WO2016064088A2 - Compound for organic electric device, organic electric device using same, and electronic device using same - Google Patents

Abstract

Disclosed are: a compound represented by chemical formula (1); an organic electric device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode; and an electronic device using same, wherein the light-emitting efficiency and the life of the organic electric device can be improved and driving voltage can be reduced by including the compound represented by chemical formula (1) in the organic layer.

Description

Compound for organic electric element, organic electric element using same and electronic device thereof

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

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

The material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. The principle is that when a small amount of 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, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

Currently, the portable display market is increasing in size with large-area displays, which requires more power consumption than that required in conventional portable displays. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and the problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases. The lifespan tends to increase. However, simply improving the organic material layer does not maximize the efficiency. This is because long life and high efficiency can be simultaneously achieved when an optimal combination of energy level and T ₁ value between each organic material layer and intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved. Therefore, there is a need for development of a light emitting material having high thermal stability and efficiently achieving a charge balance in the light emitting layer.

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

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

In one aspect, the present invention provides a compound represented by the following formula (1).

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

By using the compound according to the embodiment of the present invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and color purity and life of the device can be improved.

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

[Description of the code]

100: organic electric element 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

Hereinafter, exemplary 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 reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

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

In addition, if a component such as a layer, film, region, plate, etc. is said to be "on" or "on" another component, it is not only when the other component is "on top of" but also another component in between. It is to be understood that this may also include cases. On the contrary, when a component is said to be "directly above" another part, it should be understood to mean that there is no other part in the middle.

As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows.

The term "halo" or "halogen" as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.

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

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

As used herein, the term "alkenyl group" or "alkynyl group", unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

As used herein, the term "alkoxy group" or "alkyloxy group" means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, but is not limited thereto.

As used herein, the term "aryloxyl group" or "aryloxy group" means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.

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

As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto. The aryl group or arylene group in the present invention includes monocyclic, ring conjugate, conjugated ring system, spiro compound and the like.

As used herein, the term "heterocyclic group" includes not only aromatic rings, such as "heteroaryl groups" or "heteroarylene groups," but also non-aromatic rings, and unless otherwise specified, each carbon number includes one or more heteroatoms. It means a ring of 2 to 60, but is not limited thereto. As used herein, the term “heteroatom” refers to N, O, S, P or Si unless otherwise indicated, and heterocyclic groups are monocyclic, ring conjugates, conjugated multiple ring systems, spies, including heteroatoms. Means a compound or the like.

"Heterocyclic groups" may also include rings comprising SO ₂ in place of the carbon forming the ring. For example, a "heterocyclic group" includes the following compounds.

In the present specification, a monovalent or divalent functional group is named as a functional group name or a valence is indicated before the parent compound. For example, "bivalent benzothiophene" refers to a divalent functional group of the parent compound benzothiophene, and similarly "bivalent dibenzothiophene" refers to a divalent functional group of the parent compound dibenzothiophene. Furan "is a divalent functional group of the parent compound furan," bivalent dibenzofuran "is a divalent functional group of the parent compound dibenzofuran," divalent pyrimidine "is a divalent functional group of the parent compound pyrimidine. It shall be shown. Similarly, a trivalent functional group can also be represented by displaying a trivalent in front of the parent compound, for example, "trivalent aryl" denotes a trivalent functional group of aryl which is aromatic, and "trivalent fluorene" denotes a trivalent functional group of fluorene.

As used herein, the term "polycyclic" includes ring assemblies, fused multiple ring systems and spiro compounds, such as biphenyl, terphenyl, and the like, including aromatics as well as nonaromatics, hydrocarbons The ring as well includes heterocycles comprising at least one heteroatom.

As used herein, the term "ring assemblies" means that two or more ring systems (single or conjugated ring systems) are directly connected to each other through a single bond or a double bond and directly between such rings. It means that the number of linkages is one less than the total number of ring systems in this compound. Ring aggregates may have the same or different ring systems directly connected to each other via a single bond or a double bond.

As used herein, the term "conjugated multiple ring systems" refers to fused ring forms that share at least two atoms, including the ring systems of two or more hydrocarbons joined together and at least one heteroatom. And heterocyclic systems having at least one conjugated form. These conjugated several ring systems can be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.

As used herein, the term "spiro compound" has a "spiro union", and a spiro linkage means a linkage formed by two rings sharing one atom only. In this case, the atoms shared by the two rings are called spiro atoms, and according to the number of spiro atoms in a compound, they are respectively referred to as 'monospyro-', 'diespyro-' and 'trispyro-' It is called a compound.

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

Also, unless expressly stated, the term "substituted" in the term "substituted or unsubstituted" refers to deuterium, halogen, amino groups, nitrile groups, nitro groups, C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C alkynyl of ₂₀ group, an aryl group of C ₃ -C ₂₀ cycloalkyl, C ₆ -C _20, the fluorene group, an aryl of C ₆ -C ₂₀ aryl, C ₈ -C ₂₀ substituted by deuterium alkenyl, At least one substituent selected from the group consisting of a silane group, a boron group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P Substituted with, and are not limited to these substituents.

Also, unless otherwise stated, the formulas used in the present invention apply equally to the definitions of substituents based on the exponential definition of the following formulas.

Here, when a is an integer of 0, the substituent R ¹ is absent, so that all hydrogen is bonded to the benzene as a substituent, and when a is an integer of 1, one substituent R ¹ is one of the carbons forming the benzene ring. When bound to carbon, and a is an integer of 2 or 3, respectively, 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; In addition, the indication of the hydrogen couple | bonded with the carbon which forms the benzene ring is abbreviate | 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, a first electrode 120, and a second electrode 180 formed on a substrate 110. ) Is provided with an organic material layer containing a compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer may 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 sequence. In this case, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like. The electron transport layer 160 may serve as a hole blocking layer. You can do it.

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 one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.

Compound according to the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, light efficiency improvement layer, light emitting auxiliary layer, etc. It can be used as a material. In one example, the compound of the present invention may be used as the material of the light emitting layer 150.

On the other hand, even in the same core, the band gap, electrical characteristics, interface characteristics, etc. may vary depending on which substituents are bonded at which positions, so the selection of the cores and the combination of sub substituents bonded thereto are very important. Long life and high efficiency can be achieved at the same time when an optimal combination of energy level, T ₁ value, and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

As described above, in order to solve the problem of light emission in the hole transport layer in the organic electroluminescent device, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and correspond to each light emitting layer (R, G, B). Therefore, it is necessary to form different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.

Therefore, the light emitting layer is formed using the compound according to Chemical Formula 1 of the present invention to optimize the energy level and T ₁ value of each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) of the organic layer and the life 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 various deposition methods. It may be manufactured using a deposition method such as PVD or CVD. For example, the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130 thereon. , By forming an organic material layer including a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170, and then depositing a material that can be used as the cathode 180 thereon have. In addition, an auxiliary light emitting layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150.

In addition, the organic layer may be formed using a variety of polymer materials, such as a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It can be produced in fewer layers by a method such as a screen printing process or a thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

The organic electric element 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) has the advantage that can be manufactured using the color filter technology of the existing LCD while being easy to realize high resolution and excellent processability. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.

In addition, the organic electroluminescent 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), a monochromatic or white illumination device.

Another embodiment of the present invention may include a display device including the organic electric element 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 a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound which concerns on one aspect of this invention is demonstrated.

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

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

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

A is one of the following general formulas (2) to (4).

In Chemical Formulas 1 to 4, R ² to R ²³ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ aryl group; Fluorenyl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C ₁ -C ₅₀ ; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ It can be selected from the group consisting of.

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

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

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

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

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

L ² is C ₆ -C ₆₀ trivalent aryl; Trivalent fluorene; And C ₂ -C ₆₀ trivalent heteroaryl including at least one hetero atom selected from the group consisting of O, N, S, Si, and P.

Preferably, L ² is a C ₆ -C ₃₀ aryl of the trivalent, trivalent fluorene, O, N, S, C ₂ -C ₃₀ containing at least one heteroatom selected from the group consisting of Si and P Trivalent heteroaryl, and the like. For example, L ² may be trivalent phenyl, trivalent pyridine, trivalent pyrimidine group, trivalent triazine, or the like.

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 -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And -L'-N (R ^a ) (R ^b ); may be selected from the group consisting of.

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

L 'is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P.

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

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

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

Each symbol is an aryl group, fluorenyl group, heterocyclic group, alkyl group, fused ring group, alkenyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group, hetero arylene group, trivalent aryl, trivalent flu Orene and the like, each of which is deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxyl group of C ₁ -C ₂₀ ; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; Aryl group of C ₆ -C ₂₀ ; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A cycloalkyl group of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; And an arylalkenyl group of C ₈ -C ₂₀ It may be further substituted with one or more substituents selected from the group consisting of.

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

In Formulas 5 to 10, R ¹ to R ²³ and X are the same as defined in Formulas 1 to 4.

Also specifically, in Formula 1, when the junction position of the A and the substituents R ¹⁰ and R ¹¹ or R ²² and R ²³ combine with each other to form a ring with the benzene ring to which they are bonded, the following Formulas 1-1 to Formula It may be displayed as 1-4.

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

On the other hand, R ²⁴ to R ²⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ aryl group; Fluorenyl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C ₁ -C ₅₀ ; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ It can be selected from the group consisting of.

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

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

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

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

In this case, the organic electric element includes a first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode. The organic material layer may include a compound represented by Chemical Formula 1, and Chemical Formula 1 may include a hole injection layer, a hole transport layer, and an emission auxiliary layer of the organic material layer. Or it may be contained in at least one layer of the light emitting layer. That is, the compound represented by Formula 1 may be used as a material of a hole injection layer, a hole transport layer, a light emitting auxiliary layer or a light emitting layer. Preferably, the compound represented by Formula 1 may be used as a phosphorescent host material of the light emitting layer.

Specifically, to provide an organic electroluminescent device comprising one of the compounds represented by Formula 5 to Formula 10 in the organic material layer, and more specifically, of the compounds represented by Formula 1-1 to Formula 1-4 in the organic material layer Provided is an organic electric device comprising one, and more particularly, an organic electric device including a compound represented by the respective formula in the organic material layer. In addition, the organic layer may include one kind alone or a mixture of two or more represented by Chemical Formula 1. For example, the light emitting layer of the organic material layer may be formed of a P-1-1 compound alone, or may include a mixture of P-1-1 and P-1-2.

In still another embodiment of the present invention, the present invention provides a light efficiency improving layer formed on at least one side of the 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 element further comprising.

Hereinafter, the synthesis examples of the compounds represented by the chemical formulas according to the present invention and the production examples of the organic electric device will be described in detail by way of examples, but the present invention is not limited to the following examples.

Synthesis Example

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

I. Synthesis of Core

1.Core 1 Synthesis Example

Synthesis of Core 1-a

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

Synthesis of Core 1-b

To the core 1-a (8 g, 38.23 mmol) was added potassium hydroxide aqueous solution (12M, 40 mL) and 2-methoxyethanol (120 ml) and refluxed for 24 hours. After the reaction is completed, the temperature of the reactant is cooled to room temperature and acidified with 1N HCl. Filter the precipitate and rinse with water. The resulting product was dissolved in NaOH 1M aqueous solution, acidified with 1N HCl and the precipitate was filtered to proceed to the next reaction without separation.

Synthesis of Core 1-c

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

Synthesis of Core 1-d

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

Synthesis of Core 1-e

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

Synthesis of Core 1-f

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

Synthesis of Core 1

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

2. Core 2 Synthesis Example

Synthesis of Core 2-a

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

Synthesis of Core 2-b

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

Synthesis of Core 2-c

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

Synthesis of Core 2-d

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

Synthesis of Core 2-e

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

Synthesis of Core 2-f

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

Synthesis of Core 2

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

3.Core 3 Synthesis Example

Synthesis of Core 3-a

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

Synthesis of Core 3-b

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

Synthesis of Core 3-c

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

Synthesis of Core 3-d

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

Synthesis of Core 3-e

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

Synthesis of Core 3-f

Core 3-e (10.5 g, 34.84 mmol), POCl ₃ (3.90 mL, 41.81 mmol), N, N- diisopropylethylamine (DIEA) (3.60 g, 27.87 mmol), toluene (100 ml) Synthesis Example yielded 7.3 g (66%) of product.

Synthesis of Core 3

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

4.Core 4 Synthesis Example

Synthesis of Core 4-a

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

Synthesis of Core 4-b

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

Synthesis of Core 4-c

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

Synthesis of Core 4-d

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

Synthesis of Core 4-e

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

Synthesis of Core 4-f

Core 4-e (7.2 g, 20.48 mmol), POCl ₃ (2.29 mL, 24.58 mmol), N, N- diisopropylethylamine (DIEA) (2.12 g, 16.39 mmol), toluene (80 ml) were added to the core 1-f. Synthesis Example gave 5.2 g (69%) of product.

Synthesis of Core 4

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

5. Core 5 Synthesis Example

Synthesis of Core 5-a

3-Bromodibenzo [b, d] thiophene (7 g, 26.6 mmol), CuCN (4.76 g, 53.2 mmol), DMF (150 ml) was obtained using 4.1 g (74%) of the product using the synthesis examples of Core 1-a. Got.

Synthesis of Core 5-b

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

Synthesis of Core 5-c

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

Synthesis of Core 5-d

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

Synthesis of Core 5-e

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

Synthesis of Core 5-f

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

Synthesis of Core 5

Core 5-f (6.9 g, 21.57 mmol), bis (pinacolato) diboron (7.25 g, 25.89 mmol), PdCl ₂ (dppf) ₂ (0.53 g, 0.64 mmol), KOAc (6.35 g, 64.72 mmol), DMF ( 100 ml) was used to synthesize 7.8 g (88%) of the product.

6.Core 6 Synthesis Example

Synthesis of Core 6-a

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

Synthesis of Core 6-b

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

Synthesis of Core 6-c

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

Synthesis of Core 6-d

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

Synthesis of Core 6-e

Core 6-d (8 g, 26.36 mmol), Pd (OCOCF ₃ ) ₂ (0.61 g, 1.84 mmol), and benzoic acid (3.22 g, 26.36) were obtained using 4.1 g of the product (Synthesis Example). 52%).

Synthesis of Core 6-f

Core 6-e (6.7 g, 22.23 mmol), POCl ₃ (2.49 mL, 26.68 mmol), N, N- diisopropylethylamine (DIEA) (2.30 g, 17.78 mmol), toluene (80 ml) were added to the core 1-f. Synthesis Example gave 4.6 g (65%) of product.

Synthesis of Core 6

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

7. Core 7 Synthesis Example

Synthesis of Core 7-a

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

Synthesis of Core 7-b

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

Synthesis of Core 7-c

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

Synthesis of Core 7-d

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

Synthesis of Core 7-e

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

Synthesis of Core 7-f

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

Synthesis of Core 7

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

8. Core 8 Synthesis Example

Synthesis of Core 8-a

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

Synthesis of Core 8-b

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

Synthesis of Core 8-c

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

Synthesis of Core 8-d

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

Synthesis of Core 8-e

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

Synthesis of Core 8-f

Core 8-e (8.2 g, 23.33 mmol), POCl ₃ (2.61 mL, 28.0 mmol), N, N- diisopropylethylamine (DIEA) (2.41 g, 18.66 mmol), toluene (100 ml) were added to the core 1-f. Synthesis Example yielded 5.6 g (66%) of product.

Synthesis of Core 8

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

9.Core 9 Synthesis Example

Synthesis of Core 9-a

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

Synthesis of Core 9-b

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

Synthesis of Core 9-c

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

Synthesis of Core 9-d

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

Synthesis of Core 9-e

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

Synthesis of Core 9-f

Core 9-e (3.5 g, 11.61 mmol), POCl ₃ (1.29 mL, 13.93 mmol), N, N- diisopropylethylamine (DIEA) (1.20 g, 9.29 mmol), toluene (60 ml) Synthesis Example gave 2.4 g (66%) of product.

Synthesis of Core 9

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

10.Core 10 Synthesis Example

Synthesis of Core 10-a

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

Synthesis of Core 10-b

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

Synthesis of Core 10-c

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

Synthesis of Core 10-d

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

Synthesis of Core 10-e

Core 10-d (10.3 g, 33.95 mmol), Pd (OCOCF ₃ ) ₂ (0.79 g, 2.37 mmol), and benzoic acid (4.15 g, 33.95) were prepared using 8.49 g ( 83%).

Synthesis of Core 10-f

Core 10-e (8.4 g, 27.87 mmol), POCl ₃ (3.11 mL, 33.44 mmol), N, N- diisopropylethylamine (DIEA) (2.88 g, 22.29 mmol), toluene (100 ml) were added to the core 1-f. Synthesis Example gave 5.4 g (66%) of product.

Synthesis of Core 10

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

On the other hand, Table 1 shows the FD-MS value of the core according to an embodiment of the present invention prepared according to the synthesis example as described above.

II. Example of Sub1

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

III. Synthesis of Final Product

1.P-1-1 Synthesis Example

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

2.P-2-8 Synthesis Example

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

3.P-3-9 Synthesis Example

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

4.P-4-7 Synthesis Example

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

5.P-5-12 Synthesis Example

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

6.P-6-11 Synthesis Example

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

7.P-7-2 Synthesis Example

Core 7 (1.5 g, 3.25 mmol) in Sub 1-6 (0.87 g, 3.25 mmol), Pd (PPh ₃ ) ₄ (0.11 g, 0.09 mmol), K ₂ CO ₃ (1.35 g, 9.75 mmol), THF ( 50 ml), H ₂ O (20 ml) were obtained using the synthesis example of P-1-1 to obtain 1.34 g (73%) of the product.

8.P-8-9 Synthesis Example

Core 8 (1.6 g, 3.46 mmol) in Sub 1-13 (0.88 g, 3.46 mmol), Pd (PPh ₃ ) ₄ (0.12 g, 0.10 mmol), K ₂ CO ₃ (1.44 g, 10.40 mmol), THF ( 50 ml), H ₂ O (20 ml) were obtained using 1.3 g (69%) of the product using the above synthesis example.

9.P-9-4 Synthesis Example

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

10.P-10-6 Synthesis Example

Core 10 (1.9 g, 4.61 mmol) in Sub 1-46 (1.79 g, 4.61 mmol), Pd (PPh ₃ ) ₄ (0.16 g, 0.13 mmol), K ₂ CO ₃ (1.92 g, 13.85 mmol), THF ( 50 ml), H ₂ O (20 ml) were obtained using 1.8 g (68%) of the product using the synthesis example of P-1-1.

On the other hand, Table 3 shows the FD-MS values of the compounds P-1-1 to P-10-20 according to the embodiment of the present invention prepared according to the synthesis examples as described above.

Manufacturing Evaluation of Organic Electrical Device

Example 1 Red organic light emitting device (phosphorescent host)

An organic electroluminescent device was manufactured according to a conventional method using the compound according to an embodiment of the present invention 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) -N ¹ on the ITO layer (anode) formed on the glass substrate. -phenylbenzene-1,4-diamine (hereinafter referred to as '2-TNATA') is vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then 4,4'-bis [N- ( 1-naphthyl) -N-phenylamino] biphenyl (hereinafter referred to as 'NPD') was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, bis- (1-phenylisoquinoline) iridium (III) acetylacetonate (hereinafter, '(piq) ₂ Ir (acac)) is used as the host material of the compound P-1-1 according to an embodiment of the present invention on the hole transport layer. Using a dopant material as a dopant material to deposit a light emitting layer having a thickness of 30 nm. Subsequently, (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter referred to as 'BAlq') on the light emitting layer was vacuum deposited to a thickness of 10 nm to form a hole blocking layer. On the hole blocking layer, tris- (8-hydroxyquinoline) aluminum (hereinafter, referred to as 'Alq ₃ ') was vacuum deposited to a thickness of 40 nm to form an electron transport layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form an organic electroluminescent device.

[Example 2] to [Example 200] Red organic light emitting device (phosphorescent host)

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

[Comparative Example 1] to [Comparative Example 5] Red organic light emitting device (phosphorescent host)

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

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

From Table 4, the device using the compound according to an embodiment of the present invention as a phosphorescent host material of the light emitting layer is significantly improved the driving voltage and luminous efficiency than the device using the comparative compound A to E as a phosphorescent host material of the light emitting layer You can check it.

In general, comparison of CBP used as a host compound A, Bebq ₂ Comparative compound than the device using the B when using a de-benzothiophene (fused) comparison compound C is naphthalene (naphthalene) is joined to (Dibenzothiophen) organic electroluminescent When the comparative compound D and the comparative compound E, in which the dibenzothiophene is bonded to quinoline rather than naphthalene, are more excellent than those of the comparative compound C, the efficiency of the organic electric device is improved. It can be seen that the driving voltage is lowered. Comparative Compound D and Comparative Compound E are the same in which the quinoline is conjugated to a hetero ring such as dibenzothiophene or carbazole, but the conjugated position is different. I can confirm that Therefore, this suggests that the characteristics may be remarkably changed depending on the position and type of the junction (substituent position and number of nitrogen) of the substituent.

The compound (the substitution position of nitrogen) which is conjugated with the comparative compound E is the same or similar, but the compound according to the embodiment of the present invention in which the hetero element has sulfur (S) or oxygen (O) other than nitrogen is a comparative compound A to The best device results were obtained compared to Comparative Compound E. This suggests that the properties of the compounds and the results of the devices may vary significantly depending on the type of hetero element.

Among the compounds according to one embodiment of the present invention, compounds represented by Chemical Formulas 1-1 to 1-4 in which R ¹⁰ and R ¹¹ or R ²² and R ²³ are bonded to each other to form a ring together with the benzene ring to which they are bonded are The best device results were shown. This is because the ring-forming compound has better thermal stability and moderate energy level than other compounds in which R ¹⁰ and R ¹¹ or R ²² and R ²³ are bonded to each other and do not form a ring. This can be explained as the result of improving the energy balance.

The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications can be made without departing from the essential features of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe 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 descriptions within the scope equivalent thereto should be construed as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is related to the patent application No. 10-2014-0142331 filed in Korea on October 21, 2014 and the patent application No. 10-2015-0080742 filed in Korea on June 08, 2015. Priority is claimed under section (a) (35 USC § 119 (a)), all of which is incorporated by reference in this patent application. In addition, if this patent application claims priority for the same reason as for the above countries, all the contents are incorporated in this patent application by reference.

Claims (11)

Compound represented by the following formula (1):

In Chemical Formula 1, X is -O-, -S-, A is one of Formulas 2 to 4, R ² to R ²³ are each independently of the other hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ aryl group; Fluorenyl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C ₁ -C ₅₀ ; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ ; wherein R ¹⁰ and R ¹¹ or R ²² and R ²³ may be combined with each other to form an aromatic or heteroaromatic ring, R ¹ is -L ^1- (Ar ¹ ) or -L ^2- (Ar ¹ ) (Ar ² ), L ¹ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; And a C ₂ -C ₆₀ heteroarylene group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P, L ² is C ₆ -C ₆₀ trivalent aryl; Trivalent fluorene; And C ₂ -C ₆₀ trivalent heteroaryl including at least one hetero atom selected from the group consisting of O, N, S, Si, and P, 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 -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And -L'-N (R ^a ) (R ^b ); L 'is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P, wherein R ^a and R ^b are each independently Aryl group of C ₆ -C ₆₀ ; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ ; And C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P, The aryl group, fluorenyl group, heterocyclic group, alkyl group, fused ring group, alkenyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group, heteroarylene group are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxyl group of C ₁ -C ₂₀ ; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; Aryl group of C ₆ -C ₂₀ ; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A cycloalkyl group of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; And an arylalkenyl group of C ₈ -C ₂₀ It may be further substituted with one or more substituents selected from the group consisting of. The method of claim 1, Formula 1 is a compound characterized in that represented by one of the following formula 5 to formula 10:

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

In Chemical Formulas 1-1 to 1-4, R ¹ to R ⁹ , R ¹⁸ to R ^21, and X are the same as defined in claim 1, R ²⁴ to R ²⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₆ -C ₆₀ aryl group; Fluorenyl group; C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An alkyl group of C ₁ -C ₅₀ ; A fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkoxyl group of C ₁ -C ₃₀ ; And an aryloxy group of C ₆ -C ₃₀ It can be selected from the group consisting of. The method of claim 1, Compound represented by Formula 1 is one of the following compounds:

. An organic electric device comprising the compound of claim 1. The method of claim 5, A first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode and containing the compound. The organic material layer, characterized in that the compound contains one or two or more kinds of the compound. The method of claim 6, The organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer and a light emitting layer. The method of claim 6, And an optical 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 6, The organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electroluminescent device of claim 5; And And a controller for driving the display device. The method of claim 10, The organic electroluminescent device is an electronic device, characterized in that at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive member, an organic transistor, and a device for monochrome or white illumination.

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