KR102359840B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

Disclosed are compounds represented by formula (1). Also disclosed is an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, wherein 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, luminous efficiency, stability, lifespan, etc. may be improved.

Description

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

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

In addition, the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. can In addition, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is reduced due to the emission attenuation effect. A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through the The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is a large-area display, and the size thereof is increasing, and thus, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and the problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan. However, the efficiency cannot be maximized by simply improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time. Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer.

That is, in order to sufficiently exhibit the excellent characteristics of an organic electric device, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc. is stable and efficient. Supported by materials should be preceded, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently developed. Accordingly, the development of new materials is continuously required, and in particular, the development of the host material of the light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity and lifespan of the device, 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.

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

By using the compound according to an embodiment of the present invention, it is possible to achieve high luminous efficiency, low driving voltage, and high heat resistance of the device, and improve color purity and lifespan of the device.

1 is an exemplary view 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 the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though 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 gist of the present invention, the detailed description thereof will be omitted.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is formed between each component. It should be understood that elements may also be “connected,” “coupled,” or “connected.”

Further, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” another component, but also when another component is in between. It should be understood that cases may be included. Conversely, when it is said that an element is "on top of" another part, it should be understood to mean that there is no other part in the middle.

As used in this specification and the appended claims, unless otherwise indicated, the following terms have the following meanings.

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.

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

As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group substituted with halogen unless otherwise specified.

The term "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise specified, has a double or triple bond of 2 to 60 carbon atoms, respectively, and includes a straight or branched chain group, and is limited thereto it is not

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

As used herein, the term “alkoxy group” or “alkyloxy group” refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

As used herein, the term “aryloxyl group” or “aryloxy group” refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A 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 to It includes the case of forming a compound as a spy together.

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

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

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

As used herein, the term "ring" includes monocyclic and polycyclic rings, and includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems and spiro compounds, and includes aromatic as well as non-aromatic, hydrocarbon Rings include, of course, heterocycles containing at least one heteroatom.

As used herein, the term "ring assemblies" refers to two or more ring systems (monocyclic or fused ring systems) directly connected to each other through single or double bonds, and a direct connection between such rings It means that the number of linkages is one less than the total number of ring systems in this compound. In a ring aggregate, the same or different ring systems may be directly linked to each other through single or double bonds.

As used herein, the term "fused multiple ring system" refers to a fused ring type sharing at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. and a form in which at least one heterocyclic system is fused. The fused multiple ring system 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 means a connection formed by sharing only one atom in two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group 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 otherwise explicitly stated, in the term "substituted or unsubstituted" as used herein, "substitution" 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 group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, fluorenyl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, One or more substituents selected from the group consisting of a silane group, a boron group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P It means substituted with, but is not limited to these substituents.

In addition, unless there is an explicit explanation, the formula used in the present invention is the same as the definition of the substituent by the exponential 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 carbon of the carbons forming the benzene ring, and when 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 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 the present invention includes a first electrode 120 , a second electrode 180 , and a first electrode 120 and a second electrode 180 formed on a substrate 110 . ) and an organic material layer containing the compound according to the present invention. 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 sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 on the first electrode 120 . At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, etc. may be further included, and the electron transport layer 160 and the like serve as a hole blocking layer. you might be able to

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic layer is a hole injection layer 130 , a hole transport layer 140 , an electron transport layer 160 , an electron injection layer 170 , a light emitting layer 150 , a light efficiency improving layer, a light emitting auxiliary layer, etc. could be used as a material for For example, the compound of the present invention may be used as a material for the emission layer 150 .

On the other hand, even with the same core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of the sub-substituents bonded thereto are very important. When the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

As already described, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and corresponding to each light emitting layer (R, G, B) Therefore, it is necessary to form different light emitting auxiliary layers. On the other hand, in the case of the light emitting auxiliary layer, it is necessary to understand the relationship between the hole transport layer and the light emitting layer (host), so even if a similar core is used, it will be very difficult to infer its characteristics if the organic material layer used is different.

Therefore, by forming a light emitting layer using the compound according to Chemical Formula 1 of the present invention, the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interface characteristics, etc.) and efficiency can be improved at the same time.

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 metal oxide having conductivity or an alloy thereof on a substrate to form the anode 120, and the 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, a light emitting auxiliary layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150 .

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

The organic electric device according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent in processability, and can be manufactured using the existing color filter technology of LCD. Various structures for a white organic light emitting diode mainly used as a backlight device have been proposed and patented. Typically, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting units are mutually planar, and a stacking method in which R, G, and B light emitting layers are stacked up and down There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light emitting layer and photo-luminescence of an inorganic phosphor using the light therefrom. could also be applied to such WOLEDs.

In addition, the organic electric device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), 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. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.

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

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

<Formula 1>

<Formula 2> <Formula 3> <Formula 4>

Each symbol described in the above formula may be defined as follows.

In the above formula, X is -O- or -S-.

Ring A is one of Formulas 2 to 4.

R ² to R ²³ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ Aryl group; fluorenyl group; C ₂ -C ₆₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₁ -C ₅₀ Alkyl group; C ₆ -C ₆₀ A fused ring group of an aromatic ring and a C ₃ -C ₆₀ aliphatic ring; C ₂ -C ₂₀ alkenyl group; C ₁ -C ₃₀ alkoxyl group; and a C ₆ -C ₃₀ aryloxy group; may be selected from the group consisting of.

Preferably, R ² to R ²³ are each independently selected from the group consisting of hydrogen, deuterium, C ₆ -C ₃₀ aryl group, fluorenyl group, O, N, S, Si and P at least one heteroatom. It may be a C ₂ -C ₃₀ heterocyclic group comprising a.

In addition, R ¹⁰ and R ¹¹ or R ²² and R ²³ may be combined with each other to optionally form an aromatic or heteroaromatic ring. Illustratively, R ¹⁰ and R ¹¹ may combine with each other to form a ring such as naphthalene together with the benzene ring to which they are bonded, and R ²² and R ²³ may also form the same ring.

R ¹ may be -L ¹ -(Ar ¹ ) or -L ² -(Ar ¹ )(Ar ² ).

L ¹ is a single bond; C ₆ -C ₆₀ Arylene group; fluorenylene group; and O, N, S, Si and P, including at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ heteroarylene group; may be selected from the group consisting of.

Preferably, L ¹ is a single bond, C ₆ -C ₃₀ Arylene group, fluorenylene group, C ₂ -C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P It may be a heteroarylene group of ₃₀ or the like. Illustratively, L ¹ is a single bond, a phenylene group, a naphthylene group, a quinazolinylene group, a benzoquinazolinylene group, a benzothienopyrimidinylene group, a phenanthrenylene group, a benzofuropyrimidinylene group, a carba It may be a zolylene group, a pyridoindolylene group, a benzocarbazolylene group, or the like.

L ² is a C ₆ -C ₆₀ trivalent arylene group; trivalent fluorenylene group; And O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ A trivalent heteroarylene group; may be selected from the group consisting of.

Preferably, L ² is C ₆ -C ₃₀ including at least one heteroatom selected from the group consisting of a trivalent arylene group, a trivalent fluorenylene group, O, N, S, Si and P C ₂ - It may be a C ₃₀ trivalent heteroarylene group or the like. Exemplarily, L ² may be a trivalent phenylene group, a trivalent pyridinylene group, a trivalent pyrimidinylene group, or a trivalent triazinylene group.

Ar ¹ and Ar ² are each independently selected from a C ₆ -C ₆₀ aryl group; fluorenyl group; C ₃ -C ₆₀ A fused ring group of an aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₂ -C ₆₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L′-N(R ^a )(R ^b ); may be selected from the group consisting of.

Preferably, Ar ¹ and Ar ² are each independently a C ₆ -C ₃₀ aryl group, a fluorenyl group, a C ₃ -C ₃₀ aliphatic ring and a C ₆ -C ₃₀ aromatic ring fused ring group, O , N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₃₀ A heterocyclic group, -L'-N(R ^a ) (R ^b ) and the like may be. Illustratively, a phenyl group unsubstituted or substituted with deuterium or methyl, a naphthyl group, a biphenyl group, a triphenylenyl group, a chrysenyl group, a phenanthrenyl group, a pyrenyl group, a triazinyl group, a pyrimidinyl group, a quinazolinyl group, a benzo Quinazolinyl group, benzothienopyrimidinyl group, phenanthridinyl group, pyridyl group, benzofuropyrimidinyl group, benzoquinazolinyl group, carbazolyl group, pyridoindole group, dibenzothienyl group, dibenzofuryl group, -L'-N(R ^a )(R ^b ) and the like.

The L' is a single bond; C ₆ -C ₆₀ Arylene group; fluorenylene group; C ₃ -C ₆₀ A fused ring group of an aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And O, N, S, Si, and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ A heterocyclic group; may be selected from the group consisting of.

Preferably, L' is a single bond, C ₆ -C ₃₀ Arylene group, fluorenylene group, C ₂ -C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P It may be a heterocyclic group of ₃₀ or the like. Illustratively, L' may be a single bond, a phenylene group, or the like.

wherein R ^a and R ^b are each independently selected from a C ₆ -C ₆₀ aryl group; fluorenyl group; C ₃ -C ₆₀ A fused ring group of an aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And O, N, S, Si, and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ A heterocyclic group; may be selected from the group consisting of.

Preferably, R ^a and R ^b are each independently C ₆ -C ₃₀ C containing at least one heteroatom selected from the group consisting of an aryl group, a fluorenyl group, O, N, S, Si and P ₂ -C ₃₀ It may be a heterocyclic group or the like. Exemplarily, R ^a and R ^b may each independently represent a phenyl group, a naphthyl group, a biphenyl group, or a fluorenyl group unsubstituted or substituted with methyl or phenyl.

Here, the aryl group, fluorenyl group, heterocyclic group, alkyl group, fused ring group, alkenyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group, heteroarylene group is each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ An alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; a C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ An aryl alkenyl group; may be further substituted with one or more substituents selected from the group consisting of.

Specifically, in Chemical Formula 1, the chemical formula according to the bonding position of A may be represented by the following Chemical Formulas 5 to 10.

<Formula 5> <Formula 6> <Formula 7>

<Formula 8> <Formula 9> <Formula 10>

In Formulas 5 to 10, R ¹ to R ²³ and X are the same as defined in claim 1.

In addition, specifically, in Formula 1, the bonding position of A and the substituents R ¹⁰ and R ¹¹ or R ²² and R ²³ are bonded to each other to form a benzene ring and a ring to which the chemical formulas are represented by the following Chemical Formulas 1-1 to Formulas It can be displayed as one of 1-4.

<Formula 1-1> <Formula 1-2> <Formula 1-3> <Formula 1-4>

In Formulas 1-1 to 1-4, R ¹ to R ⁹ , R ¹⁸ to R ²¹ and X are the same as defined in claim 1.

R ²⁴ to R ²⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ Aryl group; fluorenyl group; C ₂ -C ₆₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₁ -C ₅₀ Alkyl group; C ₆ -C ₆₀ A fused ring group of an aromatic ring and a C ₃ -C ₆₀ aliphatic ring; C ₂ -C ₂₀ alkenyl group; C ₁ -C ₃₀ alkoxyl group; and a C ₆ -C ₃₀ aryloxy group; may be selected from the group consisting of.

Preferably, R ²⁴ to R ²⁷ are each independently selected from the group consisting of hydrogen, deuterium, C ₆ -C ₃₀ aryl group, fluorenyl group, O, N, S, Si and P at least one heteroatom. It may be a C ₂ -C ₃₀ heterocyclic group comprising a.

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

As another embodiment, the present invention provides a compound for an organic electric device represented by the formula (1).

In another embodiment, the present invention provides an organic electric device containing the compound represented by the formula (1).

At this time, the organic electric device includes a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer may include a compound represented by Chemical Formula 1, wherein Chemical Formula 1 is a hole injection layer, a hole transport layer, and a light emitting auxiliary layer of the organic material layer. Alternatively, it may be contained in at least one of the light-emitting layers. That is, the compound represented by Formula 1 may be used as a material for a hole injection layer, a hole transport layer, a light emitting auxiliary layer, or a light emitting layer. Preferably, the compound represented by Formula 1 may be used as a phosphorescent host material of the light emitting layer.

Specifically, an organic electric device including one of the compounds represented by Chemical Formulas 5 to 10 is provided in the organic layer, and more specifically, among the compounds represented by Chemical Formulas 1-1 to 1-4 in the organic layer. It provides an organic electric device including one, and more specifically, provides an organic electric device including a compound represented by the individual formula in the organic material layer. In addition, the compound contained in the organic material layer may be a single one or a mixture of two or more represented by the formula (1). For example, the emission layer of the organic material layer may be formed of the P-1-1 compound alone or may include a mixture of P-1-1 and P-1-2.

In another embodiment of the present invention, the present invention provides a light efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device further comprising a.

Hereinafter, examples of the synthesis of the compound represented by the formula according to the present invention and the preparation of the organic electric device will be described in detail with reference to examples, but the present invention is not limited to the following examples.

Synthesis example

The compound represented by Formula 1 according to an embodiment of the present invention (final products) is prepared by the reaction route of Scheme 1 below, but is not limited thereto.

<Scheme 1>

I. Synthesis of Core

1. of Core 1 Synthesis example

Synthesis of Core 1-a

CuCN (8.85 g, 98.8 mmol) and DMF (200 ml) were added to 2-Bromodibenzothiophene (13 g, 49.4 mmol) and refluxed at 160° C. for 24 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, diluted in CH ₂ Cl ₂ , and washed with 28% NH ₃ aqueous solution and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was washed with ethanol and filtered to obtain 7.2 g (70%) of the product.

Synthesis of Core 1-b

Add potassium hydroxide aqueous solution (12M, 40 mL) and 2-methoxyethanol (120 ml) to Core 1-a (8 g, 38.23 mmol) and reflux for 24 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, and acidified with 1N HCl. Filter the precipitate and wash with water. After dissolving in NaOH 1M aqueous solution, the product was acidified with 1N HCl and the precipitate was filtered to proceed to the next reaction without separation.

Synthesis of Core 1-c

SOCl ₂ (14.07 g, 118.28 mmol) and benzene (100 ml) were added to Core 1-b (9 g, 39.43 mmol), and refluxed at 90° C. for 3 hours. When the reaction is complete, the temperature of the reactant is cooled to room temperature and poured into ice water. Extract with ethyl acetate and wash with water. The organic layer was dried over MgSO ₄ and filtered through celite. The solvent was removed and the resulting solid was recrystallized and filtered to obtain 7.8 g (80%) of the product.

Synthesis of Core 1-d

Add triethylamine (TEA) (3.23 g, 31.92 mmol) and THF (150 mL) to aniline (2.83 g, 30.40 mmol), and slowly add Core 1-c (7.5 g, 30.40 mmol) dissolved in THF at 0°C. Stir at room temperature for 3 hours. When the reaction is complete, the reaction is filtered to remove triethylammonium chloride, and the solvent is concentrated. The resulting organic material was washed with pentane and dried to obtain 8.6 g (94%) of the product.

Synthesis of Core 1-e

Pd(OCOCF ₃ ) ₂ (0.63 g, 1.89 mmol) and benzoic acid (3.3 g, 27.02 mmol) were added to Core 1-d (8.2 g, 27.02 mmol) and stirred at 150° C. for 12 hours. When the reaction is complete, the temperature of the reactant is cooled to room temperature, dissolved in ethyl acetate, and neutralized by adding aqueous sodium carbonate solution. Extract with ethyl acetate and wash with water. The organic layer was dried over MgSO ₄ and filtered through silica. The solvent was removed and the resulting solid was recrystallized and filtered to obtain 3.4 g (42%) of the product.

Synthesis of Core 1-f

POCl ₃ (2.82 mL, 30.26 mmol), N,N -diisopropylethylamine (DIEA) (2.61 g, 20.17 mmol), toluene (80 ml) was added to Core 1-e (7.6 g, 25.22 mmol) and 3 hours at 120°C reflux When the reaction is complete, the temperature of the reactant is cooled to room temperature and poured into ice water. Extract with ethyl acetate and wash with water. The organic layer was dried over MgSO ₄ and filtered through celite. The solvent was removed and the resulting solid was recrystallized and filtered to obtain 5.6 g (71%) of the product.

Synthesis of Core 1

Core 1-f (5.4 g, 16.88 mmol) in bis(pinacolato)diboron (5.68 g, 20.26 mmol), PdCl ₂ (dppf) ₂ (0.41 g, 0.51 mmol), KOAc (4.97 g, 50.65 mmol), DMF ( 600 ml) and refluxed at 120° C. for 6 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 5.7 g (83%) of the product.

2. Core 2's Synthesis example

Synthesis of Core 2-a

5-Bromobenzo[b]naphtho[2,1-d]thiophene (9 g, 28.73 mmol), CuCN (5.15 g, 57.47 mmol), and DMF (200 ml) were prepared using the synthesis example of Core 1-a above. 5.3 g (72%) were obtained.

Synthesis of Core 2-b

Core 2-a (10 g, 38.56 mmol), aqueous potassium hydroxide solution (12M, 45 mL), and 2-methoxyethanol (130 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 2-c

Core 2-b (11 g, 39.52 mmol), SOCl ₂ (14.10 g, 118.56 mmol), and benzene (150 ml) were obtained using the synthesis example of Core 1-c above to obtain 9 g (77%) of the product.

Synthesis of Core 2-d

Core 2-c ( 9 g, 30.32 mmol), aniline (2.82 g, 30.32 mmol), triethylamine (TEA) (3.22 g, 31.84 mmol), and THF (200 mL) were prepared using the synthesis example of Core 1-d above. 9.6 g (90%) of the product were obtained.

Synthesis of Core 2-e

Core 2-d (9.5 g, 26.87 mmol), Pd(OCOCF ₃ ) ₂ (0.63 g, 1.88 mmol), benzoic acid (3.28 g, 26.87 mmol) using the synthesis example of Core 1-e above, 8.3 g of the product (88%) was obtained.

Synthesis of Core 2-f

Core 2-e (8 g, 22.76 mmol), POCl ₃ (2.55 mL, 27.31 mmol), N,N -diisopropylethylamine (DIEA) (2.35 g, 18.21 mmol), toluene (80 ml) of Core 1-f Using the synthesis example, 6.1 g (73%) of the product was obtained.

Synthesis of Core 2

Core 2-f (6 g, 16.22 mmol), bis(pinacolato)diboron (5.45 g, 19.46 mmol), PdCl ₂ (dppf) ₂ (0.40 g, 0.48 mmol), KOAc (4.78 g, 48.66 mmol), DMF ( 800 ml) using the synthesis example of Core 1 above to obtain 5.9 g (80%) of the product.

3. Core 3's Synthesis example

Synthesis of Core 3-a

1-Bromodibenzo[b,d]thiophene (5 g, 19.0 mmol), CuCN (3.40 g, 38.0 mmol), and DMF (150 ml) using the synthesis example of Core 1-a above 2.7 g (69%) of the product got

Synthesis of Core 3-b

Core 3-a (6 g, 28.67 mmol), aqueous potassium hydroxide solution (12M, 35 mL), and 2-methoxyethanol (110 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 3-c

Core 3-b (6.5 g, 28.48 mmol), SOCl ₂ (10.16 g, 85.42 mmol), and benzene (80 ml) were obtained using the synthesis example of Core 1-c above to obtain 5.5 g (79%) of the product.

Synthesis of Core 3-d

Core 3-c (11 g, 44.58 mmol), aniline (4.15 g, 44.58 mmol), triethylamine (TEA) (4.74 g, 46.81 mmol), and THF (300 mL) were prepared using the synthesis example of Core 1-d above. 12.5 g (93%) of the product were obtained.

Synthesis of Core 3-e

Core 3-d (12 g, 39.55 mmol), Pd(OCOCF ₃ ) ₂ (0.92 g, 2.76 mmol), and benzoic acid (4.83 g, 39.55 mmol) were prepared using the above synthesis example of Core 1-e to 10.8 g of the product (91%) was obtained.

Synthesis of Core 3-f

Core 3-e (10.5 g, 34.84 mmol), POCl ₃ (3.90 mL, 41.81 mmol), N,N -diisopropylethylamine (DIEA) (3.60 g, 27.87 mmol), toluene (100 ml) of Core 1-f Using the synthesis example, 7.3 g (66%) of the product was obtained.

Synthesis of Core 3

Core 3-f (7.1 g, 22.20 mmol), bis(pinacolato)diboron (7.46 g, 26.64 mmol), PdCl ₂ (dppf) ₂ (0.54 g, 0.66 mmol), KOAc (6.54 g, 66.60 mmol), DMF ( 100 ml) using the synthesis example of Core 1 above to obtain 6.6 g (73%) of the product.

4. Core 4's Synthesis example

Synthesis of Core 4-a

6-Bromobenzo[b]naphtho[2,1-d]thiophene (11 g, 35.12 mmol), CuCN (6.29 g, 70.24 mmol), and DMF (200 ml) were prepared using the synthesis example of Core 1-a above. 6 g (66%) were obtained.

Synthesis of Core 4-b

Core 4-a (12 g, 46.27 mmol), aqueous potassium hydroxide solution (12M, 50 mL), and 2-methoxyethanol (150 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 4-c

Core 4-b (10.5 g, 37.72 mmol), SOCl ₂ (13.46 g, 113.17 mmol), and benzene (100 ml) were obtained using the synthesis example of Core 1-c above to obtain 8.4 g (75%) of the product.

Synthesis of Core 4-d

Core 4-c (8.2 g, 27.63 mmol), aniline (2.57 g, 27.63 mmol), triethylamine (TEA) (2.94 g, 29.01 mmol), and THF (200 mL) were prepared using the synthesis example of Core 1-d above. 8.8 g (91%) of the product were obtained.

Synthesis of Core 4-e

Core 4-d (8.6 g, 24.33 mmol), Pd(OCOCF ₃ ) ₂ (0.57 g, 1.70 mmol), benzoic acid (2.97 g, 24.33 mmol) using the synthesis example of Core 1-e above, 7.7 g of the product (91%) was obtained.

Synthesis of Core 4-f

Core 4-e (7.2 g, 20.48 mmol), POCl ₃ (2.29 mL, 24.58 mmol), N,N -diisopropylethylamine (DIEA) (2.12 g, 16.39 mmol), toluene (80 ml) of Core 1-f Using the synthesis example, 5.2 g (69%) of the product was obtained.

Synthesis of Core 4

Core 4-f (5 g, 13.51 mmol), bis(pinacolato)diboron (4.54 g, 16.22 mmol), PdCl ₂ (dppf) ₂ (0.33 g, 0.40 mmol), KOAc (3.98 g, 40.55 mmol), DMF ( 80 ml) using the synthesis example of Core 1 above to obtain 4.3 g (70%) of the product.

5. Core 5's Synthesis example

Synthesis of Core 5-a

3-Bromodibenzo[b,d]thiophene (7 g, 26.6 mmol), CuCN (4.76 g, 53.2 mmol), and DMF (150 ml) using the synthesis example of Core 1-a above, 4.1 g (74%) of the product got

Synthesis of Core 5-b

Core 5-a (8.5 g, 40.62 mmol), aqueous potassium hydroxide solution (12M, 45 mL), and 2-methoxyethanol (140 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 5-c

Core 5-b (15 g, 65.71 mmol), SOCl ₂ (23.45 g, 197.13 mmol), and benzene (200 ml) were obtained using the synthesis example of Core 1-c above to obtain 13.7 g (85%) of the product.

Synthesis of Core 5-d

Core 5-c (13 g, 52.69 mmol), aniline (4.91 g, 52.69 mmol), triethylamine (TEA) (5.60 g, 55.32 mmol), and THF (300 mL) were prepared using the synthesis example of Core 1-d above. 14 g (88%) of the product were obtained.

Synthesis of Core 5-e

Core 5-d (13 g, 42.85 mmol), Pd(OCOCF ₃ ) ₂ (1.0 g, 3.00 mmol), and benzoic acid (5.23 g, 42.85 mmol) using the synthesis example of Core 1-e above, 4.9 g of the product (38%) was obtained.

Synthesis of Core 5-f

Core 5-e (9.6 g, 31.85 mmol), POCl ₃ (3.56 mL, 38.22 mmol), N,N -diisopropylethylamine (DIEA) (3.29 g, 25.48 mmol), toluene (100 ml) of Core 1-f Using the synthesis example, 7.3 g (72%) of the product was obtained.

Synthesis of Core 5

Core 5-f (6.9 g, 21.57 mmol), bis(pinacolato)diboron (7.25 g, 25.89 mmol), PdCl ₂ (dppf) ₂ (0.53 g, 0.64 mmol), KOAc (6.35 g, 64.72 mmol), DMF ( 100 ml) using the synthesis example of Core 1 above to obtain 7.8 g (88%) of the product.

6. Core 6's Synthesis example

Synthesis of Core 6-a

2-Bromodibenzo[b,d]thiophene (19 g, 72.2 mmol), CuCN (12.93 g, 144.4 mmol), DMF (300 ml) using the synthesis example of Core 1-a above, 9.8 g (65%) of the product got

Synthesis of Core 6-b

Core 6-a (9.5 g, 45.39 mmol), aqueous potassium hydroxide solution (12M, 50 mL), and 2-methoxyethanol (150 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 6-c

Core 6-b (7.8 g, 34.17 mmol), SOCl ₂ (12.19 g, 102.51 mmol), and benzene (100 ml) were obtained using the synthesis example of Core 1-c above to obtain 6.9 g (82%) of the product.

Synthesis of Core 6-d

Core 6-c (7 g, 28.37 mmol), aniline (2.64 g, 28.37 mmol), triethylamine (TEA) (3.01 g, 29.79 mmol), and THF (150 mL) were prepared using the synthesis example of Core 1-d above. 8 g (93%) of product were obtained.

Synthesis of Core 6-e

Core 6-d (8 g, 26.36 mmol), Pd(OCOCF ₃ ) ₂ (0.61 g, 1.84 mmol), and benzoic acid (3.22 g, 26.36) were prepared using the above synthesis example of Core 1-e to 4.1 g of the product ( 52%) was obtained.

Synthesis of Core 6-f

Core 6-e (6.7 g, 22.23 mmol), POCl ₃ (2.49 mL, 26.68 mmol), N,N -diisopropylethylamine (DIEA) (2.30 g, 17.78 mmol), toluene (80 ml) of Core 1-f Using the synthesis example, 4.6 g (65%) of the product was obtained.

Synthesis of Core 6

Core 6-f (6.6 g, 20.63 mmol), bis(pinacolato)diboron (6.94 g, 24.76 mmol), PdCl ₂ (dppf) ₂ (0.51 g, 0.62 mmol), KOAc (6.08 g, 61.91 mmol), DMF ( 80 ml) using the synthesis example of Core 1 above to obtain 7.5 g (89%) of the product.

7. Core 7's Synthesis example

Synthesis of Core 7-a

6-Bromobenzo[b]naphtho[1,2-d]thiophene (7.5 g, 23.94 mmol), CuCN (4.29 g, 47.89 mmol), and DMF (200 ml) were prepared using the synthesis example of Core 1-a above. 4 g (65%) were obtained.

Synthesis of Core 7-b

Core 7-a (15 g, 57.84 mmol), aqueous potassium hydroxide solution (12M, 65 mL), and 2-methoxyethanol (200 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 7-c

Core 7-b (16 g, 60.99 mmol), SOCl ₂ (21.77 g, 182.97 mmol), and benzene (200 ml) were obtained using the synthesis example of Core 1-c above to obtain 15.92 g (88%) of the product.

Synthesis of Core 7-d

Core 7-c (12 g, 40.43 mmol), aniline (3.77 g, 40.43 mmol), triethylamine (TEA) (4.30 g, 42.45 mmol), and THF (300 mL) were prepared using the synthesis example of Core 1-d above. 12.4 g (87%) of the product were obtained.

Synthesis of Core 7-e

Core 7-d (12.4 g, 35.08 mmol), Pd(OCOCF ₃ ) ₂ (0.82 g, 2.45 mmol), benzoic acid (4.28 g, 35.08 mmol) was prepared using the synthesis example of Core 1-e above, 11.2 g of the product (91%) was obtained.

Synthesis of Core 7-f

Core 7-e (11 g, 31.30 mmol), POCl ₃ (3.50 mL, 37.56 mmol), N,N -diisopropylethylamine (DIEA) (3.24 g, 25.04 mmol), toluene (150 ml) of Core 1-f Using the synthesis example, 7.87 g (68%) of the product was obtained.

Synthesis of Core 7

Core 7-f (7.6 g, 20.54 mmol), bis(pinacolato)diboron (6.91 g, 24.65 mmol), PdCl ₂ (dppf) ₂ (0.50 g, 0.61 mmol), KOAc (6.05 g, 61.64 mmol), DMF ( 90 ml) using the synthesis example of Core 1 above to obtain 7.6 g (81%) of the product.

8. Core 8's Synthesis example

Synthesis of Core 8-a

5-Bromobenzo[b]naphtho[1,2-d]thiophene (9 g, 28.73 mmol), CuCN (5.15 g, 57.47 mmol), and DMF (200 ml) were prepared using the synthesis example of Core 1-a above. 5 g (67%) were obtained.

Synthesis of Core 8-b

Core 8-a (13 g, 50.33 mmol), aqueous potassium hydroxide solution (12M, 55 mL), and 2-methoxyethanol (220 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 8-c

Core 8-b (12 g, 43.11 mmol), SOCl ₂ (15.39 g, 129.34 mmol), and benzene (150 ml) were obtained using the synthesis example of Core 1-c above to obtain 11.5 g (90%) of the product.

Synthesis of Core 8-d

Core 8-c (10 g, 33.69 mmol), aniline (3.14 g, 33.69 mmol), triethylamine (TEA) (3.58 g, 35.38 mmol), and THF (300 mL) were prepared using the synthesis example of Core 1-d above. 11 g (93%) of product were obtained.

Synthesis of Core 8-e

Core 8-d (10.5 g, 29.71 mmol), Pd(OCOCF ₃ ) ₂ (0.69 g, 2.08 mmol), and benzoic acid (3.63 g, 29.71) were prepared using the above synthesis example of Core 1-e to 8.77 g ( 84%) was obtained.

Synthesis of Core 8-f

Core 8-e (8.2 g, 23.33 mmol), POCl ₃ (2.61 mL, 28.0 mmol), N,N -diisopropylethylamine (DIEA) (2.41 g, 18.66 mmol), toluene (100 ml) of Core 1-f Using the synthesis example, 5.6 g (66%) of the product was obtained.

Synthesis of Core 8

Core 8-f (5.5 g, 14.87 mmol), bis(pinacolato)diboron (5.0 g, 17.84 mmol), PdCl ₂ (dppf) ₂ (0.36 g, 0.44 mmol), KOAc (4.38 g, 44.61 mmol), DMF ( 80 ml) using the synthesis example of Core 1 above to obtain 5.3 g (78%) of the product.

9. Core 9's Synthesis example

Synthesis of Core 9-a

3-Bromodibenzo[b,d]thiophene (12 g, 45.60 mmol), CuCN (8.17 g, 91.20 mmol), and DMF (250 ml) using the synthesis example of Core 1-a above, 6.8 g (72%) of the product got

Synthesis of Core 9-b

Core 9-a (14.5 g, 69.28 mmol), aqueous potassium hydroxide solution (12M, 65 mL), and 2-methoxyethanol (220 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 9-c

Core 9-b (10 g, 43.80 mmol), SOCl ₂ (15.63 g, 131.42 mmol), and benzene (200 ml) were obtained using the synthesis example of Core 1-c above to obtain 9.2 g (86%) of the product.

Synthesis of Core 9-d

Core 9-c (7.7 g, 31.21 mmol), aniline (2.91 g, 31.21 mmol), triethylamine (TEA) (3.32 g, 32.77 mmol), and THF (300 mL) were prepared using the synthesis example of Core 1-d above. 8.8 g (93%) of the product were obtained.

Synthesis of Core 9-e

Core 9-d (8.5 g, 28.01 mmol), Pd(OCOCF ₃ ) ₂ (0.65 g, 1.96 mmol), and benzoic acid (3.42 g, 28.01) were prepared using the above synthesis example of Core 1-e to 3.56 g ( 42%) was obtained.

Synthesis of Core 9-f

Core 9-e (3.5 g, 11.61 mmol), POCl ₃ (1.29 mL, 13.93 mmol), N,N -diisopropylethylamine (DIEA) (1.20 g, 9.29 mmol), toluene (60 ml) of Core 1-f Using the synthesis example, 2.4 g (66%) of the product was obtained.

Synthesis of Core 9

Core 9-f (2.30 g, 7.19 mmol), bis(pinacolato)diboron (2.42 g, 8.63 mmol), PdCl ₂ (dppf) ₂ (0.29 g, 0.35 mmol), KOAc (2.12 g, 21.57 mmol), DMF ( 50 ml) using the synthesis example of Core 1 above to obtain 2.2 g (77%) of the product.

10. Core 10's Synthesis example

Synthesis of Core 10-a

4-Bromodibenzo[b,d]thiophene (9.3 g, 35.34 mmol), CuCN (6.33 g, 70.68 mmol), and DMF (200 ml) using the synthesis example of Core 1-a above, 5.5 g (75%) of the product got

Synthesis of Core 10-b

Core 10-a (8.3 g, 39.66.33 mmol), aqueous potassium hydroxide solution (12M, 44 mL), and 2-methoxyethanol (220 ml) were obtained using the synthesis example of Core 1-b above.

Synthesis of Core 10-c

Core 10-b (11 g, 48.18 mmol), SOCl ₂ (17.20 g, 144.56 mmol), and benzene (150 ml) were obtained using the synthesis example of Core 1-c above to obtain 10.8 g (91%) of the product.

Synthesis of Core 10-d

Core 10-c (9.1 g, 36.88 mmol), aniline (3.44 g, 36.88 mmol), triethylamine (TEA) (3.92 g, 38.72 mmol), and THF (300 mL) were prepared using the synthesis example of Core 1-d above. 10.6 g (95%) of the product were obtained.

Synthesis of Core 10-e

Core 10-d (10.3 g, 33.95 mmol), Pd(OCOCF ₃ ) ₂ (0.79 g, 2.37 mmol), and benzoic acid (4.15 g, 33.95) were prepared using the above synthesis example of Core 1-e to 8.49 g ( 83%) was obtained.

Synthesis of Core 10-f

Core 10-e (8.4 g, 27.87 mmol), POCl ₃ (3.11 mL, 33.44 mmol), N,N -diisopropylethylamine (DIEA) (2.88 g, 22.29 mmol), toluene (100 ml) of Core 1-f Using the synthesis example, 5.4 g (66%) of the product was obtained.

Synthesis of Core 10

Core 10-f (4.8 g, 15.0 mmol), bis(pinacolato)diboron (5.05 g, 18.01 mmol), PdCl ₂ (dppf) ₂ (0.61 g, 0.75 mmol), KOAc (4.42 g, 45.02 mmol), DMF ( 90 ml) using the synthesis example of Core 1 above to obtain 4.6 g (75%) of the product.

Meanwhile, Table 1 below shows the FD-MS values of the core according to an embodiment of the present invention prepared according to the synthesis example as described above.

[Table 1]

II. Sub1 example of

Examples of Sub 1 of the scheme are as follows, but are not limited thereto, and Table 2 below shows their FD-MS values.

[Table 2]

III. Synthesis of Final Product

1. P-1-1 Synthesis example

Core 1 (1.7 g, 4.13 mmol) in Sub 1-1 (1.11 g, 4.13 mmol), Pd(PPh ₃ ) ₄ (0.03 g, 0.12 mmol), K ₂ CO ₃ (1.71 g, 12.39 mmol), THF ( 40 ml), H ₂ O (10 ml) was added and refluxed at 90° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 1.5 g (70%) of the product.

2. P-2-8 Synthesis example

Core 2 (2 g, 4.33 mmol) in Sub 1-27 (1.04 g, 4.33 mmol), Pd(PPh ₃ ) ₄ (0.15 g, 0.13 mmol), K ₂ CO ₃ (1.80 g, 13.0 mmol), THF ( 50 ml), H ₂ O (20 ml) was used in the above synthesis example of P-1-1 to obtain 1.4 g (65%) of the product.

3. P-3-9 Synthesis example

Core 3 (1.1 g, 2.67 mmol) in Sub 1-39 (1.0 g, 2.67 mmol), Pd(PPh ₃ ) ₄ (0.09 g, 0.08 mmol), K ₂ CO ₃ (1.11 g, 8.02 mmol), THF ( 30 ml), H ₂ O (10 ml) was used in the above synthesis example of P-1-1 to obtain 1.1 g (68%) of the product.

4. P-4-7 Synthesis example

Core 4 (1.9 g, 4.11 mmol) in Sub 1-17 (1.10 g, 4.11 mmol), Pd(PPh ₃ ) ₄ (0.14 g, 0.12 mmol), K ₂ CO ₃ (1.71 g, 12.35 mmol), THF ( 50 ml), H ₂ O (20 ml) was used in the above synthesis example of P-1-1 to obtain 1.6 g (69%) of the product.

5. P-5-12 Synthesis example

Core 5 (0.90 g, 2.18 mmol) in Sub 1-53 (0.64 g, 2.18 mmol), Pd(PPh ₃ ) ₄ (0.08 g, 0.06 mmol), K ₂ CO ₃ (0.91 g, 6.56 mmol), THF ( 30 ml), H ₂ O (10 ml) was used in the above synthesis example of P-1-1 to obtain 0.82 g (70%) of the product.

6. P-6-11 Synthesis example

Core 6 (2.0 g, 4.86 mmol) in Sub 1-61 (1.36 g, 4.86 mmol), Pd(PPh ₃ ) ₄ (0.17 g, 0.14 mmol), K ₂ CO ₃ (2.02 g, 14.58 mmol), THF ( 60 ml), H ₂ O (30 ml) was used in the above synthesis example of P-1-1 to obtain 1.93 g (75%) of the product.

7. P-7-2 Synthesis example

Sub 1-6 (0.87 g, 3.25 mmol), Pd(PPh ₃ ) ₄ (0.11 g, 0.09 mmol), K ₂ CO ₃ (1.35 g, 9.75 mmol), THF ( 50 ml), H ₂ O (20 ml) was used in the above synthesis example of P-1-1 to obtain 1.34 g (73%) of the product.

8. P-8-9 Synthesis example

Sub 1-13 (0.88 g, 3.46 mmol), Pd(PPh ₃ ) ₄ (0.12 g, 0.10 mmol), K ₂ CO ₃ (1.44 g, 10.40 mmol), THF ( 50 ml), H ₂ O (20 ml) was used in the above synthesis example of P-1-1 to obtain 1.3 g (69%) of the product.

9. P-9-4 Synthesis example

Core 9 (2.2 g, 5.34 mmol) in Sub 1-18 (1.43 g, 5.34 mmol), Pd(PPh ₃ ) ₄ (0.19 g, 0.16 mmol), K ₂ CO ₃ (2.22 g, 16.04 mmol), THF ( 50 ml), H ₂ O (20 ml) was prepared using the above synthesis example of P-1-1 to obtain 1.7 g (63%) of the product.

10. P-8-9 Synthesis example

Sub 1-46 (1.79 g, 4.61 mmol), Pd(PPh ₃ ) ₄ (0.16 g, 0.13 mmol), K ₂ CO ₃ (1.92 g, 13.85 mmol), THF ( 50 ml), H ₂ O (20 ml) was used in the above synthesis example of P-1-1 to obtain 1.8 g (68%) of the product.

Meanwhile, Table 3 below shows the FD-MS values of the compounds according to an embodiment of the present invention prepared according to the above synthesis examples.

[Table 3]

Manufacturing evaluation of organic electric devices

[ Example One] Red organic light emitting device (Phosphor Host)

An organic electroluminescent device was manufactured according to a conventional method by using the compound according to an embodiment of the present invention as a light emitting host material of the light emitting layer. First, on an ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (hereinafter referred to as '2-TNATA') was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then 4,4-bis[N-(1) -naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as 'NPD') was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Then, on the hole transport layer, compound P-1-1 according to an embodiment of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, '(piq) ₂ Ir(acac) ') was used as a dopant material and doped in a weight ratio of 95:5 to deposit a light emitting layer to a thickness of 30 nm. Subsequently, ((1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter referred to 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 referred to as 'Alq ₃ ') was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Then, an organic electroluminescent device was manufactured by depositing LiF, which is an alkali metal halide to a thickness of 0.2 nm, to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 200] Red organic light emitting device (Phosphor Host)

Except for using one of the compounds P-1-2 to P-10-20 according to an embodiment of the present invention shown in Table 4 below instead of the compound P-1-1 of the present invention as the host material of the light emitting layer, An organic electroluminescent device was manufactured in the same manner as in Example 1.

[ comparative example 1] to [ comparative example 5] Red organic light emitting device (Phosphor Host)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following comparative compounds A to E was used instead of the compound P-1-1 of the present invention as a host material for the light emitting layer.

<Comparative compound A> <Comparative compound B> <Comparative compound C>

<Comparative compound D> <Comparative compound E>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 200 and Comparative Examples 1 to 5 of the present invention, electroluminescence (EL) characteristics with PR-650 manufactured by photoresearch was measured, and the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 2500 cd/m ² standard luminance. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the device measurement results in Table 4, the device using the compound according to an embodiment of the present invention as the phosphorescent host material of the light emitting layer has a driving voltage than the device using Comparative Compounds 1 to 5 as the phosphorescent host material of the light emitting layer. and luminous efficiency were remarkably improved.

A device using Comparative Compound C, in which naphthalene is fused to dibenzothiophene, is superior to a device using Comparative Compound A, which is CBP, which is generally used as a host material, and Comparative Compound B, which is Bebq ₂ . The device results were shown, and it was confirmed that the devices using Comparative Compound D and Comparative Compound E, in which quinoline, not naphthalene, were bonded to dibenzothiene, showed lower driving voltage and higher efficiency than the device using Comparative Compound C. can Comparative Compound D and Comparative Compound E have the same quinoline bonding to a heterocyclic ring such as dibenzothiene or carbazole, but the bonding position is different. I can confirm that. Therefore, this suggests that the properties may be significantly different depending on the bonding position and type (nitrogen (N) substitution position and number).

The compound according to an embodiment of the present invention in which the position conjugated with Comparative Compound E (nitrogen substitution position) is the same or similar, but the hetero element has sulfur (S) or oxygen (O) other than nitrogen, Comparative Compounds A to Compared with the comparative compound E, it showed the best device result. This suggests that the properties of the compound and the results of the device may be significantly different depending on the type of hetero element.

Among the compounds according to an embodiment of the present invention, compounds represented by Formulas 1-1 to 1-4 in which R ¹⁰ and R ¹¹ or R ²² and R ²³ are bonded to each other to form a ring together with the benzene ring to which they are bonded It showed the best device result. This is because the compound in which a ring is formed has better thermal stability than other compounds in which R ¹⁰ and R ¹¹ or R ²² and R ²³ are bonded to each other and does not form a ring, and has an appropriate energy level, so that the energy balance in the device ( It can be explained as a result of improving energy balance).

The above description is merely 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 intended to illustrate, not to limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all descriptions within the scope equivalent thereto should be construed 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 (11)

A compound represented by the following formula (1):
<Formula 1>

<Formula 2><Formula3><Formula4>

In the above formula,
X is -O-, -S-,
Ring A is one of Formulas 2 to 4,
R ² to R ²³ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ Aryl group; fluorenyl group; C ₂ -C ₆₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₁ -C ₅₀ Alkyl group; C ₆ -C ₆₀ A fused ring group of an aromatic ring and a C ₃ -C ₆₀ aliphatic ring; C ₂ -C ₂₀ alkenyl group; C ₁ -C ₃₀ alkoxyl group; and a C ₆ -C ₃₀ aryloxy group; selected from the group consisting of, wherein R ¹⁰ and R ¹¹ or R ²² and R ²³ may be bonded to each other to selectively form an aromatic or heteroaromatic ring,
R ¹ is -L ¹ -(Ar ¹ ) or -L ² -(Ar ¹ )(Ar ² ),
L ¹ is a single bond; C ₆ -C ₆₀ Arylene group; fluorenylene group; And O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ Heteroarylene group; selected from the group consisting of,
L ² is a C ₆ -C ₆₀ trivalent arylene group; trivalent fluorenylene group; And O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ A trivalent heteroarylene group; is selected from the group consisting of,
Ar ¹ and Ar ² are each independently selected from a C ₆ -C ₆₀ aryl group; fluorenyl group; C ₃ -C ₆₀ A fused ring group of an aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₂ -C ₆₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L'-N(R ^a )(R ^b );
The L' is a single bond; C ₆ -C ₆₀ Arylene group; fluorenylene group; C ₃ -C ₆₀ A fused ring group of an aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ A heterocyclic group; is selected from the group consisting of,
wherein R ^a and R ^b are each independently selected from a C ₆ -C ₆₀ aryl group; fluorenyl group; C ₃ -C ₆₀ A fused ring group of an aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₆₀ A heterocyclic group; is selected from the group consisting of,
The aryl group, fluorenyl group, heterocyclic group, alkyl group, fused ring group, alkenyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group, and heteroarylene group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; a C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ Aryl alkenyl group; may be substituted with one or more substituents selected from the group consisting of. The method of claim 1,
Formula 1 is a compound, characterized in that represented by one of the following Formulas 5 to 10:
<Formula 5><Formula6><Formula7>

<Formula 8><Formula9><Formula10>

In Formulas 5 to 10, R ¹ to R ²³ and X are the same as defined in claim 1. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 1-1 to 1-4:
<Formula 1-1><Formula1-2><Formula1-3><Formula1-4>

In Formulas 1-1 to 1-4, R ¹ to R ⁹ , R ¹⁸ to R ²¹ and X are the same as defined in claim 1,
R ²⁴ to R ²⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ Aryl group; fluorenyl group; C ₂ -C ₆₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₁ -C ₅₀ Alkyl group; C ₆ -C ₆₀ A fused ring group of an aromatic ring and a C ₃ -C ₆₀ aliphatic ring; C ₂ -C ₂₀ alkenyl group; C ₁ -C ₃₀ alkoxyl group; and a C ₆ -C ₃₀ aryloxy group; may be selected from the group consisting of. The method of claim 1,
A compound characterized in that it is one of the following compounds:

. delete a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound of claim 1. 7. The method of claim 6,
The organic material layer is an organic electric device comprising at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and a light emitting layer. 7. The method of claim 6,
The organic electric device further comprising a light efficiency improving layer formed on at least one surface opposite to the organic material layer of one surface of the first electrode and the second electrode. 7. The method of claim 6,
The organic material layer is an organic electric device, characterized in that 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 comprising the organic electric device of claim 6; and
An electronic device comprising a; a control unit for driving the display device. 11. The method of claim 10,
The organic electroluminescent device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and an electronic device, characterized in that at least one of a single color or white lighting device.

Images