synthesis example of Sub2-32

[0187]

[0188] Sub2-II-32 (8.5 g, 50.3 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (491 ml) were added to Sub2-I-32 (19 g, 47.9 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 19.2 g of product (yield: 75.6%).

[0189] 6. Synthesis example of Sub2-39

[0190]

[0191] Sub2-II-39 (15.3 g, 53.7 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (524 ml) were added to Sub2-I-39 (20 g, 51.2 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 23.2 g of product (yield: 71%).

[0192] 7. Synthesis example of Sub2-53

[0193]

[0194] Sub2-II-53 (12.8 g, 70 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (684 ml) were added to Sub2-I-53 (21 g, 66.7 mmol) in the same manner as in the above-described synthesis of Sub2-3, to obtain 23.5 g of product (yield: 76.2%).

[0195] 8. Synthesis example of Sub2-66

[0196]

[0197] Sub2-II-66 (12.9 g, 59.1 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (577 ml) were added to Sub2-I-66 (22 g, 56.3 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 26.1 g of product (yield: 80.9%).

[0198] 9. Synthesis example of Sub2-68

[0199]

[0200] Sub2-II-68 (11 g, 63.4 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (619 ml) were added to Sub2-I-68 (19 g, 63.4 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 21 g of product (yield: 76.8%).

[0201] 10. Synthesis example of Sub2-71

[0202]

[0203] Sub2-II-71 (8.5 g, 45.7 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (446 ml) were added to Sub2-I-71 (19 g, 43.5 mmol) in the same manner as in the synthesis example of Sub2-3 above, to obtain 16.4 g of product (yield: 69.8%).

[0204] The compounds belonging to Sub2 may be, but are not limited to, the compounds described below. Table 2 shows the FD-MS values ​​of the following compounds.

[0205]

[0206]

[0207]

[0208]

[0209] [Table 2]

[0210]

[0211]

[0212] Synthesis example of the final product

[0213] 1. Synthesis example of P1-1

[0214]

[0215] Sub1-2 (32 g, 91.52 mmol) was dissolved in toluene (938 ml), and then Sub2-48 (43.01 g, 96.09 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), and NaOt-Bu (3 equivalents) were added. The mixture was stirred at 100 °C. After the reaction was complete, the product was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to obtain 44.27 g (yield: 75.6%) of the product.

[0216] 2. Synthesis examples of P1-3

[0217]

[0218] Sub2-3 (60.39 g, 115.31 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (1126 ml) were added to Sub1-2 (30 g, 109.82 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 67.8 g of product (yield: 86.2%).

[0219] 3. Synthesis examples of P1-8

[0220]

[0221] Sub2-5 (48.2 g, 107.63 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (1051 ml) were added to Sub1-2 (28 g, 102.5 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 54.1 g of product (yield: 82.4%).

[0222] 4. Synthesis examples from P1-13

[0223]

[0224] Sub2-13 (41.7 g, 93.2 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (910 ml) were added to Sub1-5 (31 g, 88.7 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 48.4 g of product (yield: 76.1%).

[0225] 5. Synthesis examples from P1-19

[0226]

[0227] Sub2-18 (45.9 g, 92.3 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (901 ml) were added to Sub1-2 (24 g, 87.9 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 43.9 g of product (yield: 72.4%).

[0228] 6. Synthesis examples on pages 1-38

[0229]

[0230] Sub2-64 (44.3 g, 84.6 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (825 ml) were added to Sub1-2 (22 g, 80.5 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 48.2 g of product (yield: 83.6%).

[0231] 7. Synthesis examples of P2-9

[0232]

[0233] Sub2-56 (28.6 g, 53.1 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (519 ml) were added to Sub1-10 (20 g, 50.6 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 30.7 g of product (yield: 71.3%).

[0234] 8. Synthesis example of P2-20

[0235]

[0236] Sub2-66 (28 g, 48.8 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (477 ml) were added to Sub1-14 (21 g, 46.5 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 30.2 g of product (yield: 68.7%).

[0237] 9. Synthesis examples of P3-8

[0238]

[0239] Sub2-20 (28.3 g, 50.2 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (490 ml) were added to Sub1-15 (19 g, 47.82 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 27.5 g of product (yield: 65.3%).

[0240] 10. Synthesis example on page 3-26

[0241]

[0242] Sub2-26 (30.3 g, 56.4 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (550 ml) were added to Sub1-22 (18 g, 53.7 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 31.5 g of product (yield: 74.1%).

[0243] 11. Synthesis example of P4-3

[0244]

[0245] Sub2-51 (29.8 g, 52.8 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (516 ml) were added to Sub1-25 (20 g, 50.3 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 33.8 g of product (yield: 76.4%).

[0246] 12. Synthesis example of P5-1

[0247]

[0248] Sub2-3 (41.4 g, 79.1 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (773 ml) were added to Sub1-28 (31 g, 74.4 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 53.5 g of product (yield: 83.1%).

[0249] 13. Synthesis examples on pages 5-16

[0250]

[0251] Sub2-73 (33.4 g, 63.8 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (623 ml) were added to Sub1-29 (25 g, 60.8 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 35.9 g of product (yield: 69.1%).

[0252] 14. Synthesis examples on pages 5-19

[0253]

[0254] Sub2-76 (29.9 g, 46.7 mmol), Pd2(dba)3 (0.03 equivalents), P(t-Bu)3 (0.06 equivalents), NaOt-Bu (3 equivalents), and toluene (456 ml) were added to Sub1-30 (19 g, 44.5 mmol) in the same manner as in the synthesis example of P1-1 above, to obtain 27 g of product (yield: 61.6%).

[0255] The FD-MS values ​​of the compounds of the present invention prepared according to the synthesis examples described above are shown in Table 3 below.

[0256] [Table 3]

[0257]

[0258]

[0259]

[0260] Evaluation of the manufacture of organic electrical components

[0261] [Example 1] Green Organic Electroluminescent Element (Hole Transport Layer)

[0262] After forming a hole injection layer of 60 nm thickness by vacuum depositing an N1-(naphth-2-yl)-N4,N4-bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N1-phenylphenyl-1,4-diamine (hereinafter referred to as "2-TNATA") film on an ITO layer (anode) formed on a glass substrate, a hole transport layer of the present invention of compound P1-1 of the present invention of 60 nm thickness is formed by vacuum depositing on the hole injection layer.

[0263] A light-emitting layer with a thickness of 30 nm was vacuum-deposited using 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") as the host material and tris(2-phenylpyridine)iridium (hereinafter referred to as "Ir(ppy)3") as the dopant material at a weight ratio of 90:10 on the hole transport layer.

[0264] Next, a hole blocking layer is formed on the light-emitting layer by vacuum deposition of (1,1'-biphenyl-4-hydroxy)bis(2-methyl-8-hydroxyquinoline)aluminum (hereinafter referred to as "BAlq") with a thickness of 5 nm, and an electron transport layer is formed on the hole blocking layer by vacuum deposition of tri(8-hydroxyquinoline)aluminum (hereinafter referred to as "Alq3") with a thickness of 40 nm.

[0265] Then, an electron injection layer is formed by depositing LiF with a thickness of 0.2 nm on the electron transport layer, and then an electron cathode is formed by depositing Al with a thickness of 150 nm.

[0266] [Example 2] to [Example 27]

[0267] Except for using the compounds of the present invention listed in Table 4 below to replace compound P1-1 of the present invention as the material for the hole transport layer, an organic electroluminescent element was prepared in the same manner as in Example 1 above.

[0268] [Comparative Example 1]

[0269] The material used as the hole transport layer was N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as "NPB"). Otherwise, an organic electroluminescent element was fabricated using the same method as in Example 1 above.

[0270] Comparative Examples 2 through 7

[0271] Organic electroluminescent elements were fabricated in the same manner as in Example 1 above, except that one of the comparative compounds ref1 to ref6, namely compound P-1, was used as the material for the hole transport layer instead of the embodiment of the present invention.

[0272] <ref1> <ref2> <ref3>

[0273]

[0274]

[0275] A forward bias DC voltage was applied to the organic electroluminescent elements prepared according to Examples 1 to 27 and Comparative Examples 1 to 7 of the present invention, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research, Inc. At 5000 cd / m²... 2 In the reference brightness test, the T95 lifetime was measured using a lifetime measurement device manufactured by Macscience, a South Korean company. The measurement results are shown in Table 4 below.

[0276] [Table 4]

[0277]

[0278]

[0279] As can be seen from Table 4, when the compounds of the present invention are used as materials for the hole transport layer, the driving voltage of the organic electrical components is reduced and the efficiency and lifespan are improved compared with the use of NPB or one of the comparative compounds ref1 to ref6.

[0280] The comparative compounds ref1 to ref6 are all tertiary amine structures, which is similar to the present invention. However, the difference is that in ref1 and ref2, the amine group is substituted with a pure aryl group, while in the chemical formula 1 of the present invention, a condensation ring containing a fluorene moiety is substituted. Although ref3 to ref6 have structures very similar to the compounds of the present invention, ref3, ref4 and ref6 differ from the compounds of the present invention in the binding positions of the linker L of the phenylene moiety and the naphthalene moiety. ref5 differs from the compounds of the present invention in that it does not contain L.

[0281] To provide a more detailed explanation, as described below, in the chemical formula 1 of the present invention, the phenylene portion directly bonded to L is referred to as composition 1, and the naphthalene portion bonded to such composition 1 is referred to as composition 2.

[0282]

[0283] In the case of the compounds of the present invention, there is a linker L and composition 2 bonded at the ortho position on the phenylene of composition 1, and in contrast, there is a linker L and composition 2 bonded at the meta position on ref3, ref4, and ref6, which is different in this respect.

[0284] Furthermore, the linker L in the compounds of the present invention cannot form a single bond, so the nitrogen of the amine group and the constituent 1 are bonded through the linker L. In contrast, ref5 is a phenylene group of the constituent 1 directly bonded to the nitrogen of the amine group, which is different in this respect.

[0285] Therefore, it can be seen that, compared to the case where only the pure aryl group is replaced by the amine group, the compound of the present invention has a amine group that is replaced by a substitute containing a specific ring morphology (fluorenyl moiety, xanthonium moiety, thioxanthonium moiety, acridine moiety), and the nitrogen of the amine group is indirectly bonded to constituent 1 through a linker L, while L and constituent 2 are bonded at the meta position of constituent 1. Thus, when the compound of the present invention is used as a material for a hole transport layer, the electrical characteristics of the device are affected by the type of core and the type of substituents constituting the compound, since the driving voltage is reduced and the efficiency and lifetime are improved at the same time.

[0286] The HOMO energy levels of ref 1 and compounds P1-49, P2-25, P3-22, P5-16, and P5-17 of the present invention are compared in Table 5 below.

[0287] [Table 5]

[0288] ref 1 P1-49 P2-25 P3-22 P5-16 P5-17 HOMO(eV) 4.897 4.773 4.785 4.794 4.820 4.764

[0289] As shown in Table 5, compared to ref1, the compounds P1-49, P2-25, P3-22, P5-16, and P5-17 of the present invention have higher HOMO energy levels. This suggests that compounds can have different physical properties depending on their core structure. When the compounds represented by chemical formula 1 of the present invention are used as materials for the hole transport layer, holes can easily move from the hole injection layer to the light-emitting layer. Therefore, the characteristics of the device are improved compared to the compounds of ref 1.

[0290] Furthermore, as already described, ref3, ref4, and ref6 differ from compounds P1-34, P1-49, and P5-16 of the present invention in the position of the linker L on the phenylene group of constituent 1 and the position of constituent 2. As a result, the compounds of the present invention tend to have resonance structures compared to the comparative compounds, thus improving the element characteristics of the embodiments using the compounds of the present invention.

[0291] Furthermore, as already explained, the difference between compound ref6 and compound P4-27 of the present invention lies in the presence or absence of a linker L between the N of the amine group and constituent 1. Due to this difference, as shown in Table 6 below, the HOMO values ​​will be different.

[0292] [Table 6]

[0293] ref 6 P4-27 HOMO(eV) 4.944 4.878

[0294] As can be seen from Table 6 above, the HOMO energy level of compound P4-27 of the present invention is higher than that of ref6. This shows that the presence or absence of the linker group has an impact on the physical properties of the compound. When the compound of the present invention with a high HOMO energy level is used as the material of the hole transport layer, holes can easily move from the hole injection layer to the light-emitting layer. Therefore, the characteristics of the device are improved compared to ref6.

[0295] Therefore, it can be seen that the types of substituents in the amine group, the presence or absence of the linker L between the amine group and constituent 1, and the position of the linker L on constituent 1 and constituent 2 will vary depending on the physical properties of these compounds (HOMO, LUMO, and T1, etc.), and these differences can have a significant impact on the performance of organic electrical components.

[0296] [Example 28] Green Organic Electroluminescent Element (Light-Emitting Auxiliary Layer)

[0297] After vacuum depositing a 2-TNATA film on an ITO layer (anode) formed on a glass substrate to form a hole injection layer with a thickness of 60 nm, a 60 nm thick NPB film is vacuum deposited on the hole injection layer to form a hole transport layer.

[0298] Next, a light-emitting auxiliary layer of the present invention, compound P1-2, was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emitting auxiliary layer. 9,10-bis(naphthyl-2-yl)anthracene was used as the host material on the light-emitting auxiliary layer, and BD-052X (manufactured by Idemitsu Kosan) was used as the dopant material and doped at a weight ratio of 96:4. The light-emitting layer was vacuum-deposited to a thickness of 30 nm.

[0299] Next, a hole blocking layer is formed by vacuum depositing BAlq to a thickness of 10 nm on the aforementioned light-emitting layer, and an electron transport layer is formed by vacuum depositing Alq3 to a thickness of 40 nm on the aforementioned hole blocking layer. Then, an electron injection layer is formed by depositing LiF to a thickness of 0.2 nm on the aforementioned electron transport layer, and then a cathode is formed by depositing Al to a thickness of 150 nm.

[0300] [Examples 29] to [Examples 41]

[0301] The material used as the light-emitting auxiliary layer was the compound of the present invention listed in Table 7 below, which was used instead of compound P1-2 of the present invention. Otherwise, the organic electroluminescent element was prepared in the same manner as in Example 28 above.

[0302] [Comparative Example 8]

[0303] Except for the absence of a light-emitting auxiliary layer, the organic electroluminescent element was fabricated using the same method as in Example 28 described above.

[0304] Comparative Examples 9 to 14

[0305] The material used as the light-emitting auxiliary layer was one of ref 1 to ref 6 instead of compound P1-2 of the present invention, and the organic electroluminescent element was otherwise made in the same manner as in Example 28 above.

[0306] A forward bias DC voltage was applied to the organic electroluminescent elements prepared according to Examples 28 to 41 and Comparative Examples 8 to 14 of the present invention, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research, Inc. At 500 cd / m²... 2 In the reference brightness test, the T95 lifetime was measured using a lifetime measurement device manufactured by Macscience, a South Korean company. The measurement results are shown in Table 7 below.

[0307] [Table 7]

[0308]

[0309] As can be seen from Table 7 above, when the compounds of the present invention are used as materials for the light-emitting auxiliary layer, the characteristics of the organic electrical components are improved compared to the case where no light-emitting auxiliary layer is formed or one of the comparative compounds ref 1 to ref 6 is used.

[0310] That is, it is known that the compounds of the present invention have substituents with specific ring morphologies (fluorene moiety, thiophene moiety, thiophene moiety, etc.) in the amine group and have the characteristics described above. Therefore, the properties of the device can be improved not only when the compounds of the present invention are used as materials for hole transport layers, but also when they are used as materials for light-emitting auxiliary layers.

[0311] Therefore, it can be seen that the compounds of the present invention can improve the charge balance in the light-emitting layer, thereby improving efficiency. By preventing electrons from transferring from the light-emitting layer, the charge balance in the light-emitting layer can be maintained, thus improving the driving voltage and lifetime. Ultimately, the features of the compounds of the present invention described above play a major role in improving the performance of the device.

[0312] The above description is merely illustrative. Those skilled in the art can make various modifications without departing from the essential characteristics of the invention. Therefore, the embodiments disclosed in this specification are not intended to limit the invention, but rather to illustrate it. The scope of the invention is not limited by such embodiments. The scope of protection of this invention should be interpreted according to the scope of the claims, and all technologies within the same scope should be interpreted as included within the scope of the invention. < / ref2> < / ref1>

Claims

1. A compound represented by chemical formula 7 or chemical formula 8: <Chemical Formula 7> <Chemical Formula 8> In the above chemical formulas 7 and 8, R1, R2, and R4 are independently chosen from hydrogen; heavy hydrogen; C6~C 12 aryl and C1-C 10 The group consisting of alkyl groups, R3 is hydrogen; or deuterium. R 11 and R 12 They are independently selected from hydrogen; deuterium, C1 to C2. 10 Alkyl groups, and C6-C 12 The group composed of aryl groups. a, c, m, and n are integers from 0 to 4, b is an integer from 0 to 3, and d is an integer from 0 to 7. When these are integers of 2 or higher, R1, R2, R3, R4, and R... 11 R respectively 12 Whether they are the same or different, R' and R” are independently chosen from C6 to C6. 12 aryl groups; and C1-C 10 The group consisting of alkyl groups, and R' and R" can be combined with each other to form a group with The ring structure, in which Corresponding to spirocyclic atoms, X is O, S, N (Ar) 1 ) or C(R 1 (R) 2 ), where Ar 1 It is C6~C 12 aryl, R 1 and R 2 C1 to C are independent of each other. 10 alkyl groups, L is selected from C6 to C. 18 arylene groups; and C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 18 A group composed of heterocyclic groups. Ar1 is a choice between C6 and C6. 18 aryl groups; and C2-C groups containing at least one heteroatom selected from O, N, S, Si, and P. 18 A group composed of heterocyclic groups. The aforementioned aryl, arylene, heterocyclic, and alkyl groups can be selected from deuterium, C1-C1, and C2, respectively. 10 Alkyl groups, and C6-C 12 One or more substituents in the group consisting of aryl groups are further substituted.

2. The compound according to claim 1, wherein, The above chemical formula 7 or chemical formula 8 is represented by the following chemical formula 11 or chemical formula 12. <Chemical Formula 11> <Chemical Formula 12> In the above chemical formulas 11 and 12, R1 to R4, R', R”, R 11 R 12 a, b, c, d, m, and n are the same as defined in claim 1. Indicates the position of combination. R5 and R6 are independently chosen from hydrogen, deuterium, and C1-C6. 10 Alkyl groups and C6-C 12 The group composed of aryl groups. e is an integer from 0 to 4, f is an integer from 0 to 5, and when they are both integers greater than 2, R5 and R6 are either the same or different.

3. The compound according to claim 1, wherein, The above chemical formula 7 is represented by chemical formula 15 or chemical formula 16. <Chemical Formula 15> <Chemical Formula 16> In the aforementioned chemical formulas 15 and 16, R1, R2, R', R'', a, and b are the same as defined in claim 1. R5 and R6 are independently chosen from hydrogen, deuterium, and C1-C6. 10 Alkyl groups and C6-C 12 The group composed of aryl groups. e is an integer from 0 to 4, f is an integer from 0 to 5, and when they are both integers greater than 2, R5 and R6 are either the same or different.

4. The compound according to claim 1, wherein, The above chemical formula 8 is represented by one of the following chemical formulas 17 and 18. <Chemical Formula 17> <Chemical Formula 18> In the aforementioned chemical formulas 17 and 18, R1, R2, and R... 11 R 12 a, b, m, and n are the same as defined in claim 1. Indicates the position of combination. R5 and R6 are independently chosen from hydrogen, deuterium, and C1-C6. 10 Alkyl groups and C6-C 12 The group composed of aryl groups. e is an integer from 0 to 4, f is an integer from 0 to 5, and when they are integers of 2 or above, R5 and R6 are either the same or different.

5. The compound according to claim 1, wherein, The above Ar1 is C 12 ~C 18 Aryl groups.

6. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 is one of the following compounds: 。 7. An organic electrical component, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein, The above-mentioned organic layer comprises the compound of claim 1.

8. The organic electrical component according to claim 7, wherein, The aforementioned organic layer includes a light-emitting layer, a hole transport layer located between the light-emitting layer and the first electrode, and a light-emitting auxiliary layer located between the hole transport layer and the first electrode, wherein the aforementioned compound is contained in at least one of the hole transport layer and the light-emitting auxiliary layer.

9. The organic electrical component according to claim 7, wherein, The aforementioned organic electrical component further includes a light efficiency improvement layer, which comprises the compound of claim 1, formed on the side of the first electrode or the second electrode that is not in contact with the organic layer.

10. The organic electrical component according to claim 7, wherein, The aforementioned organic layer comprises two or more stacks, and the aforementioned first electrode is an anode, wherein the aforementioned stack comprises a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the aforementioned anode.

11. The organic electrical component according to claim 10, wherein, The aforementioned organic layer also includes a charge generation layer formed between the two or more stacks.

12. An electronic device, wherein, include: The display device includes the organic electrical component according to claim 7; as well as The control unit is used to drive the aforementioned display device.

13. The electronic device according to claim 12, wherein, The aforementioned organic electrical components include organic light-emitting elements, organic solar cells, organic photosensitive elements, organic transistors, monochrome lighting elements, or quantum dot display elements.

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