KR102182552B1 - Compound for organic electric element, organic electric element comprising the same and electronic device thereof - Google Patents

Abstract

The present invention provides a compound represented by Formula 1. In addition, an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode is provided, and the organic material layer includes a compound represented by Chemical Formula 1. When the compound represented by Formula 1 is included in the organic material layer of the organic electric device, the driving voltage may be reduced, and luminous efficiency, color purity, and lifespan may be improved.

Description

Compound for organic electric device, organic electric device using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF}

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electronic device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as an organic material layer in an organic electronic device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

Currently, the portable display market is increasing in size as a large-area display, and for this reason, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for portable displays that have a limited power supply source, such as a battery, and efficiency and life problems are also important factors that must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize efficiency. This is because the long life and high efficiency can be achieved at the same time when the optimum combination of the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) is achieved.

In addition, in order to solve the problem of light emission and driving voltage in the hole transport layer in recent organic electroluminescent devices, a light emission auxiliary layer (multi-layer hole transport layer) must exist between the hole transport layer and the light emitting layer, and different light emission for each light emitting layer. This is the time when the development of the auxiliary layer is necessary.

In general, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and recombination is performed in the light-emitting layer to form excitons. However, if a material with fast hole mobility is used to create a low driving voltage, positive polaron accumulates at the interface between the light emitting layer and the hole transport layer, resulting in interfacial deterioration, reducing life and efficiency. , In addition, since the charge balance in the light-emitting layer does not match, the excess polaron in the light-emitting layer attacks weak bonding of the light-emitting material and deforms the light-emitting material, thus reducing lifespan and efficiency, and reducing color purity. have.

Therefore, the light-emitting auxiliary layer must be a material having an appropriate HOMO value between the light-emitting layer and the hole-transport layer in order to prevent the positive polaron from accumulating at the light-emitting layer interface as it exists between the hole transport layer and the light-emitting layer. In order to increase the balance), it must be a material having hole mobility within a suitable driving voltage range (within the ble device driving voltage range of the full device).

However, this cannot be achieved simply by the structural characteristics of the core of the light-emitting auxiliary layer material, and when an appropriate combination between the light-emitting auxiliary layer material's core and sub-substituent characteristics, and the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer is made. High-efficiency and high-life devices can be implemented.

In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials, are stable and efficient. What is supported by materials must precede, and in particular, development of materials for the light-emitting auxiliary layer and the hole transport layer is urgently required.

The present invention has been proposed in order to solve the conventional problems as described above, and at the same time provides a compound having efficient electron blocking ability and hole transport ability, and at the same time, high luminous efficiency, low driving voltage, and high heat resistance of the device by using such a compound , To provide a compound capable of improving color purity and lifespan, an organic electric device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following formula. The following formula represents a compound in which a core (dibenzofuran or dibenzothiophene) and two amine groups are bonded with a linking group, and at least one of R ¹ to R ³ in the following formula 1 is the following formula 2.

<Formula 1> <Formula 2>

In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by Formula 1 above.

According to the present invention, by using a specific compound limiting the type of linking group connected to the core, the type of amine group bonded to the linking group, the bonding position and number, etc. as the material of the organic electric device, it is possible to achieve charge balance in the light emitting layer. Due to the easy HOMO energy level and high T1 value, it is possible to improve the luminous efficiency, heat resistance, color purity, life, etc. of the organic electronic device and lower the driving voltage.

1 is an exemplary diagram of an organic electroluminescent device according to the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to elements of each drawing, it should be noted that the same elements are assigned the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof will be omitted.

In describing the constituent elements of the present invention, terms such as first, second, A, B, (a), (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected or connected to that other component, but another component between each component It will be understood that elements may be "connected", "coupled" or "connected".

In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, it is not only "directly over" another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is "directly above" another part, it means that there is no other part in the middle.

As used in this specification and the appended claims, the meaning of the following terms is as follows, unless stated otherwise.

As used herein, the term "halo" or "halogen" is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise specified.

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms unless otherwise specified, and is a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo It means a radical of a saturated aliphatic functional group, including an alkyl group and a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.

The terms "alkenyl group" or "alkynyl group" used in the present invention each have a double bond or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include a linear or branched chain group, and are limited thereto. It is not.

The term "cycloalkyl" as used in the present invention means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

The terms "alkoxyl group", "alkoxy group", or "alkyloxy group" as used in the present invention means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.

The term "aryloxyl group" or "aryloxy group" used in the present invention refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms, and is not limited thereto.

The term "fluorenyl group" or "fluorenylene group" as used in the present invention means a monovalent or divalent functional group in which R, R'and R" are all hydrogen in each of the following structures, unless otherwise specified, " Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R'are bonded to each other and the carbon to which they are bonded It includes the case of forming a compound by spy together.

The terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto, unless otherwise specified. In the present invention, the aryl group or the arylene group includes a monocyclic type, a ring aggregate, a conjugated ring system, and a spiro compound.

The term "heterocyclic group" as used in the present invention includes not only an aromatic ring such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.

In addition, the "heterocyclic group" may also include a ring including SO ₂ instead of carbon forming a ring. For example, "heterocyclic group" includes the following compounds.

In addition, the term "divalent benzothiophene" as used herein refers to the divalent functional group of the parent compound benzothiophene, and similarly, "divalent dibenzothiophene" refers to the divalent functional group of the parent compound dibenzothiophene. Valent functional group, "divalent furan" is the divalent functional group of the parent compound furan, "divalent dibenzofuran" is the divalent functional group of the parent compound dibenzofuran, and "divalent pyrimidine" is the parent compound It means a divalent functional group of pyrimidine. That is, in the present specification, when naming the divalent functional group of the parent, in some cases, the divalent may be simply indicated in front of the parent compound.

The term "ring" as used in the present invention includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" used in the present invention includes ring assemblies such as biphenyl, terphenyl, etc., several fused ring systems, and spiro compounds, and includes not only aromatic but also non-aromatic, hydrocarbon Rings of course include heterocycles containing at least one heteroatom.

The term "ring assemblies" as used in the present invention refers to two or more ring systems (single ring or fused ring system) directly connected to each other through a single bond or a double bond, and direct It means that the number of linkages is one less than the total number of ring systems in this compound. In the ring aggregate, the same or different ring systems may be directly linked to each other through a single bond or a double bond.

The term "conjugated multiple ring systems" as used in the present invention refers to a fused ring form that shares at least two atoms, and includes a form in which a ring system of two or more hydrocarbons is fused and at least one heteroatom And at least one conjugated heterocyclic system. Several such fused ring systems may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.

The term "spiro compound" used in the present invention has a'spiro union', and the spiro linkage refers to a connection made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.

In addition, when prefixes are named consecutively, it means that substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where The arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, unless explicitly stated otherwise, the term "substituted" in the term "substituted or unsubstituted" used in the present invention means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group including a group, a germanium group, and at least one heteroatom selected from the group consisting of O, N, S, Si and P And, it is not limited to these substituents.

In addition, unless there is an explicit explanation, the formula used in the present invention is applied in the same manner as the definition of the substituent group defined by the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and a is an integer of 2 or 3. Each is bonded as follows, wherein R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is indicated. Is omitted.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 formed on a substrate 110. An organic material layer including the compound according to the present invention is provided between the two electrodes 180. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, a hole transport layer 140, an emission layer 150, an electron transport layer 160, and an electron injection layer 170 sequentially on the first electrode 120. At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, a buffer layer 141, etc., and the electron transport layer 160 serves as the hole blocking layer. You might be able to do it.

In addition, although not shown, the organic electric device according to an embodiment of the present invention further includes a protective layer or a capping layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer. can do.

The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a host or a dopant of the emission layer 150, or It may be used as a material for the light efficiency improvement layer. For example, the compound of the present invention may be used as a material for the light emitting layer 150, the hole transport layer 140, and/or the light emitting auxiliary layer 151, and preferably, the material for the hole transport layer 140 and/or the light emitting auxiliary layer 151 Can be used as

On the other hand, even with the same core, the band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position, so the selection of the core and the combination of sub-substituents bonded thereto may be changed. Research is required. In particular, long life and high efficiency can be achieved at the same time when the optimum combination of energy level and T ₁ value between each organic material layer, and intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved.

As described above, in general, in order to solve the problem of light emission in the hole transport layer in an organic electroluminescent device, it is preferable to form a light emission auxiliary layer between the hole transport layer and the light emitting layer, and each light emitting layer (R, G, B) Accordingly, it is necessary to develop different light-emitting auxiliary layers.

On the other hand, in the case of the light-emitting auxiliary layer, since the correlation between the hole transport layer and the light-emitting layer (host) must be grasped, even if a similar core is used, it will be very difficult to infer its characteristics if the used organic material layer is different.

Therefore, in the present invention, by forming a hole transport layer and/or a light emission auxiliary layer using the compound represented by Formula 1, the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interface characteristics, etc.) are optimized. Thus, it is possible to simultaneously improve the life and efficiency of the organic electric device.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate to form the anode 120, and a hole injection layer 130 thereon. , After forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon. have. In addition, an auxiliary light emitting layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150.

In addition, the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.

WOLED (White Organic Light Emitting Device) is easy to realize high resolution and excellent processability, while there is an advantage that can be manufactured using the existing LCD color filter technology. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, R(Red), G(Green), B(Blue) light emitting parts are arranged side-by-side in a mutually planar way, and R, G, B light emitting layers are stacked up and down. In addition, there is a color conversion material (CCM) method that uses electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom. May be applied to such WOLED.

In addition, the organic electric device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a single color or white lighting device.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

Hereinafter, a compound according to an aspect of the present invention will be described.

A compound according to an aspect of the present invention is represented by the following formula (1).

<Formula 1> <Formula 2>

Each symbol in Formulas 1 and 2 is defined as follows.

In Formula 1, X is O or S.

In addition, R ¹ to R ³ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And it may be selected from the group consisting of Formula 2. However, at least one of R ¹ to R ³ is Formula 2.

Preferably, R ¹ to R ³ may be independently of each other hydrogen, a cyano group, a C ₆ -C ₆₀ aryl group, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxyl group or the above Formula 2, , Preferably it may be hydrogen, phenyl unsubstituted or substituted with pyridine, methoxyl group, ethoxyl group, cyano group, methyl group, and the like.

When the R ¹ to R ³ are an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an aryloxy group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group. In addition, when each of these substituents are adjacent, they may be bonded to each other to form a ring.

In Formula 1, R ⁴ to R ⁷ are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ may be selected from the group consisting of an aryloxy group. However, in R ⁴ to R ⁷ , a dibenzofuryl group and a dibenzothienyl group are excluded.

Alternatively, R ⁴ to R ⁷ may optionally be bonded to each other with neighboring groups to form a ring. Here,'neighboring groups can be bonded to each other to form a ring' means that at least one pair of R ⁴ and R ⁵ , R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each other to form a ring. It means that a ring can be formed with a benzene ring. At this time, since at least one pair of groups among each neighboring group may independently form a ring, for example, R ⁴ and R ⁵ may form a ring and the remaining R ⁵ to R ⁷ may not form a ring.

The ring formed by bonding of R ⁴ and R ^{5 to} each other, R ⁵ and R ^{6 to} each other, or between R ⁶ and R ^{7 to} each other is usually a 5 to 8 membered ring, but is preferably a 5 or 6 membered ring, more preferably a 6 membered ring. At this time, the formed ring may be an aromatic ring or an aliphatic ring, and in the case of an aromatic ring, it may be an aromatic hydrocarbon ring or an aromatic heterocycle, but is preferably an aromatic hydrocarbon ring. In addition, neighboring groups may be connected to each other by alkylene or alkenylene to form an alicyclic ring, monocyclic or polycyclic aromatic ring. Preferably, the ring formed by bonding of R ⁴ and R ^{5 to} each other, R ⁵ and R ^{6 to} each other, or R ⁶ and R ^{7 to} each other may be a benzene ring, and together with the benzene ring to which they are bonded, naphthalene, phenanthrene, etc. are formed. can do.

Preferably, R ⁴ to R ⁷ may be independently of each other hydrogen, deuterium, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heterocyclic group, C ₁ -C ₅₀ alkyl group, and the like, more preferably May be hydrogen, deuterium, tert-butyl, phenyl, naphthyl, terphenyl, quinolyl, isoquinolyl, and the like.

When R ⁴ to R ⁷ are an aryl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an aryloxy group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; O, N, S, Si, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P (excluding dibenzofuryl and dibenzothienyl groups); A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group. In addition, when each of these substituents are adjacent, they may be combined with each other to form a ring.

Meanwhile, in Formula 1, R ¹ to R ³ may be each independently represented by Formula 2.

<Formula 2>

In Formula 2, L ¹ to L ⁵ are each independently a single bond; C ₆ -C ₆₀ arylene group; A divalent C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenylene group; A divalent fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And C ₁ -C ₆₀ It may be selected from the group consisting of a divalent aliphatic hydrocarbon group, each of which (except a single bond) is deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of.

Preferably, L ¹ to L ⁵ are independently of each other a single bond, a C ₆ -C ₆₀ arylene group, an alkyl group or an aryl group substituted or unsubstituted fluorenylene group, C ₂ -C ₁₂ including S or O A heterocyclic group of, and more preferably a single bond, a phenylene group, a divalent naphthalene, a biphenylene group, a 9,9-dimethyl- 9H -fluorenylene group, a divalent dibenzothiophene, and a divalent benzo. It may be a thiophene, a divalent benzofuran, a divalent pyrimidine, and the like.

In addition, Ar ¹ to Ar ⁴ are each independently a C ₆ -C ₆₀ aryl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; Fluorenyl group; A fused ring group of a C ₆ -C ₆₀ aromatic ring and a C ₃ -C ₆₀ aliphatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ may be selected from the group consisting of an aryloxy group.

Preferably, Ar ¹ to Ar ⁴ are independently of each other C ₆ -C ₁₆ aryl group, C ₁₃ -C ₂₅ fluorenyl group, C ₃ -C ₁₂ heterocycle, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₃₀ alkoxyl group, etc., more preferably phenyl group, biphenyl group, terphenyl group, naphthyl group, 9-dimethyl-9H-fluorenyl group, 9-diphenyl -9H-fluorenyl group, 9,9'-spirobifluorenyl group, pyrenyl group, dibenzofuryl group, dibenzothienyl group, phenanthryl group, pyridyl group, benzothienyl group, methyl group, ethenyl group, It may be a propenyl group, a methoxyl group, a butoxyl group, a tert-butoxyl group, a carbazolyl, and the like.

)로 더 치환될 수 있다.At this time, when Ar ¹ to Ar ⁴ are an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an aryloxy group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group. When Ar ¹ to Ar ⁴ is an aryl group substituted with a C ₁ -C ₂₀ alkyl group, the alkyl group is an alkenylarylalkoxyl group (eg:

) Can be further substituted.

In the case where at least one of R ¹ to R ³ in Formula 1 is a compound represented by Formula 2, the type of amine group substituted with the linking group connected to the core (benzofuran or benzothiophene) having hole characteristics, the bonding position, and Depending on the number, differences in energy level (HOMO, LUMO), T1 value, thermal stability, and hole mobility occur.

In Formula 1, when R ¹ , R ² or R ³ is Formula 2, Formula 1 may be represented by one of Formulas 3 to 5 below.

<Formula 3> <Formula 4>

<Formula 5>

In Formulas 3 to 5, X, R ¹ to R ⁷ , Ar ¹ to Ar ⁴ , and L ¹ to L ⁵ are the same as defined in Formulas 1 and 2.

In Chemical Formula 1, R ⁴ to R ⁷ may be bonded to each other to form a ring. When at least a pair of adjacent groups are bonded to each other to form an aromatic ring, particularly a benzene ring, the following Chemical Formulas 6 to 9 Can be marked as one of. Specifically, the following Formula 6 is between adjacent R ⁴ and R ⁵ in Formula 1, Formula 7 is between adjacent R ⁵ and R ⁶ , Formula 8 is between adjacent R ⁶ and R ⁷ and Formula 9 is between adjacent R ⁴ and R ⁵ and adjacent R ⁶ and R ⁷ are bonded to each other to form a benzene ring. When a benzene ring is formed between adjacent groups, naphthalene or phenanthrene may be formed together with the benzene ring to which they are bonded.

<Formula 6> <Formula 7>

<Formula 8> <Formula 9>

In Formulas 6 to 9, X, R ¹ to R ⁷ are the same as defined in Formula 1, and R ⁸ to R ¹⁰ are each independently deuterium; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ may be selected from the group consisting of an aryloxy group. Further, in the above formula, m, n, and o are each independently an integer of 0 to 4, and when each of them is an integer of 2 or more, R ⁸ to R ¹⁰ may be the same or different from each other. For example, when m is 3, a plurality of R ⁸ may be identical to or different from each other.

Preferably, Formula 2 may be represented by one of the following Formulas 10 to 14.

<Formula 10> <Formula 11>

<Formula 12> <Formula 13>

<Formula 14>

In Formulas 10 to 14, Ar ² to Ar ⁴ , L ¹ to L ⁵ are the same as defined in Formula 2, and Y ¹ to Y ⁴ are independently of each other S, O, C(R ^a )(R ^b ) Or N(R ^c ), wherein R ^a to R ^c are each independently a C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ may be selected from the group consisting of aryloxy group, optionally R ^a and R ^b may be bonded to each other to form a spy compound with the carbon to which they are attached. When R ^a and R ^b are bonded to each other to form a ring, preferably 9,9'-spirobifluorene may be formed.

Further, in the above formula, R ¹¹ to R ¹⁸ are each independently deuterium; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; C ₆ -C ₃₀ aryloxy group; And it may be selected from the group consisting of a combination thereof. Or, R ¹¹ to R ¹⁸ is optionally adjacent to each other R ¹¹ between, R ¹² between, R ¹³ between, R ¹⁴ between, R ¹⁵ between, R ¹⁶ between, R ¹⁷ between, and at least one pair of R ¹⁸ between each other At least one ring may be formed, for example, R ¹¹ and R ¹² may form a ring, and the remaining R ¹³ to R ¹⁸ may not form a ring.

R ¹³ together, R ¹⁴ together, R ¹⁵ together, R ¹⁶ together, R ¹⁷ rings are bonded to each other to form together or R ¹⁸ with each other is, but usually 5 to 8-membered ring, preferably 5 or 6-membered ring, preferably 6 than It is torus. At this time, the formed ring may be an aromatic ring or an aliphatic ring, and in the case of an aromatic ring, it may be an aromatic hydrocarbon ring or an aromatic heterocycle, but is preferably an aromatic hydrocarbon ring. In addition, neighboring groups may be connected to each other by alkylene or alkenylene to form an alicyclic ring, monocyclic or polycyclic aromatic ring. Preferably, the ring formed by bonding between R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , or R ¹⁸ may be a benzene ring, and together with the benzene ring to which they are bonded, naphthalene is formed. can do.

In the above formula, p, r, t and v are each independently an integer of 0 to 3, and when each is an integer of 2 or more, R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁷ are each the same or different from each other, and q , s, u and w are each independently an integer of 0 to 4, and when each of them is an integer of 2 or more, R ¹² , R ¹⁴ , R ¹⁶ and R ¹⁸ may each be the same or different from each other.

Specifically, the compound represented by Formula 1 may be one of the following compounds.

In another aspect of the present invention, the present invention provides a first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, and a light emitting layer, and the organic material layer includes At least one may be included. That is, the organic material layer may be formed of one single compound or a mixture of two or more compounds represented by Formula 1 above.

Hereinafter, examples for synthesizing the compound represented by Formula 1 according to the present invention and an example for preparing an organic electric device will be described in detail, but the present invention is not limited to the following examples.

Synthesis example

The compound (final product) represented by Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

X, R ¹ to R ⁷ , Ar ¹ to Ar ⁴ , L ¹ to L ⁵ are the same as defined in Chemical Formulas 1 and 2, and A, B, Z are independently selected from R ¹ to R ³ And A, B, and Z may be different from each other.

I. Sub Synthesis of 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route of Scheme 2 to Scheme 5 below, but is not limited thereto.

<Scheme 2> When L ¹ is a single bond

<Reaction Scheme 3> When L ¹ is not a single bond

<Reaction Scheme 4> When X is S

<Scheme 5> When X is O

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

One. Sub 1-1 Synthesis example

<Reaction Scheme 6>

(One) Sub 1-I-1 synthesis

The starting material 3-bromo-[1,1'-biphenyl]-2-ol (32.42 g, 130.15 mmol) was added to Pd(OAc) ₂ (2.92 g, 13.01 mmol), 3-nitropyridine (1.62 g) in a round bottom flask. , 13.01 mmol) and dissolved in C ₆ F ₆ (195ml) and DMI (130ml), tert- butyl peroxybenzoate (50.56 g, 260.30 mmol) was added and stirred at 90°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 15.76 g (yield: 49%) of the product.

(2) Sub 1-1 synthesis

After dissolving the Sub 1-I-1 (15.76 g, 63.78 mmol) in a round bottom flask with DMF (320ml), Bis(pinacolato)diboron (17.82 g, 70.16 mmol), Pd(dppf)Cl ₂ (1.56 g, 1.91 mmol), KOAc (18.78 g, 191.35 mmol) was added and stirred at 90°C. When the reaction was completed, DMF was removed through distillation, and extraction was performed with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 15.38 g (yield: 82%) of the product.

2. Sub 1-8 Synthesis example

<Reaction Scheme 7>

(One) Sub 1-I-8 synthesis

The starting material 3-bromo-2-(methylsulfinyl)-1,1'-biphenyl (20.03 g, 67.85 mmol) was added to a round bottom flask with triflic acid (90ml, 1017.82 mmol) and stirred at room temperature for 24 hours, followed by stirring for 24 hours. , pyridine aqueous solution (1190ml, pyridine: H ₂ O = 1: 5) was slowly added dropwise and stirred under reflux for 30 minutes. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 14.46 g (yield: 81%) of the product.

(2) Sub 1-8 synthesis

After dissolving the Sub 1-I-8 (14.46 g, 54.95 mmol) in THF (190ml) in a round bottom flask, 1,3-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan) -2-yl)benzene (19.95 g, 60.44 mmol), Pd(PPh ₃ ) ₄ (2.10 g, 1.81 mmol), NaOH (7.25 g, 181.33 mmol), and water (95ml) were added and stirred at 80°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 13.37 g (yield: 63%) of the product.

3. Sub One- 10 Synthesis Example

<Reaction Scheme 8>

(One) Sub 1-I-10 synthesis

The starting material 4-bromo-2-(methylsulfinyl)-1,1'-biphenyl (46.25 g, 156.68 mmol) in triflic acid (208ml, 2350.18 mmol), pyridine aqueous solution (2745ml, pyridine: H ₂ O = 1: 5 ) Was obtained by using the Sub 1-I-8 synthesis method to obtain 35.87 g (yield: 87%) of the product.

(2) Sub 1-10 synthesis

Bis(pinacolato)diboron (16.89 g, 66.51 mmol), Pd(dppf)Cl ₂ (1.48 g, 1.81 mmol), KOAc in the Sub 1-I-10 (15.91 g, 60.46 mmol) (17.80 g, 181.38 mmol) and DMF (300ml) were used to obtain 15.94 g (yield: 85%) of the product using the Sub 1-1 synthesis method.

4. Sub 1-12 Synthesis example

<Reaction Scheme 9>

1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (26.60 g, 80.59 mmol) in the Sub 1-I-10 (19.28 g, 73.27 mmol) ), Pd(PPh ₃ ) ₄ (2.79 g, 2.42 mmol), NaOH (9.67 g, 241.78 mmol), THF (260ml), water (130ml) was added, and the product 15.57 g (15.57 g) (using the above Sub 1-8 synthesis method). Yield: 55%).

5. Sub 1-13 Synthesis example

<Reaction Scheme 10>

Bis(pinacolato)diboron (25.73 g,) in 1-bromodibenzo[b,d]furan (Sub 1-I-13, CAS No. 50548-45-3) (22.76 g, 92.11 mmol) purchased from Tractus-Chemistry. 101.32 mmol), Pd(dppf)Cl ₂ (2.26 g, 2.76 mmol), KOAc (27.12 g, 276.34 mmol) and DMF (460ml) were used to obtain 18.97 g (yield: 70%) of the product using the Sub 1-1 synthesis method.

6. Sub 1-24 Synthesis example

<Reaction Scheme 11>

(One) Sub 1-I-24 synthesis

Pd(OAc) ₂ (4.93 g, 21.98 mmol), 3-nitropyridine (2.73 g, 21.98 mmol), tert in the starting material 2-bromo-6-(naphthalen-1-yl)phenol (65.75 g, 219.78 mmol) -butyl peroxybenzoate (85.38 g, 439.56 mmol), C ₆ F ₆ (330ml), DMI (220ml) was obtained by using the Sub 1-I-1 synthesis method, 29.39 g (yield: 45%) of the product.

(2) Sub 1-24 synthesis

In the Sub 1-I-24 (29.39 g, 98.91 mmol) 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'- biphenyl (44.19 g, 108.80 mmol), Pd(PPh ₃ ) ₄ (3.77 g, 3.26 mmol), NaOH (13.06 g, 326.39 mmol), THF (340ml), water (170ml) were added and the Sub 1-8 synthesis method Using the product, 24.55 g (yield: 50%) was obtained.

7. Sub 1-35 Synthesis example

<Reaction Scheme 12>

(One) Sub 1-I-35 synthesis

To the starting material 1-(4-bromophenyl)-2-(methylsulfinyl)naphthalene (34.59 g, 100.19 mmol), triflic acid (133ml, 1502.82 mmol), pyridine aqueous solution (1755ml, pyridine: H ₂ O = 1: 5) was added. The product 26.67 g (yield: 85%) was obtained using the Sub 1-I-8 synthesis method.

(2) Sub 1-35 synthesis

2,2'-(9,9-dimethyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1 in the Sub 1-I-35 (26.67 g, 85.15 mmol) ,3,2-dioxaborolane) (41.79 g, 93.67 mmol), Pd(PPh ₃ ) ₄ (3.25 g, 2.81 mmol), NaOH (11.24 g, 281.00 mmol), THF (300ml), water (150ml) were added, and 28.23 g (yield: 60%) of the product was obtained by using the Sub 1-8 synthesis method.

8. Sub 1-39 Synthesis example

<Reaction Scheme 13>

(One) Sub 1-I-39 synthesis

Pd(OAc) ₂ (4.05 g, 18.02 mmol), 3-nitropyridine (2.24 g, 18.02 mmol), tert -butyl in the starting material 10-(4-bromophenyl)phenanthren-9-ol (62.94 g, 180.23 mmol) Peroxybenzoate (70.01 g, 360.46 mmol), C ₆ F ₆ (270 ml), and DMI (180 ml) were obtained by using the Sub 1-I-1 synthesis method to obtain 26.28 g (yield: 42%) of the product.

(2) Sub 1-39 synthesis

3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophene in the Sub 1-I-39 (26.28 g, 75.69 mmol) (36.32 g, 83.26 mmol), Pd(PPh ₃ ) ₄ (2.89 g, 2.50 mmol), NaOH (9.99 g, 249.78 mmol), THF (260ml), water (130ml) were added, and the Sub 1-8 synthesis method Using the product, 24.87 g (yield: 57%) was obtained.

9. Sub 1-47 Synthesis Example

<Reaction Scheme 14>

(1) Sub 1-I-47 synthesis

Starting material, 9-(2-bromo-6-(methylsulfinyl)phenyl)phenanthrene (87.09 g, 220.31 mmol) in triflic acid (292ml, 3304.62 mmol), pyridine aqueous solution (3860ml, pyridine: H ₂ O = 1: 5) Using the Sub 1-I-8 synthesis method, the product 54.42 g (yield: 68%) was obtained.

(2) Sub 1-47 synthesis

Bis(pinacolato)diboron (21.04 g, 82.85 mmol), Pd(dppf)Cl ₂ (1.85 g, 2.26 mmol) in Sub 1-I-47 (27.36 g, 75.32 mmol) obtained in the above synthesis, KOAc (22.17 g, 225.95 mmol) and DMF (380ml) were used to obtain 24.72 g (yield: 80%) of the product using the Sub 1-1 synthesis method.

10. Sub 1-49 Synthesis example

<Reaction Scheme 15>

1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (24.17 g) in Sub 1-I-47 (24.19 g, 66.59 mmol) obtained in the above synthesis. , 73.25 mmol), Pd(PPh ₃ ) ₄ (2.54 g, 2.20 mmol), NaOH (8.79 g, 219.75 mmol), THF (230ml), water (115ml) were added, and the product was prepared using the Sub 1-8 synthesis method. 19.43 g (yield: 60%) was obtained.

11.Synthesis Example of Sub 1-52

<Reaction Scheme 16>

(1) Sub 1-I-52 synthesis

Starting material 3-bromo-2-(methylsulfinyl)-1,1':4',1''-terphenyl (25.00 g, 67.33 mmol) in triflic acid (89ml, 1009.99 mmol), pyridine aqueous solution (1180ml, pyridine: H ₂ O = 1: 5) was obtained by using the Sub 1-I-8 synthesis method to obtain 12.34 g (yield: 54%) of the product.

(2) Sub 1-52 synthesis

Bis(pinacolato)diboron (10.16 g, 40.01 mmol), Pd(dppf)Cl ₂ (0.89 g, 1.09 mmol) in Sub 1-I-52 (12.34 g, 36.37 mmol) obtained in the above synthesis, KOAc (10.71 g, 109.12 mmol) and DMF (180ml) were used to obtain 11.94 g (yield: 85%) of the product using the Sub 1-1 synthesis method.

12. Sub 1-58 Synthesis Example

<Scheme 17>

(1) Sub 1-I-58 synthesis

Starting material 5-bromo-2'-hydroxy-[1,1'-biphenyl]-2-carbonitrile (49.25 g, 179.67 mmol) in Pd(OAc) ₂ (4.03 g, 17.97 mmol), 3-nitropyridine (2.23) g, 17.97 mmol), tert- butyl peroxybenzoate (69.80 g, 359.34 mmol), C ₆ F ₆ (270 ml), DMI (180 ml) using the Sub 1-I-1 synthesis method described above, the product 19.07 g (yield: 39%) ).

(2) Sub 1-58 synthesis

1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (25.44 g) to Sub 1-I-58 (19.07 g, 70.08 mmol) obtained in the above synthesis. , 77.09 mmol), Pd(PPh ₃ ) ₄ (2.67 g, 2.31 mmol), NaOH (9.25 g, 231.28 mmol), THF (240ml), water (120ml) were added, and the product using the Sub 1-8 synthesis method 14.96 g (yield: 54%) was obtained.

Meanwhile, the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS values of the compound belonging to Sub 1.

[Table 1]

II . Sub Synthesis of 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 15 below, but is not limited thereto.

<Reaction Scheme 18>

Synthesis examples of specific compounds belonging to Sub 2 are as follows.

One. Sub 2-1 Synthesis example

<Reaction Scheme 19>

(One) Sub 2-I-1 synthesis

After dissolving the starting material diphenylamine (25.74 g, 152.11 mmol) in toluene (880ml) in a round bottom flask, 1,3,5-tribromobenzene (62.25 g, 197.74 mmol), Pd ₂ (dba) ₃ (4.18 g, 4.56) mmol), PPh ₃ (3.19 g, 12.17 mmol), NaO t -Bu (58.48 g, 608.44 mmol) were added and stirred at 80°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 27.59 g (yield: 45%) of the product.

(2) Sub 2-1 synthesis

After dissolving diphenylamine (8.91 g, 52.65 mmol) in toluene (300ml) in a round bottom flask, Sub 2-I-1 (27.59 g, 68.45 mmol), Pd ₂ (dba) ₃ (1.45 g, 1.58 mmol), PPh ₃ (1.10 g, 4.21 mmol), NaO t -Bu (20.24 g, 210.61 mmol) was added and stirred at 80°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 12.16 g (yield: 47%) of the product.

2. Sub 2-6 Synthesis Example

<Reaction Scheme 20>

(1) Sub 2-I-6 synthesis

Starting materials 4-(naphthalen-1-yl)-N-phenylaniline (35.43 g, 119.95 mmol), 1,3,5-tribromobenzene (49.09 g, 155.93 mmol), Pd ₂ (dba) ₃ (3.30 g, 3.60) mmol), PPh ₃ (2.52 g, 9.60 mmol), NaO t -Bu (46.11 g, 479.79 mmol), toluene (690 ml) using the Sub 2-I-1 synthesis method, the product 34.92 g (yield: 55%) Got it.

(2) Sub 2-6 synthesis

4-(naphthalen-1-yl)-N-phenylaniline (14.99 g, 50.75 mmol), Sub 2-I-6 (34.92 g, 65.97 mmol), Pd ₂ (dba) ₃ (1.39 g, 1.52 mmol), PPh ₃ (1.06 g, 4.06 mmol), NaO t -Bu (19.51 g, 202.99 mmol), toluene (290ml) was obtained by using the Sub 2-1 synthesis method to obtain a product 18.12 g (yield: 48%).

2. Sub 2-12 Synthesis example

<Reaction Scheme 21>

(One) Sub2 -I-12 synthesis

Starting materials, N-phenyl-9,9'-spirobi[fluoren]-2-amine (38.57 g, 94.65 mmol), 1,3,5-tribromobenzene (38.73 g, 123.04 mmol), Pd ₂ (dba) ₃ ( 2.60 g, 2.84 mmol), PPh ₃ (1.99 g, 7.57 mmol), NaO t -Bu (36.39 g, 378.59 mmol), toluene (540ml) using the Sub 2-I-1 synthesis method described above using the product 29.14 g (yield) : 48%) was obtained.

(2) Sub 2-12 synthesis

N-phenyl-[1,1'-biphenyl]-2',3',4',5',6'-d ₅ -4-amine (8.75 g, 34.95 mmol), Sub 2-I-12 (29.14 g, 45.44 mmol), Pd ₂ (dba) ₃ (0.96 g, 1.05 mmol), PPh ₃ (0.73 g, 2.80 mmol), NaO t -Bu (13.44 g, 139.80 mmol), toluene (200ml) in Sub 2 Using the -1 synthesis method, the product 15.59 g (yield: 55%) was obtained.

3. Sub 2-20 Synthesis example

<Reaction Scheme 22>

(One) Sub 2-I-20 synthesis

Starting materials N-phenylphenanthren-9-amine (32.67 g, 121.30 mmol), 1,3,5-tribromobenzene (49.64 g, 157.69 mmol), Pd ₂ (dba) ₃ (3.33 g, 3.64 mmol), PPh ₃ ( 2.55 g, 9.70 mmol), NaO t -Bu (46.63 g, 485.19 mmol), toluene (700ml) was obtained by using the above Sub 2-I-1 synthesis method to obtain a product 28.69 g (yield: 47%).

(2) Sub 2-20 synthesis

diphenylamine (7.42 g, 43.85 mmol), Sub 2-I-20 (28.69 g, 57.00 mmol), Pd ₂ (dba) ₃ (1.20 g, 1.32 mmol), PPh ₃ (0.92 g, 3.51 mmol), NaO t- Bu (16.86 g, 175.39 mmol) and toluene (250ml) were used to obtain 12.97 g (yield: 50%) of the product using the Sub 2-1 synthesis method.

4. Sub 2-24 Synthesis example

<Reaction Scheme 23>

(One) Sub 2-I-24 synthesis

Starting materials, N-phenyldibenzo[b,d]thiophen-2-amine (66.57 g, 241.75 mmol), 1,3,5-tribromobenzene (98.93 g, 314.27 mmol), Pd ₂ (dba) ₃ (6.64 g, 7.25) mmol), PPh ₃ (5.07 g, 19.34 mmol), NaO t -Bu (92.94 g, 966.99 mmol), toluene (1390ml) using the Sub 2-I-1 synthesis method described above, the product 61.56 g (yield: 50%) Got it.

(2) Sub 2-24 synthesis

N-phenyl-[1,1'-biphenyl]-4-amine (22.81 g, 92.98 mmol), Sub 2-I-24 (61.56 g, 120.87 mmol), Pd ₂ (dba) ₃ (2.55 g, 2.79 mmol) ), PPh ₃ (1.95 g, 7.44 mmol), NaO t -Bu (35.75 g, 371.92 mmol), and toluene (540ml) were obtained by using the Sub 2-1 synthesis method to obtain a product 36.33 g (yield: 58%).

5. Sub 2-36 Synthesis example

<Reaction Scheme 24>

(One) Sub2 -I-36 synthesis

Starting materials 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (44.07 g, 154.43 mmol), 1,3,5-tribromobenzene (63.20 g, 200.75 mmol), Pd ₂ (dba) ₃ ( 4.24 g, 4.63 mmol), PPh ₃ (3.24 g, 12.35 mmol), NaO t -Bu (59.37 g, 617.70 mmol), and toluene (890ml) were prepared by using the Sub 2-I-1 synthesis method as the product 39.29 g (yield). : 49%) was obtained.

(2) Sub 2-36 synthesis

N-phenyl-[1,1'-biphenyl]-4-amine (14.28 g, 58.21 mmol), Sub 2-I-36 (39.29 g, 75.67 mmol), Pd ₂ (dba) ₃ (1.60 g, 1.75 mmol) ), PPh ₃ (1.22 g, 4.66 mmol), NaO t -Bu (22.38 g, 232.84 mmol), and toluene (340 ml) were obtained using the Sub 2-1 synthesis method to obtain 21.09 g (yield: 53%).

6. Sub 2-47 Synthesis example

<Reaction Scheme 25>

(One) Sub2 -I-47 synthesis

Starting materials N-(naphthalen-2-yl)naphthalen-1-amine (41.38 g, 153.63 mmol), 1,3,5-tribromobenzene (62.87 g, 199.73 mmol), Pd ₂ (dba) ₃ (4.22 g, 4.61 mmol), PPh ₃ (3.22 g, 12.29 mmol), NaO t -Bu (59.06 g, 614.54 mmol), toluene (880 ml) using the above Sub 2-I-1 synthesis method 37.11 g (yield: 48%) ).

(2) Sub 2-47 synthesis

N-(naphthalen-2-yl)naphthalen-1-amine (15.28 g, 56.73 mmol), Sub 2-I-47 (37.11 g, 73.75 mmol), Pd ₂ (dba) ₃ (1.56 g, 1.70 mmol), PPh ₃ (1.19 g, 4.54 mmol), NaO t -Bu (21.81 g, 226.93 mmol), toluene (330ml) was obtained by using the Sub 2-1 synthesis method to obtain a product 20.01 g (yield: 51%).

7. Sub 2-51 Synthesis example

<Scheme 26>

(One) Sub 2-I-51 synthesis

Starting materials di(naphthalen-1-yl)amine (40.03 g, 148.62 mmol), 1,3,5-tribromobenzene (60.82 g, 193.21 mmol), Pd ₂ (dba) ₃ (4.08 g, 4.46 mmol), PPh ₃ (3.12 g, 11.89 mmol), NaO t -Bu (57.14 g, 594.49 mmol), toluene (860ml) was obtained by using the above Sub 2-I-1 synthesis method to give a product 36.65 g (yield: 49%).

(2) Sub 2-51 synthesis

di(naphthalen-2-yl)amine (15.09 g, 56.03 mmol), Sub 2-I-51 (36.65 g, 72.83 mmol), Pd ₂ (dba) ₃ (1.54 g, 1.68 mmol), PPh ₃ (1.18 g) , 4.48 mmol), NaO t -Bu (21.54 g, 224.10 mmol), and toluene (320ml) were obtained by using the Sub 2-1 synthesis method to obtain a product 20.54 g (yield: 53%).

8. Sub 2-63 Synthesis example

<Reaction Scheme 27>

(One) Sub 2-I-63 synthesis

Starting materials 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (42.99 g, 150.64 mmol), 1,3,5-tribromobenzene (61.65 g, 195.83 mmol), Pd ₂ (dba) ₃ ( 4.14 g, 4.52 mmol), PPh ₃ (3.16 g, 12.05 mmol), NaO t -Bu (57.91 g, 602.57 mmol), toluene (870 ml) using the above Sub 2-I-1 synthesis method, the product 35.98 g (yield) : 46%) was obtained.

(2) Sub 2-63 synthesis

9,9-dimethyl-N-phenyl-9H-fluoren-4-amine (15.21 g, 53.30 mmol), Sub 2-I-63 (35.98 g, 69.29 mmol), Pd ₂ (dba) ₃ (1.46 g, 1.60) mmol), PPh ₃ (1.12 g, 4.26 mmol), NaO t -Bu (20.49 g, 213.19 mmol), and toluene (310ml) were used to obtain 18.52 g (yield: 48%) of the product using the Sub 2-1 synthesis method. .

10. Sub 2-77 Synthesis Example

<Reaction Scheme 28>

N,9-diphenyl-9H-carbazol-2-amine (18.63 g, 55.71 mmol), Sub 2-I-24 (36.88 g, 72.42 mmol), Pd ₂ (dba) ₃ (1.53 g, 1.67 mmol), PPh ₃ (1.17 g, 4.46 mmol), NaO t -Bu (21.42 g, 222.84 mmol), toluene (320ml) was obtained by using the Sub 2-1 synthesis method to obtain a product 22.95 g (yield: 54%).

11.Synthesis Example of Sub 2-91

<Reaction Scheme 29>

bis(3,5-dimethylphenyl)amine (11.88 g, 52.72 mmol), Sub 2-I-51 (34.49 g, 68.54 mmol), Pd ₂ (dba) ₃ (1.45 g, 1.58 mmol), PPh ₃ (1.11 g , 4.22 mmol), NaO t -Bu (20.27 g, 210.89 mmol), and toluene (300ml) were obtained by using the Sub 2-1 synthesis method to obtain 15.71 g (yield: 46%).

12. Sub 2-104 Synthesis Example

<Reaction Scheme 30>

N,7-diphenyldibenzo[b,d]furan-3-amine (16.92 g, 50.45 mmol), Sub 2-I-1 (26.44 g, 65.58 mmol), Pd ₂ (dba) ₃ (1.39 g, 1.51 mmol) , PPh ₃ (1.06 g, 4.04 mmol), NaO t -Bu (19.39 g, 201.79 mmol), toluene (290ml) was obtained by using the Sub 2-1 synthesis method to obtain a product 17.58 g (yield: 53%).

Meanwhile, the compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS values of the compound belonging to Sub 2.

[Table 2]

III . Product synthesis

After dissolving Sub 1 (1 eq) in THF in a round bottom flask, add Sub 2 (1 eq), Pd(PPh ₃ ) ₄ (0.03 eq), NaOH (3 eq), and H ₂ O and stir at 80℃ I did. When the reaction was completed, CH ₂ Cl ₂ and water were extracted, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain a final product.

1.P-1 Synthesis example

<Reaction Scheme 31>

After dissolving the Sub 1-1 (6.83 g, 23.23 mmol) in THF (80ml) in a round bottom flask, Sub 2-1 (11.42 g, 23.23 mmol), Pd(PPh ₃ ) ₄ (0.81 g, 0.70 mmol) , NaOH (2.79 g, 69.69 mmol) and water (40ml) were added and stirred at 80°C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 10.08 g (yield: 75%) of the product.

2. P-12 Synthesis example

<Reaction Scheme 32>

Sub 1-8 (6.40 g, 16.56 mmol) in Sub 2-12 (13.43 g, 16.56 mmol), Pd(PPh ₃ ) ₄ (0.57 g, 0.50 mmol), NaOH (1.99 g, 46.69 mmol), THF ( 60ml), water (30ml) was added, and the product 10.66 g (yield: 65%) was obtained using the P-1 synthesis method.

3. P-20 Synthesis example

<Reaction Scheme 33>

Sub 1-12 (7.09 g, 18.34 mmol) in Sub 2-20 (10.85 g, 18.34 mmol), Pd(PPh ₃ ) ₄ (0.64 g, 0.55 mmol), NaOH (2.20 g, 55.03 mmol), THF ( 60ml), water (30ml) was added, and 11.32 g (yield: 80%) of the product was obtained using the P-1 synthesis method.

4. P-24 Synthesis example

<Reaction Scheme 34>

Sub 1-13 (8.64 g, 29.36 mmol) to Sub 2-24 (19.78 g, 29.36 mmol), Pd(PPh ₃ ) ₄ (1.02 g, 0.88 mmol), NaOH (3.52 g, 88.08 mmol), THF ( 100ml), water (50ml) was added, and the product 14.08 g (yield: 63%) was obtained using the P-1 synthesis method.

5. P-36 Synthesis example

<Reaction Scheme 35>

Sub 1-24 (12.42 g, 25.02 mmol) to Sub 2-36 (17.10 g, 25.02 mmol), Pd(PPh ₃ ) ₄ (0.87 g, 0.75 mmol), NaOH (3.00 g, 75.05 mmol), THF (THF) 80ml) and water (40ml) were added, and 12.17 g (yield: 50%) of the product was obtained using the P-1 synthesis method.

6. P-47 Synthesis example

<Reaction Scheme 36>

Sub 1-35 (12.90 g, 23.35 mmol) to Sub 2-47 (16.15 g, 23.35 mmol), Pd(PPh ₃ ) ₄ (0.81 g, 0.70 mmol), NaOH (2.80 g, 70.04 mmol), THF (THF) 80ml) and water (40ml) were added, and 11.87 g (yield: 49%) of the product was obtained using the P-1 synthesis method.

7. P-51 Synthesis example

<Scheme 37>

Sub 1-39 (11.77 g, 20.41 mmol) to Sub 2-51 (14.12 g, 20.41 mmol), Pd(PPh ₃ ) ₄ (0.71 g, 0.61 mmol), NaOH (2.45 g, 61.25 mmol), THF ( 70ml) and water (35ml) were added, and 9.75 g (yield: 45%) of the product was obtained using the P-1 synthesis method.

8. P-63 Synthesis example

<Scheme 38>

Sub 1-49 (9.33 g, 19.18 mmol) to Sub 2-63 (13.88 g, 19.18 mmol), Pd(PPh ₃ ) ₄ (0.66 g, 0.58 mmol), NaOH (2.30 g, 57.54 mmol), THF ( 60ml), water (30ml) was added, and 13.09 g (yield: 68%) of the product was obtained using the P-1 synthesis method.

9. P-76 Synthesis example

<Reaction Scheme 39>

Sub 1-10 (7.05 g, 22.73 mmol) in Sub 2-24 (15.31 g, 22.73 mmol), Pd(PPh ₃ ) ₄ (0.79 g, 0.68 mmol), NaOH (2.73 g, 68.18 mmol), THF ( 80ml) and water (40ml) were added, and 12.71 g (yield: 72%) of the product was obtained using the P-1 synthesis method.

10. Synthesis Example of P-81

<Reaction Scheme 40>

Sub 1-77 (20.65 g, 27.08 mmol), Pd(PPh ₃ ) ₄ (0.94 g, 0.81 mmol), NaOH (3.25 g, 81.23 mmol) in Sub 1-10 (8.40 g, 27.08 mmol) obtained in the above synthesis , THF (90ml), and water (45ml) were added, and 16.42 g (yield: 70%) of the product was obtained using the above P-1 synthesis method.

11. Synthesis Example of P-100

<Reaction Scheme 41>

Sub 1-52 (8.18 g, 21.17 mmol) obtained in the above synthesis, Sub 2-91 (13.71 g, 21.17 mmol), Pd(PPh ₃ ) ₄ (0.73 g, 0.64 mmol), NaOH (2.54 g, 63.52 mmol) , THF (70ml) and water (35ml) were added, and 11.38 g (yield: 65%) of the product was obtained using the P-1 synthesis method.

12. Synthesis Example of P-102

<Scheme 42>

Sub 2-6 (15.99 g, 21.50 mmol), Pd(PPh ₃ ) ₄ (0.75 g, 0.65 mmol), NaOH (2.58 g, 64.51 mmol) in Sub 1-58 (8.50 g, 21.50 mmol) obtained in the above synthesis , THF (70ml) and water (35ml) were added, and 11.63 g (yield: 58%) of the product was obtained using the P-1 synthesis method.

13. Synthesis Example of P-121

<Reaction Scheme 43>

Sub 1-47 (10.00 g, 24.37 mmol) obtained in the above synthesis, Sub 2-104 (16.03 g, 24.37 mmol), Pd(PPh ₃ ) ₄ (0.84 g, 0.73 mmol), NaOH (2.92 g, 73.11 mmol) , THF (80ml) and water (40ml) were added, and 13.64 g of a product (yield: 65%) was obtained using the P-1 synthesis method.

On the other hand, the FD-MS values of the compounds P-1 to P-96 of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.

[Table 3]

Meanwhile, in the above, exemplary synthesis examples of the present invention represented by Chemical Formula 1 have been described, but all of them are Suzuki cross-coupling reaction, Miyaura boration reaction, Intramolecular acid-induced cyclization reaction ( J. mater. Chem. 1999, 9 , 2095 .), Pd(II)-catalyzed oxidative cyclization reaction ( Org. Lett. 2011, 13 , 5504) and Buchwald-Hartwig cross coupling reaction, and other substituents defined in Formula 1 (X, R ¹ to R ⁷ , Ar ¹ to Ar ⁴ , L ¹ to L ⁵ Even if a substituent such as) is bonded, it will be readily understood by those skilled in the art that the reaction proceeds.

For example, Sub 1 and Sub 2 -> Final Products reaction in Scheme 1 and Sub 1-I -> Sub 1 reaction in Scheme 3 are based on Suzuki cross-coupling reaction, and Sub 1-I -> Sub 1 reaction in Scheme 2 Is based on the Miyaura boration reaction, and the starting material -> Sub 1-I reaction in Scheme 4 is based on the Intramolecular acid-induced cyclization reaction. Subsequently, in Scheme 5, the starting material -> Sub 1-I reaction is based on the Pd(II)-catalyzed oxidative cyclization reaction, and in Scheme 18, the starting material -> Sub 2-I reaction and Sub 2-I -> Sub 2 reaction Is based on the Buchwald-Hartwig cross coupling reaction. Even if substituents not specifically specified are attached to them, the reactions will proceed.

Manufacturing evaluation of organic electric devices

[ Example I-1] Green organic electroluminescent device ( Hole transport layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a material for a hole transport layer. First, a vacuum of 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as “2-TNATA”) to a thickness of 60 nm on the ITO layer (anode) formed on the organic substrate. After depositing to form a hole injection layer, the compound P-1 of the present invention was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Then, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter, abbreviated as “CBP”) on the hole transport layer as a host material, tris(2-phenylpyridine)-iridium (hereinafter, “Ir (ppy ) ₃ ") was used as a dopant material and vacuum-deposited to a thickness of 30 nm as a doping test at a weight ratio of 90:10 to form a light emitting layer. Subsequently, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as “BAlq”) was vacuum deposited to a thickness of 10 nm on the light emitting layer. A hole blocking layer was formed, and tris(8-quinolinol) aluminum (hereinafter abbreviated as “Alq ₃ ”) was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Example I-2] to [ Example I-58] Green organic electroluminescent device ( Hole transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that the compounds P-2 to P-96 of the present invention described in Table 4 below were used instead of the compound P-1 of the present invention as the hole transport layer material. I did.

[ Comparative example I-1] to [ Comparative example I-5]

An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compounds 1 to 5 shown in Table 4 below were used instead of Compound P-1 of the present invention as a hole transport layer material. .

<Comparative compound 1> <Comparative compound 2> <Comparative compound 3>

<Comparative compound 4> <Comparative compound 5>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples I-1 to I-58 and Comparative Examples I-1 to I-5 of the present invention, PR- from photoresearch Electroluminescence (EL) characteristics were measured at 650, and as a result of the measurement, T95 life was measured using a life measurement equipment manufactured by McScience at a reference luminance of 5000 cd/m ² , and the measurement results are shown in Table 4 below.

[Table 4]

From the results of Table 4, it can be seen that the luminous efficiency and lifetime of the organic electroluminescent device using the compound of the present invention as a material for the hole transport layer are improved.

In particular, compared to Comparative Compound 1, which is NPB, which is generally widely used as a hole transport layer, one amine group is bonded to a dibenzofuran or dibenzothiophene core by a linking group (including direct bonds). The result was higher in terms of luminous efficiency, and the compound of the present invention, which has a structure in which two amine groups are bonded to a dibenzofuran or dibenzothiophene core, with a linking group, has higher luminous efficiency and higher luminous efficiency than Comparative Compounds 1 to 5. Showed lifespan.

In the case of the compound of the present invention, which has a structure in which two amine groups are bonded to a hetero ring (dibenzofuran or dibenzothiophene) core with a linking group, one amine group is used as a linking group (including direct bonds) to the hetero ring core during device deposition The packing density is higher than that of Comparative Compounds 2 to 5, which are the combined structures, and as a result, Joule heating caused by overvoltage is less, which is judged to have thermal stability, and a relatively high T1 value. Therefore, it can be seen that the lifespan is increased by preventing excess electrons from passing over from the light emitting layer to the hole transport layer, resulting in an increase in color purity and reduction of thermal damage caused by light emission at the hole transport layer interface.

In addition, in the case of the hole transport layer, it is necessary to grasp the correlation with the light emitting layer (host). Even if a similar core is used, it will be very difficult for a person skilled in the art to infer the characteristics exhibited in the hole transport layer in which the compound according to the present invention is used. .

[ Example II -1] Green organic electroluminescent device ( Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. First, a hole injection layer was formed by vacuum depositing 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the glass substrate, and then N,N'-Bis(1-naphthalenyl)-N on the hole injection layer. ,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as “NPB”) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, after vacuum deposition of the compound P-1 of the present invention to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer, CBP as a host material and Ir(ppy) ₃ are coated on the light emission auxiliary layer. A light emitting layer was formed by using it as a material and doping at a weight ratio of 90:10 and vacuum deposition to a thickness of 30 nm. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer, and Alq ₃ was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Example II -2] to [ Example II -62] Green organic electroluminescent device ( Light-emitting auxiliary layer )

An organic electroluminescent device was prepared in the same manner as in Example II-1, except that the compounds P-2 to P-96 of the present invention described in Table 5 below were used instead of the compound P-1 of the present invention as a light emitting auxiliary layer material. Was produced.

[ Comparative example II -1] to [ Comparative example II -6]

In Comparative Example II-1, an organic electroluminescent device was manufactured in the same manner as in Example II-1, except that an emission auxiliary layer was not formed, and Comparative Examples II-2 to II-6 were materials for the emission auxiliary layer. Example II-1, except that Comparative Compound 4, Comparative Compound 5, Comparative Compound 6, Comparative Compound 7, and Comparative Compound 8 were used as shown in Table 5 below instead of Compound P-1 of the present invention. An organic electroluminescent device was manufactured in the same manner as described above.

<Comparative compound 6> <Comparative compound 7>

<Comparative compound 8>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples II-1 to II-62 and Comparative Examples II-1 to II-6 of the present invention, PR- from photoresearch Electroluminescence (EL) characteristics were measured at 650, and as a result of the measurement, T95 life was measured using a life measurement equipment manufactured by McScience at a reference luminance of 5000 cd/m ² , and the measurement results are shown in Table 5 below.

[Table 5]

[ Example III -One] Red organic electroluminescent device ( Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. First, 2-TNATA was vacuum-deposited to a thickness of 60 nm on the ITO layer (anode) formed on the glass substrate to form a hole injection layer, and then NPB was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. I did. Subsequently, after vacuum-depositing the compound P-1 of the present invention to a thickness of 20 nm on the hole transport layer to form an emission auxiliary layer, CBP as a host material on the emission auxiliary layer, bis-(1-phenylisoquinolyl) iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir(acac)") was used as a dopant material, doped at a weight ratio of 95:5, and vacuum deposited to a thickness of 30 nm to form a light emitting layer. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer, and Alq ₃ was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Example III -2] to [ Example III -48] Red organic electroluminescent device ( Light-emitting auxiliary layer )

An organic electroluminescent device was prepared in the same manner as in Example III-1, except that the compounds P-2 to P-96 of the present invention described in Table 6 were used instead of the compound P-1 of the present invention as the light emitting auxiliary layer material. Was produced.

[ Comparative example III -1] to [ Comparative example III -6]

In Comparative Example III-1, an organic electroluminescent device was manufactured in the same manner as in Example III-1, except that the light emission auxiliary layer was not formed, and Comparative Examples III-2 to III-6 were Except for using the Comparative Compound 4, Comparative Compound 5, Comparative Compound 6, Comparative Compound 7, and Comparative Compound 8 shown in Table 6 below, respectively, instead of Compound P-1 of the present invention as a light emitting auxiliary layer material. An organic electroluminescent device was manufactured in the same manner as in Example III-1.

By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples III-1 to III-48, Comparative Example III-1 and Comparative Example III-6 of the present invention, PR- Electroluminescence (EL) characteristics were measured at 650, and as a result of the measurement, T95 life was measured through a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m ² , and the measurement results are shown in Table 6 below.

[Table 6]

As can be seen from the results of Tables 5 and 6, the organic electroluminescent device using the compound of the present invention as a material for the light emitting auxiliary layer has luminous efficiency compared to the organic electroluminescent devices of Comparative Examples II-1 to III-5. This improved and the lifespan was significantly improved.

These results can be seen that the luminous efficiency and lifespan of the devices using Comparative Compound 4 to Comparative Compound 8 and the compound of the present invention as the emission auxiliary layer were improved compared to the device without forming the luminescent auxiliary layer. Among them, the compound of the present invention It can be seen that the result is remarkably high in terms of luminous efficiency and lifetime. This is because the structure in which the heterocyclic (dibenzofuran or dibenzothiophene) core and two amine groups are bonded with a linking group acts as a major factor in improving the performance of the device not only in the hole transport layer but also in the light emission auxiliary layer (green phosphorescence, red phosphorescence). This is believed to be because it achieves charge balance and plays an effective electron blocking role.

The compound of the present invention used as a light-emitting auxiliary layer material has a deep HOMO energy level, while holes are transported smoothly to the light-emitting layer, and as a result, positive polaron is prevented from accumulating at the light-emitting layer interface, thereby reducing interfacial deterioration. It can be seen that the charge balance is increased, thereby improving the luminous efficiency and lifespan.

When the aforementioned characteristics such as high thermal stability, high T1 value, and deep HOMO energy level are summarized, the band gap, electrical characteristics, and interface characteristics can be significantly changed depending on the number of amine groups substituted in the heterocyclic core and 　 connector. It can be seen that this acts as a major factor in improving the performance of the device.

In addition, in the evaluation results of the device fabrication described above, the device characteristics in which the compound of the present invention was applied to only one of the hole transport layer and the light-emitting auxiliary layer were described, but the compound of the present invention may be applied to both the hole transport layer and the light-emitting auxiliary layer.

The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the claims, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

100: organic electric device 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (10)

Compound represented by the following formula (1):
<Formula 1><Formula2>

In Formula 1,
X is O or S,
R ¹ is independently of each other hydrogen; heavy hydrogen; Cyano group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₁ -C ₅₀ alkyl group; And C ₁ -C ₃₀ alkoxyl group; is selected from the group consisting of,
R ² and R ³ are each independently hydrogen; heavy hydrogen; Cyano group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₁ -C ₅₀ alkyl group; An alkoxyl group of C ₁ -C ₃₀ ; And Formula 2; is selected from the group consisting of, provided that at least one of R ² and R ³ is Formula 2,
R ⁴ to R ⁷ are each independently hydrogen; heavy hydrogen; Cyano group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₁ -C ₅₀ alkyl group; And C ₁ -C ₃₀ alkoxyl group; is selected from the group consisting of, provided that in R ⁴ to R ⁷ dibenzofuryl group and dibenzothienyl group are excluded,
In Chemical Formula 2,
Ar ¹ to Ar ⁴ are each independently a C ₆ -C ₆₀ aryl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; Fluorenyl group; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; And C ₁ -C ₃₀ alkoxyl group; is selected from the group consisting of,
L ¹ to L ⁵ are each independently a single bond; C ₆ -C ₆₀ arylene group; A divalent C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And a fluorenylene group; is selected from the group consisting of,
L ¹ is deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of N, Si and P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of,
Each of L ² to L ⁵ is deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of,
When the R ¹ to R ³ , and Ar ¹ to Ar ⁴ are an aryl group, a fluorenyl group, a heterocyclic group, an alkyl group or an alkoxy group, or the Ar ¹ to Ar ⁴ is an alkenyl group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl groups, and when each of these substituents are adjacent, they may be bonded to each other to form a ring,
When the R ⁴ to R ⁷ is an aryl group, a fluorenyl group, a heterocyclic group, an alkyl group or an alkoxy group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; O, N, S, Si, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P (excluding dibenzofuryl and dibenzothienyl groups); A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group. The method of claim 1,
Formula 1 is a compound characterized in that represented by Formula 4 or Formula 5:
<Formula 4><Formula5>

,

In Formulas 4 and 5, X, R ¹ to R ⁷ , Ar ¹ to Ar ⁴ , and L ¹ to L ⁵ are the same as defined in claim 1. The method of claim 1,
Formula 2 is a compound characterized in that represented by one of the following formulas 10 to 14:
<Formula 10><Formula11>

<Formula 12><Formula13>

<Formula 14>

In Formulas 10 to 14, Ar ² to Ar ⁴ , L ¹ to L ⁵ are the same as defined in claim 1,
Y ¹ to Y ⁴ are each independently S, O, C(R ^a )(R ^b ) or N(R ^c ), wherein R ^a to R ^c are each independently an aryl group of C ₆ -C ₆₀ ; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ is selected from the group consisting of aryloxy group, R ^a and R ^b may be bonded to each other to form a spy compound with the carbon to which they are bonded,
R ¹¹ to R ¹⁸ are each independently deuterium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ is selected from the group consisting of an aryloxy group, and when a plurality of R ¹¹ to R ¹⁸ are present, each independently neighboring R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , and R ¹⁵ , At least one pair of R ¹⁶ , R ¹⁷ and R ¹⁸ may be bonded to each other to form a ring,
p, r, t and v are each independently an integer of 0 to 3, and when each of them is an integer of 2 or more, R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁷ are each the same or different from each other,
q, s, u and w are each independently an integer of 0 to 4, and when each is an integer of 2 or more, R ¹² , R ¹⁴ , R ¹⁶ and R ¹⁸ are each the same or different from each other. Compound represented by the following formula (1):
<Formula 1><Formula2>

In Formula 1,
X is O or S,
R ¹ is Formula 2, wherein Formula 2 is represented by one of Formulas 10 to 14 below,
<Formula 10><Formula11>

<Formula 12><Formula13>

<Formula 14>

R ² and R ³ are each independently hydrogen; heavy hydrogen; Cyano group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₁ -C ₅₀ alkyl group; An alkoxyl group of C ₁ -C ₃₀ ; And is selected from the group consisting of Formula 2,
R ⁴ to R ⁷ are each independently hydrogen; heavy hydrogen; Cyano group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₁ -C ₅₀ alkyl group; And C ₁ -C ₃₀ alkoxyl group; is selected from the group consisting of, provided that in R ⁴ to R ⁷ dibenzofuryl group and dibenzothienyl group are excluded,
Ar ¹ to Ar ⁴ are each independently a C ₆ -C ₆₀ aryl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; Fluorenyl group; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; And C ₁ -C ₃₀ alkoxyl group; is selected from the group consisting of,
L ¹ to L ⁵ are each independently a single bond; C ₆ -C ₆₀ arylene group; A divalent C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And a fluorenylene group; is selected from the group consisting of,
L ¹ is deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of N, Si and P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of,
Each of L ² to L ⁵ is deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of,
Y ¹ to Y ⁴ are each independently S, O, C(R ^a )(R ^b ) or N(R ^c ), wherein R ^a to R ^c are each independently an aryl group of C ₆ -C ₆₀ ; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ is selected from the group consisting of aryloxy group, R ^a and R ^b may be bonded to each other to form a spy compound with the carbon to which they are bonded,
R ¹¹ to R ¹⁸ are each independently deuterium; Tritium; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And C ₆ -C ₃₀ is selected from the group consisting of an aryloxy group, and when a plurality of R ¹¹ to R ¹⁸ are present, each independently neighboring R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , and R ¹⁵ , At least one pair of R ¹⁶ , R ¹⁷ and R ¹⁸ may be bonded to form a ring,
p, r, t and v are each independently an integer of 0 to 3, and when each of them is an integer of 2 or more, R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁷ are each the same or different from each other,
q, s, u and w are each independently an integer of 0 to 4, and when each is an integer of 2 or more, R ¹² , R ¹⁴ , R ¹⁶ and R ¹⁸ are each the same or different from each other,
When the R ¹ to R ³ , and Ar ¹ to Ar ⁴ are an aryl group, a fluorenyl group, a heterocyclic group, an alkyl group or an alkoxy group, or the Ar ¹ to Ar ⁴ is an alkenyl group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl groups, and when each of these substituents are adjacent, they may be bonded to each other to form a ring,
When the R ⁴ to R ⁷ is an aryl group, a fluorenyl group, a heterocyclic group, an alkyl group or an alkoxy group, each of them is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; O, N, S, Si, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P (excluding dibenzofuryl and dibenzothienyl groups); A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group,
However, the following compounds in Formula 1 are excluded:

. A compound characterized by being one of the following compounds:

. A first electrode; A second electrode; And an organic material layer formed between the first electrode and the second electrode,
An organic electric device comprising the compound of any one of claims 1 to 5 in the organic material layer. The method of claim 6,
The organic material layer includes an emission layer, a hole transport layer, and an emission auxiliary layer, and the hole transport layer or the emission auxiliary layer is formed of one type of the compound. The method of claim 6,
The organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process. A display device including the organic electric device of claim 6; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 9,
The organic electroluminescent device is an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and an electronic device, characterized in that one of a single color or white lighting device.

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