KR102516579B1 - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are an organic electric device including a compound represented by Formula 1, a first electrode, a second electrode, and an organic material layer between the first and second electrodes, and an electronic device including the same, wherein the compound represented by Formula 1 is present in the organic material layer. By including the, it is possible to lower the driving voltage of the organic electric element, it is possible to improve high heat resistance, color purity, luminous efficiency and lifespan.

Description

Compound for organic electric element, organic electric element using the 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, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.

An organic electric device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may include, 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 organic layers in organic electric devices may 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.

Polycyclic cyclic compounds containing heteroatoms have very large differences in properties depending on their material structure, and are applied to various layers as materials for organic electric devices. In particular, it has different characteristics such as band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. depending on the number of rings (rings), fused position (junction position), and type and arrangement of heteroatoms. Development of application to the layer of the electric element has been progressing.

In addition, until now, the development of materials for organic electric devices for the type, number and position of heteroatoms in five-ring compounds has been actively progressed. can be heard The prior patent discloses an embodiment in which a 5-ring compound is applied to a hole transport layer or a light emitting layer (host) of an organic electric device.

Since the invention of patents US 5843607 and KR 2008-7016107, which are indolocarbazole cores in which heteroatoms in five-ring compounds are composed only of nitrogen (N), benzobisbenzofuran cores in which heteroatoms are composed of only oxygen (O) Patent KR 1523124 was disclosed, and an indenofluorene core composed of only carbon (C) atoms in a five-ring compound was disclosed in patent KR 1346467.

As described above, after the development of the five-ring compound of the isomorphic type, the development of the five-ring compound of the heteroatom type was made, which has the low charge carrier mobility of the conventional five-ring compound of the isotype of the atom. and attempts to overcome low oxidative stability.

In general, when molecules are stacked, as the number of adjacent π-electrons increases, they have strong electrical interactions, which are closely related to charge carrier mobility.

That is, in the NN type isotype 5-ring compound, when the molecules are stacked, the arrangement order between the molecules has an edge-to-face form, whereas in the case of the heteroatom 5-ring compound having different heteroatoms, the packing structure of the molecule is It has an antiparallel cofacial π-stacking structure, so that the order of arrangement between molecules has a face-to-face form. At the asymmetrically arranged heteroatom N, which is the cause of this layered structure, The steric effect of the substituent to be substituted causes relatively high carrier mobility and high oxidation stability ( Org . Lett . 2008, 10, 1199).

In spite of these advantages described above, stable and efficient organic material layer materials for organic electric devices have not been sufficiently developed. Therefore, the development of new materials is continuously required, and in particular, development of a host material and a hole transport layer material of the light emitting layer is urgently required.

The present invention has been proposed to solve the above conventional problems, and provides a compound having high carrier mobility, high oxidation stability and high thermal stability, and at the same time, high luminous efficiency and low drive of a device using such a compound. An object of the present invention is to provide a compound capable of improving voltage, high heat resistance, color purity and lifetime, an organic electric device using the same, and an electronic device thereof.

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

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

According to the present invention, by introducing a core (6-ring heterocycle containing a phenanthrene structure) to increase packing density and using a specific compound limited in the type and number of heteroatoms as a material for an organic electric device, It exhibits stability, high carrier mobility and high oxidation stability, and has a T1 value and energy band gap that are easy to achieve charge balance in the light emitting layer, so that the luminous efficiency, heat resistance, lifespan, etc. of the organic electric device can be improved and the driving voltage can be lowered. can

1 is an exemplary diagram 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 components of each drawing, it should be noted that the same components have the same numerals as much as possible even if they are displayed on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the corresponding component is not limited by the term. When an element is described as being “connected,” “coupled to,” or “connected” to another element, that element is or may be directly connected to the other element, but there is another element between the elements. It will be understood that elements may be “connected”, “coupled” or “connected”.

Also, when a component such as a layer, film, region, or plate is said to be “on” or “on” another component, this is not only when it is “directly on” the other component, but also when there is another component in between. It should be understood that the case may also be included. Conversely, when an element is said to be “directly on” another part, it should be understood that there is no intervening part.

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

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

As used herein, unless otherwise specified, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, and includes a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and the like. A radical of a saturated aliphatic functional group, including an alkyl group, a cycloalkyl-substituted alkyl group.

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

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

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

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

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

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structure, respectively, unless otherwise specified, " Substituted fluorenyl group" or "substituted fluorenyl group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a This includes cases where they form a spy compound together.

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

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

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

In addition, in the present specification, a monovalent or divalent functional group is named by a functional group name or by indicating a valency in front of the parent compound. For example, "divalent benzothiophene" refers to a divalent functional group of the parent compound, benzothiophene, and similarly, "divalent dibenzothiophene" refers to a divalent functional group of the parent compound, dibenzothiophene. "Furan" refers to the divalent functional group of the parent compound, furan, "divalent dibenzofuran" refers to the divalent functional group of the parent compound, dibenzofuran, and "divalent pyrimidine" refers to the divalent functional group of the parent compound, pyrimidine. to indicate Similarly, a trivalent functional group can be represented by indicating trivalent in front of the parent compound. For example, "trivalent aryl" represents a trivalent functional group of an aromatic aryl, and "trivalent fluorene" represents a trivalent functional group of fluorene.

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

As used herein, the term "polycyclic" includes ring assemblies such as biphenyls and terphenyls, fused multiple ring systems, and spiro compounds, including aromatic as well as non-aromatic hydrocarbons. Rings include, of course, heterocycles that contain at least one heteroatom.

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

As used herein, the term "multiple fused ring system" refers to a fused ring form in which at least two atoms are shared, and includes a form in which two or more hydrocarbon ring systems are fused and at least one heteroatom. It includes a form in which at least one heterocyclic system is conjugated. These fused multiple ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings, or combinations of these rings.

As used herein, the term "spiro compound" has a 'spiro union', which means a connection formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called 'spiro atoms', and according to the number of spiro atoms in a compound, they are called 'monospiro-', 'dispiro-', and 'trispiro-', respectively. ' It's called a compound.

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

In addition, unless explicitly stated otherwise, “substituted” in the term “substituted or unsubstituted” as used herein means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, deuterium-substituted C ₆ -C ₂₀ aryl group, C ₈ -C ₂₀ arylalkenyl group, silane group, boron At least one substituent selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of a group, a germanium group, a fluorenyl group, and O, N, S, Si and P It means substituted with, but is not limited to these substituents.

In addition, unless explicitly stated otherwise, the chemical formula used in the present invention applies the same as the substituent definition by the exponent definition of the following formula.

Here, when a is an integer of 0, substituent R ¹ does not exist, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbon atoms forming the benzene ring, and when a is an integer of 2 or 3 Each is combined as follows, wherein R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while indicating the hydrogen bonded to the carbon forming the benzene ring. is omitted.

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

Referring to FIG. 1 , an organic electric element 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110, and An organic material layer containing the compound according to the present invention is provided between the two electrodes 180 . In this case, the first electrode 120 may be an anode (anode), and the second electrode 180 may be a cathode (negative electrode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 on the first electrode 120 . At this time, at least one of these layers may be omitted or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 and the like play a role as the hole blocking layer. you might be able to do

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

The compound according to an embodiment of the present invention applied to the organic material layer is a host or dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the light emitting layer 150, or It may be used as a material for a light efficiency improvement layer. For example, the compound of the present invention may be used as the light emitting layer 150, the hole transport layer 140, and/or the light emitting auxiliary layer 151.

On the other hand, since the band gap, electrical properties, interface properties, etc. may vary depending on which substituent is attached to which position even in the same core, the selection of the core and the combination of sub-substituents bound thereto Research is required, and in particular, long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interfacial property, etc.) is achieved.

As described above, in order to generally solve the light emission problem in the hole transport layer in organic electroluminescent devices, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and each light emitting layer (R, G, B) It is time to develop different light emitting auxiliary layers according to the present invention. On the other hand, in the case of the light emitting auxiliary layer, since it is necessary to understand the relationship between the hole transport layer and the light emitting layer (host), even if a similar core is used, it will be very difficult to infer its characteristics if the organic material layer used is different.

Therefore, in the present invention, by forming a phosphorescent host and / or a hole transport layer using the compound represented by Formula 1, by optimizing the energy level and T ₁ value between each organic material layer, the intrinsic properties of the material (mobility, interface properties, etc.) The lifetime and efficiency of the organic electric element can be simultaneously improved.

An organic light emitting device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode 120, and a hole injection layer 130 thereon , After 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, depositing a material that can be used as the cathode 180 thereon can be manufactured. there is. In addition, an auxiliary light emitting layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150 .

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

An organic electric device according to an embodiment of the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

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

In addition, the organic electric device according to an embodiment of the present invention may be one of an organic light emitting device, an organic solar cell, an organic photoreceptor, an organic transistor, and a device for monochromatic or white lighting.

Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention and a control unit controlling the display device. At this time, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

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

A compound according to one aspect of the present invention is represented by Formula 1 below.

<Formula 1>

In Formula 1,

Ring A is an aromatic ring of C ₆ ,

X may be selected from the group consisting of S, O and C(R ^a )(R ^b ).

Ar ¹ is a C ₆ -C ₆₀ aryl group; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; -L ^a -N(R ^c )(R ^d ); C ₁ -C ₃₀ alkoxyl group; And it may be selected from the group consisting of a C ₆ -C ₃₀ aryloxy group. Preferably, Ar ¹ is a C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₂₀ aliphatic ring and a C ₆ -C ₁₀ aromatic ring; C ₂ -C ₁₀ alkenyl group; and -L ^a -N(R ^c )(R ^d ); etc., and as a specific example, Ar ¹ is phenyl, biphenyl, pyrenyl, naphthyl, fluoranthenyl, phenanthryl, triphenylenyl, terphenyl, fluorenyl, pyridyl, dibenzofuryl, carbazolyl , Pyrimidinyl, triazinyl, quinazolyl, benzoquinazolyl, dibenzoquinazolyl, pyrimidobenzothienyl, pyrimidobenzofuryl, benzoindenopyrimidinyl, pyrimidophenanthrofuryl, benzothienopyridyl, Indolocarbazole, pyrimidonaphthofuryl, indolopyrimidinyl, spirobifluorenyl, quinoxanyl, pyridoquinazolyl, quinolyl, pyridopyrimidinyl, pyrimidonaphthothienyl, imida zolyl, thianthrene, vinyl, -L ^a -N(R ^c )(R ^d ) and the like.

R ¹ to R ³ are each independently deuterium; tritium; halogen; cyano group; nitro group; C ₆ -C ₆₀ aryl group; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; -L ^a -N(R ^c )(R ^d ); C ₁ -C ₃₀ alkoxyl group; And it may be selected from the group consisting of a C ₆ -C ₃₀ aryloxy group. Preferably, R ¹ to R ³ are each independently a cyano group; C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L ^a -N(R ^c )(R ^d ); etc. As a specific example, R ¹ to R ³ may be each independently cyano, phenyl, fluorenyl, benzophenanthryl, chrysenyl, carbazolyl, -L ^a -N(R ^c )(R ^d ), and the like.

In addition, R ¹ to R ³ may be independently bonded to each other to form at least one ring, wherein R ¹ to R ³ that do not form a ring may be defined the same as those defined above. there is.

m is an integer of 0 to 4, and when m is an integer of 2 or greater, a plurality of R ¹ may be the same as or different from each other.

n is an integer from 0 to 1;

o is an integer of 0 to 5, and when o is an integer of 2 or more, a plurality of R ³ may be the same as or different from each other.

R ^a to R ^d are each independently a C ₆ -C ₆₀ aryl group; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₁ -C ₃₀ alkoxyl group; And it may be selected from the group consisting of a C ₆ -C ₃₀ aryloxy group. Preferably, R ^a to R ^d are each independently a C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ -C ₃₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; etc. As a specific example, R ^a to R ^d are each independently phenyl, biphenyl, naphthyl, triphenylenyl, phenanthryl, fluorenyl, spirobifluorenyl, dibenzothienyl, carbazolyl, dibenzofuryl , fluorenyl, benzonaphthothienyl, benzocarbazolyl, and the like.

In addition, R ^a and R ^b may be bonded to each other to form a spiro compound together with C (carbon) to which they are bonded, and R ^c and R ^d may be bonded to each other to form a ring.

L ¹ and L ^a are each independently a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ divalent heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; A divalent fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And it may be selected from the group consisting of a divalent aliphatic hydrocarbon group. Preferably, L ¹ and L ^a are each independently a single bond; C ₆ -C ₃₀ arylene group; Fluorenylene group; A C ₂ -C ₃₀ divalent heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; etc. As specific examples, L ¹ and L ^a are each independently selected from a single bond, phenylene, biphenylene, fluorenylene, pyrimidinylene, triazinylene, quinazolylene, benzoquinazolylene, dibenzoquinazolylene, Pyrimidobenzothienylene, pyrimidobenzofurylene, benzoindenopyrimidinylene, phenanthrofuropyrimidinylene, dibenzofurylene, pyridonaphthofurylene, pyridonaphthothothienylene, indolopyrimidinylene, It may be quinoxanylene, quinolylene, pyridopyrimidinylene, pyrimidonaphthothienylene, imidazolylene, pyridoquinazolylene, carbazolylene, pyridylene, and the like.

In addition, except for the case of a single bond, L ¹ and L ^a are each deuterium; halogen; silane group; Siloxane group; boron group; Germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; -N(R ^e )(R ^f ); And a C ₈ -C ₂₀ arylalkenyl group; may be substituted with one or more substituents selected from the group consisting of.

R ^e and R ^f are each independently a C ₆ -C ₆₀ aryl group; fluorenyl group; and a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; it may be selected from the group consisting of.

Each of the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; boron group; Germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; And it may be further substituted with one or more substituents selected from the group consisting of a C ₈ -C ₂₀ arylalkenyl group.

Specifically, Formula 1 may be represented by one of Formulas 2 to 5 below.

<Formula 2> <Formula 3> <Formula 4> <Formula 5>

In Chemical Formulas 2 to 5, X, R ¹ to R ³ , L ¹ , Ar ¹ , m, n and o may be defined the same as those defined in Chemical Formula 1 above.

In addition, Ar ¹ in Formula 1 may be represented by Formula A-1 or A-2 below.

<Formula A-1> <Formula A-2>

The Z ring is a C ₆ -C ₆₀ monocyclic or polycyclic aromatic ring; Or it may be a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P.

In Formula A-1, Q ¹ to Q ⁴ may each independently be N, C(R ^g ) or C, but, when combined with L ¹ , they are C.

In Formula A-2, Q ⁵ to Q ⁹ are each independently N or C(R ^g ).

R ^g is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; boron group; Germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group.

More specifically, ring Z of Chemical Formula A-1 may be represented by one of the following Chemical Formulas Z-1 to Z-15.

In the above formulas Z-1 to Z-15, marks (*) are binding moieties bonded to the ring containing Q ¹ to Q ⁴ of the above formula A-1 to form a fused ring.

W ¹ and W ² may be independently selected from the group consisting of a single bond, NL ² -Ar ² , S, O, and C(R ^h )(R ⁱ ), and V is independently of each other, N or C (R ^g ) is,

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

Ar ² , R ^h and R ⁱ are C ₆ -C ₆₀ aryl groups; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₁ -C ₃₀ alkoxyl group; And it may be selected from the group consisting of a C ₆ -C ₃₀ aryloxy group.

Also, R ^h and R ⁱ may be bonded to each other to form a spiro compound together with C (carbon) to which they are bonded, and R ^g may be defined the same as defined in Formulas A-1 and A-2 above. .

Meanwhile, a structure in which at least one of Q ¹ to Q ⁴ in Formula A-1 includes N (nitrogen) may be represented by one of Formulas Z-16 to Z-50.

In Formulas Z-16 to Z-50, R ^g may be defined the same as defined in Formulas A-1 and A-2.

Also specifically, Formula 1 may be represented by Formula 6 below.

<Formula 6>

In Formula 6, ring A, X, R ¹ to R ³ , R ^c , R ^d , L ¹ , L ^a , Ar ¹ , m, n, and o may be defined the same as those defined in Formula 1.

p is an integer from 0 to 4, and m+p≤4. In this case, when p is an integer of 2 or more, a plurality of L ^a -N(R ^c )(R ^d ) may be the same as or different from each other.

q is an integer of 0 or 1, and n+q≤1.

r is an integer from 0 to 5, and o+r≤5. In this case, when r is an integer of 2 or more, a plurality of L ^a -N(R ^c )(R ^d ) may be the same as or different from each other.

Also specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

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

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

At this time, the organic electric element includes a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, and the organic material layer may include a compound represented by Chemical Formula 1. In addition, the compound represented by Formula 1 may be contained in at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, and the light emitting layer as a single compound or a mixture of two or more. That is, the compound represented by Formula 1 may be used as a material for a hole injection layer, a hole transport layer, an auxiliary light emitting layer, or a light emitting layer. Preferably, the compound represented by Formula 1 is used as a phosphorescent host material and a hole transport layer material of the light emitting layer. can be used

Hereinafter, a synthesis example of the compound represented by Formula 1 and an example of manufacturing an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

synthesis example

Illustratively, the compound (Final Products) according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1> X= S, O, C (R ^a ) (R ^b )

(Ring A, X, R ¹ to R ³ , L ¹ , Ar ¹ , m, n and o are the same as those defined in Formula 1, and Hal ¹ is Br or Cl.)

I. Sub Synthesis of 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction pathways of Reaction Scheme 2 and Reaction Scheme 3 below, but is not limited thereto.

<Scheme 2>

<Scheme 3>

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

One. Sub 1-1 and Sub 1-7 synthesis example

<Scheme 4>

(One) Sub Synthesis of 1-I-1

After dissolving the starting material 2-bromo-4H-benzo[def]carbazole (59.41 g, 219.93 mmol) in THF (730mL), (2-(methylsulfinyl)phenyl)boronic acid (40.47 g, 219.93 mmol), Pd( PPh ₃ ) ₄ (10.17 g, 8.80 mmol), NaOH (26.39 g, 659.79 mmol) and water (365 mL) were added and stirred at 80 °C. After the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 54.34 g of product (yield: 75%).

(2) Sub 1-1; Sub 1-7 synthesis

Sub 1-I-1 (54.34 g, 164.96 mmol) obtained in the above synthesis was added together with triflic acid (219 mL, 2474.35 mmol), stirred at room temperature for 24 hours, and then a pyridine aqueous solution (2890 mL, pyridine: H ₂ O = 1 : 5) was slowly added dropwise and stirred at reflux for 30 minutes. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 23.55 g of Sub 1-1 (yield: 48%) and Sub 1-7. 15.21 g (yield: 31%) was obtained.

2. Sub 1-4; Sub 1-10 synthesis example

<Scheme 5>

(One) Sub Synthesis of 1-I-4

(2-hydroxyphenyl)boronic acid (13.11 g, 95.07 mmol), Pd(PPh ₃ ) ₄ (4.39 g, 3.80 mmol) to the starting material 2-bromo-4H-benzo[def]carbazole (25.68 g, 95.07 mmol) , NaOH (11.41 g, 285.20 mmol), THF (320 mL), and water (160 mL) were added to obtain 22.63 g of product (yield: 84%) using the above Sub 1-I-1 synthesis method.

(2) Sub 1-4; Sub 1-10 synthesis

Sub 1-I-4 (22.63 g, 79.87 mmol) obtained in the above synthesis was added together with Pd(OAc) ₂ (1.79 g, 7.99 mmol) and 3-nitropyridine (0.99 g, 7.99 mmol), and C ₆ F ₆ (120mL) ), after dissolving with DMI (80mL), tert -butyl peroxybenzoate (31.03 g, 159.74 mmol) was added and stirred at 90°C. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 8.99 g of Sub 1-4 (yield: 40%) and Sub 1-10 as products. 6.52 g (yield: 29%) was obtained.

3. Sub 1-11 synthesis example

<Scheme 6>

(One) Sub Synthesis of 1-I-11

(2-(methoxycarbonyl)phenyl)boronic acid (14.06 g, 78.11 mmol), Pd(PPh ₃ ) ₄ (3.61 g, 3.12 mmol), NaOH (9.37 g, 234.33 mmol), THF (260 mL) and water (130 mL) were added and 20.84 g (yield: 82%) of the product was obtained using the Sub 1-I-1 synthesis method.

(2) Sub 1-11 synthesis

After dissolving Sub 1-I-11 (20.84 g, 64.05 mmol) obtained in the above synthesis in THF (320 mL), methylmagnesium bromide 1.0M in THF (256.2 mL, 256.20 mmol) was slowly added dropwise, followed by stirring at room temperature. Upon completion of the reaction, the mixture was extracted with diethyl ether and water, and the organic layer was dried over MgSO ₄ and concentrated to obtain an intermediate product. This intermediate product was dissolved in acetic acid solution (250mL) and refluxed after adding HCl (5mL). When the reaction was completed, water was added, stirred, and the resulting solid was filtered under reduced pressure and washed with water and methanol to obtain 8.47 g of the product as a white powder (yield: 43% over two steps).

4. Sub 1-13 synthesis example

<Scheme 7>

(One) Sub Synthesis of 1-I-13

(2-(methylsulfinyl)phenyl)boronic acid (10.50 g, 57.08 mmol), Pd(PPh ₃ ) ₄ (2.64 g, 2.28 mmol), NaOH (6.85 g, 171.25 mmol), THF (190 mL), and water (95 mL) were added and 13.35 g (yield: 71%) of the product was obtained using the Sub 1-I-1 synthesis method.

(2) Sub 1-13 synthesis

To Sub 1-I-13 (13.35 g, 40.53 mmol) obtained in the above synthesis, triflic acid (53.8 mL, 607.89 mmol) and pyridine aqueous solution (710 mL, pyridine : H ₂ O = 1 : 5) were added and the Sub 1- 8.07 g (yield: 67%) of the product was obtained using the synthesis method 1.

5. Sub 1-20 synthesis example

<Scheme 8>

(One) Sub Synthesis of 1-I-20

(2-(methylsulfinyl)phenyl)boronic acid (9.88 g, 53.68 mmol), Pd(PPh ₃ ) ₄ (2.48 g, 2.15 mmol), NaOH (6.44 g, 161.03 mmol), THF (180 mL), and water (90 mL) were added and 11.49 g (yield: 65%) of the product was obtained using the Sub 1-I-1 synthesis method.

(2) Sub 1-20 synthesis

To Sub 1-I-20 (11.49 g, 34.88 mmol) obtained in the above synthesis, triflic acid (46.3 mL, 523.19 mmol) and pyridine aqueous solution (610 mL, pyridine : H ₂ O = 1 : 5) were added, and the Sub 1- 7.26 g of product (yield: 70%) was obtained using the synthesis method 1.

6. Sub 1-31 synthesis example

<Scheme 9>

(One) Sub Synthesis of 1-I-31

Starting material N-([1,1'-biphenyl]-4-yl)-6-bromo-N-(9-phenyl-9H-carbazol-2-yl)-4H-benzo[def]carbazol-2- amine (39.89 g, 58.78 mmol), (2-(methylsulfinyl)phenyl)boronic acid (10.82 g, 58.78 mmol), Pd(PPh ₃ ) ₄ (2.72 g, 2.35 mmol), NaOH (7.05 g, 176.34 mmol), THF (200mL) and water (100mL) were added and 28.63 g (yield: 66%) of a product was obtained using the Sub 1-I-1 synthesis method.

(2) Sub 1-31 synthesis

Triflic acid (51.5ml, 581.97 mmol) and pyridine aqueous solution (680ml, pyridine : H ₂ O = 1 : 5) were added to Sub 1-I-31 (28.63 g, 38.80 mmol) obtained in the synthesis above, and the Sub 1- 1 synthesis method was used to obtain 10.95 g of product (yield: 40%).

7. Sub 1-40 synthesis example

<Scheme 10>

(One) Sub Synthesis of 1-I-40

To the starting material 2-bromo-6-phenyl-4H-benzo[def]carbazole (20.71 g, 59.82 mmol) (5-(diphenylamino)-2-(methylsulfinyl)phenyl)boronic acid (21.01 g, 59.82 mmol), Pd(PPh ₃ ) ₄ (2.76 g, 2.39 mmol), NaOH (7.18 g, 179.45 mmol), THF (200 mL), water (100 mL) were added and the product 25.01 g ( Yield: 73%) was obtained.

(2) Sub 1-40 synthesis

To Sub 1-I-40 (25.01 g, 43.67 mmol) obtained in the above synthesis, triflic acid (58.0 mL, 655.02 mmol) and pyridine aqueous solution (765 mL, pyridine : H ₂ O = 1 : 5) were added, and the Sub 1- 1 synthesis method was used to obtain 10.62 g of product (yield: 45%).

8. Sub 1-43 synthesis example

<Scheme 11>

(One) Sub Synthesis of 1-I-43

Starting material N-(2-(6-bromo-4H-benzo[def]carbazol-2-yl)phenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (34.62g, 58.72mmol ) in (2-(methylsulfinyl)phenyl)boronic acid (10.81 g, 58.72 mmol), Pd(PPh ₃ ) ₄ (2.71 g, 2.35 mmol), NaOH (7.05 g, 176.17 mmol), THF (200mL), water ( 100 mL) was added, and 25.91 g (yield: 68%) of the product was obtained using the Sub 1-I-1 synthesis method.

(2) Sub 1-43 synthesis

To Sub 1-I-43 (25.91 g, 39.93 mmol) obtained in the above synthesis, triflic acid (53.0 mL, 599.01 mmol) and aqueous pyridine solution (700 mL, pyridine : H ₂ O = 1 : 5) were added, and the Sub 1- 1 synthesis method was used to obtain 10.34 g of product (yield: 42%).

Compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 1.

[Table 1]

II. Sub Composite of 2

Sub 2 of Scheme 1 may be synthesized by the reaction pathway of Scheme 12, but is not limited thereto. Hal ¹ and Hal ² are Br or Cl.

<Scheme 12>

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

One. Sub 2-28 synthesis example

<Scheme 13>

After dissolving the starting material 1,4-dibromobenzene (17.37 g, 73.63 mmol) in THF (260mL), 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (25.13 g, 80.99 mmol), Pd(PPh ₃ ) ₄ (3.40 g, 2.95 mmol), K ₂ CO ₃ (30.53 g, 220.89 mmol), water (130 mL) and stirred at 90 °C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ , concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 18.23 g (yield: 73%) of the product.

2. Sub 2-35 synthesis example

<Scheme 14>

4,4,5,5-tetramethyl-2-(naphthalen-1-yl-d7)-1,3,2-dioxaborolane (29.54 g, 113.11 mmol), Pd(PPh ₃ ) ₄ (4.75 g, 4.11 mmol), K ₂ CO ₃ (42.63 g, 308.47 mmol), THF (360 mL), water (180 mL) were added and the product was 18.03 g (yield: 60%) using the Sub 2-28 synthesis method above. got

3. Sub 2-53 synthesis example

<Scheme 15>

4,4,5,5 -tetramethyl-2-(naphthalen-2-yl)- 1,3,2-dioxaborolane (35.07 g, 138.02 mmol), Pd(PPh ₃ ) ₄ (5.80 g, 5.02 mmol), K ₂ CO ₃ (52.02 g, 376.41 mmol), THF (440 mL), water (220 mL) were added and the product was 19.58 g (yield: 45%) using the Sub 2-28 synthesis method above. got

4. Sub 2-64 synthesis example

<Scheme 16>

4,4,5,5-tetramethyl-2-(3-(naphthalen-1- yl)phenyl)-1,3,2-dioxaborolane (35.44 g, 107.32 mmol), Pd(PPh ₃ ) ₄ (4.51 g, 3.90 mmol), K ₂ CO ₃ (40.45 g, 292.69 mmol), THF (170 mL), water (340 mL) were added and the product was 19.81 g (yield: 48%) using the Sub 2-28 synthesis method above. got.3

5. Sub 2-85 synthesis example

<Scheme 17>

(One) Sub Synthesis of 2-I-85

The starting material, 1-amino-2-naphthoic acid (75.11 g, 401.25 mmol) was added to a round bottom flask together with urea (168.69 g, 2808.75 mmol) and stirred at 160°C. After confirming the reaction by TLC, the mixture was cooled to 100° C., water (200 mL) was added, and the mixture was stirred for 1 hour. Upon completion of the reaction, the resulting solid was filtered under reduced pressure, washed with water and dried to obtain 63.86 g of the product (yield: 75%).

(2) Sub Synthesis of 2-II-85

Sub 2-I-85 (63.86 g, 300.94 mmol) obtained in the above synthesis was dissolved in POCl ₃ (200 mL) at room temperature, N , N -Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise thereto, and at 90 ° C. Stir. When the reaction was complete, ice water (500mL) was added after concentration and the mixture was stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 67.47 g of product (yield: 90%).

(2) Sub 2-85 synthesis

4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (60.80 g, 297.94 mmol) and Pd (PPh) were added to Sub 2-II-85 (67.47 g, 270.86 mmol) obtained in the above synthesis. ₃ ) ₄ (12.52 g, 10.83 mmol), K ₂ CO ₃ (112.30 g, 812.57 mmol), THF (950 mL), water (475 mL) were added and the product was 44.89 g (yield: 57%) using the Sub 2-28 synthesis method above. got

Compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 2.

[Table 2]

III. Product synthesis

After dissolving Sub 1 (1 equivalent) with Toluene, Sub 2 (1 equivalent), Pd ₂ (dba) ₃ (0.03 equiv.), (t-Bu)3P (0.06 equiv.), NaOt-Bu (3 equiv.) were added and stirred at 100°C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ , concentrated, and the resulting compound was recrystallized using a silica gel column to obtain a final product.

1. P1-1 synthesis example

<Scheme 18>

After dissolving Sub 1-1 (10.01 g, 33.66 mmol) obtained in the above synthesis in toluene (335 mL), Sub 2-1 (5.29 g, 33.66 mmol), Pd ₂ (dba) ₃ (0.92 g, 1.01 mmol), 50% P( t -Bu) ₃ (1.0 mL, 2.02 mmol), NaO t -Bu (9.71 g, 100.98 mmol) was added and stirred at 100 °C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with MgSO ₄ , concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 10.06 g (yield: 80%) of the product.

2. P1-6 synthesis example

<Scheme 19>

Sub 2-43 (6.92 g, 22.16 mmol), Pd ₂ (dba) ₃ (0.61 g, 0.66 mmol) 50% P( t -Bu) ₃ to Sub 1-1 (6.59 g, 22.16 mmol) obtained in the synthesis above (0.6mL, 1.33 mmol), NaO t -Bu (6.39 g, 66.48 mmol), and toluene (220mL) were added, and 9.84 g (yield: 84%) of a product was obtained using the P 1-1 synthesis method.

3. P1-10 synthesis example

<Scheme 20>

Sub 2-85 (6.72 g, 23.10 mmol), Pd ₂ (dba) ₃ (0.63 g, 0.69 mmol) 50% P( t -Bu) ₃ to Sub 1-1 (6.87 g, 23.10 mmol) obtained in the above synthesis (0.7mL, 1.39 mmol), NaO t -Bu (6.66 g, 69.31 mmol), and toluene (230mL) were added, and 9.69 g (yield: 76%) of a product was obtained using the P 1-1 synthesis method.

4. P1-20 synthesis example

<Scheme 21>

Sub 2-17 (7.03 g, 24.99 mmol), Pd ₂ (dba) ₃ (0.69 g, 0.75 mmol) 50% P( t -Bu) ₃ to Sub 1-4 (7.03 g, 24.99 mmol) obtained in the synthesis above (0.7mL, 1.50 mmol), NaO t -Bu (7.21 g, 74.97 mmol), and toluene (250mL) were added, and 9.51 g of product (yield: 79%) was obtained using the P 1-1 synthesis method.

5. P1-35 synthesis example

<Scheme 22>

Sub 2-28 (7.28 g, 21.45 mmol), Pd ₂ (dba) ₃ (0.59 g, 0.64 mmol) 50% P( t -Bu) ₃ to Sub 1-7 (6.38 g, 21.45 mmol) obtained in the synthesis above (0.6mL, 1.29 mmol), NaO t -Bu (6.19 g, 64.36 mmol), and toluene (215mL) were added, and 9.06 g of product (yield: 76%) was obtained using the P 1-1 synthesis method.

6. P1-37 synthesis example

<Scheme 23>

Sub 2-35 (6.44 g, 22.03 mmol), Pd ₂ (dba) ₃ (0.61 g, 0.66 mmol) 50% P( t -Bu) ₃ to Sub 1-7 (6.55 g, 22.03 mmol) obtained in the synthesis above (0.6mL, 1.32 mmol), NaO t -Bu (6.35 g, 66.08 mmol), and toluene (220mL) were added to obtain 9.19 g of product (yield: 82%) using the P 1-1 synthesis method.

7. P1-58 synthesis example

<Scheme 24>

Sub 2-53 (7.55 g, 21.76 mmol), Pd ₂ (dba) ₃ (0.60 g, 0.65 mmol) 50% P( t -Bu) ₃ to Sub 1-10 (6.12 g, 21.76 mmol) obtained in the synthesis above (0.6mL, 1.31 mmol), NaO t -Bu (6.27 g, 65.27 mmol), and toluene (220mL) were added, and 9.40 g (yield: 73%) of a product was obtained using the P 1-1 synthesis method.

8.P1-60 synthesis example

<Scheme 25>

Sub 2-64 (8.59 g, 20.30 mmol), Pd ₂ (dba) ₃ (0.56 g, 0.61 mmol) 50% P( t -Bu) ₃ to Sub 1-11 (6.24 g, 20.30 mmol) obtained in the synthesis above (0.6mL, 1.22 mmol), NaO t -Bu (5.85 g, 60.90 mmol), and toluene (200mL) were added, and 9.16 g of product (yield: 65%) was obtained using the P 1-1 synthesis method.

9. P1-69 synthesis example

<Scheme 26>

Sub 2-85 (6.76 g, 23.24 mmol), Pd ₂ (dba) ₃ (0.64 g, 0.70 mmol) 50% P( t -Bu) ₃ to Sub 1-13 (6.91 g, 23.24 mmol) obtained in the synthesis above (0.7mL, 1.39 mmol), NaO t -Bu (6.70 g, 69.71 mmol), and toluene (230mL) were added, and 9.23 g (yield: 72%) of a product was obtained using the P 1-1 synthesis method.

10. P1-84 synthesis example

<Scheme 27>

Sub 2-85 (6.70 g, 23.03 mmol), Pd ₂ (dba) ₃ (0.63 g, 0.69 mmol) 50% P( t -Bu) ₃ to Sub 1-20 (6.85 g, 23.03 mmol) obtained in the synthesis above (0.7mL, 1.38 mmol), NaO t -Bu (6.64 g, 69.10 mmol), and toluene (230mL) were added, and 9.40 g (yield: 74%) of a product was obtained using the P 1-1 synthesis method.

11.P2-7 synthesis example

<Scheme 28>

Sub 2-1 (2.37 g, 15.07 mmol), Pd ₂ (dba) ₃ (0.41 g, 0.45 mmol) 50% P( t -Bu) ₃ to Sub 1-31 (10.64 g, 15.07 mmol) obtained in the above synthesis (0.4mL, 0.90 mmol), NaO t -Bu (4.35 g, 45.22 mmol), and toluene (150mL) were added, and 8.02 g of product (yield: 68%) was obtained using the P 1-1 synthesis method.

12.P2-16 synthesis example

<Scheme 29>

Sub 2-1 2-7 (2.83 g, 18.03 mmol), Pd ₂ (dba) ₃ (0.50 g, 0.54 mmol) 50% P( t - Bu) ₃ (0.5mL, 1.08 mmol), NaO t -Bu (5.20 g, 54.10 mmol), and toluene (180mL) were added and 8.23 g of product (yield: 74%) was obtained using the above P 1-1 synthesis method. .

13. P2-19 synthesis example

<Scheme 30>

Sub 2-1 (2.60 g, 16.54 mmol), Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol) 50% P( t -Bu) ₃ to Sub 1-43 (10.20 g, 16.54 mmol) obtained in the synthesis above (0.5mL, 0.99mmol), NaO t -Bu (4.77 g, 49.61mmol), and toluene (165mL) were added, and 8.14 g of product (yield: 71%) was obtained using the P 1-1 synthesis method.

FD-MS values of some compounds of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.

[Table 3]

Meanwhile, in the above, exemplary synthesis examples of the present invention represented by Formula 1 have been described, but they are all Buchwald-Hartwig cross coupling reactions, Suzuki cross-coupling reactions, and intramolecular acid-induced cyclization reactions ( J. mater . Chem . 1999, 9 , 2095.), Pd(II)-catalyzed oxidative cyclization reaction ( Org . Lett . 2011, 13 , 5504), Grignard reaction and Cyclic Dehydration reaction, etc. Other substituents defined in Formula 1 in addition to the substituents specified in the specific synthesis examples Those skilled in the art will easily understand that the reaction proceeds even when (ring A, X, R ¹ to R ³ , L ¹ and substituents such as Ar ¹ ) are bonded.

For example, the reaction of Sub 1 and Sub 2 -> Final Product in Scheme 1 is based on the Buchwald-Hartwig cross coupling reaction, the starting material -> Sub 1-I reaction in Scheme 2, and the starting material -> Sub 2 reaction in Scheme 12 All are based on the Suzuki cross-coupling reaction, (At this time, in the case of reactants containing amines, Korea Patent No. 10-1251451 (registration announcement dated 2013.04.05) and No. 10-1298483 (2013.08.21 Date registration notification) was used.) In Scheme 3, Sub 1-I -> Sub 1 (when X is S) is an intramolecular acid-induced cyclization reaction ( J. mater . Chem . 1999, 9 , 2095.). Subsequently, Sub 1-I -> Sub 1 (when X is O) in Scheme 3 is based on the Pd(II)-catalyzed oxidative cyclization reaction ( Org. Lett . 2011, 13 , 5504), and in Scheme 3 Sub 1-I -> Sub 1 (when X is C(R ^a )(R ^b )) The reaction is based on Grignard reaction and Cyclic Dehydration reaction.

Thus, even if a substituent not specifically specified is attached, the above reactions will proceed. In addition, the benzocarbazole-type material used as a starting material in the starting material of Scheme 2 -> Sub 1-I reaction is synthesized by the following reaction scheme 31 (Method A, Method B (Korean Patent Publication No. 2015-0039486) Ho), Method C (Korean Patent Publication No. 2015-0077219)) was used.

<Scheme 31>

Manufacturing evaluation of organic electric devices

[ Example One] red organic light emitting device (phosphorescent host)

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a light emitting host material for the light emitting layer. First, a 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as "2-TNATA") film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to have a thickness of 60 nm. After forming the hole injection layer, a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as "NPD") film as a hole transport compound was vacuum deposited on the hole injection layer to a thickness of 60 nm. Thus, a hole transport layer was formed. The compound P 1-9 of the present invention was used as a host on the hole transport layer, and bis-(1-phenylisoquinoline)iridium(III)acetylacetonate (hereinafter referred to as "(piq) ₂ Ir(acac)") was used as a dopant material at 95 A light emitting layer having a thickness of 30 nm was deposited by doping at a weight ratio of 5:5. Subsequently, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminu (hereinafter referred to as "BAlq") was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and tris-( A film of 8-hydroxyquinoline)aluminum (hereinafter referred to as "Alq ₃ ") was formed to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light emitting device.

[ Example 2] to [ Example 37] red organic light emitting device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 was used instead of Compound P 1-9 according to Example 1 of the present invention as a host material for the light emitting layer. .

[ comparative example 1] to [ comparative example 3]

Organic electrolysis was performed in the same manner as in Example 1, except that one of Comparative Compounds 1 to 3 listed in Table 4 was used instead of Compound P 1-9 according to Example 1 of the present invention as a host material of the light emitting layer. A light emitting device was manufactured.

<Comparative compound 1> <Comparative compound 2> <Comparative compound 3>

Electroluminescence (EL) characteristics with PR-650 of Photoresearch Co., Ltd. by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 1 to 37 and Comparative Examples 1 to 3 of the present invention was measured, and as a result of the measurement, T95 life was measured through life measurement equipment manufactured by McScience at a standard luminance of 2500 cd / m ² , and the measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the measurement results of Table 4, it was confirmed that the device using the compound according to an embodiment of the present invention as a phosphorescent red host material of the light emitting layer had significantly improved luminous efficiency and lifetime than Comparative Compounds 1 to 3. .

Comparing the heteroatoms in the 6-ring compound, one pentagonal ring contains N as the core element, and the other pentagonal ring contains the core elements S, O , C (R ^a ) (R ^b ) It can be confirmed that the compound of the present invention, which is a heteroatom type containing one, exhibits higher efficiency and higher lifetime.

In general, when molecules are stacked, as the number of adjacent π-electrons increases, they have strong electrical interactions, which are closely related to charge carrier mobility.

Comparative Compound 2, which is an N-N type 6-ring heterocyclic compound, has an N-N type isomorphic heterocyclic core when the molecules are stacked, so the arrangement order between molecules has an edge-to-face form, which has low charge carrier mobility. and low oxidative stability.

In the case of the compound of the present invention, since the heteroatoms in the cyclic compound have heterocyclic cores different from each other, the packing structure of the molecule has an antiparallelcofacial π-stacking structure. This makes the arrangement sequence between molecules face-to-face, and it is judged to have high efficiency by causing remarkably high carrier mobility due to the steric effect of Ar ¹ of the asymmetrically arranged heteroatom N, which is the cause of this layered structure. , it is judged that the lifetime is remarkably increased because it has high oxidation stability.

In addition, as in Comparative Compound 3, when the ring condensed into a pentagonal ring includes Sp3 carbon, it has a lower packing density than the compound of the present invention and exhibits low thermal stability, so that during electroluminescence, the organic layer among the organic layers It can be seen that the heat resistance to Joule's heat generated between the organic layer and the metal electrode and the resistance under a high temperature environment are reduced.

On the other hand, the compound of the present invention, in which phenanthrene is introduced into the core, has a high packing density, so the lifespan is significantly increased compared to Comparative Compound 3 due to its high thermal stability due to a relatively low driving voltage and reduced Joule's heat generated during device driving. can confirm that

Among the compounds of the present invention, when a specific substituent such as benzothienopyrimidine, benzofuropyrimidine, or benzoquinazoline is introduced, a structural form suitable for accommodating both holes and electrons is selected. At the same time, it can be seen that it has an appropriate T1 value to facilitate charge transfer from the host to the dopant, resulting in the best device results in luminous efficiency and lifetime.

[ Example 38] Green organic light emitting device (phosphorescent host)

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a light emitting host material for the light emitting layer. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 60 nm-thick hole injection layer, and then a 60-nm-thick NPD film was vacuum-deposited as a hole transport compound on the hole injection layer to form a hole injection layer. A transport layer was formed. The compound P 1-62 of the present invention was used as a host on the hole transport layer, and tris(2-phenylpyridine)-iridium (hereinafter referred to as "Ir(ppy) ₃ ") was doped at a weight ratio of 95:5 as a dopant material to form 30 nm A light emitting layer was deposited to a thickness. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and Alq ₃ was deposited to a thickness of 40 nm as an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light emitting device.

[ Example 39] to [ Example 57] Green organic light emitting device

An organic light emitting device was prepared in the same manner as in Example 38, except that the compound of the present invention shown in Table 5 was used instead of the compound P 1-62 according to Example 38 of the present invention as the host material of the light emitting layer. .

[ comparative example 4] to [ comparative example 6]

Same as Example 38 except that one of Comparative Compound 1, Comparative Compound 5 and Comparative Compound 6 described in Table 5 was used instead of Compound P 1-62 according to Example 38 as the host material of the light emitting layer. An organic electroluminescence device was manufactured by the method.

<Comparative compound 5> <Comparative compound 6>

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices prepared by Examples 38 to 57 and Comparative Examples 4 to 6 of the present invention with PR-650 of Photoresearch Co., Ltd. was measured, and as a result of the measurement, the T95 life was measured through a life measurement equipment manufactured by McScience at a standard luminance of 5000 cd / m ² , and the measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the measurement results of Table 5, the device using the compound according to an embodiment of the present invention as a phosphorescent green host material of the light emitting layer significantly improved the luminous efficiency and lifetime compared to Comparative Compound 1, Comparative Compound 5, and Comparative Compound 6. confirmed that it has been This is because the heteroatom in the cyclic compound has a different heterocyclic core and the structure having high thermal stability is not only in the light emitting layer of the red organic light emitting device (used as a host) but also in the light emitting layer of the green organic light emitting device (used as a host). It can be confirmed that it acts as a major factor in improving the performance of the device.

The compound of the present invention used as a host material in the light emitting layer has high oxidation stability and high charge carrier mobility, as well as the most appropriate T1 value and energy band gap so that charges can be smoothly transferred from the host to the dopant. It can be seen that it exhibits remarkably high luminous efficiency and high lifetime.

In addition, in the case of a phosphorescent host, it is necessary to understand the relationship between the hole transport layer and the dopant. Even if a similar core is used, it will be very difficult to infer the excellent electrical properties of the phosphorescent host of the compound of the present invention.

[ Example 58] Green organic light emitting device ( hole transport layer )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a hole transport layer material. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 60 nm thick hole injection layer, and then the compound P 2-1 of the present invention was applied on the hole injection layer to a thickness of 60 nm. A hole transport layer was formed by vacuum deposition. 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") was used as a host on the top of the hole transport layer, and tris(2-phenylpyridine)-iridium (hereinafter referred to as "Ir(ppy)) was used as a dopant material. ₃ ″) at a weight ratio of 90:10 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and Alq ₃ was deposited to a thickness of 40 nm as an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light emitting device.

[ Example 59] to [ Example 80] Green organic light emitting device

An organic electroluminescent device was prepared in the same manner as in Example 58, except that the compound of the present invention shown in Table 6 was used instead of Compound P 2-1 according to Example 58 as the hole transport layer material.

[ comparative example 7]

An organic electroluminescent device was manufactured in the same manner as in Example 58, except that Comparative Compound 7 was used instead of Compound P 2-1 according to Example 58 as the hole transport layer material.

<Comparative compound 7>

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Examples 58 to 80 and Comparative Example 7 of the present invention to measure electroluminescence (EL) characteristics with PR-650 of Photoresearch, As a result of the measurement, the life of T95 was measured using life measurement equipment manufactured by McScience at a standard luminance of 5000 cd/m ² , and the measurement results are shown in Table 6 below.

[Table 6]

As can be seen from the measurement results of Table 6, it was confirmed that the device using the compound according to one embodiment of the present invention as a hole transport layer material had significantly improved luminous efficiency and lifetime compared to Comparative Compound 7.

As a result, since it has a deep HOMO energy level and a high T1 value, which are inherent characteristics of the compound of the present invention, the ability to block electrons is improved and holes are smoothly transported to the light emitting layer, resulting in excitons passing through the light emitting layer. It is judged that the efficiency is improved as it is more easily generated within. In addition, it can be confirmed that the lifespan is increased due to high thermal stability.

Combining the characteristics described above, such as deep HOMO energy level, high T1 value, and high thermal stability, the amine group (-L ^a -N (R ^c ) (R ^d )) in the same 6-ring heterocycle as the compound of the present invention It can be seen that the band gap, electrical properties, interface properties, etc. can be greatly changed according to the introduction, and it can be confirmed that this acts as a major factor in improving the performance of the device. In addition, in the case of the hole transport layer, it is necessary to understand the mutual relationship with the light emitting layer (host). Even if a similar core is used, it will be very difficult even for a person skilled in the art to infer the characteristics of the hole transport layer in which the compound of the present invention is used.

The above description is merely illustrative of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are intended to explain rather than limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed according to the claims, and all techniques within the equivalent range should be construed as being included in the scope of the present invention.

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

Claims (13)

A compound represented by Formula 1 below:
<Formula 1>

In Formula 1,
Ring A is an aromatic ring of C ₆ ,
X is selected from the group consisting of S, O and C(R ^a )(R ^b );
Ar ¹ is a C ₆ -C ₆₀ aryl group; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; -L ^a -N(R ^c )(R ^d ); C ₁ -C ₃₀ alkoxyl group; And C ₆ -C ₃₀ It is selected from the group consisting of an aryloxy group,
R ¹ to R ³ are each independently deuterium; halogen; cyano group; C ₆ -C ₆₀ aryl group; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; -L ^a -N(R ^c )(R ^d ); C ₁ -C ₃₀ alkoxyl group; And C ₆ -C ₃₀ It is selected from the group consisting of an aryloxy group, adjacent groups may be bonded to each other to form a ring,
m is an integer from 0 to 4, and when m is an integer of 2 or more, R ¹ may be the same as or different from each other;
n is an integer from 0 to 1;
o is an integer from 0 to 5, and when o is an integer of 2 or more, R ³ may be the same as or different from each other;
R ^a to R ^d are each independently a C ₆ -C ₆₀ aryl group; fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; C ₁ -C ₅₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₁ -C ₃₀ alkoxyl group; And C ₆ -C ₃₀ It is selected from the group consisting of an aryloxy group, R ^a and R ^b are bonded to each other to form a spiro compound together with C to which they are bonded, or R ^c and R ^d are bonded to each other can form a ring
L ¹ and L ^a are each independently a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ divalent heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; and a C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring selected from the group consisting of a divalent fused ring group, except for a single bond, L ¹ and L ^a are each deuterium; halogen; silane group; cyano group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; -N(R ^e )(R ^f ); And a C ₈ -C ₂₀ arylalkenyl group; may be substituted with one or more substituents selected from the group consisting of,
R ^e and R ^f are each independently a C ₆ -C ₆₀ aryl group; fluorenyl group; and a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;
Each of the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group is deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; cyano group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; And it may be further substituted with one or more substituents selected from the group consisting of a C ₈ -C ₂₀ arylalkenyl group. According to claim 1,
Formula 1 is a compound characterized in that represented by one of the following formulas 2 to 5:
<Formula 2><Formula3><Formula4><Formula5>

In Chemical Formulas 2 to 5, X, R ¹ to R ³ , L ¹ , Ar ¹ , m, n and o are the same as those defined in claim 1. According to claim 1,
A compound characterized in that Ar ¹ of Formula 1 is represented by the following Formula A-1 or A-2:
<Formula A-1><FormulaA-2>

The Z ring is a C ₆ -C ₆₀ monocyclic or polycyclic aromatic ring; Or a C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P;
In Formula A-1, Q ¹ to Q ⁴ are each independently N, C (R ^g ) or C, but, when combined with L ¹ , it is C,
In Formula A-2, Q ⁵ to Q ⁹ are each independently N or C (R ^g ),
R ^g is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; cyano group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group. According to claim 3,
A compound characterized in that the Z ring of Formula A-1 is one of the following Formulas Z-1 to Z-15:

In the above formulas Z-1 to Z-15, the mark (*) is a binding moiety bonded to a ring containing Q ¹ to Q ⁴ of formula A-1 to form a fused ring,
W ¹ and W ² are each independently selected from the group consisting of a single bond, NL ² -Ar ² , S, O, and C(R ^h )(R ⁱ );
V is independently of each other N or C (R ^g ) is,
L ² is a single bond; C ₆ -C ₂₀ arylene group; Fluorenylene group; And it is selected from the group consisting of a C ₂ -C ₂₀ divalent heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P,
Ar ² , R ^h and R ⁱ are each independently a C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; And it is selected from the group consisting of a C ₁ -C ₂₀ alkoxyl group, R ^h and R ⁱ may bond to each other to form a spiro compound together with C (carbon) to which they are bonded,
R ^g is as defined in claim 3. According to claim 3,
A compound characterized in that at least one of Q ¹ to Q ⁴ in Formula A-1 is N. According to claim 1,
Formula 1 is a compound characterized in that represented by the following formula (6):
<Formula 6>

In Formula 6, ring A, X, R ¹ to R ³ , R ^c , R ^d , L ¹ , L ^a , Ar ¹ , m, n, and o are the same as those defined in claim 1,
p is an integer from 0 to 4, m+p≤4, and when p is an integer of 2 or greater, a plurality of L ^a -N(R ^c )(R ^d ) are the same as or different from each other;
q is an integer of 0 or 1, n+q≤1,
r is an integer from 0 to 5, o+r≤5, and when r is an integer of 2 or greater, a plurality of L ^a -N(R ^c )(R ^d ) are the same as or different from each other. According to claim 1,
Formula 1 is a compound characterized in that one of the following compounds:

.
a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode.
An organic electric device characterized in that the organic material layer contains the compound of any one of claims 1 to 7. According to claim 8,
The organic electric device, characterized in that the compound is contained in at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer and the light emitting layer of the organic material layer as a single compound or a mixture of two or more. According to claim 9,
The organic electric device, characterized in that the compound is used as a phosphorescent host material of the light emitting layer. According to claim 8,
The organic 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 electric element of claim 8; and
An electronic device comprising a controller for driving the display device. 13. The electronic device according to claim 12, wherein the organic electric element is at least one of an organic light emitting element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white light.

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