KR20210040895A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

An object of the present invention is to provide a compound capable of improving high luminous efficiency, lower driving voltage and improve lifespan of an element, and an electronic device thereof. In one aspect, the present invention provides the compound represented by the following chemical formula. By using the compound according to the present invention, it is possible to achieve high luminous efficiency and low driving voltage of the element, and to greatly improve lifespan of the element.

Description

Compound for organic electric device, organic electric device using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT 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 emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic electric device using the 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.

The light-emitting material can be classified into a high-molecular type and a low-molecular type according to its molecular weight, and can be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emitting mechanism. . In addition, the light-emitting material may be classified 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 light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a long wavelength due to the interaction between molecules, and the color purity decreases or the efficiency of the device decreases due to the light-emitting attenuation effect. A host/dopant system may be used as a light-emitting material in order to increase the luminous efficiency through. The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light-emitting layer is mixed in the light-emitting layer, excitons generated in the light-emitting 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 of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

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 a very important factor for portable displays that have a limited power supply source, such as batteries, and efficiency and life issues must also be solved.

Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the life span. However, simply improving the organic material layer cannot maximize the efficiency. This is because long life and high efficiency can be achieved at the same time 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.

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. Supported by the material must precede, but the development of a stable and efficient organic material layer material for an organic electric device has not been made sufficiently. Therefore, the development of new materials continues to be required. In particular, development of a light emitting layer material is also urgently required.

In the case of polycyclic cyclic compounds containing heteroatoms, the difference in properties according to the material structure is very large, so they are applied to various layers as OLED materials.

In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, and physical properties are different depending on the number of rings and fused positions, and the type and arrangement of heteroatoms. come. (HTL or phosphorescent host application: US 8334058, KR 1108398; ETL application: KR 0813385, KR 0765078) In addition, recently, OLED material development for the type, number, and location of heteroatoms of a 5-cyclic cyclic compound is actively progressing. (KR 1418146, KR 0938796, KR 2011-0043439, KR2012-0140557, KR 2013-0071547, JP2010-230312, etc.)

An object of the present invention is to provide a compound capable of improving a high luminous efficiency, a low driving voltage, and a lifetime of a device, an organic electric device using the same, and an electronic device thereof.

Our company has been developing materials related to 7-ring cyclic compounds (KR 1108512, US13/390043) in 2009 using the properties of the polycyclic cyclic compounds. However, in the case of the 7-ring cyclic compound, the efficiency is good, but the lifespan is relatively low, so it is very difficult to apply it to the current OLED panel. Therefore, although the present invention has the same 7 ring structure as KR 1108512, the fused position constituting the 7 ring cyclic compound and the type and arrangement of heteroatoms were different to develop a high-efficiency, long-lived material.

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 the present invention, high luminous efficiency and low driving voltage of the device can be achieved, and the life of the device can be greatly improved.

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 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, when 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 addition, in describing the constituent elements of the present invention, terms such as first, second, A, B, (a) and (b) may be used. These terms are for distinguishing the constituent element from other constituent elements, and the nature, order, or order of the constituent element is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, the 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”.

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 saturated aliphatic functional groups including alkyl groups and cycloalkyl-substituted alkyl groups.

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.

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 straight or branched chain group, and are limited thereto. It is not.

The term "cycloalkyl" as used herein refers to 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 herein refers to 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 terms "alkenyl group", "alkenoxy group", "alkenyloxy group", or "alkenyloxy group" as used in the present invention mean an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It has a carbon number of, but is not limited thereto.

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

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatics, and includes an aromatic ring formed by neighboring substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorene group, a spirofluorene group, or a spirobifluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has the number of carbon atoms described herein.

In addition, when the prefixes are named consecutively, it means that the 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 alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group. And the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term "heteroalkyl" means an alkyl containing one or more heteroatoms unless otherwise specified. The term "heteroaryl group" or "heteroarylene group" as used herein refers to an aryl group or arylene group having 2 to 60 carbon atoms each including one or more heteroatoms, unless otherwise specified, and is limited thereto. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

The term "heterocyclic group" as used in the present invention includes one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, unless otherwise specified, heteroaliphatic ring and hetero It contains an aromatic ring. It may be formed by combining adjacent functional groups.

As used herein, the term "heteroatom" refers to N, O, S, P or Si unless otherwise specified.

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.

Unless otherwise specified, the term "aliphatic" as used herein refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" used in the present invention refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms, or a combination thereof, It contains saturated or unsaturated rings.

Other hetero compounds or hetero radicals other than the aforementioned hetero compounds include one or more heteroatoms, but are not limited thereto.

Unless otherwise specified, the term "carbonyl" as used herein is represented by -COR', where R'is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Is a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise stated, the term "ether" used in the present invention is represented by -RO-R', wherein R or R'are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, and 6 to 30 carbon atoms. It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

In addition, unless expressly stated, the term "substituted or unsubstituted" used in the present invention means "substituted" deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkylamine group, C ₁ to C ₂₀ alkylthiophene group, C ₆ to C ₂₀ arylthiophene group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a 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 group, a germanium group, and a C ₂ ~ C _{20 heterocyclic group, and is not limited to these substituents.}

In addition, unless there is an explicit description, the formula used in the present invention is applied in the same manner as the definition of the substituent 　 in 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 carbons forming a 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, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode 180 formed on a substrate 110. ) Between the organic material layer containing the compound according to the present invention. At this time, 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. In this case, other layers other than the emission layer 150 may not be formed. A hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, a buffer layer 141, etc. may be further included, and the electron transport layer 160 may serve as a hole blocking layer.

Further, although not shown, the organic electric device according to the present invention may further include 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.

The compound according to the present invention applied to the organic material layer is the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150, or the dopant or the light efficiency improvement layer. It could be used as a material. Preferably, the compound of the present invention may be used as the light emitting layer 150.

On the other hand, even with the same core, the band gap, electrical characteristics, and interfacial characteristics 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 are also very It is important, and in particular, long life and high efficiency can be achieved at the same time when an optimum combination of energy level and T1 value between each organic material layer, and intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved.

Therefore, in the present invention, by forming a light emitting layer using the compound represented by Formula 1, the lifespan of the organic electronic device is optimized by optimizing the energy level and T1 value between each organic material layer, and 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 a physical vapor deposition (PVD) method. For example, an anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer ( After forming an organic material layer including 160) and the electron injection layer 170, it may be manufactured by depositing a material that can be used as the cathode 180 thereon.

In addition, the organic material layer is a solution process or a solvent process other than a 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 method of forming the organic material layer.

The organic electric device according to the present invention may be a top emission type, a bottom emission type, or a double-sided 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 using electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom. May be applied to these WOLEDs as well.

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 photoconductor (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 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>

In Formula 1,

Ar ¹ and Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _{60; And a C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; And -N(R')(R"); may be selected from the group consisting of.

Wherein the R'and R" are independently of each other C ₆ ~ C _{60 aryl group; fluorenyl group; C 2} ~ C ₆₀ heterocycle containing at least one hetero atom of O, N, S, Si and P Group; And C ₁ ~ C ₅₀ It may be selected from the group consisting of an alkyl group.

L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; _{A C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; A fused ring group of a C ₃ to C ₆₀ divalent aliphatic ring and a C ₆ to C _{60 divalent aromatic ring;} And a divalent aliphatic hydrocarbon group; it may be selected from the group consisting of. Here, each of these (except for a single bond) is deuterium; Nitro group; Nitrile group; Halogen group; A C ₁ to C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; C ₂ ~ C ₂₀ Heterocyclic group; C ₁ ~ C ₂₀ alkoxy group; And an amino group; may be substituted with one or more substituents selected from the group consisting of.

X ¹ to X ⁸ are each independently CR ¹ or N.

R ¹ is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P; A fused ring group of an aromatic ring of C ₆ to C _{60 and an aliphatic ring of C 3} to C _60; A C ₁ to C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And it may be selected from the group consisting of _{C 6} ~ C _{30 aryloxy group.}

In addition, when a plurality of R ¹ is present, they are the same as or different from each other, and each adjacent R ¹ may be bonded to each other to form at least one ring. In this case, R ¹ not forming a ring may be defined in the same manner as defined above. In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring, a C ₂ ~ C ₆₀ heterocycle, a C ₃ ~ C ₆₀ alicyclic ring, or a fused ring consisting of a combination thereof And the like, and may be a single ring or multiple rings, as well as a saturated or unsaturated ring.

For example, when Ar ¹ , Ar ² , R', R", L ¹ , L ² , R ¹ is an aryl group or an arylene group, Ar ¹ , Ar ² , R', R", L ¹ , L ² , R ¹ may be, independently of each other, a phenyl group or a phenylene group, a biphenyl group or a biphenylene group, a terphenyl group or a terphenylene group, a naphthyl group or a naphthylene group, a phenanthryl group or a phenanthrylene group.

_{Ring A is a C 6} ~ C ₂₀ aromatic ring condensed with two adjacent rings (thiophene, pyrrole). Here, the aromatic ring of the _{C 6} ~ C _{20 of the A ring is deuterium;} halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P; Halogen group; A C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C _{60 and an aliphatic ring of C 3} to C _60; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And C ₆ ~ C ₃₀ may be substituted with one or more groups selected from the group consisting of aryloxy groups, and when a plurality of substituents are present, they are the same as or different from each other, and adjacent substituents may be bonded to each other to form at least one ring. . In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring, a C ₂ ~ C ₆₀ heterocycle, a C ₃ ~ C ₆₀ alicyclic ring, or a fused ring consisting of a combination thereof And the like, and may be a single ring or multiple rings, as well as a saturated or unsaturated ring.

In this case, the _{aromatic ring of C 6} ~ C ₂₀ of the A ring may be benzene, naphthalene, or phenanthrene, but is not limited thereto.

Specifically, in Formula 1, each A ring is independently It may be represented by one of the following formulas A1 to A6.

The * of A1 to A6 is a bonding site that shares any one side of each of the rings (thiophene, pyrrole) adjacent to the A ring and condenses.

l is an integer of 0 to 2, and m is an integer of 0 to 4.

Wherein R ² and R ³ are deuterium; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P; Halogen group; A C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C _{60 and an aliphatic ring of C 3} to C _60; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And it may be selected from the group consisting of _{C 6} ~ C _{30 aryloxy group.}

In addition, when a plurality of R ² and R ³ are present, a plurality of R ² or a plurality of R ³ are the same as or different from each other, and Adjacent R ² and adjacent R ³ may be bonded to each other to form at least one ring. At this time, R ² and R ³ that do not form a ring may each be defined the same as defined above. In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring, a C ₂ ~ C ₆₀ heterocycle, a C ₃ ~ C ₆₀ alicyclic ring, or a fused ring consisting of a combination thereof And the like, and may be a single ring or multiple rings, as well as a saturated or unsaturated ring.

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

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

In Formulas 2 to 5,

The X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ and L ² may be the same as X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ and L ² defined in Formula 1 above.

n is an integer from 0 to 2.

R ⁴ is heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P; Halogen group; A C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C _{60 and an aliphatic ring of C 3} to C _60; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And it may be selected from the group consisting of _{C 6} ~ C _{30 aryloxy group.}

In addition, when a plurality of R ⁴ is present, they are the same as or different from ^{each other, and adjacent R 4} may be bonded to each other to form at least one ring. At this time, R ⁴ that does not form a ring may be defined in the same manner as defined above. In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring, a C ₂ ~ C ₆₀ heterocycle, a C ₃ ~ C ₆₀ alicyclic ring, or a fused ring consisting of a combination thereof And the like, and may be a single ring or multiple rings, as well as a saturated or unsaturated ring.

In Formulas 1 to 5, each of the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxyl group, and aryloxy group 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 to C _20; A C ₁ to C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C _20; C ₆ ~ C ₂₀ aryl group; _{C 6} ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; C ₈ ~ C ₂₀ arylalkenyl group; And -N (R ^a ) (R ^b ); may be substituted with one or more substituents selected from the group consisting of.

R ^a and R ^b 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 hetero atom of P; And C ₁ ~ C ₅₀ Alkyl group; It may be selected from the group consisting of.

Here, in the case of the aryl group, the number of carbon atoms may be 6 to 60, preferably 6 to 40, more preferably an aryl group having 6 to 30 carbon atoms,

In the case of the heterocyclic group, the number of carbon atoms may be 2 to 60, preferably 2 to 30, more preferably 2 to 20 carbon atoms,

In the case of the alkyl group, the number of carbon atoms may be 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms.

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

<Formula 6> <Formula 7>

<Formula 8> <Formula 9>

In Chemical Formulas 6 to 9,

The X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ and L ² may be the same as X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ and L ² defined in Formula 1 above.

More specifically, the compound represented by Chemical Formulas 1 to 9 may be any one of the following compounds.

As another embodiment, the present invention provides a compound for an organic electric device represented by Formula 1 above.

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

In this case, 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 Formula 1, and the compound represented by Formula 1 is a hole injection layer and a hole transport layer of the organic material layer. , A light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer may be contained in at least one layer. In particular, the compound represented by Formula 1 may be included in the emission layer.

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 emission auxiliary layer, a light emitting layer, an electron transport layer, or an electron injection layer. In particular, the compound represented by Formula 1 may be used as a material for the light emitting layer. Specifically, an organic electric device including one of the compounds represented by Formulas 2 to 9 is provided in the organic material layer, and more specifically, the An organic electric device including a compound represented by the individual formulas (P-1 to P-171) is provided in the organic material layer.

In another embodiment, the compound alone is contained in at least one of the hole injection layer, the hole transport layer, the emission auxiliary layer, the emission layer, the electron transport layer, and the electron injection layer of the organic material layer, or the It provides an organic electric device, characterized in that the compound is contained in a combination of two or more different from each other, or the compound is contained in a combination of two or more of the other compounds. In other words, each of the layers may contain a compound corresponding to Formula 1 to Formula 9 alone, and a mixture of two or more compounds of Formula 1 to Formula 9 may be included, and the compounds of claims 1 to 5 and the present Mixtures with compounds that do not correspond to the invention may be included. Here, the compound not applicable to the present invention may be a single compound or may be two or more types of compounds. In this case, when the compound is contained in a combination of two or more of the other compounds, the other compound may be a known compound of each organic material layer or may be a compound to be developed in the future. At this time, the compound contained in the organic material layer may be composed of only the same type of compound, but may be a mixture of two or more different types of compounds represented by the formula (1).

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.

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 ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ , L ² and ring A are the same as defined in Formula 1 above)

Ⅰ. Synthesis Example of Sub 1

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

<Reaction Scheme 2>

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

1. Sub 1-24 synthesis

<Reaction Scheme 3>

(1) Sub 1-II-24 synthesis

Put Sub 1-I-24 (160 g, 151.9 mmol) in a round bottom flask, (2-nitrophenyl)boronic acid (86.1 g, 515.9 mmol), Pd(PPh ₃ ) ₄ (17.9 g, 15.5 mmol), NaOH (61.9 g, 1548 mmol), THF (2270 ml), and water (1134 ml) are added. Then, it is heated to reflux at 80℃~90℃. When the reaction is complete, dilute with distilled water at room temperature and extract with _{CH 2} Cl _{2 and water.} The organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 152.6 g of the product. (Yield: 77%)

(2) Sub 1-III-24 synthesis

Sub 1-II-24 (151 g, 393.97 mmol) obtained in the above synthesis was dissolved in o-dichlorobenzene (1572 ml) in a round bottom flask, triphenylphosphine (309.2 g, 1179 mmol) was added and stirred at 200°C. When the reaction was completed, o-dichlorobenzene was removed through distillation, followed by _{extraction 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 59.5 g of a product. (Yield: 43%)

(3) Sub 1-IV-24 synthesis

Sub 1-III-24 (59 g, 167.5 mmol) was dissolved in nitrobenzene (838 ml) in a round bottom flask, and then 2-iodonaphthalene (46.8 g, 184.2 mmol), Na ₂ SO ₄ (23.8 g, 167.5 mmol), K ₂ CO ₃ (23.1 g, 167.5 mmol) and Cu (3.2 g, 50.2 mmol) were added and stirred at 200°C. When the reaction was completed, nitrobenzene was removed through distillation and 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 41.7 g of the product. (Yield: 52%)

(4) Sub 1-V-24

Sub 1-IV-24 in round bottom flask (40 g, 83.6 mmol) was added, (2-nitrophenyl)boronic acid (14 g, 83.6 mmol), Pd(PPh ₃ ) ₄ (2.9 g, 2.5 mmol), NaOH (10 g, 251 mmol), THF ( 368 ml) and water (184 ml) are added. Then, it is heated to reflux at 80℃~90℃. When the reaction is complete, dilute with distilled water at room temperature and extract with _{CH 2} Cl _{2 and water.} The organic layer was dried over MgSO 4, concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 34 g of a product. (Yield: 78%)

(5) Sub 1-24 synthesis

Sub 1-V-24 (28 g, 53.8 mmol) obtained in the above synthesis was dissolved in o-dichlorobenzene (215 ml) in a round bottom flask, triphenylphosphine (42.3 g, 161.4 mmol) was added and stirred at 200°C. When the reaction was completed, o-dichlorobenzene was removed through distillation, followed by _{extraction 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 16.6 g of a product. (Yield: 63%)

2. Sub 1-36 synthesis

<Reaction Scheme 4>

(1) Sub 1-II-36 synthesis

Sub 1-I-36 (241 g, 518.1 mmol), (2-nitrophenyl)boronic acid (86.5 g, 518.1 mmol), Pd(PPh ₃ ) ₄ (18 g, 15.5 mmol), NaOH (62.2 g, 1554 mmol) ), THF (2280 ml), and water (1140 ml) were obtained using the Sub 1-II-24 synthesis method to obtain 188.4 g of the product. (Yield: 79%)

(2) Sub 1-III-36 synthesis

Sub 1-II-36 (187 g, 406.2 mmol), o-dichlorobenzene (1645 ml), and triphenylphosphine (319.6 g, 1218.7 mmol) were obtained using the Sub 1-III-24 synthesis method to obtain 71.3 g of the product. (Yield: 41%)

(3) Sub 1-IV-36 synthesis

Sub 1-III-36 (70.5 g, 164.6 mmol), nitrobenzene (823 ml), 2-iodo-1,1'-biphenyl (50.7 g, 181 mmol), Na ₂ SO ₄ (23.4 g, 164.6 mmol), K ₂ CO ₃ (22.7 g, 164.6 mmol), Cu (3.1 g, 49.4 mmol) was obtained using the Sub 1-IV-24 synthesis method to obtain 46.8 g of the product. (Yield: 49%)

(4) Sub 1-V-36 synthesis

Sub 1-IV-36 (46 g, 79.2 mmol), (2-nitrophenyl)boronic acid (13.2 g, 79.2 mmol), Pd(PPh ₃ ) ₄ (2.7 g, 2.4 mmol), NaOH (9.5 g, 238 mmol), THF (349 ml ), water (174 ml) was obtained using the Sub 1-V-24 synthesis method to obtain 35.5 g of the product. (Yield: 72%)

(5) Sub 1-36 synthesis

Sub 1-V-36 obtained in the above synthesis (33 g, 53 mmol), o-dichlorobenzene (212 ml), and triphenylphosphine (41.7 g, 159 mmol) were used to obtain 16.4 g of a product using the Sub 1-24 synthesis method. (Yield: 60%)

3. Sub 1-59 synthesis

<Reaction Scheme 5>

(1) Sub 1-II-59 synthesis

Sub 1-I-59 (357.5 g, 918.9 mmol), (2-nitropyridin-3-yl)boronic acid (154.3 g, 918.9 mmol), Pd(PPh ₃ ) ₄ (31.9 g, 27.6 mmol), NaOH (110.3 g, 2757 mmol), THF (4043 ml), and water (2021 ml) were obtained by using the Sub 1-II-24 synthesis method to obtain 215.9 g of the product. (Yield: 61%)

(2) Sub 1-III-59 synthesis

Sub 1-II-59 (215.5 g, 559.4 mmol), o-dichlorobenzene (2237 ml), and triphenylphosphine (440.2 g, 1678.2 mmol) were obtained using the Sub 1-III-24 synthesis method to obtain 84.97 g of the product. (Yield: 43%)

(3) Sub 1-IV-59 synthesis

Sub 1-III-59 (84.6 g, 239.5 mmol), nitrobenzene (1200 ml), 2-iodo-1,1'-biphenyl (73.8 g, 263.4 mmol), Na ₂ SO ₄ (34 g, 239.5 mmol), K ₂ CO ₃ (33.1 g, 239.5 mmol), Cu (4.6 g, 71.8 mmol) was obtained by using the Sub 1-IV-24 synthesis method 50.8 g. (Yield: 42%)

(4) Sub 1-V-59 synthesis

Sub 1-IV-59 (50 g, 98.9 mmol), (5-(naphthalen-2-yl)-2-nitrophenyl)boronic acid (29 g, 98.9 mmol), Pd(PPh ₃ ) ₄ (3.4 g, 2.97 mmol), NaOH (11.9 g, 297 mmol), THF (435 ml), and water (218 ml) were obtained using the Sub 1-V-24 synthesis method to obtain 41.3 g of the product. (Yield: 62%)

(5) Sub 1-59 synthesis

Sub 1-V-59 (40 g, 59.4 mmol), o-dichlorobenzene (237 ml), triphenylphosphine (46.7 g, 178 mmol) obtained in the above synthesis was obtained using the Sub 1-24 synthesis method to obtain 16 g of a product. (Yield: 42%)

4. Sub 1-71 synthesis

<Reaction Scheme 6>

(1) Sub 1-II-71 synthesis

Sub 1-I-71 (308 g, 701.4 mmol), (2-nitrophenyl)boronic acid (117.1 g, 701.4 mmol), Pd(PPh ₃ ) ₄ (24.3 g, 21 mmol), NaOH (84.2 g, 2104 mmol) ), THF (3086 ml), and water (1543 ml) were obtained using the Sub 1-II-24 synthesis method to obtain 219.3 g of the product. (Yield: 72%)

(2) Sub 1-III-71 synthesis

Sub 1-II-71 (220 g, 506.5 mmol), o-dichlorobenzene (2026 ml), triphenylphosphine (398.6 g, 1519.7 mmol) was obtained by using the Sub 1-III-24 synthesis method, 87.6 g of the product. (Yield: 43%)

(3) Sub 1-IV-71 synthesis

Sub 1-III-71 (79 g, 196.4 mmol), nitrobenzene (982 ml), 4-iodo-1,1'-biphenyl (60.5 g, 216 mmol), Na ₂ SO ₄ (27.9 g, 196.4 mmol), K ₂ CO ₃ (27.1 g, 196.4 mmol), Cu (3.7 g, 58.9 mmol) was obtained by using the Sub 1-IV-24 synthesis method , 49 g of the product. (Yield: 45%)

(4) Sub 1-V-71 synthesis

Sub 1-IV-71 (48 g, 86.6 mmol), (2-nitrophenyl)boronic acid (14.5 g, 86.6 mmol), Pd(PPh ₃ ) ₄ (3 g, 2.6 mmol), NaOH (10.4 g, 259.7 mmol ), THF (381 ml), and water (190 ml) were obtained using the Sub 1-V-24 synthesis method to obtain 35.1 g of the product. (Yield: 68%)

(5) Sub 1-71 synthesis

Sub 1-V-71 (31 g, 52 mmol), o-dichlorobenzene (208 ml), and triphenylphosphine (40.9 g, 156 mmol) obtained in the synthesis were obtained by using the Sub 1-24 synthesis method to obtain 13.2 g of a product. (Yield: 45%)

5. Sub 1-63 synthesis

<Reaction Scheme 7>

(1) Sub 1-II-63 synthesis

Sub 1-I-63 (251 g, 645.2 mmol), (2-nitrophenyl)boronic acid (107.7 g, 645.2 mmol), Pd(PPh ₃ ) ₄ (22.4 g, 19.4 mmol), NaOH (77.4 g, 1935 mmol) ), THF (2839 ml), and water (1419 ml) were obtained using the Sub 1-II-24 synthesis method to obtain 188.4 g of the product. (Yield: 76%)

(2) Synthesis of Sub 1-III-63

Sub 1-II-63 (105 g, 273.3 mmol), o-dichlorobenzene (1093 ml), and triphenylphosphine (215 g, 819.8 mmol) were obtained using the Sub 1-III-24 synthesis method to obtain 40.4 g of a product. (Yield: 42%)

(3) Sub 1-IV-63 synthesis

Sub 1-III-63 (38 g, 107.9 mmol), nitrobenzene (540 ml), iodobenzene (24.2 g, 118.7 mmol), Na ₂ SO ₄ (15.3 g, 107.9 mmol), K ₂ CO ₃ (14.9 g, 107.9 mmol), Cu (2.1 g, 32.4 mmol) was obtained using the Sub 1-IV-24 synthesis method to obtain 31.9 g of the product. (Yield: 69%)

(4) Sub 1-V-63 synthesis

Sub 1-IV-63 (31 g, 72.4 mmol), (2-nitrophenyl)boronic acid (12.1 g, 72.4 mmol), Pd(PPh ₃ ) ₄ (2.5 g, 2.2 mmol), NaOH (8.7 g, 217.1 mmol) ), THF (318 ml), and water (159 ml) were obtained using the Sub 1-V-24 synthesis method to obtain 26.9 g of the product. (Yield: 79%)

(5) Sub 1-63 synthesis

Sub 1-V-63 (26 g, 55 mmol), o-dichlorobenzene (221 ml), triphenylphosphine (43.5 g, 166 mmol) obtained in the synthesis was obtained by using the Sub 1-24 synthesis method to obtain 16.5 g of a product. (Yield: 68%)

6. Sub 1-107 synthesis

<Reaction Scheme 8>

(1) Sub 1-II-107 synthesis

Sub 1-I-107 (275 g, 626.3 mmol), (2-nitrophenyl)boronic acid (104.5 g, 626.3 mmol), Pd(PPh ₃ ) ₄ (21.7 g, 18.8 mmol), NaOH (75.2 g, 1879 mmol) ), THF (2756 ml), and water (1378 ml) were obtained by using the Sub 1-II-24 synthesis method to obtain 190.4 g of the product. (Yield: 70%)

(2) Synthesis of Sub 1-III-107

Sub 1-II-107 (189.5 g, 436.3 mmol), o-dichlorobenzene (1745 ml), triphenylphosphine (343.3 g, 1309 mmol) was obtained by using the Sub 1-III-24 synthesis method, 82.5 g of the product. (Yield: 47%)

(3) Sub 1-IV-107 synthesis

Sub 1-III-107 (82.2 g, 204.3 mmol), nitrobenzene (1022 ml), 5'-bromo-1,1':3',1''-terphenyl (69.5 g, 224.8 mmol), Na ₂ SO ₄ (29 g, 204.3 mmol), K ₂ CO ₃ (28.2 g, 204.3 mmol), and Cu (3.9 g, 61.3 mmol) were obtained using the Sub 1-IV-24 synthesis method to obtain 60.6 g of the product. (Yield: 47%)

(4) Sub 1-V-107 synthesis

Sub 1-IV-107 (60 g, 95.1 mmol), (4-nitro-[1,1'-biphenyl]-3-yl)boronic acid (23.1 g, 95.1 mmol), Pd(PPh ₃ ) ₄ (3.3 g, 2.9 mmol), NaOH (11.4 g, 285.4 mmol), THF (419 ml), and water (209 ml) were obtained using the Sub 1-V-24 synthesis method to obtain 36.3 g of the product. (Yield: 51%)

(5) Sub 1-107 synthesis

Sub 1-V-107 (35 g, 46.7 mmol), o-dichlorobenzene (187 ml), and triphenylphosphine (36.8 g, 140 mmol) obtained in the synthesis were obtained by using the Sub 1-24 synthesis method to obtain 16.4 g of a product. (Yield: 49%)

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

[Table 1]

II. Synthesis of Sub 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 9 below, but is not limited thereto.

1.Synthesis of Sub 2-18

<Reaction Scheme 9>

After dissolving phenylboronic acid pinacol ester (26 g, 90.4 mmol) in THF (398 ml), 3,7-dibromo-1,5-naphthyridine (18 g, 90.4 mmol), Pd(PPh ₃ ) ₄ (3.1 g, 2.7 mmol), K ₂ CO ₃ (37.5 g, 271 mmol), and water (200 ml) were added, followed by stirring at 90°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 organic material was recrystallized with a silicagel column to obtain 12.4 g of the product. (Yield: 48%)

2. Sub 2-21 synthesis

<Reaction Scheme 10>

Phenylboronic acid pinacol ester (31.2 g, 152.7 mmol), THF (336 ml), 2,4,6-trichloropyrimidine (14 g, 76 mmol), Pd(PPh ₃ ) ₄ (5.3 g, 4.58 mmol), K ₂ CO ₃ (63.3 g, 458 mmol) and water (168 ml) were used to obtain 13.2 g of the product using the Sub 2-18 synthesis method. (Yield: 65%)

3. Sub 2-33 synthesis

<Reaction Scheme 11>

Phenylboronic acid pinacol ester (24.6 g, 120.5 mmol), THF (531 ml), 2,4-dichloroquinazoline (24 g, 120.5 mmol), Pd(PPh ₃ ) ₄ (4.2 g, 3.62 mmol), K ₂ CO ₃ ( 50 g, 361.7 mmol) and water (265.3 ml) were used to obtain 13.93 g of the product using the Sub 2-18 synthesis method. (Yield: 48%)

4. Sub 2-53 synthesis

<Reaction Scheme 12>

Phenylboronic acid pinacol ester (21.6 g, 106 mmol), THF (466 ml), 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (27 g, 106 mmol), Pd(PPh ₃ ) ₄ (3.7 g, 3.18 mmol), K ₂ CO ₃ (43.9 g, 317.5 mmol), and water (233 ml) were obtained using the Sub 2-18 synthesis method to obtain 13.8 g of the product. (Yield: 44%)

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

[Table 2]

III. Final Product Synthesis

In a round bottom flask, Sub 1 compound (1.1 equivalent), Sub 2 compound (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), P(t-Bu) ₃ (0.1 equivalent), NaO t -Bu (3 equivalent) ), toluene (10.5 mL / 1 mmol) was added and the reaction was proceeded at 100 °C. When the reaction was completed, the product was extracted with ether and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain a product.

1. Synthesis of P-31

<Reaction Scheme 13>

In a round bottom flask, Sub 1-24 (14 g, 28.7 mmol), Sub 2-33 (7.6 g, 31.5 mmol), Pd ₂ (dba) ₃ (1.3 g, 1.4 mmol), P(t-Bu) ₃ ( 0.6 g, 2.87 mmol), NaO t -Bu (8.3 g, 86 mmol), and toluene (301 ml) were added, and the reaction was proceeded at 100 °C. When the reaction was completed, the product was extracted with ether and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 11 g of the product. (Yield: 55%)

2. Synthesis of P-69

<Reaction Scheme 14>

Sub 1-36 (14 g, 23.7 mmol), Sub 2-18 (7.4 g, 26 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), P(t-Bu) ₃ (0.5 g, 2.4 mmol), NaO t -Bu (6.8 g, 71 mmol), and toluene (250 ml) were obtained using the P-31 synthesis method to obtain 10.9 g of the product. (Yield: 58%)

3. Synthesis of P-91

<Reaction Scheme 15>

Sub 1-59 (15 g, 23.4 mmol), Sub 2-3 (5.3 g, 25.7 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.17 mmol), P(t-Bu) ₃ (0.5 g, 2.3 mmol), NaO t -Bu (6.7 g, 70 mmol), and toluene (245 ml) were obtained using the P-31 synthesis method to obtain 10.4 g of the product. (Yield: 62%)

4. Synthesis of P-118

<Reaction Scheme 16>

In a round bottom flask, Sub 1-79 (12 g, 21.3 mmol), Sub 2-21 (6.3 g, 23.4 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P(t-Bu) ₃ ( 0.4 g, 2.1 mmol), NaO t -Bu (6.1 g, 63.8 mmol), and toluene (223 ml) were obtained using the P-31 synthesis method to obtain 12.2 g of the product. (Yield: 72%)

5. P-96 synthesis

<Scheme 17>

Sub 1-63 (10 g, 22.8 mmol), Sub 2-54 (12.4 g, 25.1 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P(t-Bu) ₃ (0.5 g, 2.3 mmol), NaO t -Bu (6.6 g, 68.4 mmol), and toluene (240 ml) were obtained using the P-31 synthesis method to obtain 14.2 g of the product. (Yield: 73%)

6. Synthesis of P-152

<Reaction Scheme 18>

Sub 1-107 (14 g, 19.5 mmol), Sub 2-10 (4.5 g, 21.5 mmol), Pd ₂ (dba) ₃ (0.9 g, 0.98 mmol), P(t-Bu) ₃ (0.4 g, 1.95 mmol), NaO t -Bu (5.6 g, 58.6 mmol), and toluene (205 ml) were obtained using the P-31 synthesis method to obtain 10.55 g of the product. (Yield: 64%)

[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, Diazotization-Thiocyanation reaction ( Org. Biomol. Chem . 2011, 9 , 6066), MW (Microwave). -assisted cyclization reaction ( Org. Biomol. Chem. 2011, 9 , 6066), PPh3-mediated reductive cyclization reaction ( J. Org. Chem. 2005, 70 , 5014.), Ullmann reaction and Buchwald-Hartwig cross coupling reaction, etc. In addition to the substituents specified in the specific synthesis example, even if other substituents defined in Formula 1 (Ar ¹ , Ar ² , R ¹ , R ² , R ³ , L ¹ , L ² , X ¹ to X ⁸ etc.) are bonded to the above It will be readily understood by those skilled in the art that the reaction proceeds.

Manufacturing evaluation of organic electric devices

[Example 1] Green organic electroluminescent device (phosphorescent host)

An organic electroluminescent device was fabricated according to a conventional method using the compound obtained through synthesis as a light emitting host material of the light emitting layer. First, on the ITO layer (anode) formed on the glass substrate, as a hole injection layer, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl )-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[ N- (1-naphthyl) -N -phenylamino]biphenyl (hereinafter abbreviated as NPD) was vacuum-deposited to a thickness of 60 nm on the film to form a hole transport layer. Formed. The compound of the invention P-4 was used as a host on the hole transport layer, and Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] was doped with 95:5 weight as a dopant to have a thickness of 30 nm on the light emitting auxiliary layer. The emissive layer was deposited. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and electron injection As a layer, tris(8-quinolinol)aluminum (hereinafter _{abbreviated as Alq 3} ) was deposited to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm, and the Al/LiF was used as a cathode, thereby manufacturing an organic electroluminescent device.

[Example 2] to [Example 21] Green organic electroluminescent device (phosphorescent host)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 below was used instead of the compound P-4 according to the embodiment of the present invention as the host material of the emission layer.

[Comparative Example 1] to [Comparative Example 5]

<Comparative Compound A> <Comparative Compound B> <Comparative Compound C>

<Comparative Compound D> <Comparative Compound E>

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compounds A to E were used instead of P-4 of the present invention as the host material of the emission layer.

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 21 and Comparative Examples 1 to 5 of the present invention with PR-650 of photoresearch Was measured, and the T95 life was measured through 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]

As can be seen from the results of Table 4, when comparing Comparative Compounds B, C, D, E, which are 7-cyclic cyclic compounds similar to the compounds of the present invention, and Comparative Compound A, which is generally widely used, the efficiency was the highest in Comparative Compound E. It was good, and it was confirmed that the lifespan of Comparative Compound D appeared the best.

In particular, as a result of checking the lifespan of Comparative Compound B and Comparative Compound C, it can be confirmed that the lifespan is lowered when fluorene is included in the 7-ring cyclic compound. In particular, it has two more than Comparative Compound C, which has one fluorene. It was found that Comparative Compound B with a longer lifespan appeared.

It can be seen in Table 4 that the inventive compound having a fused position similar to that of the core of Comparative Compound D and having the same N-S-N type as Comparative Compound E exhibits higher efficiency and life than that of Comparative Compounds D and E.

This means that even if the 7-ring cyclic compound has the same NSN type heteroatom, the lifespan may vary depending on the fused position, and the efficiency may vary depending on the type and arrangement of the heteroatoms contained in the 7-ring cyclic compound. Is shown.

Therefore, in the case of a 7-ring cyclic compound, it is judged that it is difficult to easily infer the efficiency and lifetime due to the difference in the type and arrangement of the fused position and the hetero atom in the compound.

[Example 22] Red organic electroluminescent device (phosphorescent host)

An organic electroluminescent device was fabricated according to a conventional method using the compound obtained through synthesis as a light emitting host material of the light emitting layer. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and then an NPD film was vacuum-deposited to a thickness of 60 nm as a hole transport compound on the hole injection layer. A transport layer was formed. The compound of the invention P-16 was used as a host on the hole transport layer, and a light emitting layer was deposited to a thickness of 30 nm by doping _{(piq) 2 Ir (acac) as a dopant material at a weight ratio of 95:5.} Subsequently, BAlq was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Alq ₃ was deposited as an electron transport layer to a thickness of 40 nm. Thereafter, as an electron injection layer, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic electroluminescent device.

[Example 23] to [Example 42] Red organic electroluminescent device (phosphorescent host)

An organic electroluminescent device was manufactured in the same manner as in Example 22, except that the compound of the present invention described in Table 5 below was used instead of the compound P-16 according to the embodiment of the present invention as the host material of the emission layer.

[Comparative Example 6] to [Comparative Example 9]

<Comparative Compound A> <Comparative Compound D>

<Comparative compound F> <Comparative compound G>

An organic electroluminescent device was manufactured in the same manner as in Example 22, except that Comparative Compound A or Comparative Compound D or Comparative Compound F or Comparative Compound G was used instead of P-16 of the present invention as the host material of the emission layer. I did.

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 22 to 42 and Comparative Examples 6 to 9 of the present invention with PR-650 of photoresearch Was measured, and the 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 5 below.}

[Table 5]

As can be seen from the results of Table 5, when comparing Comparative Compounds D, F, G, which are 7-cyclic cyclic compounds similar to the compounds of the present invention, and Comparative Compound A, which is widely used, the efficiency was the best in Comparative Compound G. In terms of lifespan, it could be confirmed that Comparative Compound D appeared best.

Likewise, as a result of checking the lifespan of Comparative Compound F, it can be seen that the lifespan is lowered when fluorene is included in the 7-ring cyclic compound. In particular, it has a fused position similar to that of the core of Comparative Compound D, and has a similar fused position to Comparative Compound G. In the case of the compounds of the present invention of the same NSN type, it was confirmed in Table 5 that the compounds of the present invention exhibit higher efficiency and life than the comparative compounds D and G.

This means that even if the 7-ring cyclic compound has the same NSN type heteroatom, the lifespan may vary depending on the fused position, and the efficiency may vary depending on the type and arrangement of the heteroatoms contained in the 7-ring cyclic compound. Is shown.

Therefore, in the case of a 7-ring cyclic compound, it is judged that it is difficult to easily infer the efficiency and lifetime due to the difference in the type and arrangement of the fused position and the hetero atom in the compound.

In addition, in the evaluation result of the above-described device fabrication, the device characteristics were described in terms of the light-emitting layer, but the materials commonly used as the light-emitting layer include organic electronic devices such as the aforementioned electron transport layer, electron injection layer, hole injection layer, hole transport layer, and light-emitting auxiliary layer. It can be used as a single layer of organic material or mixed with other materials. Therefore, for the above-described reasons, the compound of the present invention may be used as a single material or mixed with other materials, such as an electron transport layer, an electron injection layer, a hole injection layer, a hole transport layer, and a light emission auxiliary layer, in addition to the light emitting layer.

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 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 following claims, and all technologies 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 (9)

Compound represented by the following formula 1 or formula 2-1
<Formula 1><Formula2-1>

[In Chemical Formula 1,
Ar ¹ and Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _{60; And a C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; And -N(R')(R"); is selected from the group consisting of,
The R′ and R” are independently of each other C ₆ to C _{60 aryl group; fluorenyl group; C 2} to C ₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si and P ; And C ₁ ~ C ₅₀ Alkyl group; is selected from the group consisting of,
L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; _{A C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; A fused ring group of a C ₃ to C ₆₀ divalent aliphatic ring and a C ₆ to C _{60 divalent aromatic ring;} And a divalent aliphatic hydrocarbon group; is selected from the group consisting of, and each of these (except a single bond) is deuterium; Nitro group; Nitrile group; Halogen group; A C ₁ to C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; C ₂ ~ C ₂₀ Heterocyclic group; C ₁ ~ C ₂₀ alkoxy group; And an amino group; may be substituted with one or more substituents selected from the group consisting of,
X ¹ to X ⁸ are each independently CR ¹ or N,
Wherein R ¹ is i) hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P; A fused ring group of an aromatic ring of C ₆ to C _{60 and an aliphatic ring of C 3} to C _60; A C ₁ to C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And C ₆ ~ C ₃₀ is selected from the group consisting of an aryloxy group, or ii) when a plurality of R ¹ is present, they are the same or different from each other, and each adjacent R ¹ may be bonded to each other to form at least one ring, ^{(However, R 1} that does not form a ring is the same as defined in i) above),
Ring A is represented by the following formula A2,

In A2 above,
* Is a bonding site to be condensed by sharing any one side of each of the rings (thiophene, pyrrole) adjacent to the A ring,
l is an integer from 0 to 2,
R ² is i) deuterium; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Halogen group; A C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ ~ C _{60 and an aliphatic ring of C 3} ~ C _60; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And C ₆ ~ C ₃₀ is selected from the group consisting of an aryloxy group, or ii) when a plurality of R ² is present, they are the same or different from ^{each other, and adjacent R 2} may be bonded to each other to form at least one ring ( ^{However, R 2} that does not form a ring is the same as defined in i) above),
In Formula 2-1,
X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ and L ² are the same as defined in Formula 1,
n is an integer from 0 to 2,
R ⁴ is i) deuterium; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Halogen group; A C ₁ to C ₅₀ alkyl group; A fused ring group of an aromatic ring of C ₆ ~ C _{60 and an aliphatic ring of C 3} ~ C _60; C ₂ ~ C ₂₀ alkenyl group; An alkoxyl group of C ₁ to C _30; And C ₆ ~ C ₃₀ is selected from the group consisting of aryloxy group, or ii) when a plurality of R ⁴ is present, they are the same or different from ^{each other, and adjacent R 4} may be bonded to each other to form at least one ring ( ^{However, R 4} not forming a ring is the same as defined in i) above),
Each of the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxyl group, and aryloxy group 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 to C _20; A C ₁ to C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C _20; C ₆ ~ C ₂₀ aryl group; _{C 6} ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; C ₈ ~ C ₂₀ arylalkenyl group; And -N (R ^a ) (R ^b ); may be substituted with one or more substituents selected from the group consisting of,
R ^a and R ^b 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 hetero atom of P; And C ₁ ~ C ₅₀ Alkyl group; is selected from the group consisting of.] The method of claim 1,
A compound characterized in that it is represented by one of the following formulas.
<Formula 2><Formula3-1>

<Formula 4><Formula5>

(In Formulas 2, 3-1, 4 and 5,
X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ and L ² are the same as defined in Formula 1,
n and R ⁴ are the same as defined in Formula 2-1) The method of claim 1,
A compound, characterized in that one of the following compounds.

A first electrode;
A second electrode; And
In the organic electric device comprising; an organic material layer positioned between the first electrode and the second electrode,
An organic electric device, characterized in that the organic material layer contains the compound of any one of claims 1 to 3. The method of claim 4,
The compound contained in the organic material layer is an organic electric device, characterized in that a mixture of two or more different types of compounds represented by Formula 1 or Formula 2-1. The method of claim 4,
An organic electric device further comprising a light efficiency improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer. The method of claim 4,
Wherein 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 4; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 8,
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 one of a single color or white lighting device.

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