KR102229862B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving luminous efficiency, stability, and lifespan of a device, an organic electric device using the same, and an electronic device thereof.

Description

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

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

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

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

On the other hand, it delays the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of the organic electronic device, and is stable against Joule heating, i.e., high glass transition when the device is driven There is a need to develop a material for a hole injection layer having a temperature. In addition, it has been reported that the low glass transition temperature of the material for the hole transport layer has a great influence on the life of the device, depending on the characteristics of the uniformity of the thin film surface being collapsed during device driving. In addition, a vapor deposition method is the mainstream in the formation of an OLED device, and a material that can withstand such a vapor deposition method for a long time, that is, a material having strong heat resistance properties, is required.

In order to fully exhibit the excellent features of the above-described organic electronic device, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. Although this should be preceded, development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently developed, and therefore, development of a new material is continuously 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 a device, an organic electric device using the same, and an electronic device thereof.

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

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

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

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

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

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

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

Meanwhile, the term "halo" or "halogen" used herein includes fluorine, chlorine, bromine, and iodine unless otherwise specified.

The term "alkyl" or "alkyl group" as used herein has a carbon number of 1 to 60 unless otherwise specified, and is not limited thereto.

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

The term "cycloalkyl" as used herein refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise specified, and is not limited thereto.

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto.

In the present invention, an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

As used herein, the term "heteroalkyl" means an alkyl containing one or more heteroatoms unless otherwise specified. The term "heteroaryl group" or "heteroarylene group" as used herein refers to an aryl group or arylene group having 3 to 60 carbon atoms each including one or more heteroatoms, unless otherwise specified, and is limited thereto. No, it includes not only a single ring but also a heterocycle, and may be formed by combining adjacent groups.

The terms "heterocycloalkyl" and "heterocyclic group" as used in the present invention include one or more heteroatoms, have 2 to 60 carbon atoms, and include heterocycles as well as monocyclic rings unless otherwise specified. , May be formed by combining adjacent groups. In addition, "heterocyclic group" may mean an alicyclic and/or aromatic containing a hetero atom.

The term "heteroatom" as used herein refers to N, O, S, P and Si unless otherwise specified.

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

Unless otherwise stated, the term "saturated or unsaturated ring" as used herein refers to a saturated or unsaturated aliphatic ring or an aromatic ring or heterocycle having 6 to 60 carbon atoms.

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

In addition, unless expressly stated, the term "substituted or unsubstituted" used in the present invention means "substituted" deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxy group, C ₁ to C ₂₀ alkylamine group, C ₁ to C ₂₀ alkylthiophene group, C ₆ to C ₂₀ arylthiophene group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group _{substituted with deuterium, C 8} ~ C ₂₀ arylalkenyl group, silane group, boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₅ ~ C _{20 heterocyclic group, and is not limited to these substituents.}

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

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode 180 formed on a substrate 110. ) Between the organic material layer containing the compound according to the present invention. At this time, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120. In this case, other layers other than the emission layer 150 may not be formed. A hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, a buffer layer 141, etc. may be further included, and the electron transport layer 160 may serve as a hole blocking layer.

Further, although not shown, the organic electric device according to the present invention may further include a protective layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer is a material of a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a host of the light emitting layer 150, or a dopant or a capping layer. Can be used as

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, an anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer ( After forming an organic material layer including 160) and the electron injection layer 170, it may be manufactured by depositing a material that can be used as the cathode 180 thereon.

In addition, the organic material layer is made of a variety of polymeric materials, so that less than a solution process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method, is used. It can be made in a number of layers. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

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

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

In addition, the organic electric device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or white lighting device.

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

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

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

<Formula 1>

In Formula 1, the total number of nitrogen atoms (N) in Formula 1 is an integer of 3 to 7, X is CR ₁ ; Or N; is selected from the group consisting of, wherein R ₁ is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A C ₁ to C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And fluorenyl group; is selected from the group consisting of.

Ar ₁ and Ar ₂ are each independently a C ₆ ~ C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And fluorenyl group; is selected from the group consisting of.

L ₁ is a phenylene group; Naphthalenylene group; And biphenylene group; is selected from the group consisting of, each of which is a nitro group; Cyano group; Halogen group; A C ₁ to C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; C ₂ ~ C ₂₀ Heterocyclic group; C ₁ ~ C ₂₀ alkoxy group; And an amino group; may be substituted with one or more substituents selected from the group consisting of.

_{HAr is composed of a C 2} ~ C ₃₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, wherein HAr is a bicyclic hetero having the same skeletal structure as naphthalene In the case of an aromatic ring, it must have two or more nitrogen atoms.

The R ₁ , Ar ₁ , and Ar ₂ are If an aryl group, which is hydrogen, deuterium, a halogen, a silane group, a boron group, a germanium group, a cyano group, an import nitro group, C ₁ ~ alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of the alkyl group, C of ₂ ~ C ₂₀ of alkenyl groups _{(alkenyl), C 2 ~ C} 20 of the alkynyl group (alkynyl), a C ₆ ~ C ₂₀ substituted with an aryl group, a heavy hydrogen of C ₆ ~ C ₂₀ aryl group, C ₂ to C ₂₀ heterocyclic group, C ₃ to C ₂₀ cycloalkyl group, C ₇ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group.}

When the R ₁ , Ar ₁ , Ar ₂ , and HAr are heterocyclic groups, it is hydrogen, deuterium, halogen, silane group, cyano group, nitro group, C ₁ to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkyl group , C ₂ ~ C ₂₀ of alkenyl groups (alkenyl), C ₆ ~ heterocyclic group of C ₂₀ aryl group, a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ substituted by deuterium, C ₃ ~ C ₂₀ Of a cycloalkyl group, C ₇ ~ C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group.}

When the R ₁ , Ar ₁ , and Ar ₂ are fluorenyl groups, it is hydrogen, deuterium, halogen, silane group, cyano group, C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, substituted with one or more substituents selected from the group consisting of a cycloalkyl group of C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₂ ~ C ₂₀ heterocyclic group and C ₃ ~ C ₂₀ of Can be.

When R ₁ is an alkyl group, it is hydrogen, deuterium, halogen, silane group, boron group, cyano group, C ₁ to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group ( the alkenyl), C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group, C ₇ ~ C ₂₀ substituted by deuterium It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group.}

When R ₁ is an alkenyl group, it is hydrogen, deuterium, halogen, silane group, cyano group, C ₁ to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group (alkenyl) , a C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ aryl group substituted with a heavy hydrogen, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ of the It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group.}

When the R ₁ is an alkoxy group, which is hydrogen, deuterium, a halogen, a silane group, a C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted with a heavy hydrogen aryl, C It may be substituted with one or more substituents selected from the group consisting of a ₂ ~ C ₂₀ heterocyclic group and a C ₃ ~ C _{20 cycloalkyl group.}

When R ₁ is an aryloxy group, it is hydrogen, deuterium, a silane group, a cyano group, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, It may be substituted with one or more substituents selected from the group consisting of a C ₂ ~ C ₂₀ heterocyclic group and a C ₃ ~ C _{20 cycloalkyl group.}

_{Ar 1} and Ar ₂ of Formula 1 may be independently selected from the group consisting of the following groups.

In addition, Formula 1 may be represented by the following Formula 2 or Formula 3.

<Formula 2> <Formula 3>

Here, R ₁ , L ₁ , Ar ₁ and Ar ₂ are the same as defined in Formula 1, HAr of Formula 2 is one selected from the group consisting of the following H1 to H29, and HAr of Formula 3 is It is one selected from the group consisting of the following H1 to H26, R ₂ and R ₃ of the following H1 to H29 are the same as the definition _{of R 1 of Formula 1, and R 1} , R ₂ and R ₃ are independent of each other .

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

On the other hand, the compound according to an aspect of the present invention is represented by the following formula (4).

<Formula 4>

In Chemical Formula 4,

또는

이고,Ar ₃ is

or

ego,

Ar ₄ to Ar ₆ are each independently a C ₆ to C ₆₀ aryl group; _{C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N and S; C ₆ ~ C ₃₀ aryloxy group; And fluorenyl group; is selected from the group consisting of.

L ₂ is a C ₆ ~ C ₆₀ arylene group; _{A C 2} ~ C ₆₀ heteroarylene group containing at least one heteroatom of O, N and S; And it is selected from the group consisting of a fluorenylene group.

n and m are each an integer of 1 to 4, and when n or m is 2 or more, _{each of a plurality of R 4} and R ₅ is the same as or different from each other, wherein i) R ₄ and R ₅ are independently of each other, hydrogen; heavy hydrogen; Tritium; C ₆ ~ C ₆₀ aryl group; A C ₁ to C ₅₀ alkyl group; C ₂ ~ C ₄₀ alkenyl group; _{C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N and S; Fluorenyl group; A fused ring group of a C ₆ ~ C ₆₀ aromatic ring and a C ₄ ~ C _{60 aliphatic ring;} Amine group; Nitro group; Nitrile group; Amide group; And a silane group; or ii) when n or m is an integer of 2 or more, adjacent R ₄ or adjacent R ₅ are bonded to each other to form at least one saturated or unsaturated cyclic compound.

When the R ₄ , R ₅ , and Ar ₄ to Ar ₆ are an aryl group, it is hydrogen, deuterium, halogen, a C ₁ to C ₆₀ alkyl group, a C ₁ to C ₆₀ alkoxy group, and a C ₁ to C ₆₀ alkylamine group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C import of ₆₀ alkylthio, C ₆ ~ C ₆₀ coming aryl Ti, C ₂ ~ alkynyl group of C ₆₀ alkenyl group, C ₂ ~ C ₆₀ of, C ₃ ~ cycloalkyl group of C _60, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, a C ₈ ~ arylalkenyl group, a substituted or unsubstituted silane group, a substituted ring of C ₆₀ Or it may be substituted with one or more substituents selected from the group consisting of an unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C ₂ to C _{60 heterocyclic group,}

When the R ₄ , R ₅ , and Ar ₄ to Ar ₆ are heterocyclic groups, it is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₆₀ alkyl group, C ₁ to C ₆₀ alkoxy group, C ₁ ~ C for ₆₀ alkyl amine group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C import of ₆₀ alkylthio, C ₂ ~ C ₆₀ alkenyl group, C ₂ ~ C ₆₀ alkynyl group, C ₃ ~ of for C ₆₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium A group, and a substituted or unsubstituted C ₂ ~ C ₆₀ heterocyclic group may be substituted with one or more substituents selected from the group consisting of,

When the R ₄ , R ₅ , and Ar ₄ to Ar ₆ are fluorenyl groups, it is hydrogen, deuterium, halogen, silane group, cyano group, C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group ( alkenyl), C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₂ ~ C ₂₀ of the heterocyclic group and C ₃ ~ C ₂₀ from the group consisting of a cycloalkyl group at least one group selected in the May be substituted with a substituent,

When the R ₄ and R ₅ are an alkyl group or an alkenyl group, it is hydrogen, deuterium, halogen, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, C ₆ to C ₆₀ aryl group, C ₆ to C ₆₀ aryl group _{substituted with deuterium, C 7} to C ₂₀ arylalkyl group, C ₈ to C ₂₀ arylalkenyl group, C ₂ to C ₆₀ heterocyclic group, nitrile group And it may be substituted with one or more substituents selected from the group consisting of an acetylene group,

When R ₄ and R ₅ are amine groups, it is It may be substituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ aryl group or C ₂ ~ C _{60 heterocyclic group,}

When the R ₄ and R ₅ fused ring group, which come alkylthio of hydrogen, deuterium, a halogen, a silane group, a boron group, a germanium group, a cyano group, a nitro group, C ₁ ~ C _20, C of ₁ ~ C ₂₀ Alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group (alkynyl), C ₆ ~ C ₂₀ aryl group, C substituted with deuterium ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ heterocyclic group, C ₃ to C ₂₀ cycloalkyl group, C ₇ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group,}

When Ar ₄ to Ar ₆ is an aryloxy group, it is hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ Of an alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₆₀ aryl group substituted with deuterium, and a C ₂ to C It may be substituted with one or more substituents selected from the group consisting of _{60 heteroaryl groups,}

When L ₂ is an arylene group or a heteroarylene group, it is hydrogen, deuterium, tritium, nitro, nitrile, halogen, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, an amino group, C ₂ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group and a C ₆ ~ C _{20 aryl group,}

When L ₂ is a fluorenylene group, it is hydrogen, deuterium, a halogen group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, C ₇ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group, C ₈ ~ C ₂₀ arylalkenyl group, C ₁ ~ C ₅₀ alkyl group, C ₂ ~ C _{20 heterocyclic group, nitrile group, and acetylene group.}

In addition, Ar ₄ to Ar ₆ of Formula 4 is represented by one selected from the group consisting of the following groups, but is not limited thereto.

Meanwhile, Ar ₃ of Formula 4 is represented by one selected from the group consisting of Formulas 5 to 13, but is not limited thereto.

<Formula 5> <Formula 6> <Formula 7> <Formula 8> <Formula 9>

<Formula 10> <Formula 11> <Formula 12> <Formula 13>

At this time, Ar ₆ , R ₄ , L ₂ and n in Formulas 5 to 13 are the same as defined in Formula 4.

In addition, the compound represented by Formula 4 may be one of the following compounds.

The compounds represented by Chemical Formulas 1 to 4 may be one of the specific compounds presented above, but are not limited thereto.

In another aspect, the present invention provides an electronic device including an organic electric device to which the compound represented by the above formula is applied.

Meanwhile, in an embodiment of the present invention, in an organic electric device including a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode, the organic material layer is a hole transport layer, a light emitting layer, and an electron transport layer. Including, wherein the electron transport layer contains the compound represented by the formula (1), the hole transport layer provides an organic electric device containing the compound represented by the formula (4).

In another embodiment of the present invention, the first electrode, the second electrode, the organic material layer positioned between the first electrode and the second electrode, and the light efficiency of at least one of the lower portion of the first electrode or the upper portion of the second electrode are improved. In the organic electrical device characterized in that the layer is formed, the organic material layer provides an organic electrical device containing the compound represented by the formula (1).

Hereinafter, examples for synthesizing the compounds represented by Formulas 1 and 4 according to the present invention and examples for preparing an organic electric device will be described in detail with reference to examples, but the present invention is not limited to the following examples.

Synthesis example

Ⅰ. Synthesis of Formula 1

Exemplarily, the compounds (Final Products: products 1-1 to 3-112) according to the present invention may be prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below.

<Reaction Scheme 1>

One. Sub Synthesis of 1

Sub 1 of Scheme 1 can be synthesized by the reaction route of Method 1 or Method 2 of Scheme 2 below.

<Reaction Scheme 2>

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

(One) Sub 1-1 Synthesis example

<Reaction Scheme 3>

After dissolving the starting material, 2,4,6-trichloropyrimidine (78.91g, 430.2mmol) in THF in a round bottom flask, naphthalen-2-ylboronic acid (147.99g, 860.4mmol), Pd(PPh ₃ ) ₄ (24.86g) , 21.5mmol), K ₂ CO ₃ (237.84g, 1720.9mmol), water was added and stirred at 70°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 110.47 g (yield: 70%) of the product.

(2) Sub 1-3 Synthesis example

<Reaction Scheme 4>

Dissolve the starting material 2,4,6-trichloro-1,3,5-triazine (55.64g, 301.7mmol) with THF in a round bottom flask, lower the temperature of the reaction to -10℃, and naphthalen-2-ylmagnesium bromide 2.0M in THF (331.9ml, 663.8mmol) was slowly added dropwise, followed by stirring at 60°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 79.91 g (yield: 72%) of the product.

(3) Sub 1-5 Synthesis example

<Reaction Scheme 5>

Starting material 2,4,6-trichloro-5-methylpyrimidine (29.96g, 151.7mmol) naphthalen-1-ylboronic acid (52.19g, 303.5mmol), Pd(PPh ₃ ) ₄ (8.77g, 7.6mmol), K ₂ CO ₃ (83.88g, 606.9mmol), THF, and water using the Sub 1-1 synthesis method to give a product 33.52g (yield: 58%).

(4) Sub 1-6 Synthesis example

<Reaction Scheme 6>

Starting material 2,4,6-trichloro-1,3,5-triazine (51.35g, 278.5mmol) naphthalen-1-ylmagnesium bromide 2.0M in THF (306.3ml, 612.6mmol), THF is added to the Sub 1- 3 The product 74.77g (yield: 73%) was obtained using a synthesis method.

(5) Sub 1-7 Synthesis example

<Reaction Scheme 7>

Intermediate Sub 1-I-7 synthesis

After dissolving the starting material 2,4,6-trichloropyrimidine (76.33g, 416.1mmol) in THF in a round bottom flask, naphthalen-2-ylboronic acid (71.57g, 416.1mmol), Pd(PPh ₃ ) ₄ (14.43g) , 12.5mmol), K ₂ CO ₃ (115.03g, 832.3mmol), and water were added and stirred at 70°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 73.28 g (yield: 64%) of the product.

Sub 1-7 synthesis

After dissolving Sub 1-I-7 (73.28g, 266.3mmol) obtained in the above synthesis with THF in a round bottom flask, naphthalen-1-ylboronic acid (45.81g, 266.3mmol), Pd(PPh ₃ ) ₄ (9.23g , 8mmol), K ₂ CO ₃ (73.62g, 532.7mmol), water was added and stirred at 70°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried with MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 58.62 g (yield: 60%) of the product.

(6) Sub 1-11 Synthesis example

<Reaction Scheme 8>

Intermediate Sub 1-I-11 synthesis

Dissolve the starting material 2,4,6-trichloro-1,3,5-triazine (74.78g, 405.5mmol) with THF in a round bottom flask, lower the temperature of the reaction to -10℃, and naphthalen-2-ylmagnesium bromide 2.0M in THF (223ml, 446.1mmol) was slowly added dropwise, followed by stirring at 0°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 78.38 g (yield: 70%) of the product.

Sub 1-11 synthesis

After dissolving Sub 1-I-11 (78.38g, 283.9mmol) obtained in the above synthesis with THF in a round bottom flask, the temperature of the reactant was lowered to -10°C, and naphthalen-2-ylmagnesium bromide 2.0M in THF (156.1ml , 312.2mmol) was slowly added dropwise, followed by stirring at 60°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 63.69 g (yield: 61%) of the product.

(7) Sub 1-28 Synthesis example

<Reaction Scheme 9>

Starting material 2,4,6-trichloropyrimidine (20.93g, 114.1mmol) in pyridin-4-ylboronic acid (28.05g, 228.2mmol), Pd(PPh ₃ ) ₄ (6.59g, 5.7mmol), K ₂ CO ₃ (63.08g, 456.4mmol), THF, and water were used to obtain 19.62g (yield: 64%) of the product using the Sub 1-1 synthesis method.

(8) Sub 1-38 Synthesis example

<Reaction Scheme 10>

Sub 1-3 Using a synthetic method, the product 25.28g (yield: 72%) was obtained.

Meanwhile, examples of Sub 1 are as follows, but are not limited thereto, and their FD-MS is shown in Table 1 below.

[Table 1]

2. Sub Synthesis of 2

Sub 2 of Scheme 1 can be synthesized by the reaction route of Scheme 11.

<Reaction Scheme 11>

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

(One) Sub 2-14 Synthesis example

<Reaction Scheme 12>

After dissolving the starting material 4-(4-bromophenyl)-2-phenylquinazoline (54.66g, 151.3mmol) in DMF in a round bottom flask, Bis(pinacolato)diboron (42.27g, 166.4mmol), Pd(dppf)Cl ₂ (3.71g, 4.5mmol), KOAc (44.55g, 453.9mmol) was added and stirred at 90°C. Upon completion of the reaction, DMF was removed through distillation and extracted with _{CH 2} Cl _{2 and water.} The organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 49.43g (yield: 80%) of the product.

(2) Sub 2-16 Synthesis example

<Reaction Scheme 13>

Bis(pinacolato)diboron (38.29g, 150.8mmol), Pd(dppf)Cl ₂ (3.36g, 4.1mmol), KOAc in the starting material 2-(4-bromophenyl)-4-phenylquinazoline (49.52g, 137.1mmol) (40.36g, 411.3mmol), DMF was obtained by using the Sub 2-14 synthesis method, the product 47.58g (yield: 85%).

(3) Sub 2-34 Synthesis example

<Reaction Scheme 14>

Bis(pinacolato)diboron (45.43g, 178.9mmol), Pd in the starting material 2-(4-bromophenyl)-5-(naphthalen-1-yl)-1,3,4-oxadiazole (57.12g, 162.6mmol) (dppf)Cl ₂ (3.98g, 4.9mmol), KOAc (47.89g, 487.9mmol), DMF was obtained by using the Sub 2-14 synthesis method 50.52g (yield: 78%) of the product.

(4) Sub 2-96 Synthesis example

<Reaction Scheme 15>

Bis in the starting material 2-(4'-bromo-[1,1'-biphenyl]-4-yl)-1-methyl-1 H -phenanthro [9,10- d ]imidazole (56.35g, 121.6mmol) (pinacolato)diboron (33.97g, 133.8mmol), Pd(dppf)Cl ₂ (2.98g, 3.6mmol), KOAc (35.8g, 364.8mmol), DMF was obtained by using the Sub 2-14 synthesis method, the product 47.18g (yield: 76%).

(5) Sub 2-101 Synthesis example

<Reaction Scheme 16>

Bis(pinacolato)diboron (44.59g, 175.6mmol), Pd(dppf)Cl ₂ (3.91g, in the starting material 2-(6-bromonaphthalen-2-yl)benzo[ d]thiazole (54.31g, 159.6mmol) 4.8mmol), KOAc (47g, 478.9mmol), DMF was obtained by using the Sub 2-14 synthesis method 50.69g (yield: 82%) of the product.

(6) Sub 2-115 Synthesis example

<Scheme 17>

Bis(pinacolato)diboron (42.58g, 167.7mmol), Pd(dppf)Cl ₂ (3.73g, 4.6) in the starting material 6-(3-bromophenyl)-2-phenylbenzo[ d]oxazole (53.38g, 152.4mmol) mmol), KOAc (44.88g, 457.3mmol), DMF was obtained 50.86g (yield: 84%) of the product using the Sub 2-14 synthesis method.

(7) Sub 2-119 Synthesis example

<Reaction Scheme 18>

_{Bis(pinacolato)diboron (29.2g, 115mmol), Pd(dppf)Cl 2 in the} starting material 2-(4-bromophenyl)-4,6-di(naphthalen-1-yl)pyrimidine (50.95g, 104.5mmol) (2.56g, 3.1mmol), KOAc (30.78g, 313.6mmol), DMF was obtained by using the above Sub 2-14 synthesis method 45.25g (yield: 81%) of the product.

Meanwhile, examples of Sub 2 are as follows, but are not limited thereto, and their FD-MS is shown in Table 2 below.

[Table 2]

3. Formula 1 Product synthesis

After dissolving Sub 1 (1 equivalent) in THF in a round bottom flask, Sub 2 (1.1 equivalent), Pd(PPh ₃ ) ₄ (0.03 equivalent), K ₂ CO ₃ (2 equivalent) were added and stirred at 80°C. . When the reaction was completed, CH ₂ Cl ₂ and water were extracted, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain a final product.

(One) Product 1-34 Synthesis example

<Reaction Scheme 19>

After dissolving Sub 1-1 (11.54g, 31.5mmol) obtained in the above synthesis with THF in a round bottom flask, Sub 2-34 (13.78g, 34.6mmol), Pd(PPh ₃ ) ₄ (1.09g, 0.9mmol) , K ₂ CO ₃ (8.7g, 62.9mmol), and water were added and stirred at 80°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 12.32 g (yield: 65%) of the product.

(2) Product 1-76 Synthesis example

<Reaction Scheme 20>

Sub 1-3 (11.09g, 30.1mmol) obtained in the above synthesis Sub 2-14 (13.54g, 33.2mmol), Pd (PPh ₃ ) ₄ (1.05g, 0.9mmol), K ₂ CO ₃ (8.33g, 60.3mmol), THF, and water were used to obtain 11.29g (yield: 61%) of the product using the Synthesis of Product 1-34.

(3) Product 2-53 Synthesis example

<Reaction Scheme 21>

Sub 1-5 (10.82g, 28.4mmol) obtained in the above synthesis Sub 2-96 (15.95g, 31.2mmol), Pd(PPh ₃ ) ₄ (0.98g, 0.9mmol), K ₂ CO ₃ (7.85g, 56.8 mmol), THF, and water were used to obtain 12.22 g of a product (yield: 59%) using the Synthesis of Product 1-34.

(4) Product 2-109 Synthesis example

<Reaction Scheme 22>

Sub 1-6 (10.24g, 27.8mmol) obtained in the above synthesis Sub 2-119 (16.37g, 30.6mmol), Pd(PPh ₃ ) ₄ (0.97g, 0.8mmol), K ₂ CO ₃ (7.7g, 55.7 mmol), THF, and water were used to obtain 12.98 g (yield: 63%) of the product using the Synthesis of Product 1-34.

(5) Product 3-40 Synthesis example

<Reaction Scheme 23>

Sub 1-7 (10.24g, 27.9mmol) obtained in the above synthesis Sub 2-101 (11.89 g, 30.7mmol), Pd(PPh ₃ ) ₄ (0.97g, 0.8mmol), K ₂ CO ₃ (7.72g, 55.8mmol), THF, and water were used to obtain 10.08g (yield: 61%) of the product using the Synthesis of Product 1-34.

(6) Product 3-80 Synthesis example

<Reaction Scheme 24>

Sub 1-11 (10.78g, 29.3mmol) obtained in the above synthesis Sub 2-115 (12.81g, 32.2mmol), Pd(PPh ₃ ) ₄ (1.02g, 0.9mmol), K ₂ CO ₃ (8.1g, 58.6mmol), THF, and water were used to obtain 10.24g (yield: 58%) of the product using the Synthesis of Product 1-34.

(7) Product 3-89 Synthesis example

<Reaction Scheme 25>

Sub 1-28 (9.55g, 35.5mmol) obtained in the above synthesis Sub 2-14 (15.96g, 39.1mmol), Pd(PPh ₃ ) ₄ (1.23g, 1.1mmol), K ₂ CO ₃ (9.82g, 71.1mmol), THF, and water were used to obtain 10.79g (yield: 59%) of the product using the Synthesis of Product 1-34.

(8) Product 3-107 Synthesis example

<Reaction Scheme 26>

Sub 1-38 (10.09g, 27.3mmol) obtained in the above synthesis Sub 2-16 (12.25g, 30mmol), Pd(PPh ₃ ) ₄ (0.95g, _{0.8mmol), K 2} CO ₃ (7.54g, 54.6 mmol), THF, and water were used to obtain 10.58 g of a product (yield: 63%) using the Synthesis of Product 1-34.

Meanwhile, FD-MS values of compounds 1-1 to 3-112 prepared according to the synthesis example as described above are shown in Table 3 below.

[Table 3]

Ⅱ. Of formula 4 synthesis

Illustratively, the compounds (final products: products 4-1 to 10-32) according to the present invention may be prepared by reacting one of Sub 3 or Sub 4 with Sub 5 as shown in Scheme 27 below.

<Scheme 27>

One. Sub Synthesis of 3

Sub 3 can be synthesized by Scheme 39 or Scheme 40 of Example 4 disclosed in patent application 10-2012-0090101.

<Reaction Scheme 28>

<Reaction Scheme 29>

2. Sub Synthesis of 4

Sub 4 can be synthesized by Scheme 55 of Example 4 disclosed in Patent Application 10-2012-0090101.

<Reaction Scheme 30>

3. Sub Synthesis of 5

Sub 5 can be synthesized according to Scheme 16 of Example 2 disclosed in patent application 10-2012-0090101.

<Reaction Scheme 31>

4. Formula 4 Product synthesis

After dissolving Sub 5 (1 equivalent) in toluene in a round bottom flask, Sub 3 or Sub 4 (1.2 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P( t -Bu) ₃ (0.08 equivalent), NaO t- Bu (3 eq) was added and stirred at 100°C. When the reaction was completed, CH ₂ Cl ₂ and water were extracted, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain a final product.

(One) Product 4-36 Synthesis example

<Reaction Scheme 32>

After dissolving the starting material Sub 5-1 (7.26g, 22.6mmol) in toluene in a round bottom flask, Sub 3-1 (11.88g, 27.1mmol), Pd ₂ (dba) ₃ (0.62g, 0.7mmol), 50% P( t- _{Bu) 3} (0.9ml, 1.8mmol), NaO t- Bu (6.51g, 67.8mmol) was added and stirred at 100°C. When the reaction was completed, the product was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 11.19 g (yield: 73%) of the product.

(2) Product 5-3 Synthesis example

<Reaction Scheme 33>

Starting material Sub 5-1 (8.09g, 25.2mmol) Sub 4-1 (12.03g, 30.2mmol), Pd ₂ (dba) ₃ (0.69g, 0.8mmol), 50% P( t _{-Bu) 3} (1ml, 2mmol), NaO t -Bu (7.26g, 75.5mmol), toluene was obtained by using the product 4-36 synthesis method 12.86g (yield: 80%)

(3) Product 5-29 Synthesis example

<Reaction Scheme 34>

Starting material Sub 5-2 (7.74g, 18.9mmol) Sub 4-2 (10.76g, 22.7mmol), Pd ₂ (dba) ₃ (0.52g, 0.6mmol), 50% P( t _{-Bu) 3} (0.7ml, 1.5mmol), NaO t -Bu (5.45g, 56.7mmol), toluene was obtained by using the Synthesis of Product 4-36, 11.38g (yield: 75%)

(4) Product 5-37 Synthesis example

<Reaction Scheme 35>

Starting material Sub 5-3 (7.58g, 15.6mmol) Sub 4-3 (8.89g, 18.7mmol), Pd ₂ (dba) ₃ (0.43g, 0.5mmol), 50% P( t -Bu) ₃ (0.6ml, 1.2mmol), NaO t -Bu (4.5g, 46.8 mmol), toluene was obtained by using the Synthesis Method of Product 4-36, 10.02g (yield: 73%) of the product.

(5) Product 6-28 Synthesis example

<Reaction Scheme 36>

Starting material Sub 5-1 (9.73g, 30.3mmol) Sub 3-2 (17.74g, 36.3mmol), Pd ₂ (dba) ₃ (0.83g, 0.9mmol), 50% P( t -Bu) ₃ (1.2ml, 2.4mmol), NaO t -Bu (8.74g, 90.9mmol), toluene was obtained by using the Synthesis of Product 4-36, the product 15.68g (yield: 71%).

(6) Product 7-15 Synthesis example

<Scheme 37>

Starting material Sub 5-3 (9.98g, 20.6mmol) Sub 3-3 (11.06g, 24.7mmol), Pd ₂ (dba) ₃ (0.57g, 0.6mmol), 50% P( t _{-Bu) 3} (0.8ml, 1.6mmol), NaO t -Bu (5.93g, 61.7mmol), toluene was obtained by using the Synthesis of Product 4-36, the product 13.5g (yield: 77%).

Meanwhile, FD-MS values of compounds 4-1 to 10-32 prepared according to the synthesis example as described above are shown in Table 4 below.

[Table 4]

Meanwhile, the exemplary synthesis examples of the present invention represented by Chemical Formula 1 or Chemical Formula 4 have been described above, but all of them are based on Suzuki cross-coupling reaction, Grignard reaction, Miyaura boration reaction, and Buchwald-Hartwig cross coupling reaction. It will be readily understood by those skilled in the art that the above reaction proceeds even if other substituents (such as X, HAr, L ₁ , L ₂ , Ar1 to Ar6, R ₁ to R _{5, etc.) are bonded in addition to the substituents specified in.} For example, starting material in Scheme 2 -> Sub 1 (Method 1), Product synthesis reaction formula of Formula 1 (Scheme 19 to Scheme 26), etc. are based on Suzuki cross-coupling reaction, and starting material in Scheme 2 -> Sub 1 ( Method 2) The reaction is based on the Grignard reaction, and the starting material -> Sub 2 reaction in Scheme 9 is based on the Miyaura boration reaction, and the Product synthesis scheme of Formula 4 (Scheme 28 to Scheme 33) is based on the Buchwald-Hartwig cross coupling reaction. As a basis, the reactions will proceed even if substituents not specifically specified are attached to them.

Manufacturing evaluation of organic electric devices

[ Experimental example One] Hole transport layer ( HTL )

An organic electroluminescent device was manufactured according to a conventional method using one of the compounds of the present invention obtained through synthesis as a material for a hole transport layer. First, on the ITO layer (anode) formed on a glass substrate, 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter, abbreviated as 2-TNATA) was vacuum deposited to form a hole having a thickness of 60 nm. After the injection layer was formed, the compound of the present invention (one of 4-1 to 10-32) was vacuum deposited on the hole injection layer to a thickness of 20 nm to form a hole transport layer. Next, CBP [4,4'-N,N'-dicarbazole-biphenyl] as a host material on the hole transport layer, Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant material 90: By doping at a weight ratio of 10, a light emitting layer was deposited to a thickness of 30 nm. Subsequently, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter, abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm on the light emitting layer to block holes. A layer was formed, and tris(8-quinolinol) aluminum (hereinafter, _{abbreviated as Alq 3} ) was formed on the hole blocking layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Comparative example 1 to Comparative example 8]

An organic electroluminescent device was manufactured in the same manner as in Experimental Example 1, except that the hole transport layer was formed by using the following Comparative Compounds 1 to 8 instead of the compound of the present invention.

Electroluminescence (EL) characteristics were measured with a PR-650 of Photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Experimental Example 1 and Comparative Examples 1 to 8, and the measurement result 300cd The T90 life was measured using a life measurement equipment manufactured by McScience at the luminance of /m².

Table 5 below shows the evaluation results of the organic electroluminescent devices manufactured according to Experimental Example 1 and Comparative Examples 1 to 8.

[Table 5]

As can be seen from the results of Table 5, the organic electroluminescent device using the compounds of the present invention represented by Chemical Formula 4 was used as a material for the hole transport layer, and the NPB-type derivatives of Comparative Examples 1 to 8, which have been widely used in the past. It showed relatively lower driving voltage and higher life than the compound. In particular, among the compounds represented by Formula 4, Ar ₃ is a compound represented by Formula 4b (5-3, 5-7 to 5-10, 5-23, 5-26, 5-27, 3-35 to 5-37 , 5-39, 5-47, 5-49, 5-50, 5-53, 5-77 and 5-78) showed relatively low driving voltage and high lifespan, and compound 5-9 showed a relatively low driving voltage. It was the lowest measured.

Accordingly, in order to obtain remarkably high results not only in the drop in driving voltage but also in luminous efficiency and lifetime, compound 5-9 was used in the hole transport layer, and the following organic electroluminescent device was manufactured by using the compounds of Formula 1 as the electron transport layer.

[ Experimental example 2] Hole transport layer +Electron transport layer (HTL+ ETL )

The compound of the present invention obtained through synthesis was used as a material for a hole transport layer and an electron transport layer to fabricate an organic electroluminescent device according to a conventional method. First, 2-TNATA was vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, and then Compound 5-9 as a hole transport compound was vacuum deposited on the hole injection layer to a thickness of 20 nm. A hole transport layer was formed. Next, CBP [4,4'-N,N'-dicarbazole-biphenyl] as a host material on the hole transport layer, Ir (ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant material 90: By doping at a weight ratio of 10, a light emitting layer was deposited to a thickness of 30 nm. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer, and an electron transport layer was formed on the hole blocking layer with a thickness of 40 nm of the compound of the present invention (one of 1-1 to 3-112). I did. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Comparative example 9] to [ Comparative example 16]

An organic electroluminescent device was manufactured in the same manner as in Experimental Example 2, except that the electron transport layer was formed by using the following Comparative Compounds 9 to 16 instead of the compound of the present invention.

Electroluminescence (EL) characteristics were measured with a PR-650 of Photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Experimental Example 2 and Comparative Examples 9 to 16, and the measurement result was 300cd. The T90 life was measured using a life measurement equipment manufactured by McScience at the luminance of /m².

Table 6 below shows the evaluation results for the organic electroluminescent device manufactured by Experimental Example 2 and Comparative Examples 9 to 16.

[Table 6]

As can be seen from the results of Table 6, the compounds of Comparative Examples 9 to 16 generally exhibit higher driving voltage, lower efficiency, and lower lifetime than the compounds of the present invention. In particular, Comparative Examples 11 to 16 are pyrimidine and triazine types similar to the compounds of the present invention, but show different results depending on the type and position of the substituent.

In the case of Comparative Examples 11 to 16, which are comparative compounds having the same core (pyrimidine and triazine) as the compound of the present invention and having a bicyclic heteroaromatic ring containing one N as a substituent, Compared with the compounds of the present invention, they exhibited relatively similar or high driving voltage, low efficiency, and low lifetime. In the case of a bicyclic heteroaromatic ring having a certain number of carbon atoms, it is judged that the difference in electron mobility appears differently depending on the number of hetero atoms included in the ring or the type in which the hetero atom is included. In other words, when the organic electroluminescent device is driven, holes are transferred to the light emitting layer very quickly, so that a material having fast electron mobility in the electron transport layer can expect high efficiency and high lifespan, which is consistent with the electron mobility of the compound of the present invention. As a result, it was confirmed that holes and electrons achieve charge balance and light emission is formed inside the light emitting layer rather than the interface of the electron transport layer, and as a result, the compounds of the present invention show higher efficiency and lifespan than Comparative Examples 9 to 16. I can.

[ Experimental example 3] Hole transport layer +Electron transport layer ( HTL + ETL )

The compound of the present invention obtained through synthesis was used as a material for a hole transport layer and an electron transport layer to fabricate an organic electroluminescent device according to a conventional method. First, after vacuum deposition of 2-TNATA on the ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, the compounds of the present invention (4-1 to 6) as a hole transport compound on the hole injection layer One of 32) was vacuum deposited to a thickness of 20 nm to form a hole transport layer. Next, CBP [4,4'-N,N'-dicarbazole-biphenyl] as a host material on the hole transport layer, Ir (ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant material 90: By doping at a weight ratio of 10, a light emitting layer was deposited to a thickness of 30 nm. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer, and an electron transport layer of Compound 1-76 of the present invention was formed on the hole blocking layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

Electroluminescence (EL) characteristics were measured by applying a forward bias DC voltage to the organic electroluminescent device manufactured according to Experimental Example 3 with a PR-650 of photoresearch. T90 life was measured through the life measurement equipment manufactured in.

Table 7 below shows the evaluation results for the organic electroluminescent device manufactured according to Experimental Example 3.

[Table 7]

As can be seen from the results of Table 7, it can be seen that Experimental Example 3 was significantly improved in terms of luminous efficiency than Experimental Example 1.

_{When Alq 3} is used as the electron transport layer as in Experimental Example 1, there is a remarkable difference in the movement speed of holes and electrons, whereas, as in Experimental Example 3, the compound 1-76 of the present invention, which has a faster electron mobility than _{Alq 3, was used} By introducing it, it is judged that the density of holes and electrons is balanced in the light emitting layer, thereby increasing the recombination efficiency and ultimately increasing the luminous efficiency.

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

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

Claims (13)

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

[In Chemical Formula 1,
The total number of nitrogen atoms (N) in Formula 1 is an integer of 3 to 7,
HAr is one selected from the group consisting of the following H13 ~ H24 and H26 ~ H29,

X is CR ₁ ; Or N; is selected from the group consisting of,
R ₁ to R ₃ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₃₀ aryl group; And C ₁ ~ C ₂₀ alkyl group; is selected from the group consisting of,
Ar ₁ and Ar ₂ are

ego,
L ₁ is a phenylene group; Naphthalenylene group; And biphenylene group; is selected from the group consisting of, each of which is a C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₀ aryl group; And C ₂ ~ C ₂₀ Heterocyclic group; It may be substituted with one or more substituents selected from the group consisting of.
(When the R _1, Ar _1, and Ar ₂ is an aryl group, which is hydrogen, deuterium, C ₁ to alkynyl of C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group (alkenyl), C ₂ ~ C ₂₀ of the diary (alkynyl), it may be optionally substituted with one or more substituents selected from the group consisting of a heterocyclic C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ aryl group and C ₂ ~ C ₂₀ substituted by deuterium,
When R ₁ is an alkyl group, it is hydrogen, deuterium, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₆ ~ C ₂₀ aryl group, C ₆ ~ C substituted with deuterium It may be substituted with one or more substituents selected from the group consisting of an aryl group of _{20 and a heterocyclic group of C 2} to C _{20 )]} delete The method of claim 1,
The compound represented by Formula 1 is a compound represented by Formula 2 or Formula 3.
<Formula 2><Formula3>

(Here, HAr, R ₁ , L ₁ , Ar ₁ and Ar ₂ are the same as defined in Formula 1) The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds.

In the organic electric device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,
The organic electroluminescent device, characterized in that the organic material layer contains the compound represented by the formula (1) according to claim 1. The method of claim 5,
An organic electric device, characterized in that a light efficiency improvement layer is formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode. In the organic electric device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer comprises a hole transport layer, a light emitting layer and an electron transport layer, the electron transport layer contains a compound represented by Formula 1 according to claim 1, and the hole transport layer contains a compound represented by the following Formula 4 Organic electric device.
<Formula 4>

[In Chemical Formula 4,
Ar ₃ is

or

ego,
Ar ₄ to Ar ₆ are each independently a C ₆ to C ₃₀ aryl group; _{C 2} ~ C ₃₀ heterocyclic group containing at least one heteroatom of O, N and S; And fluorenyl group; is selected from the group consisting of,
L ₂ is a C ₆ ~ C ₃₀ arylene group; And it is selected from the group consisting of a fluorenylene group,
n and m are each an integer of 1 to 4, and when n or m is 2 or more, _{each of a plurality of R 4} and R ₅ is the same as or different from each other, wherein i) R ₄ and R ₅ are independently of each other, hydrogen; heavy hydrogen; Tritium; C ₆ ~ C ₃₀ aryl group; _{And a heterocyclic group of C 2} to C ₃₀ containing at least one heteroatom of O, N and S; or ii) when n or m is an integer of 2 or more, neighboring R ₄ between or Adjacent R ₅ are bonded to each other to form at least one saturated or unsaturated cyclic compound.
(Wherein R _4, R _5, and Ar ₄ ~ Ar ₆ is an aryl group cases, this hydrogen, deuterium, C ₁ ~ alkyl group of C _30, C ₆ ~ substituted C aryl group, a heavy hydrogen of C _{30 6} ~ C ₃₀ May be substituted with one or more substituents selected from the group consisting of an aryl group and a substituted or unsubstituted C ₂ ~ C _{30 heterocyclic group,}
Wherein R _4, R _5, and Ar ₄ ~ Ar ₆ In this case, a heterocyclic group, which is a C ₆ ~ C ₃₀ substituted with a hydrogen, deuterium, an aryl group, a heavy hydrogen of the C ₁ ~ C ₃₀ alkyl group, C ₆ ~ C ₃₀ of May be substituted with one or more substituents selected from the group consisting of an aryl group and a substituted or unsubstituted C ₂ ~ C _{30 heterocyclic group,}
When L ₂ is an arylene group, it will be substituted with one or more substituents selected from the group consisting of _{hydrogen, deuterium, a C 1} to C ₂₀ alkyl group, a C ₂ to C ₂₀ heterocyclic group, and a C ₆ to C _{20 aryl group.} I can,
When L ₂ is a fluorenylene group, it is substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, _{an aryl group of C 6} to C _20, an alkyl group of C ₁ to C ₂₀ and _{a heterocyclic group of C 2} to C ₂₀ Can be)] The method of claim 7,
The Ar ₄ to Ar ₆ is an organic electric device, characterized in that one selected from the group consisting of the following groups.

The method of claim 7,
The _{organic electric device, characterized in that Ar 3} is one selected from the group consisting of the following Chemical Formulas 5 to 13.
<Formula 5><Formula6><Formula7><Formula8><Formula9>

<Formula 10><Formula11><Formula12><Formula13>

(Wherein, Ar ₆ , R ₄ , L ₂ and n in Formulas 5 to 13 are the same as defined in Formula 4) The method of claim 7,
The compound represented by Formula 4 is an organic electric device, characterized in that one of the following compounds.

The method of claim 5,
An organic electric device, characterized in that the compound is formed into the organic material layer by a soluble process. A display device including the organic electric device of claim 5; And a control unit for driving the display device. The method of claim 12,
The organic electroluminescent device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or white lighting device.

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