KR102331466B1 - 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, low driving voltage and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

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 generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multilayer 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, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

The light emitting material can be classified into a high molecular type and a low molecular type according to 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 a light emitting mechanism. . 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 moves 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 a 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 its size is increasing, and thus, a larger 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 efficiency and lifespan problems 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 simply by 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.

That is, in order to sufficiently exhibit the excellent characteristics of an organic electric device, materials constituting the organic 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. are stable and efficient. It should be supported by materials, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently made. Therefore, the development of new materials continues to be demanded. In particular, the development of the light emitting layer material is also urgently required.

In the case of polycyclic cyclic compounds containing heteroatoms, the difference in properties depending on the material structure is very large, so it is 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, 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) Also, recently, OLED material development for the type, number, and position of heteroatoms of the pentacyclic compound is being actively developed. (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 high luminous efficiency, low driving voltage and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

Our company has been developing a 7-cyclic cyclic compound-related (KR 1108512, US13/390043) material in 2009 by using the characteristics of the polycyclic cyclic compound. 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 to the current OLED panel. Therefore, the present invention has the same seven-ring structure as that of KR 1108512, but by changing the fused position and heteroatom type and arrangement constituting the seven-ring compound, development of a high-efficiency, long-life material was progressed.

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 lifespan 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 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 addition, 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 components from other components, and the essence, order, or order of the components are not limited by the terms. When a component is described as being “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may be “connected,” “coupled,” or “connected.”

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" is 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 having 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, 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.

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

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, but is not limited thereto.

As used herein, the term "alkoxyl group", "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. it is not

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 has a carbon number of, 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.

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, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by a neighboring substituent joining or participating in a 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” refers to 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 the radical substituted with an aryl group has the number of carbon atoms described herein.

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 alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group and wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

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

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes a heteroaliphatic ring and a heterocyclic group. aromatic rings. 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 include a ring including _{SO 2 instead of carbon forming the ring.} For example, "heterocyclic group" includes the following compounds.

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

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a combination thereof, saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the above-mentioned heterocompounds include one or more heteroatoms, but are not limited thereto.

Unless otherwise specified, the term "carbonyl" used in the present invention 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. of 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 specified, as used herein, the term "ether" is represented by -RO-R', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 6 to 30 carbon atoms. An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

In addition, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in the present invention, "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 alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of 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, 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 110 and a second electrode 180 formed on a substrate 110 . ), an organic layer containing the compound according to the present invention is provided. 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 . In this case, the remaining layers except for the emission layer 150 may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151 , a buffer layer 141 , and the like, and the electron transport layer 160 and the like may serve as a hole blocking layer.

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 host or dopant of the hole injection layer 130 , the hole transport layer 140 , the electron transport layer 160 , the electron injection layer 170 , the light emitting layer 150 or the light efficiency improvement layer. material could be used. 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 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 coupled thereto are also very In particular, 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, in the present invention, by forming a light emitting layer using the compound represented by Formula 1, the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interface characteristics, etc.) of the material are optimized, and the lifespan of the organic electric device. 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 PVD (physical vapor deposition) method. For example, the anode 120 is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer ( 160) and an organic material layer including the electron injection layer 170 may be formed, and then a material that can be used as the cathode 180 is deposited thereon.

In addition, the organic layer is a solution process or a solvent process rather than a deposition method 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, Dr. Blay It can be manufactured with a smaller number of 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 formation method.

The organic electric device according to the present invention may be a top emission type, a back emission type, or a double side 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 color filter technology of the existing LCD. Various structures for a white organic light emitting diode mainly used as a backlight device have been proposed and patented. Typically, the R (Red), G (Green), and B (Blue) light emitting units are arranged in parallel in a planar manner (side-by-side), and the R, G, and B light emitting layers are stacked up and down in a stacking method. 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, and the present invention 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>

In Formula 1,

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

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

L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of a divalent aliphatic ring and a C ₆ ~ C _{60 divalent aromatic ring;} and a divalent aliphatic hydrocarbon group; may be selected from the group consisting of. Here, each of these (except for single bonds) is deuterium; nitro group; nitrile group; halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₆ ~ C ₂₀ Aryl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₁ ~ C ₂₀ Alkoxy group; And 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 hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one hetero atom of C ₂ ~ C ₆₀ A heterocyclic group; C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and a C ₃ ~ C _{60 aliphatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ It may be selected from the group consisting of an 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} which does not form a ring may be defined the same as defined above. In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or C ₆ ~ C ₆₀ aromatic ring, C ₂ ~ C ₆₀ heterocycle, 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 each independently represent 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 C ₆ ~ C ₂₀ aromatic ring of the A ring is deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one hetero atom of C ₂ ~ C ₆₀ A heterocyclic group; halogen group; 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 An alkoxyl group; and C ₆ to C ₃₀ may be substituted with one or more groups selected from the group consisting of an aryloxy group, 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 C ₆ ~ C ₆₀ aromatic ring, C ₂ ~ C ₆₀ heterocycle, 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 C ₆ ~ C ₂₀ aromatic ring of the A ring may be benzene, naphthalene, or phenanthrene, but is not limited thereto.

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

* in A1 to A6 is a bonding position at which one side of each of the rings (thiophene, pyrrole) adjacent to the A ring is shared and condensed.

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

The R ² and R ³ are deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one hetero atom of C ₂ ~ C ₆₀ A heterocyclic group; halogen group; 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 An alkoxyl group; And C ₆ ~ C ₃₀ It may be selected from the group consisting of an aryloxy group.

In addition, when a plurality of R ² and R ³ is present, a plurality of R ² or a plurality of R ³ are the same as or different from each other, Adjacent R ² and adjacent R ³ may be bonded to each other to form at least one ring. In this case, R ² and R ³ that do not form a ring may be defined the same as those defined above, respectively. In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or C ₆ ~ C ₆₀ aromatic ring, C ₂ ~ C ₆₀ heterocycle, 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 Chemical Formula 1 may be represented by one of the following Chemical Formulas.

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

In Formulas 2 to 5,

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 P containing at least one hetero atom of C ₂ ~ C ₆₀ A heterocyclic group; halogen group; 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 An alkoxyl group; And C ₆ ~ C ₃₀ It may be selected from the group consisting of an 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. ^{In this case, R 4} which does not form a ring may be defined the same as defined above. In this case, the formed ring is a C ₃ ~ C ₆₀ aliphatic ring or C ₆ ~ C ₆₀ aromatic ring, C ₂ ~ C ₆₀ heterocycle, 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, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxyl group, and the aryloxy group is 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; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; C ₇ ~ C ₂₀ Arylalkyl group; C ₈ ~ C ₂₀ Aryl alkenyl group; and -N(R ^a )(R ^b ); may be substituted with one or more substituents selected from the group consisting of.

The R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one hetero atom of C ₂ ~ C ₆₀ A heterocyclic group; And C ₁ ~ C ₅₀ Alkyl group; may be selected from the group consisting of.

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

In the case of the heterocyclic group, it may be a heterocyclic ring having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms,

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

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

<Formula 6> <Formula 7>

<Formula 8> <Formula 9>

In Formulas 6 to 9,

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.

In 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 Formula 1, wherein the compound represented by Formula 1 is a hole injection layer and a hole transport layer of the organic material layer , it may be contained in at least one of the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection 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 emitting 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 Chemical 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) in the organic material layer is provided.

In another embodiment, in at least one of the hole injection layer, the hole transport layer, the light emission auxiliary layer, the light emitting layer, the electron transport layer, and the electron injection layer of the organic material layer, the compound is contained alone, or It provides an organic electric device, characterized in that the compound is contained in a combination of two or more different compounds, or the compound is contained in a combination of two or more other compounds. In other words, each of the layers may contain a compound corresponding to Formulas 1 to 9 alone, or a mixture of two or more compounds of Formulas 1 to 9, and the compound of claims 1 to 5 and the present invention. Mixtures with compounds not subject to the invention may be included. Here, the compound not falling under 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 other compounds, the other compound may be a known compound of each organic layer, or a compound to be developed in the future. In this case, the compound contained in the organic material layer may consist only of the same kind of compound, or may be a mixture in which two or more heterogeneous compounds represented by Formula 1 are mixed.

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

Hereinafter, a synthesis example of the compound represented by Formula 1 and a manufacturing example of an organic electric device according to the present invention will be described in detail with reference to examples, 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.

<Scheme 1>

(X ¹ to X ⁸ , Ar ¹ , Ar ² , L ¹ , L ² and A ring 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.

<Scheme 2>

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

1. Sub 1-24 Synthesis

<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 and refluxed at 80°C to 90°C. When the reaction is completed, dilute by adding distilled water at room temperature, and extract with _{CH 2} Cl _{2 and water.} The organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized by silicagel column to obtain 152.6 g of the product. (Yield: 77%)

(2) Synthesis of Sub 1-III-24

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 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 by silicagel column to obtain 59.5 g of a product. (Yield: 43%)

(3) Synthesis of Sub 1-IV-24

Sub 1-III-24 (59 g, 167.5 mmol) was dissolved in nitrobenzene (838 ml) in a round-bottom flask, 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), 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 by 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). Then, it is heated and refluxed at 80°C to 90°C. When the reaction is completed, dilute by adding distilled water at room temperature, and extract with _{CH 2} Cl _{2 and water.} The organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized using silicagel column to obtain 34 g of the 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 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 by silicagel column to obtain 16.6 g of a product. (Yield: 63%)

2. Sub 1-36 Synthesis

<Scheme 4>

(1) Synthesis of Sub 1-II-36

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 by using the Sub 1-II-24 synthesis method above to obtain 188.4 g of the product. (Yield: 79%)

(2) Synthesis of Sub 1-III-36

Sub 1-II-36 (187 g, 406.2 mmol), o-dichlorobenzene (1645 ml), triphenylphosphine (319.6 g, 1218.7 mmol) aboveSub 1-III-24 synthesis method71.3 g of product were obtained. (Yield: 41%)

(3) Synthesis of Sub 1-IV-36

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) and Cu (3.1 g, 49.4 mmol) were obtained by using the above 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 ) and water (174 ml), 35.5 g of the product was obtained by using the Sub 1-V-24 synthesis method. (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 synthesized using the Sub 1-24 synthesis method to obtain 16.4 g of the product. (Yield: 60%)

3. Sub 1-59 Synthesis

<Scheme 5>

(1) Synthesis of Sub 1-II-59

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 prepared using the Sub 1-II-24 synthesis method above to obtain 215.9 g of the product. (Yield: 61%)

(2) Synthesis of Sub 1-III-59

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

(3) Synthesis of Sub 1-IV-59

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), 50.8 g of K ₂ CO ₃ (33.1 g, 239.5 mmol) and Cu (4.6 g, 71.8 mmol) was obtained by using the above Sub 1-IV-24 synthesis method. (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 by using the Sub 1-V-24 synthesis method above 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), and triphenylphosphine (46.7 g, 178 mmol) obtained in the above synthesis were synthesized using the Sub 1-24 synthesis method to obtain 16 g of the product. (Yield: 42%)

4. Sub 1-71 Synthesis

<Scheme 6>

(1) Synthesis of Sub 1-II-71

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 by using the Sub 1-II-24 synthesis method above to obtain 219.3 g of the product. (Yield: 72%)

(2) Synthesis of Sub 1-III-71

Sub 1-II-71 (220 g, 506.5 mmol), o-dichlorobenzene (2026 ml), and triphenylphosphine (398.6 g, 1519.7 mmol) were synthesized using the above Sub 1-III-24 synthesis method to obtain 87.6 g of the product. (Yield: 43%)

(3) Synthesis of Sub 1-IV-71

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) and Cu (3.7 g, 58.9 mmol) were obtained by using the above Sub 1-IV-24 synthesis method to obtain 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 by using the Sub 1-V-24 synthesis method above 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 above synthesis were synthesized using the above Sub 1-24 synthesis method to obtain 13.2 g of the product. (Yield: 45%)

5. Sub 1-63 Synthesis

<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 by using the Sub 1-II-24 synthesis method above 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 synthesized using the above Sub 1-III-24 synthesis method to obtain 40.4 g of the product. (Yield: 42%)

(3) Synthesis of Sub 1-IV-63

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) and Cu (2.1 g, 32.4 mmol) were obtained by using the Sub 1-IV-24 synthesis method above 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 by using the Sub 1-V-24 synthesis method above 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), and triphenylphosphine (43.5 g, 166 mmol) obtained in the above synthesis were synthesized using the above Sub 1-24 synthesis method to obtain 16.5 g of the product. (Yield: 68%)

6. Sub 1-107 Synthesis

<Scheme 8>

(1) Synthesis of Sub 1-II-107

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 above 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), and triphenylphosphine (343.3 g, 1309 mmol) were synthesized using the above Sub 1-III-24 synthesis method to obtain 82.5 g of the product. (Yield: 47%)

(3) Synthesis of Sub 1-IV-107

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 by using the above 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 by using the above 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 above synthesis were synthesized using the above Sub 1-24 synthesis method to obtain 16.4 g of the product. (Yield: 49%)

On the other hand, the compound belonging to Sub 1 may be the following compounds, but is not limited thereto, and Table 1 below shows the FD-MS values of the compounds 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. Sub 2-18 Synthesis

<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 and stirred at 90°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting organic material was recrystallized by silicagel column to obtain 12.4 g of the product. (Yield: 48%)

2. Sub 2-21 Synthesis

<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

<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

<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 by using the Sub 2-18 synthesis method above to obtain 13.8 g of the product. (Yield: 44%)

On the other hand, the compound belonging to Sub 2 may be a compound as follows, 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

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

1. Synthesis of P-31

<Scheme 13>

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 then the reaction was carried out at 100 °C. When the reaction was completed, the organic layer was extracted with ether and water, dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized by silicagel column to obtain 11 g of the product. (Yield: 55%)

2. Synthesis of P-69

<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 by using the above P-31 synthesis method to obtain 10.9 g of the product. (Yield: 58%)

3. Synthesis of P-91

<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 by using the above P-31 synthesis method to obtain 10.4 g of the product. (Yield: 62%)

4. Synthesis of P-118

<Scheme 16>

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 by using the above 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 by using the above P-31 synthesis method to obtain 14.2 g of the product. (Yield: 73%)

6. Synthesis of P-152

<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 by using the above P-31 synthesis method to obtain 10.55 g of the product. (Yield: 64%)

[Table 3]

Meanwhile, although exemplary synthesis examples of the present invention represented by Chemical Formula 1 have been described above, these are all 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 examples, 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. Substituents) are bonded 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 manufactured according to a conventional method by using the compound obtained through synthesis as a light emitting host material of the light emitting layer. ^{First, N 1} -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl as a hole injection layer on the ITO layer (anode) formed on the glass substrate. )-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) as a hole transport compound was vacuum deposited on the film to a thickness of 60 nm to form a hole transport layer. formed. The compound P-4 of the invention was used as a host on the hole transport layer, and as a dopant, Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] was doped at a weight of 95:5 by doping at a weight of 30 nm on the light emitting auxiliary layer. A light emitting layer was deposited. (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, and electron injection was performed. 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 to manufacture 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 was used instead of the compound P-4 according to an embodiment of the present invention as the host material of the light emitting 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 a host material for the emission layer.

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 21 and Comparative Examples 1 to 5 of the present invention with PR-650 manufactured by photoresearch was measured, and the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 5000 ^{cd/m 2 standard luminance, and the measurement results are shown in Table 4 below.}

[Table 4]

As can be seen from the results in Table 4, when Comparative Compounds B, C, D, and E, which are 7-ring compound similar to the present compound, are compared with Comparative Compound A, which is widely used, the efficiency is the highest with Comparative Compound E. It was good, and it was confirmed that Comparative Compound D showed the best lifespan.

In particular, as a result of checking the lifespans of Comparative Compound B and Comparative Compound C, it can be seen that the lifespan is lowered when fluorene is included in the 7-ring compound. It was found that the comparative compound B had a lower lifespan.

In the case of the compound of the present invention 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, it was confirmed from Table 4 that the compounds of the present invention exhibit higher efficiency and lifetime than those of Comparative Compounds D and E.

This means that even if the 7-ring cyclic compound has the same NSN-type heteroatom, the lifetime may vary depending on the fused position, and the efficiency may vary depending on the type and arrangement of heteroatoms included in the 7-ring cyclic compound. is indicating

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

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

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

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 22 to 42 and Comparative Examples 6 to 9 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, and the measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results in Table 5, when the comparative compounds D, F, and G, which are 7-ring compound similar to the present invention compound, were compared with the commonly used comparative compound A, the efficiency of the comparative compound G was the best. , it was confirmed that the comparative compound D showed the best lifespan.

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

This means that even if the 7-ring cyclic compound has the same NSN-type heteroatom, the lifetime may vary depending on the fused position, and the efficiency may vary depending on the type and arrangement of heteroatoms included in the 7-ring cyclic compound. is indicating

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

In addition, although the device characteristics were described in terms of the light emitting layer in the evaluation results of the above-described device fabrication, materials typically used as the light emitting layer are organic electric 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 alone or mixed with other materials as an organic layer of Therefore, for the above reasons, the compound of the present invention may be used alone or in combination with other materials in other organic layers other than the light emitting layer, for example, an electron transport layer, an electron injection layer, a hole injection layer, a hole transport layer and a light emission auxiliary 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 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 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)

A compound represented by one of the following formulas.
<Formula 2><Formula3-1>

<Formula 4><Formula5>

[In Formulas 2, 3-1, 4 and 5,
Ar ¹ and Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; and -N(R')(R");
The R' and R" are each independently a C ₆ ~ C _{60 aryl group; a fluorenyl group; C 2} ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P And C ₁ ~ C ₅₀ Alkyl group; 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; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of a divalent aliphatic ring and a C ₆ ~ C _{60 divalent aromatic ring;} and a divalent aliphatic hydrocarbon group; selected from the group consisting of, and each of these (except for a single bond) is deuterium; nitro group; nitrile group; halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₆ ~ C ₂₀ Aryl group; C ₂ ~ C ₂₀ A 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; C ₆ ~ C ₂₀ Aryl group; fluorenyl group; and O, N, and S _{selected from the group consisting of a C 5} ~ C ₁₂ heterocyclic group comprising at least one hetero atom, or ii) when a plurality of R ¹ is present, they are the same as or different from each other and each adjacent R ^{1 may} combine with each other to form at least one ring (provided that R ¹ which does not form a ring is the same as defined in i) above),
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 P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; halogen group; 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 An alkoxyl group; And C ₆ ~ C ₃₀ selected from the group consisting of an aryloxy group, or ii) 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 ( ^{provided that R 4} which does not form 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; 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; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; C ₇ ~ C ₂₀ Arylalkyl group; C ₈ ~ C ₂₀ Aryl alkenyl group; and -N(R ^a )(R ^b ); may be substituted with one or more substituents selected from the group consisting of;
The R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one hetero atom of C ₂ ~ C ₆₀ A heterocyclic group; And C ₁ ~ C ₅₀ Alkyl group; is selected from the group consisting of.] delete A compound which is 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,
The organic layer is an organic electric device, characterized in that it contains the compound of claim 1 or 3. 5. The method of claim 4,
The compound contained in the organic material layer is an organic electric device, characterized in that two or more heterogeneous compounds represented by any one of Chemical Formulas 2, 3-1, 4 and 5 are mixed and used. 5. The method of claim 4,
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. 5. The method of claim 4,
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 4; and
An electronic device comprising a; a control unit for driving the display device. 9. The method of claim 8,
The organic electric 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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