Organic electronic elements comprising a compound for an organic electronic element and electronic devices thereof

Abstract

Provided are an organic electronic element including an anode, a cathode, and an organic material layer between the anode and the cathode, and an electronic device including the organic electronic element, wherein the organic material layer contains a compound represented by Formula 1 and Formula 2, respectively, of the present invention, thus enabling a reduction in driving voltage of the organic electronic element and improvement in luminous efficiency and service life of the organic electronic element.

Description

Technical Field

[0001] This invention relates to organic electronic components and electronic devices using compounds for organic electronic components. Background Technology

[0002] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electronic components utilizing organic light emission generally have a structure comprising an anode, a cathode, and layers of organic material interposed therebetween. To increase the efficiency and stability of the organic electronic components, the organic material layers are typically composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic material layers in organic electronic components can be classified into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0004] The biggest challenges in organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. As displays become larger, these two issues must be addressed. Efficiency, lifespan, and drive voltage are interrelated; as efficiency increases, the drive voltage relatively decreases. Conversely, as the drive voltage decreases, the crystallization of the organic material due to Joule heating during drive decreases, thus increasing the lifespan.

[0005] However, simply improving the organic material layers cannot maximize efficiency. This is because long lifetime and high efficiency can only be achieved simultaneously when the energy levels and T1 values ​​between the organic material layers, as well as the inherent properties of the materials (mobility, interfacial characteristics, etc.), are optimally combined.

[0006] Furthermore, in recent years, in order to solve the problem of light emission in the hole transport layer in organic electroluminescent devices, a light emission auxiliary layer must exist between the hole transport layer and the light emission layer, and different light emission auxiliary layers need to be developed according to each light emission layer (R, G, B).

[0007] Typically, electrons transfer from the electron transport layer to the luminescent layer, and holes transfer from the hole transport layer to the luminescent layer, thereby generating excitons through recombination.

[0008] However, the materials used for the hole transport layer should have low HOMO values, and therefore most have low T1 values. As a result, excitons generated in the luminescent layer are transferred to the hole transport layer, causing a charge imbalance in the luminescent layer and luminescence at the interface of the hole transport layer.

[0009] When light is emitted at the interface of the hole transport layer, the color purity and efficiency of organic electronic components decrease, and their lifespan is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer with a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

[0010] Simultaneously, it is necessary to develop hole injection layer materials with stable properties, namely a high glass transition temperature, to resist Joule heating generated during device driving, while delaying the penetration of metal oxides from the inductively coupled oxide (ITO) electrode into the organic layer, which is one of the reasons for the shortened lifespan of organic electronic devices. The low glass transition temperature of hole transport layer materials has the following characteristics: when driving the device, the uniformity of the thin film surface decreases, which has reportedly had a significant impact on the device's lifespan. Furthermore, OLED devices are mainly formed through deposition methods, and it is necessary to develop materials that can withstand long-term deposition, i.e., materials with high heat resistance.

[0011] In other words, to fully realize the superior properties of organic electronic components, the materials used to form organic material layers in the components (e.g., hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and luminescent auxiliary layer materials) should be supported by stable and effective materials. However, such stable and effective organic material layer materials for organic electronic components have not yet been fully developed. Therefore, there is a continuous need to develop new materials, and there is an urgent need to develop materials for hole transport layers or luminescent auxiliary layers.

[0012] KR020190038246 A is a prior art document used for reference. Summary of the Invention

[0013] The purpose of this invention is to provide organic electronic components and electronic devices thereof that contain compounds that can reduce the driving voltage of the components and improve the luminous efficiency, color purity, stability and lifespan of the components.

[0014] Technical solution

[0015] In one aspect, the present invention provides an organic electronic element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a light-emitting layer and a hole transport band layer formed between the light-emitting layer and the anode, wherein the hole transport band layer comprises a compound represented by Formula 1, and wherein the light-emitting layer provides an organic electronic element comprising a compound represented by Formula 2.

[0016]

[0017] In another aspect, the present invention provides an electronic device comprising the organic electronic components.

[0018] Invention Effects

[0019] By using the compounds according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the element can be achieved, and the color purity and lifespan of the element can be significantly improved. Attached Figure Description

[0020] Figures 1 to 3 Examples of organic electronic components according to the present invention are shown.

[0021] 100, 200, 300: Organic electronic components; 110: First electrode

[0022] 120: Hole injection layer; 130: Hole transport layer

[0023] 140: Emissive layer; 150: Electron transport layer

[0024] 160: Electron injection layer; 170: Second electrode

[0025] 180: Light efficiency enhancement layer; 210: Buffer layer

[0026] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0027] 330: First hole transport layer; 340: First luminescent layer

[0028] 350: First electron transport layer; 360: First charge generation layer

[0029] 361: Second charge generation layer; 420: Second hole injection layer

[0030] 430: Second hole transport layer; 440: Second luminescent layer

[0031] 450: Second electron transport layer; CGL: Charge generation layer

[0032] ST1: First stack; ST2: Second stack Detailed Implementation

[0033] Some embodiments of the invention will be described in detail below. Furthermore, in the following description of the invention, detailed descriptions of known functions and configurations incorporated herein will be omitted where such inclusion would make the subject matter of the invention considerably unclear.

[0034] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b) may be used herein. Each of these terms is not intended to define the substance, order, or sequence of the respective component, but only to distinguish the respective component from other components. It should be noted that if a component is described as “connected,” “linked,” or “attached” to another component, the component may be directly connected to or connected to other components, but may be “connected,” “linked,” or “attached” between components.

[0035] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0036] Unless otherwise stated, the term "halogenated" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine.

[0037] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein means having a single bond of 1 to 60 carbon atoms and refers to a saturated aliphatic functional group, including straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups (alicyclic), alkyl-substituted cycloalkyl groups, or cycloalkyl-substituted alkyl groups.

[0038] Unless otherwise stated, the terms “alkenyl” or “alkynyl” as used herein have, but are not limited to, two to 60 carbon atoms in double or triple bonds, and include straight or branched groups.

[0039] Unless otherwise stated, the term "cycloalkyl" as used herein means, but is not limited to, an alkyl group that forms a ring having 3 to 60 carbon atoms.

[0040] Unless otherwise stated, the terms “alkoxy,” “alkoxy group,” or “alkyloxy” as used herein mean, but are not limited to, an oxygen group attached to an alkyl group having 1 to 60 carbon atoms.

[0041] Unless otherwise stated, the terms “aryloxy group” or “aryloxy group” as used herein mean, but are not limited to, an oxygen group attached to an aryl group having 6 to 60 carbon atoms.

[0042] Unless otherwise stated, the terms "aryl group" or "arylene group" as used herein refer to, but are not limited to, a group having 6 to 60 carbon atoms. In this document, aryl group or arylene group means monocyclic and polycyclic aromatic groups, and can also be formed by combining with adjacent groups. Examples of "aryl group" may include phenyl groups, biphenyl groups, fluorene groups, or spirofluorene groups.

[0043] The prefix “aryl” or “aromatic” indicates a group that is substituted by an aryl group. For example, an arylalkyl group can be an aryl-substituted alkyl group, and an arylalin group can be an aryl-substituted alkenyl group, and the aryl-substituted group has the number of carbon atoms as defined herein.

[0044] Furthermore, when prefixes are named sequentially, this means that substituents are listed in the order they are first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0045] Unless otherwise stated, the term "heterocyclic group" as used herein contains one or more heteroatoms and has, but is not limited to, 2 to 60 carbon atoms, including any of monocyclic and polycyclic rings, and may include heteroaliphatic and / or heteroaromatic rings. Furthermore, it may combine with adjacent groups to form a heterocyclic group.

[0046] Unless otherwise stated, the term "heteroatom" as used herein means at least one of N, O, S, P, or Si.

[0047] Furthermore, the term "heterocyclic group" can include rings in which SO2 replaces the carbon atoms that make up the ring. For example, "heterocyclic group" includes the following compounds.

[0048]

[0049] Unless otherwise stated, the terms “fluorenyl group” or “fluoreneyl group” as used herein mean that R, R' and R” are all monovalent or divalent functional groups of hydrogen in the following structures, and the terms “substituted fluorenyl group” or “substituted fluoreneyl group” mean that at least one of the substituents R, R', and R” is a substituent other than hydrogen, and include those in which R and R' are bonded to each other to form a spiro compound together with the carbons they are bonded to.

[0050]

[0051] As used in this article, the term "spiro compound" has a "spiral connection," and a spiral connection means a connection in which two rings share only one atom. In this case, the atom shared by the two rings is called a "spiro atom," and these compounds are called "single-spiro," "double-spiro," and "triple-spiro," respectively, depending on the number of atoms in the compound.

[0052] Unless otherwise stated, as used herein, the term "aliphatic" means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0053] Unless otherwise stated, as used herein, the term "ring" means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by combination thereof, and includes saturated or unsaturated rings.

[0054] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups contain one or more hetero atoms, but are not limited thereto.

[0055] Unless otherwise specified, the term "substituted or unsubstituted" as used herein means that the substitution is made by at least one substituent selected from deuterium, halogens, amino groups, nitrile groups, nitro groups, C1-C6 groups, etc. 20 Alkyl groups, C1-C 20 alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 aryl group, deuterated C6-C 20 aryl group, C8-C 20 Aryl alkenyl groups, silyl groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups, but not less than these.

[0056] Unless otherwise explicitly stated, the formulas used herein for the purposes of this invention are applied in the same manner as the substituents defined according to the definition of the exponents in the following formulas.

[0057]

[0058] Where, when a is a zero integer, the substituent R 1 There is no unique substituent R when a is an integer of 1. 1 When a is an integer of 2 or 3, each substituent R is attached to any one of the carbons constituting the benzene ring. 1 They can be the same or different. When a is an integer from 4 to 6, they are connected to the benzene ring in a similar manner, but the indication of the hydrogen that binds to the carbon that forms the benzene ring is omitted.

[0059]

[0060] In the following text, reference will be made to Figures 1 to 3 Describe the layered structure of organic electronic devices comprising the compounds of the present invention.

[0061] When adding reference numerals to the components in each figure, it should be noted that even if the same component is shown in different figures, the same component should have the same numerals as much as possible. Furthermore, in describing the invention, detailed descriptions will be omitted if it is determined that a detailed description of a related known configuration or function might obscure the essential points of the invention.

[0062] Figures 1 to 3 This is an exemplary view of an organic electronic component according to an embodiment of the present invention.

[0063] refer to Figure 1 According to an embodiment of the present invention, an organic electronic component (100) includes a first electrode (110), a second electrode (170) formed on a substrate (not shown) and an organic material layer formed between the first electrode (110) and the second electrode (170).

[0064] The first electrode (110) can be an anode (anode), and the second electrode (170) can be a cathode (cathode). In the case of the inverted type, the first electrode can be a cathode and the second electrode can be an anode.

[0065] The organic material layer may include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160). Specifically, the hole injection layer (120), the hole transport layer (130), the light-emitting layer (140), the electron transport layer (150), and the electron injection layer (160) may be sequentially formed on the first electrode (110).

[0066] Preferably, the light efficiency enhancement layer (180) can be formed on one surface of the organic material layer that is not in contact with the first electrode (110) or the second electrode (170), and when the light efficiency enhancement layer (180) is formed, the light efficiency of the organic electronic component can be improved.

[0067] For example, a light efficiency enhancement layer (180) can be formed on the second electrode (170). In the case of top-emitting organic light-emitting device, the light energy loss caused by surface plasmon polaritons (SPP) in the second electrode (170) can be reduced by forming the light efficiency enhancement layer (180), and in the case of bottom-emitting organic light-emitting device, the light efficiency enhancement layer (180) can be used as a buffer for the second electrode (170).

[0068] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will refer to Figure 2 Describe it.

[0069] refer to Figure 2According to another embodiment of the present invention, an organic electronic element (200) includes a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) sequentially formed on a first electrode (110), and a light efficiency enhancement layer (180) may be formed on the second electrode.

[0070] although Figure 2 The electron transport auxiliary layer may be further formed between the light-emitting layer (140) and the electron transport layer (150), but it is not shown in the figure.

[0071] Furthermore, according to another embodiment of the invention, the organic material layer can have the form of a plurality of stacks in which a hole transport layer, a light-emitting layer, and an electron transport layer are formed. This will be referred to Figure 3 Describe it.

[0072] refer to Figure 3 In an organic electronic component (300) according to another embodiment of the present invention, a stack of two or more sets of organic material layers (ST1, ST2) comprising a multilayer structure may be formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stack of organic material layers.

[0073] Specifically, an organic electronic component according to an embodiment of the present invention 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 light efficiency enhancement layer (180).

[0074] The first stack (ST1), which is an organic material 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), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450). Thus, the first stack and the second stack can be organic material layers having the same stack structure or organic material layers having different stack structures.

[0075] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). The charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to smoothly distribute the charge.

[0076] like Figure 3 As shown, when multiple light-emitting layers are formed by a multilayer stacked structure method, it is possible to manufacture an organic light-emitting device that emits white light through the mixing effect of light emitted from each light-emitting layer, as well as an organic light-emitting device that emits light of various colors.

[0077] The compounds represented by Formula 1 of the present invention can be used as materials for hole injection layers (120, 320, 420), hole transport layers (130, 330, 430), buffer layers (210), light-emitting auxiliary layers (220), electron transport layers (150, 350, 450), electron injection layers (160), light-emitting layers (140, 340, 440), or light efficiency enhancement layers (180). However, preferably, the compounds represented by Formula 1 of the present invention can be used as materials for light-emitting auxiliary layers (220), and the compounds represented by Formula 2 of the present invention can be used as the main body of light-emitting layers (140, 340, 440).

[0078] Even with identical or similar nuclei, band gaps, electrical properties, and interfacial properties can vary depending on the position of the substituents. Therefore, it is necessary to study the selection of the nucleus and the combination of substituents bonded to it. In particular, when the energy levels and T1 values ​​between the layers of organic materials are optimally combined with the inherent properties of the material (mobility, interfacial properties, etc.), long service life and high efficiency can be achieved simultaneously.

[0079] The organic electroluminescent device according to embodiments of the present invention can be manufactured using various deposition methods. It can be manufactured using deposition methods such as PVD or CVD, for example, by depositing a conductive metal or metal oxide or alloy thereof on a substrate to form an anode (110), and after forming an organic material layer thereon comprising 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), it can be manufactured by depositing a material thereon that can serve as a cathode (170). 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 also be formed between the light-emitting layer (140) and the electron transport layer (150), which can also be formed as a stacked structure as shown.

[0080] Furthermore, organic material layers can be manufactured with fewer layers using various polymer materials, without vapor deposition methods, but through methods such as solution or solvent processes, for example, spin coating or nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll coating, doctor blade coating, screen printing, or thermal transfer. Since the organic material layers according to the invention can be formed by various methods, the scope of the invention is not limited to the method of formation.

[0081] Furthermore, the organic electronic components according to embodiments of the present invention can be selected from organic electroluminescent devices, organic solar cells, organic photosensitive materials, organic transistors, monochrome lighting devices, and quantum dot display devices.

[0082] Another embodiment of the present invention may include: a display device comprising the organic electronic elements of the present invention described above, and an electronic device including a control unit for driving the display device. In this case, the electronic device may be a current or future wired / wireless communication terminal, and includes all electronic devices, such as mobile communication terminals like portable phones, PDAs, electronic dictionaries, PMPs, remote controllers, navigation systems, game consoles, various TVs, and various computers.

[0083] Organic electrical devices according to aspects of the present invention will be described below.

[0084] An organic electronic component according to an embodiment of the present invention includes an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes a light-emitting layer and a hole transport band layer formed between the light-emitting layer and the anode, wherein the hole transport band layer contains a compound represented by Formula 1, and the light-emitting layer contains a compound represented by Formula 2.

[0085]

[0086] In Equations 1 and 2, each symbol can be defined as follows.

[0087] 1) X is O, S, or NR, but when X is NR, i is 0 and j is 1.

[0088] 2)X 1 X 2 and X 3 Each is independently either CR' or N, provided that X 1 X 2 and X 3 At least two of them are N.

[0089] 3)R 1 R 2 R 3 R 4R and R' are each independently the same or different from each other, and are each independently selected from hydrogen; deuterium; halogen; C1-C. 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; and -L'-NR a R b Or if a, b, c, and d are 2 or greater, multiple adjacent R 1 One or more R 2 One or more R 3 One or more R 4 They can bond together to form a ring.

[0090] Where R 1 R 2 R 3 R 4 R and R' are alkyl groups, which can preferably be C1-C2. 30 Alkyl groups, more preferably C1-C 24 alkyl groups,

[0091] Where R 1 R 2 R 3 R 4 R and R' are alkenyl groups, which can preferably be C2-C. 30 Alkenyl groups, more preferably C2-C 24 alkenyl group,

[0092] Where R 1 R 2 R 3 R 4 R and R' are alkynyl groups, which can preferably be C2-C. 30 Alkyne group, more preferably C2-C 24 acetylation group,

[0093] Where R 1 R 2 R 3 R 4 R and R' are alkoxy groups, which can preferably be C1-C. 30 Alkoxy groups, more preferably C1-C24 alkoxy group,

[0094] Where R 1 R 2 R 3 R 4 R and R' are aryloxy groups, which can preferably be C6-C. 30 Aryloxy groups, more preferably C6-C 24 aryloxy group,

[0095] Where R 1 R 2 R 3 R 4 R and R' are aryl groups, which can preferably be C6-C. 30 Aryl groups, more preferably C6-C 24 The aryl group, for example, can be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0096] Where R 1 R 2 R 3 R 4 R and R' are heterocyclic groups, which can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidin[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0097] Where R 1 R 2 R 3 R 4 R and R' are fused ring groups, which can preferably be C3-C. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0098] 4) L', L 1 L 2 L 3 L 4 and L 5 Each is independently selected from a single bond; C6-C 60 arylene group; fluorene group; C3-C 60 Aliphatic rings and C6-C 60Fused ring groups of aromatic rings; C2-C 60 Heterocyclic groups;

[0099] Where L', L 1 L 2 L 3 L 4 and L 5 It is an aryl group, which can preferably be C6-C. 30 arylene groups, more preferably C6-C 24 Aromatic groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.

[0100] Where L', L 1 L 2 L 3 L 4 and L 5 It is a fused ring group, and it can preferably be C3-C. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings,

[0101] Where L', L 1 L 2 L 3 L 4 and L 5 It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0102] 5) Where R a and R b Each is independently selected from C6-C 60 Aryl group; fluorenyl group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups;

[0103] Where R a and R b It is an aryl group, and it can preferably be C6-C. 30 Aryl groups, more preferably C6-C 24Aryl groups, such as phenylene, biphenyl, naphthalene, terphenyl, etc.

[0104] Where R a and R b It is a fused ring group, and it can preferably be C3-C. 30 Aliphatic rings and C6-C 30 The fused ring group of the aromatic ring, more preferably C3-C, is preferred. 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings,

[0105] Where R a and R b It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, such as pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidin[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, triazine, quinoxaline, etc.

[0106] 6) a, b, c, and d are each an independent integer from 0 to 4.

[0107] 7) i and j are independent integers from 0 to 2, provided that i + j is an integer of 1 or greater;

[0108] 8)Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 Each is independently selected from C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; alternatively, Ar 1 and Ar 2 Or Ar 3 and Ar 4 They can bond together to form a ring.

[0109] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is an alkyl group, which can preferably be C1-C. 30 Alkyl groups, more preferably C1-C 24 Alkyl groups.

[0110] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is an alkenyl group, which can preferably be C2-C. 30 Alkenyl groups, more preferably C2-C 24 alkenyl group,

[0111] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is an alkynyl group, which can preferably be C2-C. 30 Alkyne group, more preferably C2-C 24 acetylation group,

[0112] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is an alkoxy group, which can preferably be C1-C. 30 Alkoxy groups, more preferably C1-C 24 alkoxy group,

[0113] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is an aryloxy group, which can preferably be C6-C. 30 Aryloxy groups, more preferably C6-C 24 aryloxy group,

[0114] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is an aryl group, and it can preferably be C6-C. 30 Aryl groups, more preferably C6-C 24 The aryl group, for example, can be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0115] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 It is a heterocyclic group, and it can preferably be C2-C. 30 Heterocyclic groups, more preferably C2-C 24 Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidin[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0116] If Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 When it is a fused ring group, it can preferably be C3-C. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0117] 9) Wherein, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorene group, fused ring group, alkyl group, alkenyl group, alkoxy group, and aryloxy group may be replaced by one or more substituents, wherein the substituents are selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 alkoxy group; C1-C 20 Alkyl group; C2-C 20alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl groups; C7-C 20 arylalkyl groups; and C8-C 20 aryl alkenyl groups; and -L'-NR a R b Furthermore, substituents can bond with each other to form saturated or unsaturated rings, where the term "ring" refers to C3-C. 60 Aliphatic rings or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by their combination.

[0118] Furthermore, the compounds represented by Formula 1 are represented by any one of Formulas 1-1 to 1-7.

[0119]

[0120] in:

[0121] 1) X, R 1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 and Ar 4 Same as defined in Equation 1,

[0122] 2) aa, bb, cc, and dd are each an independent integer from 0 to 3.

[0123] 3) bb' and dd' are each an integer from 0 to 2.

[0124] Furthermore, the compounds represented by Formula 1 are represented by any one of Formulas 1-8 to 1-9.

[0125]

[0126]

[0127] Where R 1 R 2 R 3 R 4 a, b, c, d, L 1 L2 Ar 1 Ar 2 Ar 3 Ar 4 i and j are the same as those defined in Equation 1.

[0128] Furthermore, Ar in Equation 1 1 To Ar 4 At least one of them is represented by equation B-1.

[0129] Formula B-1

[0130]

[0131] in

[0132] 1)V 1 and V 2 Each is an independent single bond, NR 5 CR 6 R 7 O or S

[0133] 2)R 5 R 6 and R 7 With R in Equation 1 1 The definitions are the same, provided that R is... 6 and R 7 They can bond together to form a ring.

[0134] 3) Ring A and ring B are independently substituted or unsubstituted C6-C. 20 aryl group; or substituted or unsubstituted C4-C 20 Heterocyclic groups;

[0135] Specifically, the compound represented by Formula 1 can be any of the following compounds.

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] Furthermore, Ar in Equation 2 5 To Ar 7 At least one of the expressions in is represented by any one of Equations 2-1 to 2-6.

[0147]

[0148] in

[0149] 1)X 4 and X 5 Each is independent of the NAr 8 O, S or CR c R d ,

[0150] 2)Ar 8 Ar in Equation 1 1 The definitions are the same.

[0151] 3)R 8 R 9 R 10 R c and R d Each is independently selected from hydrogen; deuterium; halogen; unsubstituted or C1-C. 20 alkyl groups or C6-C 20 aryl-substituted silane groups; cyano groups; nitro groups; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and C3-C 20 Aliphatic ring; alternatively, adjacent groups may bond to each other to form a ring, and adjacent substituents may bond to form a ring.

[0152] 4) e, f, and h are integers from 0 to 4, and g is an integer from 0 to 6.

[0153] Furthermore, the compounds represented by Formula 2 are represented by any one of Formulas 2-7 to 2-9.

[0154]

[0155] in

[0156] 1)X 3 L 3 L 4 L 5 Ar 6 and Ar 7 Same as defined in Equation 2,

[0157] 2)X 4 X 6 and X 8 Each is independently O, S, NAr 9 or CR c R d ,

[0158] 3)X 5 X 7 and X 9 Each is independently O, S, NAr 10 CR e R f Or a single key,

[0159] 4) a', d', and f' are integers from 0 to 4, and b', c', and e' are integers from 0 to 3.

[0160] 5)Ar 9 and Ar 10 Ar in Equation 1 1 The definitions are the same.

[0161] 6)R c R d R e R f R 12 R 13 R 14 R 15 R 16 and R 17 R in Equation 2-1 8 The definitions are the same.

[0162] Furthermore, L in Equations 1 and 2 1 To L 5 At least one of the following formulas is represented by one of the following formulas b-1 to b-13.

[0163]

[0164] in

[0165] 1) Z is O, S, NL 6 -Ar 11 Or CR6R7,

[0166] 2)L6 With L in Equation 1 1 The definitions are the same.

[0167] 3)Ar 11 Ar in Equation 1 1 The definitions are the same.

[0168] 4) R6, R7, R8, R9 and R 10 They may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and C3-C 20 Aliphatic rings; and adjacent groups can bond with each other to form rings.

[0169] 5) a", c", d", and e" are each an integer from 0 to 4, b" is an integer from 0 to 6, f" and g" are each an integer from 0 to 3, h" is an integer from 0 to 2, and i" is 0 or 1.

[0170] 6)Z 49 Z 50 and Z 51 Each is CR independently g Or N, and Z 49 Z 50 and Z 51 At least one of them is N,

[0171] 7)R g Selected from hydrogen; deuterium; halogen; unsubstituted or C1-C 20 alkyl groups or C6-C 20 aryl-substituted silane groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and C3-C 20 Aliphatic ring; C7-C 20 arylalkyl groups; and C8-C 20 aryl alkenyl groups;

[0172] Specifically, the compound represented by Formula 2 can be any of the following compounds.

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] Furthermore, the present invention provides a compound comprising one or more hole transport band layers between an anode and a light-emitting layer, wherein the hole transport band layer comprises a hole transport layer, a light-emitting auxiliary layer, or both, wherein the hole transport band layer comprises a compound represented by Formula 1, and wherein the light-emitting layer comprises a compound represented by Formula 2.

[0181] The luminescent layer may contain a compound represented by Formula 2 as a first host, and may also contain a second host different from the first host.

[0182] For example, the second subject may be selected from formula 3-1, formula 3-2, and compounds 3-1 to 3-135 and compounds 4-1 to 4-65, but is not limited thereto.

[0183]

[0184] in

[0185] 1) R1 and R2 are the same as R in Equation 1 1 The definitions are the same.

[0186] 2) a1 and a2 are each independent integers from 0 to 5, and a1' and a2' are each independent integers from 0 to 4.

[0187] 3) L and L in Equation 1 1 The definitions are the same.

[0188] 4)Ar 12 Ar in Equation 1 1 The definitions are the same.

[0189] However, the first host compound may not include formula C.

[0190] Formula C

[0191]

[0192] 1) Ring A and ring B are each independently C6-C 14 aryl group,

[0193] 2) L1 is selected from single bonds; C6-C 60 arylene group; fluorene group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C2-C 60 Heterocyclic groups;

[0194] 3) ET is a C2-C bond containing one or more N atoms. 60 Heterocyclic groups.

[0195] The compound represented by formula C can be any of the following compounds.

[0196]

[0197]

[0198] The organic electronic component also includes a light efficiency enhancement layer formed on at least one surface of the anode and cathode, which is opposite to the organic material layer.

[0199] In addition, the organic material layer may include two or more stacks, each stack including a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the anode, and the organic material layer may also include a charge-generating layer formed between the two or more stacks.

[0200] In another aspect, the present invention provides an electronic device comprising a display device including organic electronic components; and a control unit for driving the display device. In this case, the organic electronic components are at least one of OLED, organic solar cell, organic photoconductor (OPC), organic transistor (organic TFT), and components for monochrome or white illumination.

[0201] In the following, examples of the synthesis of compounds represented by formulas according to the present invention and examples of the preparation of organic electronic devices will be described in detail with reference to the embodiments, but the present invention is not limited to the following embodiments.

[0202] [Synthesis example 1]

[0203] The compound represented by Formula 1 according to the invention (final product 1) can be prepared by reacting as shown in reaction scheme 1, but is not limited thereto.

[0204] <Reaction Scheme 1>

[0205]

[0206] In reaction scheme 1, Hal is Cl, Br, or I, and G1 is Ar.1 Or Ar 3 G2 is Ar 2 Or Ar 4 .

[0207] I. Example of Sub 1 Synthesis

[0208] Sub 1 of reaction scheme 1 can be synthesized using reaction scheme 2, but is not limited to this.

[0209] <Reaction Scheme 2>

[0210]

[0211]

[0212] Examples of the synthesis of specific compounds belonging to Sub 1 are as follows.

[0213] Synthesis example of Sub 1-1

[0214]

[0215] (1) Synthesis of Sub 1-1A

[0216] After dissolving 4-chloro-9H-xanthon-9-one (20 g, 86.71 mmol) and 2-bromo-1,1'-biphenyl (21.22 g, 91.05 mmol) in THF (600 mL), the reaction mixture was cooled to -78 °C, and n-BuLi (2.5 M in hexane) (6.11 g, 95.38 mmol) was slowly added. The reaction mixture was stirred at room temperature for 4 hours. When the reaction was complete, the reactants were quenched in H₂O, then the water was removed, the mixture was filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated by column chromatography to obtain 29.7 g of product (yield: 89%).

[0217] (2) Synthesis of Sub 1-1

[0218] Sub 1-1A (20 g, 51.97 mmol), HCl (4 ml), and acetic acid (208 ml) were added, and the mixture was stirred at 80 °C for 1 hour. When the reaction was complete, the organic solvent was concentrated after filtration under reduced pressure, and the resulting product was separated by column chromatography to obtain 17.54 g of product. (Yield: 92%)

[0219] Synthesis examples in Sub 1-6

[0220]

[0221] (1) Synthesis of Sub 1-6A

[0222] By using the method for synthesizing Sub 1-1A, 33.3 g of the product was obtained using 4-chloro-9H-xanthon-9-one (20 g, 101.93 mmol) and 2-bromo-1,1'-biphenyl (28.64 g, 107.03 mmol), THF (680 ml), and n-BuLi (2.5 M in hexane) (7.18 g, 112.12 mmol). (Yield: 85%)

[0223] (2) Synthesis of Sub 1-6

[0224] Using the Sub 1-1 synthetic method, Sub 1-6A (20 g, 51.97 mmol), HCl (4 ml), and acetic acid (208 ml) were used to obtain 16.78 g of product. (Yield: 88%)

[0225] Synthesis examples in Sub 1-46

[0226]

[0227] (1) Synthesis of Sub 1-46A

[0228] By using the method for synthesizing Sub 1-1A, 25.7 g of the product was obtained using 3-chloro-9H-thioxanthone-9-one (20 g, 81.07 mmol), 2-bromo-1,1'-biphenyl (19.84 g, 85.12 mmol), THF (600 ml), and n-BuLi (2.5 M in hexane) (5.71 g, 89.17 mmol). (Yield: 79%)

[0229] (2) Synthesis of Sub 1-46

[0230] Using the Sub 1-1 synthetic method, Sub 1-46A (20.8 g, 51.97 mmol), HCl (4 ml), and acetic acid (200 ml) were used to obtain 15.47 g of product. (Yield: 81%)

[0231] Synthesis examples in Sub 1-55

[0232]

[0233] (1) Synthesis of Sub 1-55A

[0234] By using the method for synthesizing Sub 1-1A, 2-chloro-9H-thioxanthone-9-one (20 g, 81.07 mmol), 4-bromo-2-iodo-1,1'-biphenyl (30.56 g, 85.12 mmol), THF (600 ml), and n-BuLi (2.5 M in hexane) (5.71 g, 89.17 mmol) were used to obtain 33.06 g of the product. (Yield: 85%)

[0235] (2) Synthesis of Sub 1-55

[0236] Using the Sub 1-1 synthetic method, Sub 1-55A (20 g, 41.68 mmol), HCl (3.5 ml), and acetic acid (167 ml) were used to obtain 16.75 g of product. (Yield: 87%)

[0237] Synthesis examples in Sub 1-72

[0238]

[0239] (1) Synthesis of Sub 1-72A

[0240] Using the synthetic method of Sub 1-1A, 25 g of product was obtained using 3-(3-chlorophenyl)-10-phenylacridin-9(10H)-one (20 g, 52.38 mmol), 2-bromo-1,1'-biphenyl (12.82 g, 54.99 mmol), THF (500 ml), and n-BuLi (2.5 M in hexane) (3.7 g, 57.61 mmol). (Yield: 89%)

[0241] (2) Synthesis of Sub 1-72

[0242] Using the Sub 1-1 synthetic method, Sub 1-72A (20 g, 37.31 mmol), HCl (3 ml), and acetic acid (150 ml) were used to obtain 17.59 g of product. (Yield: 91%)

[0243] The compounds belonging to Sub 1 can be, but are not limited to, the following compounds.

[0244]

[0245]

[0246]

[0247] Table 1 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to Sub 1.

[0248] [Table 1]

[0249]

[0250]

[0251]

[0252] II. Example of Sub 2 Synthesis

[0253] Sub 2 of Scheme 1 can be synthesized through the reaction pathway of Scheme 3, but is not limited to this.

[0254] <Reaction Scheme 3>

[0255]

[0256] In reaction scheme 3, G1 is Ar 1 Or Ar 3 G2 is Ar 2 Or Ar 4 .

[0257] Synthesis example in Sub 2-1

[0258]

[0259] After dissolving bromobenzene (37.1 g, 236.2 mmol) in toluene (2200 ml) in a round-bottom flask, aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83 g, 10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol), and NaOt-Bu (62 g, 644.3 mmol) were added sequentially and stirred at 100 °C. After the reaction was complete, the mixture was extracted with diethyl ether and water, and the organic layer was dried over MgSO₄, concentrated, and recrystallized from the resulting compound using a silica gel column to obtain 28 g of Sub₂⁻ (yield: 77%).

[0260] Synthesis example in Sub 2-37

[0261]

[0262] Using the Sub 2-1 synthetic method, 37.9 g of Sub 2-37 was obtained using 3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol), toluene (1550 ml), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol), Pd2(dba)3 (6.76 g, 7.4 mmol), P(t-Bu)3 (3 g, 14.8 mmol), and NaOt-Bu (42.6 g, 443.2 mmol). (Yield: 73%)

[0263] The compounds belonging to Sub 2 can be, but are not limited to, the following compounds.

[0264]

[0265]

[0266] Table 2 shows the FD-MS (field desorption-mass spectrometry) values ​​of compounds belonging to Sub 2.

[0267] [Table 2]

[0268]

[0269]

[0270] III. Synthesis Example of Final Product 1

[0271] Synthesis example 1-1

[0272]

[0273] After dissolving Sub 1-1 (10 g, 27.26 mmol) in toluene (300 mL) in a round-bottom flask, Sub 2-1 (5.07 g, 29.99 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were added and stirred at 100 °C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4, concentrated, and recrystallized from the compound using a silica gel column to obtain 11.7 g of the product (yield: 86%).

[0274] Synthesis examples 1-15

[0275]

[0276] Using the 1-1 synthetic method, Sub 1-3 (10 g, 27.26 mmol), toluene (500 ml), Sub 2-27 (12.22 g, 29.99 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were used to obtain 15.89 g of product. (Yield: 79%)

[0277] Synthesis examples 1-27

[0278]

[0279] Using the 1-1 synthetic method, Sub 1-3 (10 g, 27.26 mmol), toluene (500 ml), Sub 2-56 (9.22 g, 29.99 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were used to obtain 14.6 g of product. (Yield: 84%)

[0280] Synthesis examples 1-42

[0281]

[0282] Using the 1-1 synthetic method, Sub 1-50 (10 g, 23.40 mmol), toluene (500 ml), Sub 2-14 (5.64 g, 25.74 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were used to obtain 10.85 g of product. (Yield: 82%)

[0283] Synthesis examples 1-74

[0284]

[0285] Using the 1-1 synthetic method, Sub 1-59 (10 g, 18.07 mmol), toluene (500 ml), Sub 2-1 (3.36 g, 19.87 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were used to obtain 9.9 g of product. (Yield: 85%)

[0286] Synthesis example 1-103

[0287]

[0288] Using the 1-1 synthetic method, Sub 1-56 (10 g, 21.65 mmol), toluene (500 ml), Sub 2-1 (4.03 g, 23.82 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were used to obtain 12.63 g of product. (Yield: 90%)

[0289] Synthesis examples 1-126

[0290]

[0291] Using the 1-1 synthetic method, Sub 1-70 (10 g, 20.32 mmol), toluene (500 ml), Sub 2-12 (7.2 g, 22.36 mmol), Pd2(dba)3 (1.25 g, 1.36 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (7.86 g, 81.78 mmol) were used to obtain 14 g of product. (Yield: 89%)

[0292] Table 3 shows the FD-MS (field desorption-mass spectrometry) values ​​of the compounds belonging to final product 1.

[0293] [Table 3]

[0294]

[0295]

[0296]

[0297]

[0298] [Synthesis example 2]

[0299] The compound represented by Formula 2 according to the invention (final product 2) is synthesized as shown in reaction scheme 4, but is not limited thereto.

[0300] G 1 It is L 5 or L 6 G 2 It is Ar 5 Or Ar 6 X 1 To X 3 L4 To L 6 And Ar 4 To Ar 6 Same as defined in Equation 1, Hal 3 and Hal 4 Each can be I, Br, or Cl independently.

[0301] <Reaction Scheme 4>

[0302]

[0303] I. Example of Sub 3 Synthesis

[0304] Synthesis example in Sub 3-1

[0305]

[0306] 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (CAS Registry No.: 10202-45-6) (20 g, 66.19 mmol) and 4-biphenylboronic acid (CAS Registry No.: 5122-94-1) (13.1 g, 66.19 mmol) were dissolved in THF (370 ml), and Pd(PPh3)4 (3.8 g, 3.31 mmol), K2CO3 (27.4 g, 198.57 mmol), and water (165 ml) were added and stirred under reflux. When the reaction was complete, the organic layer was concentrated after extraction with diethyl ether and water. The concentrated organic layer was dried over MgSO4 and concentrated again. The final concentrate was passed through a silica gel column and recrystallized to obtain 20.8 g of product (75% yield).

[0307] Synthesis examples in Sub 3-8

[0308]

[0309] 2,4-Dichloro-6-(naphth-2-yl)-1,3,5-triazine (20 g, 72.43 mmol), (3-(pyridin-2-yl)phenyl)boronic acid (14.3 g, 72.43 mmol), Pd(PPh3)4 (0.05 equivalents), K2CO3 (3 equivalents), anhydrous THF, and a small amount of water were added, and 20.3 g of the product was synthesized in the same manner as in the synthesis of Sub 3-1 (yield 71%).

[0310] Synthesis example in Sub 3-19

[0311]

[0312] 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (15 g, 49.64 mmol), (9,9-dimethyl-9H-fluorene-3-yl)boronic acid (11.8 g, 49.64 mmol), Pd(PPh3)4 (0.05 equivalents), K2CO3 (3 equivalents), anhydrous THF, and a small amount of water were added, and 15.7 g of the product was synthesized in the same manner as in the synthesis of Sub 3-1 (yield 69%).

[0313] Synthesis examples in Sub 3-35

[0314]

[0315] 2,4-Dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol), dibenzo[b,d]furan-2-ylboronic acid (28.1 g, 132.71 mmol), Pd(PPh3)4 (0.05 equivalents), K2CO3 (3 equivalents), anhydrous THF, and a small amount of water were added, and 30.8 g of the product was synthesized in the same manner as in the synthesis of Sub 3-1 (yield 65%).

[0316] Compounds belonging to Sub 3 can be, but are not limited to, the following compounds, and Table 4 shows the field desorption-mass spectrometry (FD-MS) values ​​of some compounds belonging to Sub 3.

[0317]

[0318]

[0319] [Table 4]

[0320]

[0321]

[0322] II. Example of Sub 4 Synthesis

[0323] Sub 4 of reaction scheme 1 can be synthesized via the reaction pathway of reaction scheme 5, but is not limited to this. 5 It is I, Br, or Cl.

[0324] <Reaction Scheme 5>

[0325]

[0326] Synthesis example in Sub 4-2

[0327]

[0328] 4-Bromo-1,1'-biphenyl (5 g, 21.45 mmol), bis(pinacol)diboron (7.1 g, 27.89 mmol), PdCl2 (dppf) (0.78 g, 1.07 mmol), KOAc (6.3 g, 64.35 mmol), and DMF (270 mL) were added and stirred under reflux at 120 °C. When the reaction was complete, the reactants were cooled to room temperature, extracted with MC, and washed with water. After drying the organic layer with MgSO4 and concentrating it, the resulting organic material was separated by silica gel column chromatography to obtain 3.4 g of Sub 4-2 (yield: 80%).

[0329] Synthesis example in Sub 4-37

[0330]

[0331] 2-Bromodibenzo[b,d]furan (10 g, 40.47 mmol), bis(pinacol)diboron (13.3 g, 52.61 mmol), PdCl2 (dppf), (0.05 equivalents), KOAc (3 equivalents), and anhydrous DMF were added, and 7 g of the product was synthesized in the same manner as in the synthesis of Sub 4-2. (Yield: 82%)

[0332] Compounds belonging to Sub 4 can be, but are not limited to, the following compounds, and Table 5 shows the field desorption-mass spectrometry (FD-MS) values ​​of some compounds belonging to Sub 4.

[0333]

[0334]

[0335] [Table 5]

[0336]

[0337]

[0338] III. Synthesis Example of Final Product 2

[0339] Sub 5 (1 equivalent) and Sub 6 (1-2 equivalents) were placed in a round-bottom flask, dissolved in THF, and Pd(PPh3)4 (0.05 equivalent), K2CO3 (3 equivalent), and water were added and the mixture was stirred and refluxed. When the reaction was complete, the organic layer was extracted with ether and water, dried over MgSO4, concentrated, and recrystallized from the resulting compound using a silica gel column to obtain the final product 2.

[0340] Synthesis examples 2-9

[0341]

[0342] Sub 3-1 (5 g, 11.91 mmol) was dissolved in 70 mL of THF containing Sub 4-36 (2.8 g, 13.1 mmol). Pd(PPh3)4 (0.7 g, 0.6 mmol), K2CO3 (5 g, 35.73 mmol), and water (30 mL) were added and stirred under reflux. When the reaction was complete, the organic layer was concentrated after extraction with ether and water. The concentrated organic layer was dried over MgSO4 and concentrated again. The final concentrate was passed through a silica gel column and recrystallized to obtain 5.4 g of product. (Yield: 71%)

[0343] Synthesis example 2-29

[0344]

[0345] Sub 3-39 (4 g, 14.94 mmol), Sub 4-47 (6.2 g, 16.43 mmol), Pd(PPh3)4 (0.05 equivalent), K2CO3 (3 equivalent), anhydrous THF, and a small amount of water were added, and 8.1 g of the product was synthesized in the same manner as in synthetic methods 2-9 above (yield 84%).

[0346] Synthesis example 2-62

[0347]

[0348] Sub 3-33 (4 g, 10.7 mmol), Sub 4-32 (2.7 g, 11.8 mmol), Pd(PPh3)4 (0.05 equivalent), K2CO3 (3 equivalent), anhydrous THF, and a small amount of water were added, and 4.4 g of the product was synthesized in the same manner as in methods 2-9 above. (Yield 80%)

[0349] Synthesis example 2-115

[0350]

[0351] Sub 3-41 (10 g, 37.35 mmol), Sub 4-48 (4.7 g, 18.5 mmol), Pd(PPh3)4 (0.1 equivalent), K2CO3 (6 equivalent), anhydrous THF, and a small amount of water were added, and 9.1 g of the product was synthesized in the same manner as in synthetic methods 2-9 above. (Yield 78%)

[0352] Furthermore, the FD-MS values ​​of compounds 2-1 to 2-118 of the present invention prepared according to the synthesis examples described above are shown in Table 6.

[0353] [Table 6]

[0354]

[0355]

[0356]

[0357] Organic Electronic Component Manufacturing Evaluation

[0358] [Example 1] Red Organic Light-Emitting Device

[0359] First, an N1-(naphthyl-2-yl)-N4,N4-bis(4-(naphthyl-2-yl(phenyl)amino)phenyl)-N1-phenylphenyl-1,4-diamine (hereinafter abbreviated as 2-TNATA) film as a hole injection layer is vacuum deposited on an ITO layer (anode) formed on a glass substrate to a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound is vacuum deposited on the film to a thickness of 60 nm to form a hole transport layer. Then, compounds 1-3 of the present invention are vacuum deposited as materials for the light-emitting auxiliary layer to a thickness of 30 nm to form the light-emitting auxiliary layer. Then, on the light-emitting auxiliary layer, compound 2-36 of the present invention, as the main component, is deposited at a weight ratio of 95:5 with (piq)2Ir(acac)[bis-(1-phenylisoquinolinyl)acetylacetone iridium(III)] as a dopant to form a light-emitting layer with a thickness of 30 nm. Then, (1,1'-biphenyl)-4-oxo)bis(2-methyl-8-quinoline oxo)aluminum (hereinafter abbreviated as BAlq) is vacuum-deposited on the light-emitting layer to a thickness of 10 nm to form a hole-blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) is deposited on the hole-blocking layer to a thickness of 40 nm to form an electron transport layer. Then, LiF, as an alkali metal halide, is deposited on the electron transport layer to a thickness of 0.2 nm as an electron injection layer, and then Al is deposited to a thickness of 150 nm and used as a cathode, thereby fabricating an organic light-emitting device.

[0360] [Example 2] to [Example 16]

[0361] The organic electroluminescent device was manufactured in the same manner as in Example 1, but the compounds of the present invention shown in Table 7 were used for the light-emitting auxiliary layer and the light-emitting layer.

[0362] [Example 17] and [Example 18]

[0363] The organic electroluminescent device was manufactured in the same manner as in Example 1, but compounds 1-54 of the present invention were used in the hole transport layer and compounds 1-61 of the present invention were used in the light-emitting auxiliary layer, and for the light-emitting layer, as shown in Table 7, the compounds of the present invention were used in a 5:5 ratio.

[0364] [Comparative Example 1] and [Comparative Example 2]

[0365] The organic light-emitting device was manufactured in the same manner as in Example 1, but using the host material instead of the light-emitting auxiliary layer as shown in Table 7.

[0366] Comparative Examples 3 through 7

[0367] As shown in Table 7, the organic light-emitting device was manufactured in the same manner as in Example 1, but using the light-emitting auxiliary layer material and the main material.

[0368] <Comparing Compound 1> <Comparing Compound 2> <Comparing Compound 3> <Comparing Compound 4> <Comparing Compound 5>

[0369]

[0370] Electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 18 and Comparative Examples 1 to 7 of the present invention, and at a lifetime of 2500 cd / m² was measured using a lifetime measuring device manufactured by McScience. 2 The lifespan of the T95 was measured under standard brightness. The measurement results are shown in Table 7.

[0371] [Table 7]

[0372]

[0373] According to the results in Table 7, when the material of the organic light-emitting device of the present invention represented by Formula 1 is used as the light-emitting auxiliary layer and the material of the organic light-emitting device of the present invention represented by Formula 2 is used as the phosphorescent host, it can be seen that, compared with Comparative Examples 1 to 7, the driving voltage is reduced and the efficiency and service life are improved.

[0374] Compared to Comparative Examples 1 and 2, which used Comparative Compound 4 or Comparative Compound 5 as the main body without forming a light-emitting auxiliary layer, Comparative Examples 3 to 6, which used one of Comparative Compounds 1 to 3 in the light-emitting auxiliary layer, showed improved driving voltage, efficiency, and lifetime. Furthermore, compared to Comparative Examples 1 to 7, Examples 1 to 18, in which the light-emitting auxiliary layer was formed using the compound of the present invention represented by Formula 1 and the material represented by Formula 2 was used as the main body, showed significant improvements.

[0375] It is speculated that this is because the compound of the present invention, represented by Formula 1, has a deep HOMO energy level, so when used as a light-emitting auxiliary layer, holes and electrons achieve charge balance, and light emission occurs within the light-emitting layer rather than at the hole transport layer interface, thereby maximizing efficiency. Furthermore, by using the compound of the present invention, represented by Formula 2, as the phosphorescent host, it is determined that the combination of devices exhibits an electrochemical synergistic effect to improve the overall performance of the device.

[0376] Therefore, when organic electronic devices are prepared by appropriately combining the compounds represented by Formulas 1 and 2, more holes move rapidly and easily to the emissive layer. Consequently, the charge balance between holes and electrons in the emissive layer increases, resulting in good luminescence within the emissive layer rather than at the interface of the hole transport layer. This also reduces degradation at the interface between ITO and HTL, lowers the overall drive voltage of the device, and improves efficiency and lifespan. In other words, when the compounds represented by Formulas 1 and 2 are appropriately combined, synergistic electrochemical effects appear to improve the overall performance of the device.

[0377] While exemplary embodiments of the invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and spirit of the invention as disclosed in the appended claims. Therefore, the embodiments disclosed herein are intended to illustrate the scope of the inventive concept, and the scope of the invention is not limited by the embodiments. The scope of the invention should be interpreted based on the appended claims, and should be construed as including all inventive concepts within the scope of equivalent claims.

[0378] Industrial applicability

[0379] According to the present invention, an organic device with excellent device characteristics such as high brightness, high luminescence and long service life can be manufactured, and therefore it has industrial applicability.

Claims

1. Organic electronic components, including: An anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes a light-emitting layer and a hole transport band layer formed between the light-emitting layer and the anode, wherein the hole transport band layer comprises a compound represented by Formula 1, and wherein the light-emitting layer comprises a compound represented by Formula 2. Formula 1 Formula 2 in: 1) X is O, S, or NR, but when X is NR, i is 0 and j is 1. 2) X 1 X 2 and X 3 Each is independently either CR' or N, provided that X 1 X 2 and X 3 At least two of them are N. 3) R 1 R 2 R 3 R 4 R and R' are each independently the same or different from each other, and are each independently selected from hydrogen; deuterium; halogen; C1-C. 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; and -L'-NR a R b Or if a, b, c, and d are 2 or greater, multiple adjacent R 1 One or more R 2 One or more R 3 One or more R 4 They can bond together to form a ring. 4) L', L 1 L 2 L 3 L 4 and L 5 Each is independently selected from a single bond; C6-C 60 arylene group; fluorene group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C2-C 60 Heterocyclic groups; 5) Where R a and R b Each is independently selected from C6-C 60 Aryl group; fluorenyl group; C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups; 6) a, b, c, and d are each an independent integer from 0 to 4. 7) i and j are independent integers from 0 to 2, provided that i+j is an integer of 1 or greater; 8) Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Ar 6 and Ar 7 Each is independently selected from C6-C 60 aryloxy group; C6-C 60 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and C3-C 60 Aliphatic rings and C6-C 60 Fused ring groups of aromatic rings; alternatively, Ar 1 and Ar 2 Or Ar 3 and Ar 4 They can bond together to form a ring. 9) wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenyl group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group, and the aryloxy group are optionally substituted by one or more substituents selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 alkoxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 Aryl group; C6-C substituted with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl groups; C7-C 20 arylalkyl groups; and C8-C 20 Aryl alkenyl group.

2. The organic electronic device of claim 1, wherein the compound represented by formula 1 is represented by any one of formulas 1-1 to 1-7: Equation 1-1 Equation 1-2 Equation 1-3 Equation 1-4 Equation 1-5 Equation 1-6 Equation 1-7 in: 1) X, R 1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 and Ar 4 Same as defined in claim 1, 2) aa, bb, cc, and dd are each an independent integer from 0 to 3. 3) bb' and dd' are each an integer from 0 to 2 independently.

3. The organic electronic device of claim 1, wherein the compound represented by formula 1 is represented by any one of formulas 1-8 to 1-9: Formula 1-8 Formula 1-9 Where R 1 R 2 R 3 R 4 a, b, c, d, L 1 L 2 Ar 1 Ar 2 Ar 3 Ar 4 i and j are the same as those defined in claim 1.

4. The organic electronic device of claim 1, wherein Ar in formula 1 1 To Ar 4 At least one of them is represented by equation B-1: Formula B-1 in: 1) V 1 and V 2 Each is an independent single bond, NR 5 CR 6 R 7 O or S 2) R 5 R 6 and R 7 With R in Equation 1 1 The definitions are the same, however, R 6 and R 7 They can bond together to form a ring. 3) Ring A and ring B are independently substituted or unsubstituted C6-C. 20 aryl group; or substituted or unsubstituted C4-C 20 Heterocyclic groups.

5. The organic electronic device of claim 1, wherein the compound represented by formula 1 is any one of the following compounds: 。 6. The organic electronic component of claim 1, wherein Ar in formula 2 5 To Ar 7 At least one of the following can be represented by any one of Equations 2-1 to 2-6: Equation 2-1 Equation 2-2 Equation 2-3 Equation 2-4 Equation 2-5 Equation 2-6 in: 1) X 4 and X 5 Each is independent of the NAr 8 O, S or CR c R d , 2) Ar 8 Ar in Equation 1 1 The definitions are the same. 3) R 8 R 9 R 10 R c and R d Each is independently selected from hydrogen; deuterium; halogen; unsubstituted or C1-C. 20 alkyl groups or C6-C 20 aryl-substituted silane groups; cyano groups; nitro groups; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and C3-C 20 Aliphatic ring; alternatively, adjacent groups can bond with each other to form a ring, and adjacent substituents can bond with each other to form a ring. 4) e, f, and h are integers from 0 to 4, and g is an integer from 0 to 6.

7. The organic electronic device of claim 1, wherein the compound represented by formula 2 is represented by any one of formulas 2-7 to 2-9: Equation 2-7 Equation 2-8 Formula 2-9 in: 1) X 3 L 3 L 4 L 5 Ar 6 and Ar 7 Same as defined in claim 1, 2) X 4 X 6 and X 8 Each is independently O, S, NAr 9 or CR c R d , 3) X 5 X 7 and X 9 Each is independently O, S, NAr 10 CR e R f Or a single key, 4) a', d', and f' are integers from 0 to 4, and b', c', and e' are integers from 0 to 3. 5) Ar 9 and Ar 10 Ar in claim 1 1 The definitions are the same. 6) R c R d R e R f R 12 R 13 R 14 R 15 R 16 and R 17 With R in claim 6 8 The definitions are the same.

8. The organic electronic device of claim 1, wherein L in formula 1 to formula 2 1 To L 5 At least one of the following equations b-1 to b-13 is represented by: Formula b-1 Formula b-2 Formula b-3 Formula b-4 Formula b-5 Formula b-6 Formula b-7 Formula b-8 Formula b-9 Formula b-10 Formula b-11 Formula b-12 Formula b-13 in: 1) Z is O, S, NL 6 -Ar 11 Or CR6R7, 2) L 6 With L in claim 1 1 The definitions are the same. 3) Ar 11 Ar in claim 1 1 The definitions are the same. 4) R6, R7, R8, R9 and R 10 They may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and C3-C 20 Aliphatic rings; and adjacent groups can combine with each other to form rings. 5) a", c", d", and e" are each an integer from 0 to 4, b" is an integer from 0 to 6, f" and g" are each an integer from 0 to 3, h" is an integer from 0 to 2, and i" is 0 or 1. 6) Z 49 Z 50 and Z 51 Each is CR independently g Or N, and Z 49 Z 50 and Z 51 At least one of them is N, 7) R g Selected from hydrogen; deuterium; halogen; unsubstituted or C1-C 20 alkyl groups or C6-C 20 aryl-substituted silane groups; cyano groups; nitro groups; C1-C 20 Alkyl thio group; C1-C 20 Alkoxy group; C6-C 20 aryloxy group; C1-C 20 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 aryl group; fluorenyl group; C2-C group containing at least one heteroatom of O, N, S, Si or P. 20 Heterocyclic groups; and C3-C 20 Aliphatic ring; C7-C 20 arylalkyl groups; and C8-C 20 Aryl alkenyl group.

9. The organic electronic device of claim 1, wherein the compound represented by formula 2 is any one of the following compounds: 。 10. The organic electronic device of claim 1, comprising at least one hole transport band layer between the anode and the light-emitting layer, wherein the hole transport band layer comprises a hole transport layer, a light-emitting auxiliary layer, or both, wherein the hole transport band layer comprises a compound represented by Formula 1.

11. The organic electronic component of claim 1, further comprising a light efficiency enhancement layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.

12. The organic electronic component of claim 1, wherein the organic material layer comprises two or more stacks, the stacks comprising a hole transport layer, a light-emitting layer and an electron transport layer sequentially formed on the anode.

13. The organic electronic component of claim 12, wherein the organic material layer further comprises a charge-generating layer formed between the two or more stacks.

14. Electronic devices, including: A display device comprising the organic electronic components as described in claim 1; And a control unit for driving the display device.

15. The electronic device of claim 14, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white lighting.

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