KR20170099476A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed is a compound represented by chemical formula 1; an organic electronic element comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode; and an electronic device including the organic electronic element. The organic layer of the organic electronic element includes the compound represented by the chemical formula 1, thereby reducing the driving voltage of the organic electronic element, and improving high heat resistance, color purity, luminous efficiency, life span, etc.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electronic device, an organic electronic device using the compound, and an electronic device using the compound.

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

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multi-layered structure made of different materials, and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

In the case of a polycyclic ring compound containing a hetero atom, the difference in characteristics depending on the material structure is very large and is applied to various layers as a material of an organic electric device. Especially, it has characteristics of different bandgap (HOMO, LUMO), electrical characteristic, chemical property and physical property depending on the number of rings and fused position, type and arrangement of heteroatoms, Has progressed.

For example, U.S. Patent Application Publication No. 2008/0145708 A1 (2008.06.19) discloses an embodiment in which a polycyclic ring compound is applied to a hole transporting layer or a phosphorescent host of an organic electronic device, and Korean Patent Laid-Open Publication No. 10-2007-0012218 (Jan. 25, 2007) discloses an embodiment in which a polycyclic ring compound is applied to an electron transport layer of an organic electronic device. Currently, development of materials for organic electronic devices with respect to kinds, number, and positions of heteroatoms of polycyclic ring compounds is actively under progress. In particular, development of a light emitting layer for a host material and a hole transporting layer material is urgently required.

Disclosure of the Invention An object of the present invention is to provide a compound capable of improving the luminous efficiency and lifetime of a device while lowering the driving voltage of the device using the characteristics of the cyclic ring compound, an organic electric device using the same, and an electronic device thereof.

In one aspect, the invention provides compounds represented by the formula:

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

According to the present invention, by using a specific compound in which a core (8-ring heterocycle including a phenanthrene structure) which increases packing density is used as a material for an organic electric device, it is possible to achieve high thermal stability and easy charge balance in a light emitting layer A T1 value and an energy band gap can be obtained, thereby improving the luminous efficiency, heat resistance, lifetime and the like of the organic electronic device and lowering the driving voltage.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, the terms first, second, A, B, (a), (b), and the like can be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

In addition, when an element such as a layer, film, region, plate, or the like is referred to as being "on" or "on" another element, And the like. On the contrary, when an element is referred to as being "directly on " another element, it should be understood that it does not have another element in the middle.

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

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

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term "alkenyl group" or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxyl group," alkoxy group "or" alkyloxy group "as used in the present invention means an alkyl group to which an oxygen radical is attached and has a carbon number of 1 to 60, no.

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

The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R 'and R" is a substituent other than hydrogen, and R and R' Together with a spy compound.

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.

The term "heterocyclic group" as used herein includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group ", but also nonaromatic rings, Means a ring of 2 to 60 rings, but is not limited thereto. The term "heteroatom ", as used herein, unless otherwise indicated, refers to N, O, S, P, or Si, wherein the heterocyclic group includes single ring, ring, And the like.

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

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

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, and the like, as well as various fused ring systems and spiro compounds, including aromatic as well as non- The ring includes, of course, a heterocycle containing at least one heteroatom.

As used herein, the term "ring assemblies" means that two or more ring systems (a single ring or a fused ring system) are directly connected to each other through a single bond or a double bond, Means that the number of linkages is one less than the total number of rings in the compound. The ring assemblies may be directly connected to each other through a single bond or a double bond.

As used herein, the term " conjugated ring system "refers to a fused ring form shared by at least two atoms, in which the ring system of two or more hydrocarbons is conjugated and contains at least one heteroatom And at least one hetero ring system bonded thereto. Such conjugated ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings or a combination of these rings.

The term "spiro compound" used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom. In this case, the atoms shared in the two rings are called 'spyro atoms', and depending on the number of spyro atoms contained in one compound, they are referred to as' monospyros,' 'diospyros,' ' 'Compounds.

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

In addition, a no explicit description, the terms used in this invention in the "unsubstituted or substituted", "substituted" is an alkyl group of deuterium, a halogen, an amino group, a nitrile group, a nitro _{group, C 1 -C 20, C 1} -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl amine group, C ₁ -C ₂₀ alkyl thiophene group, C ₆ -C ₂₀ aryl thiophene group, C ₂ -C ₂₀ alkenyl, C ₂ -C of ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron And a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and at least one substituent selected from the group consisting of a halogen atom, , And it is not limited to these substituents.

In the present specification, the 'group name' corresponding to the aryl group, the arylene group, the heterocyclic group and the like exemplified as the examples of the respective symbols and substituents thereof may be described as 'the name of the group reflecting the singer' You may. For example, in the case of phenanthrene, which is a kind of aryl group, a monovalent 'group' may be named 'phenanthryl' and a bivalent group may be named 'phenanthrylene' It may be described as "phenanthrene" which is the name of the parent compound. Similarly, in the case of pyrimidine, it may also be described as 'pyrimidine' irrespective of the valence number, or may be described as the 'name of the group' of the corresponding singer, such as pyrimidine and pyrimidine have.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, and when a is an integer of 4 to 6 and bonded to the carbon of the benzene ring in a similar way, while in the hydrogen bonded to the carbon to form a benzene ring The display is omitted.

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

1, an organic electroluminescent device 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 a compound according to the present invention is provided between the two electrodes 180. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially 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, an electron transporting auxiliary layer, a buffer layer 141, It may also serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to an embodiment of the present invention further includes a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer can do.

The compound according to the present invention applied to the organic layer includes a hole injecting layer 130, a hole transporting layer 140, an electron transporting auxiliary layer, an electron transporting layer 160, an electron injecting layer 170, a light emitting layer 150, , The light-emitting auxiliary layer 151, and the like. For example, the compound of the present invention may be used as the material of the light emitting layer 150 and / or the hole transporting layer 140.

On the other hand, even if the core is the same core, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at which position, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T ₁ value between the organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.

As described above, in order to solve the problem of light emission in the hole transporting layer in an organic electroluminescent device, it is preferable that a light-emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer. It is necessary to develop different luminescence-assisting layers according to the above. On the other hand, in the case of the light-emission-assisting layer, it is difficult to deduce the characteristics of the organic layer to be used even if a similar core is used because the relationship between the hole-transport layer and the light-emitting layer (host)

Accordingly, in the present invention, by forming a phosphorescent host and / or a hole transport layer using the compound represented by the formula (1), the energy level and T ₁ value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) It is possible to simultaneously improve the lifetime and efficiency of the organic electronic device.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. An emission auxiliary layer 151 may be further formed between the hole transport layer 140 and the emission layer 150 and an electron transport auxiliary layer may be further formed between the emission layer 150 and the electron transport layer 160

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. 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 forming method.

The organic electroluminescent device according to an embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic or white illumination.

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

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

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

≪ Formula 1 >

In Formula 1,

A ring and B ring are C ₆ aromatic rings.

X may be selected from the group consisting of NL ² -Ar ² , S, O and C (R ^a ) (R ^b )

Y may be selected from the group consisting of NL ³ -Ar ³ , S, O and C (R ^c ) (R ^d ).

Ar ¹ To Ar ³ independently represent an aryl group of C ₆ -C ₆₀ with each other; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; -L ^a -N (R ^e ) (R ^f ); A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group.

Preferably, Ar < ^{1 >} To Ar ³ are independently of each other a C ₆ -C ₃₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 30 containing at least one heteroatom selected from the group consisting of Si and P; And a C ₂ -C ₁₀ alkenyl group; Etc., more preferably a C ₆ -C ₂₀ aryl group; A fluorenyl group; A C ₂ -C ₁₈ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And an alkenyl group of C ₂ -C _4; And the like, illustratively, phenyl, pyrene yl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene renil, fluoran butenyl, 9,9-dimethyl -9 H - fluorenyl, 9,9 '- spirobifluorenyl, pyridine, pyrimidine, triazine, quinazoline, pyridopyrimidine, quinoxaline, benzoquinazoline, dibenzoquinazoline, benzothienopyrimidine, benzopurpyrimidine, Dibenzothiophene, dibenzofuran, pyridoquinazoline, naphthothienopyrimidine, naphthopyropyrimidine, carbazole, indolocarbazole, benzoindenopyrimidine, benzofurpyridine, benzothiophene, Napyridine, isoquinoline, imidazole, vinyl, and the like.

R ¹ to R ⁵ independently of one another are deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; -L ^a -N (R ^e ) (R ^f ); A C ₁ -C ₃₀ alkoxyl group; And an aryloxy group of C ₆ -C ₃₀ .

Preferably, R ¹ to R ⁵ independently of one another are halogen; A C ₆ -C ₃₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 30 containing at least one heteroatom selected from the group consisting of Si and P; And -L ^a -N (R ^e ) (R ^f ), and more preferably, halogen; A C ₆ -C ₂₄ aryl group; A fluorenyl group; A C ₂ -C ₁₆ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And ^{-L a -N (R e) (} R f) , and the like, illustratively, F, phenyl, biphenyl, carbazole, acridine Ben Joa, ^{-L a -N (R e) (} R f) And so on. In addition, R ¹ to R ⁵ independently of each other may be bonded to each other to form at least one ring, wherein R ¹ to R ⁵ which do not form a ring may be defined as defined above have.

m and q are independently an integer of 0 to 4, and when m and q are each an integer of 2 or more, a plurality of R ¹ and R ⁵ may be the same or different from each other.

o is an integer of 0 to 2, and when o is 2, the plurality of R ³ may be the same or different from each other. N and p are integers of 0 or 1.

L ¹ to L ³ , and L ^a independently of one another are a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And aliphatic hydrocarbon groups; ≪ / RTI >

Preferably, L ¹ to L ³ , and L ^a independently of one another are a single bond; A C ₆ -C ₃₀ arylene group; And 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 more preferably a single bond; A C ₆ -C ₂₀ arylene group; And a C ₂ -C ₁₆ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and illustratively includes a single bond, phenylene, biphenylene, Pyridine, pyridine, pyrimidine, triazine, quinazoline, pyridopyrimidine, quinoxaline, benzoquinazoline, dibenzoquinazoline, benzothienopyrimidine, benzopuropyrimidine, dibenzofurane, pyridoquinazoline, Naphthosophenes, naphthosienopyrimidines, naphthopyrimirines, carbazoles, benzoindenopyrimidines, benzofurpyridines, benzothienopyridines, isoquinolines, imidazoles, and the like. In addition, L ¹ to L ³ , and L ^a are each a hydrogen atom, halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A 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; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; -L ^a -N (R ^e ) (R ^f ); And an arylalkenyl group having from _{8 to 20} carbon atoms.

R ^a to R ^f are independently of each other a C ₆ -C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And an aryloxy group of C ₆ -C ₃₀ . Also, R ^a and R ^b or R ^c and R ^d may combine with each other to form a spiro compound together with the carbon (C) to which they are bonded, or R ^e and R ^f may bond to each other to form a ring.

The aryl group, the arylene group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group and the aryloxy group of each of the above symbols may be substituted with deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A 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; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; And an arylalkenyl group having from _{8 to 20} carbon atoms.

Specifically, the formula (1) may be represented by one of the following formulas (2) to (11).

&Lt; Formula 2 > < EMI ID =

&Lt; Formula 5 > < EMI ID =

&Lt; Formula 8 > < EMI ID =

&Lt; Formula 11 >

X, Y, R ¹ to R ⁵ , L ¹ , Ar ¹ , m, n, o, p and q in the general formulas 2 to 11 may be defined as defined in the general formula (1).

In addition, Ar ¹ of Formula ¹ To Ar ³ may be represented by the following formula (A-1) or (A-2).

&Lt; Formula A-1 > < Formula A-2 &

Q ¹ to Q ⁴ may independently be N (nitrogen), C (R ⁱ ) or C (carbon), provided that Q ¹ to Q ⁴ are each ^one of L ¹ to L ³ C (carbon) when combined with.

In the above formula (A-2), Q ⁵ to Q ⁹ are independently N (nitrogen) or C (R ¹ ).

In the formula A-1) and (A-2, R ⁱ is hydrogen; heavy hydrogen; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A 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; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; And C ₈ may be selected from the group consisting of aryl alkenyl group of -C _20.

The Z ring of the above formula (A-1) is a C ₆ -C ₆₀ aromatic ring group; Or a heterocyclic date of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P.

 Preferably, the Z ring of the formula (A-1) may be represented by one of the following formulas (Z-1) to (Z-15).

In the above formulas (Z-1) to (Z-15), the symbol (*) is a bonding moiety which bonds with a ring containing Q ¹ to Q ⁴ of the above formula A-1 to form a fused ring.

V is independently N or C (R &^lt; ¹ &gt;),

W ¹ and W ² may be independently selected from the group consisting of a single bond, NL ⁴ -Ar ⁴ , S, O and C (R ^j ) (R ^k ).

L ⁴ is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And an aliphatic hydrocarbon group.

Ar ⁴ , R ^j and R ^k are each independently a C ₆ -C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group.

Also, R ^j And R ^k may combine with each other to form a spiro compound together with C (carbon) to which they are bonded, and R ⁱ may be defined as defined in the above formulas A-1 and A-2 .

In formula (A-1), when at least one of Q ¹ to Q ⁴ is N (nitrogen), the formula (A-1) may be represented by one of the following formulas Z-16 to Z-50.

In the above formulas Z-16 to Z-50, R ⁱ may be defined as defined in the above formulas A-1 and A-2.

At least one of R ¹ to R ⁵ in Formula 1 may be represented by Formula B below.

&Lt; Formula B >

The R ^e , R ^f, and L ^a may be defined as defined in Formula 1 above.

More specifically, when R ¹ to R ⁵ in the above formula (1) are of the above formula (B), they may be represented by the following formula (12).

&Lt; Formula 12 >

In Formula 12, A ring, B ring, X, Y, R ¹ to R ⁵ , L ¹ , Ar ¹ , m, n, o, p and q may be defined as defined in Formula 1 .

r and v are each independently an integer of 0 to 4, m + r? 4, and q + v? 4. When each of r and v is an integer of 2 or more, a plurality of L ^a , (R ^e ) and (R ^f ) may be the same or different from each other.

s and u are each independently an integer of 0 to 1, n + s? 1, and p + u? 1.

t is an integer of 0 to 2, and o + t? 2. Here, when t is 2, a plurality of L ^a , (R ^e ) and (R ^f ) may be the same or different from each other.

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

In another embodiment, the present invention provides a compound for an organic electroluminescent device represented by the general formula (1).

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

The organic electroluminescent device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer may include a compound represented by the general formula (1). The compound represented by the general formula (1) may be used as a single compound or a mixture of two or more compounds in at least one of a hole injection layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, . That is, the compound represented by the general formula (1) can be used as a material for the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting auxiliary layer, the electron transporting layer and the electron injecting layer, May be used as the phosphorescent host material and / or the hole transport layer material in the light emitting layer.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

The compounds represented by formula (1) according to the present invention are synthesized by reacting one of Sub 1A and Sub 1B with Sub 2 as shown in Reaction Scheme 1, but are not limited thereto.

A ring, B ring, X, Y, R ¹ to R ⁵ , L ¹ to L ³ , Ar ¹ And Ar ³ , m, n, o, p and q are the same as defined in formula (1), and Hal ¹ and Hal ³ are Br or Cl.

When X = S, O or C (R ^a ) (R ^b ) and Y = S, O or C (R ^c ) (R ^d )

When X = S, O, C (R ^a ) (R ^b ) or NL ² -Ar ² and Y = NL ³ -Ar ³ ,

I. Sub  1A, Sub  Synthesis of 1B

Sub 1A of Reaction Scheme 1 and Sub 1B of Reaction Scheme 2 can be synthesized by the reaction path of the following Reaction Schemes 3 to 7, but are not limited thereto.

<Reaction Scheme 3>

<Reaction Scheme 4>

<Reaction Scheme 5>

<Reaction Scheme 6>

<Reaction Scheme 7>

Examples of the synthesis of specific compounds belonging to Sub 1 are as follows.

One. Sub  1A-1, Sub  1A-7 Synthetic example

<Reaction Scheme 8>

(One) Sub  1A-I-1 synthesis

2- (methylsulfinyl) phenyl) boronic acid (259.19 g, 1408.47 mmol), and Pd (PPh 3) were dissolved in THF (3700 mL) ₃ ) ₄ (65.10 g, 56.34 mmol), NaOH (169.02 g, 4225.42 mmol) and water (1850 mL) were added and stirred at 80 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 356.56 g (yield: 62%) of the product.

(2) Sub  1A-II-1, Sub  1A-II-47 Synthesis

Back into the Sub 1A-I-1 (356.56 g, 873.26 mmol) and triflic acid (772.8mL, 8732.58 mmol) obtained in the above synthesis with stirring for 24 hours at room temperature, aqueous solution of pyridine _{(10200mL, pyridine: H 2 O} = 1: 5) was slowly added dropwise and refluxed with stirring for 30 minutes. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give the product, Sub 1A-II-1 (147.86 g, yield: 45% Sub 1A-II-47 (108.43 g, yield: 33%).

(3) Sub  1A-III-1 Synthesis

After the Sub 1A-II-1 (61.61 g, 163.74 mmol) obtained in the above Synthesis was dissolved in THF (540mL), (2- ( methylsulfinyl) phenyl) boronic acid (30.13 g, 163.74 mmol), Pd (PPh 3) 4 (7.57 g, 6.55 mmol), NaOH (19.65 g, 491.22 mmol) and water (270 mL) were added and stirred at 80 &lt; 0 &gt; C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 49.21 g (yield 69%).

(4) Sub  1A-1, Sub  1A-7 synthesis

Sub-1A-III-1 (49.21 g, 112.98 mmol) obtained in the above synthesis was mixed with triflic acid (150 ml, 1694.71 mmol) and stirred at room temperature for 24 hours. A pyridine aqueous solution (1980 ml, pyridine: H ₂ O = 1 : 5) was slowly added dropwise and refluxed with stirring for 30 minutes. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give the product Sub 1A-1 (119.60 g, 7 (714.59 g, yield: 32%).

2. Sub  1A- 2, Sub  1A-8 Synthetic example

<Reaction Scheme 9>

(One) Sub  1A-III-2 synthesis

(2-hydroxyphenyl) boronic acid ( 10.14 g, 73.54 mmol) in Sub 1A-II-1 (27.67 g, 73.54 mmol) obtained in the synthesis, Pd (PPh _{3) 4} (23.49 g, yield: 82%) was obtained using the above Sub 1A-III-1 synthesis method by adding sodium hydride (3.40 g, 2.94 mmol), NaOH (8.82 g, 220.61 mmol), THF (240 mL) &Lt; / RTI &gt;

(2) Sub  1A-2, Sub  1A-8 synthesis

Sub 1A-III-2 (23.49 g, 60.31 mmol) obtained in the above synthesis and Pd (OAc) ₂ (1.35 g, 6.03 mmol) and 3-nitropyridine (0.75 g, 6.03 mmol) were added together and dissolved in C ₆ F ₆ (90 mL) and DMI (60 mL), followed by the addition of tert- butylperoxybenzoate (23.43 g, 120.63 mmol) 90 C &lt; / RTI &gt; After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give Sub 1A-2 (28.88 g, yield: 38% 8 (87.01 g, yield: 30%).

3. Sub  1A-30 Synthetic example

<Reaction formula 10>

(One) Sub  1A-III- 30 synthesis

(9 - dimethyl - 9H - fluoren - 2 - yl) (phenyl - d5) amino) -2- (methylsulfinyl) phenyl) boronic acid (31.44 g, 66.55 mmol), Pd (PPh 3) 4 (28.91 g, yield: 60%) was prepared using the sub-1A-III-1 synthesis method by the addition of water (3.08 g, 2.66 mmol), NaOH (7.99 g, 199.64 mmol) .

(2) Sub  1A-30 synthesis

Triflic acid (53 mL, 599.00 mmol) and pyridine aqueous solution (700 mL, pyridine: H ₂ O = 1: 5) were added to Sub 1A-III-30 (28.91 g, 39.93 mmol) The product (11.33 g, yield: 41%) was obtained using the synthetic method.

4. Sub  1A-47 Synthetic example

<Reaction Scheme 11>

(One) Sub  1A-III- 47 synthesis

Dibenzo [b, d] furan-2-yl (4- (naphthalen-1-yl) phenyl) amino) -2- (methoxycarbonyl) phenyl) boronic acid ( 64.03 g, 113.64 mmol), Pd (PPh 3) 4 (53.72 g, yield: 58%) was obtained using the sub-1A-III-1 synthesis method by adding NaOH (5.25 g, 4.55 mmol), NaOH (13.64 g, 340.93 mmol), THF (380 mL) &Lt; / RTI &gt;

(2) Sub  1A-47 synthesis

Sub 1A-III-47 (53.72 g, 65.92 mmol) obtained in the above synthesis was dissolved in THF (330 mL), then methylmagnesium bromide 1.0 M in THF (263.7 mL, 263.67 mmol) was slowly added dropwise and stirred at room temperature. After the reaction was completed, the reaction mixture was extracted with diethyl ether and water. The organic layer was dried over MgSO ₄ and concentrated to obtain an intermediate product. This intermediate was dissolved in acetic acid solution (250 mL), HCl (5 mL) was added, and the mixture was refluxed. When the reaction was completed, water was added and stirred. The resulting solid was filtered under reduced pressure and washed with water and methanol to give the product (17.34 g, yield: 33% over two steps) as a white powder.

5. Sub  1B-2, Sub  1B-9 Synthetic example

<Reaction Scheme 12>

(One) Sub  1B-III- 2 synthesis

(2-nitrophenyl) boronic acid ( 14.57 g, 87.28 mmol) in Sub 1A-II-1 (32.84 g, 87.28 mmol) obtained in the synthesis, Pd (PPh _{3) 4} (28.12 g, yield: 77%) was obtained using the above Sub 1A-III-1 synthesis method by adding sodium hydride (4.03 g, 3.49 mmol), NaOH (10.47 g, 261.83 mmol), THF (290 mL) &Lt; / RTI &gt;

(2) Sub  1B-IV-2 synthesis

Sub 2B-9 (15.66 g, 67.20 mmol), Pd ₂ (dba) ₃ ( ₂ ) were dissolved in toluene (670 mL) (1.85 g, 2.02 mmol), 50% P ( t- Bu) ₃ (2.0 mL, 4.03 mmol) and NaO t- Bu (19.37 g, 201.59 mmol) were added and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 27.23 g (yield: 71%) of the product.

(3) Sub  1B-2, Sub  1B-9 synthesis

Sub 1B-IV-2 (27.23 g, 47.72 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene (420 mL), triphenylphosphine (31.29 g, 119.29 mmol) was added and stirred at 200 ° C. When the reaction was complete, o- dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give the product, Sub 1B-2 (11.57 g, yield: 45%) and Sub 1B-9 (8.74 g, yield: 34%) .

6. Sub  1B-27 Synthetic example

<Reaction Scheme 13>

(One) Sub  1B-I-27 Synthesis

1,7-dibromo-4H-benzo [ def] carbazole (63.04g, 180.61 mmol) in (2-nitrophenyl) boronic acid ( 30.15 g, 180.61 mmol), Pd (PPh 3) 4 (44.52 g, yield: 63%) was obtained using the sub-1A-I-1 synthesis method by adding sodium hydride (8.35 g, 7.22 mmol), NaOH (21.67 g, 541.84 mmol), THF (600 mL) &Lt; / RTI &gt;

(2) Sub  1B-II'-27 Synthesis

Was dissolved the Sub 1B-I-27 (44.52 g, 113.80 mmol) obtained in the above synthesis with toluene (1140mL), Sub 2-1 ( 17.87 g, 113.80 mmol), Pd 2 (dba) 3 (3.13 g, 3.41 mmol), 50% P ( t- Bu) ₃ (3.3 mL, 6.83 mmol) and NaO t- Bu (32.81 g, 341.39 mmol) were added and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silica gel column chromatography and recrystallized to obtain 34.57 g (yield 65%).

(3) Sub  1B-III'-27 Synthesis

Sub 1B-II'-27 (34.57 g, 73.98 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene (520 mL), triphenylphosphine (48.51 g, 184.94 mmol) was added and stirred at 200 ° C. When the reaction was complete, o- dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give the product (22.54 g, yield: 70%).

(4) Sub  1B-IV'-27 Synthesis

Was dissolved the Sub 1B-III'-27 (22.54 g, 51.78 mmol) obtained in the above synthesis in THF (170mL), (2- nitrophenyl) boronic acid (8.64 g, 51.78 mmol), Pd (PPh 3) 4 (2.39 g, 2.07 mmol), NaOH (6.21 g, 155.33 mmol), water (85 mL) and the mixture was stirred at 80 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 21.26 g (yield: 86%) of the product.

(5) Sub  1B-V'-27 Synthesis

Was dissolved the Sub 1B-IV'-27 (21.26 g, 44.52 mmol) obtained in the above synthesis with toluene (45mL), Sub 2-1 ( 6.99 g, 44.52 mmol), Pd 2 (dba) 3 (1.22 g, 1.34 mmol), 50% P ( t- Bu) ₃ (1.3 mL, 2.67 mmol) and NaO t- Bu (12.84 g, 133.57 mmol) were added and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 18.24 g (yield 74%).

(6) Sub  1B-27 Synthesis

Sub 1B-V'-27 (18.24 g, 32.95 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene (230 mL), triphenylphosphine (21.60 g, 82.37 mmol) was added and stirred at 200 ° C. When the reaction was complete, o- dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain the product (12.37 g, yield: 72%).

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

[Table 1]

II. Sub  Synthesis of 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 14, but is not limited thereto. At this time, Ar ^A is Ar ¹ To Ar ³ , L ^A is L ¹ to L ³ , and Hal ^A is Hal ¹ To Hal ³ . In addition, Hal ¹ To Hal ³ is Br or Cl.

<Reaction Scheme 14>

Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

One. Sub  2-28 Synthetic example

<Reaction Scheme 15>

1,4-dibromobenzene (17.37 g, 73.63 mmol) was dissolved in THF (260 mL) and then 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) and water (130 mL) were added and stirred at 90 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 18.23 g (yield: 73%) of the product.

2. Sub  2-35 Synthetic example

<Reaction Scheme 16>

4,4,5,5-tetramethyl-2- (naphthalen-1-yl-d7) -1,3,2-dioxaborolane (29.54 g, 113.11 _{mmol), Pd (PPh 3)} 4 (18.03 g, yield: 60%) was obtained using the Sub 2-28 synthesis method by the addition of water (4.75 g, 4.11 mmol), K ₂ CO ₃ (42.63 g, 308.47 mmol), THF (360 mL) ).

3. Sub  2-52 Synthetic example

<Reaction Scheme 17>

4,4,5,5-tetramethyl-2- (naphthalen-2-yl) - (4-methylphenyl) pyridine was added to the starting material 2,4- dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (32.01 g, 125.47 mmol) 1,3,2-dioxaborolane (35.07 g, 138.02 mmol), Pd (PPh 3) 4 (19.58 g, yield: 45%) was obtained using the above Sub 2-28 synthesis method by the addition of triethylamine (5.80 g, 5.02 mmol), K ₂ CO ₃ (52.02 g, 376.41 mmol), THF (440 mL) ).

4. Sub  2-57 Synthetic example

<Reaction Scheme 18>

To a solution of 4,4,5,5-tetramethyl-2- (3- (naphthalen-1-yl) pyrimidine, 24.89 g, 97.56 mmol) was added to the starting material 2,4- dichlorobenzo [4,5] thieno [ yl) phenyl) -1,3,2-dioxaborolane ( 35.44 g, 107.32 mmol), Pd (PPh 3) 4 (19.81 g, yield: 48%) was obtained using the Sub 2-28 synthesis method by the addition of potassium carbonate (4.51 g, 3.90 mmol), K ₂ CO ₃ (40.45 g, 292.69 mmol), THF (170 mL) ).

5. Sub  2-78 Synthetic example

<Reaction Scheme 19>

(One) Sub  2-I-78 Synthesis

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

(2) Sub 2-II-78 Synthesis

N , N- Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise to the round bottom flask, and Sub 2-I-78 (63.86 g, 300.94 mmol) and POCl ₃ , And stirred at 90 ° C. After completion of the reaction, the reaction mixture was concentrated, and then ice water (500 ml) was added thereto, followed by stirring at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain the product (67.47 g, yield: 90%).

(2) Sub  2-78 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-78 (67.47 g, 270.86 mmol) ₃ ) ₄ (44.89 g, yield: 57%) was obtained using the Sub 2-28 synthesis method by the addition of water (12.52 g, 10.83 mmol), K ₂ CO ₃ (112.30 g, 812.57 mmol), THF (950 mL) ).

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

[Table 2]

III. Product  synthesis

Sub 1A or Sub 1B (1 eq.) Was placed in a round bottom flask and dissolved in toluene. Sub 2 (1 equivalent), Pd ₂ (dba) ₃ (0.03 eq.), (T-Bu) ₃ P (0.06 eq.) And NaOt-Bu (3 eq.) Were added and stirred at 100 &lt; 0 &gt; C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was subjected to silicagel column and recrystallization to obtain final product.

1. P 1-8 Synthetic example

<Reaction Scheme 20>

Once placed in the Sub 1A-1 (7.87 g, 19.50 mmol) obtained in the above Synthesis round bottom flask was dissolved in toluene (195mL), Sub 2-78 ( 5.67 g, 19.50 mmol), Pd 2 (dba) 3 (0.54 g, 0.59 mmol), 50% P ( t- Bu) ₃ (0.6 mL, 1.17 mmol) and NaO t- Bu (5.62 g, 58.51 mmol) were added and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 9.11 g (yield: 71%) of the product.

2. P 1-12 Synthetic example

<Reaction Scheme 21>

To Sub 1B-2 (8.93 g, 16.58 mmol) obtained in the above synthesis, Sub 2-7 (3.86 g, 16.58 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.50 mmol), 50% P ( t- Bu) ₃ (0.5 mL, 0.99 mmol), NaO t- Bu (4.78 g, 49.73 mmol) Was used to obtain the product (8.82 g, yield: 77%).

3. P 1-17 Synthetic example

<Reaction Formula 22>

To Sub-1A-2 (7.36 g, 19.00 mmol) obtained in the above synthesis, Sub 2-35 (5.55 g, 19.00 mmol), Pd ₂ (dba) ₃ (0.52 g, 0.57 mmol), 50% P ( t- Bu) ₃ (0.6 mL, 1.14 mmol), NaO t- Bu (5.48 g, 56.99 mmol) (8.53 g, yield: 75%) was obtained.

4. P 1-32 Synthesis Example

<Reaction Scheme 23>

To Sub 1A-7 (7.52 g, 18.64 mmol) obtained in the above synthesis, Sub 2-11 (5.76 g, 18.64 mmol), Pd ₂ (dba) ₃ (0.51 g, 0.56 mmol), 50% P ( t- Bu) ₃ (0.5 mL, 1.12 mmol), NaO t- Bu (5.37 g, 55.91 mmol) Was used to obtain the product (8.24 g, yield: 70%).

5. P 1-37 Synthetic example

<Reaction Scheme 24>

To Sub-1A-7 (7.03 g, 17.42 mmol) obtained in the above synthesis, Sub 2-52 (6.04 g, 17.42 mmol), Pd ₂ (dba) ₃ (0.48 g, 0.52 mmol), 50% P ( t- Bu) ₃ (0.5 mL, 1.05 mmol), NaO t- Bu (5.02 g, 52.27 mmol) Was used to obtain the product (8.46 g, yield: 68%).

6. P 1-39 Synthetic example

<Reaction Scheme 25>

To Sub 1A-8 (6.75 g, 17.42 mmol) obtained in the above synthesis, Sub 2-28 (5.91 g, 17.42 mmol), Pd ₂ (dba) ₃ (0.48 g, 0.52 mmol), 50% P ( t- Bu) ₃ (0.5 ml, 1.05 mmol), NaO t- Bu (5.02 g, 52.26 mmol) Was used to obtain the product (8.21 g, yield: 73%).

7. P 1-42 Synthesis Example

<Reaction Scheme 26>

To Sub 1B-9 (8.01 g, 14.87 mmol) obtained in the above synthesis, Sub 2-2 (4.32 g, 14.87 mmol), Pd ₂ (dba) ₃ (0.41 g, 0.45 mmol), 50% P ( t- Bu) ₃ (0.4 ml, 0.89 mmol), NaO t- Was used to obtain the product (8.25 g, yield: 70%).

8. P 1-91 Synthetic example

<Reaction Scheme 27>

To Sub 1B-27 (7.52 g, 14.42 mmol) obtained in the above synthesis, Sub 2-57 (6.10 g, 14.42 mmol), Pd ₂ (dba) ₃ (0.40 g, 0.43 mmol), 50% P ( t- Bu) ₃ (0.4 mL, 0.86 mmol), NaO t- Bu (4.16 g, 43.25 mmol) and toluene (145 mL) (8.38 g, yield: 64%) was obtained.

9. P 1-103 Synthetic example

<Reaction Scheme 28>

To Sub 1A-30 (10.08 g, 14.57 mmol) obtained in the above synthesis, Sub 2-7 (3.40 g, 14.57 mmol), Pd ₂ (dba) ₃ (0.40 g, 0.44 mmol), 50% P ( t- Bu) ₃ (0.4 mL, 0.87 mmol), NaO t- Bu (4.2 g, 43.70 mmol) Was used to obtain the product (8.36 g, yield: 68%).

10. P 1-128 Synthetic example

<Reaction Scheme 29>

To Sub 1A-47 (11.58 g, 14.53 mmol) obtained in the above synthesis, Sub 2-6 (3.01 g, 14.53 mmol), Pd ₂ (dba) ₃ (0.40 g, 0.44 mmol), 50% P ( t- Bu) ₃ (0.4 mL, 0.87 mmol), NaO t- Bu (4.19 g, 43.59 mmol) Was used to obtain the product (8.18 g, yield: 61%).

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

[Table 3]

On the other hand, the above has been described in an illustrative synthesis of the present invention represented by the general formula (1), all of Buchwald-Hartwig cross coupling reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd (II ) -catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13 , 5504), Grignard reaction, Cyclic Dehydration reaction and PPh ₃ -mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.) as the other substituents as defined in formula (I) in addition to the substituents specifically set forth in synthetic example, based or the like (a ring, B ring, X, Y, R ¹ to ^{R 5, L 1, L 2} , L 1 to L ³ , Substituents such as Ar ¹ to Ar ³ ) are bonded to each other, it will be easily understood by those skilled in the art. Sub 2 -> Final Product reaction with one of Sub 1A and Sub 1B in Scheme 1 and Scheme 2, Sub 1-III -> Sub IV reaction in Scheme 6, Sub 1 -I -> Sub II 'reaction with Scheme 7 , Sub 1-IV '-> Sub V' reactions are all based on the Buchwald-Hartwig cross coupling reaction and the starting material -> Sub 1-I reaction in Scheme 3, Sub 1-II -> Sub 1-III Sub 1 - III '-> Sub 1 - IV' reaction in Scheme 7 and starting material -> Sub 2 reaction in Scheme 14 are based on the Suzuki cross-coupling reaction, The synthesis method disclosed in Korean Patent No. 10-1251451 (registered in the date of April, 2013) and No. 10-1298483 (registered in the date of August 31, 2013) were used. > Sub 1-II (when X is S) reaction, in scheme 5 Sub 1-III -> Sub 1A ( when Y is S) the reaction is acid-induced cyclization reaction Intramolecular (J. mater Chem 1999, 9. . , 2 095. Sub 1-III -> Sub 1A (when Y is O) in the reaction scheme 1, Sub 1-I -> Sub 1-II (when X is O) in Scheme 4 and Pd (II) -catalyzed oxidative cyclization reaction (.. Org Lett 2011, 13 , 5504) it will, based on, in scheme 3 Sub 1-I -> Sub 1-II ( when X is ^{C (R a) (R b} )) reaction, scheme 5 Sub 1-III -> Sub 1A (where Y is C (R ^c ) (R ^d )) The reaction is based on the Grignard reaction and the cyclic dehydration reaction. in 7 Sub 1-II '-> Sub 1-III' reaction, Sub 1-V '-> Sub 1B reaction is based on PPh ₃ -mediated reductive cyclization reaction (J. Org Chem 2005, 70, 5014...) will be. The above reactions will proceed even if a substituent not specifically mentioned is attached.

The benzocarbazole type material used as the starting material in the starting material -> Sub 1-I reaction of the above reaction scheme 3 can be synthesized according to the synthesis method (Method A, Method B (Korean Patent Laid-Open Publication No. 2015-0039486 , Method C (Korean Patent Laid-Open Publication No. 2015-0077219)) was used.

<Reaction Scheme 30>

Evaluation of manufacturing of organic electric device

[ Example  One] Red organic electroluminescent 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 of a 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 the ITO layer (anode) (1-naphthyl) -N-phenylamino] biphenyl (hereinafter referred to as NPD) film as a hole transporting compound was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer . The compound P 1-5 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) 5 by weight to form a light emitting layer with a thickness of 30 nm. Subsequently, bis (2-methyl-8-quinolinolato) aluminum (hereinafter referred to as BAlq) was vapor-deposited to a thickness of 10 nm as a hole blocking layer to form tris- (8- hydroxyquinoline) aluminum (hereinafter referred to as Alq ₃ ) was deposited to a thickness of 40 nm. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm as an electron injecting layer, and then Al was deposited to a thickness of 150 nm as an anode to produce an organic electroluminescent device.

[ Example  2] to [ Example  38] Red organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P 1-5 according to Example 1 of the present invention as a host material of the light emitting layer .

[ Comparative Example  1] to [ Comparative Example  3]

Except that one of Comparative Compounds 1 to 3 described in the following Table 4 was used in place of the compound P 1-5 according to Example 1 of the present invention as a host material of the light emitting layer, Thereby preparing a light emitting device.

&Lt; Comparative Compound 1 > < Comparative Compound 2 > < Comparative Compound 3 &

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 38 and Comparative Examples 1 to 3 of the present invention And the T95 lifetime was measured by a life measuring apparatus manufactured by Mac Science Inc. at a reference brightness of 2500 cd / m ^2. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the measurement results in Table 4, the device using the compound according to one embodiment of the present invention as the phosphorescent red host material of the light emitting layer is superior to the device using Comparative Compounds 1 to 3 as the phosphorescent red host material of the light emitting layer It was confirmed that the efficiency and the lifetime were remarkably improved.

This is presumably because the compound of the present invention, which is an 8-ring cyclic compound having phenanthrene introduced into the core, has a high packing density and thus has a relatively low driving voltage and a high thermal stability due to a decrease in joule heat generated when the device is driven. As a result, it can be seen that the compound of the present invention which is an 8-ring cyclic compound is significantly more improved in luminous efficiency and lifetime than Comparative Compound 2 which is a 7-ring compound and Comparative Compound 3.

When a specific substituent such as benzothienopyrimidine, benzofuropyrimidine, or benzoquinazoline is introduced into the compound of the present invention, a structure suitable for accepting both holes and electrons And at the same time, a proper T1 value is provided so as to facilitate the charge transfer from the host to the dopant. As a result, it can be confirmed that the device results show the best emission efficiency and lifetime.

[ Example  39] Green organic electroluminescent 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 of a light emitting layer. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm. Then, an NPD film as a hole transporting compound was vacuum- To form a transport layer. The above compound P 1-66 of the present invention was used as a host on the hole transport layer and tris (2-phenylpyridine) -iridium (hereinafter abbreviated as "Ir (ppy) ₃ " Doped to form a light emitting layer with a thickness of 30 nm. Subsequently, BAlq was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Alq ₃ was formed to a thickness of 40 nm as an electron transporting layer. Then, LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm as an anode to produce an organic electroluminescent device

[ Example  40] to [ Example  55] Green organic electroluminescent device

An organic electroluminescence device was prepared in the same manner as in Example 39 except that the compound of the present invention described in Table 5 was used instead of the compound P 1-66 according to the embodiment 39 of the present invention as a host material of the light emitting layer .

[ Comparative Example  4] to [ Comparative Example  6]

As the host material of the light emitting layer, in place of the compound P 1-66 according to Example 39 of the present invention, one of the comparative compound 1, the comparative compound 4 and the comparative compound 5 described in the following Table 5 was used, Thereby preparing an organic electroluminescent device.

&Lt; Comparative Compound 4 > < Comparative Compound 5>

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 39 to 55 and Comparative Examples 4 to 6 of the present invention And the T95 lifetime was measured through a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 5000 cd / m ^2. The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the measurement results in Table 5, the device using the compound according to one embodiment of the present invention as the phosphorescent green host material of the light emitting layer has significantly improved luminescence efficiency and lifetime than the comparative compound 1, the comparative compound 4 and the comparative compound 5 . It can be confirmed that the structure having a high thermal stability acts as a main factor for improving the performance of a device in a light emitting layer (used as a host) of a green organic electroluminescent device as well as a light emitting layer (used as a host) of a red organic electroluminescent device .

The compound of the present invention used as a host material in the light emitting layer has a high thermal stability and a most suitable T1 value and energy band gap so that the charge transfer from the host to the dopant can be smoothly performed. It can be confirmed that it shows a high lifetime.

In addition, in the case of a phosphorescent host, it is necessary to grasp the correlation with the hole transporting layer and the dopant, so that it is very difficult to use the similar cores to infer the excellent electrical characteristics of the compound of the present invention.

[ Example  56] Green organic electroluminescent 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 hole injection layer having a thickness of 60 nm. Then, the compound P 1-101 of the present invention was deposited on the hole injection layer to a thickness of 60 nm Vacuum vapor deposition was performed to form a hole transport layer. 4,4'-N, N'-dicarbazole-biphenyl (hereinafter abbreviated as "CBP") was used as a host on the hole transport layer and doped with Ir (ppy) ₃ as a dopant in a 90:10 weight ratio A light emitting layer was deposited to a thickness of 30 nm. Subsequently, BAlq was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Alq ₃ was formed to a thickness of 40 nm as an electron transporting layer. Then, LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm as an anode to produce an organic electroluminescent device.

[ Example  57] to [ Example  89] Green organic electroluminescent device

An organic electroluminescence device was prepared in the same manner as in Example 56, except that the compound of the present invention described in Table 6 was used instead of the compound P 1-101 according to Example 56 of the present invention as a hole transport layer material.

[ Comparative Example  7]

 An organic electroluminescence device was prepared in the same manner as in Example 56, except that the compound 6 described in the following Table 6 was used instead of the compound P 1-101 according to Example 56 of the present invention as the hole transport layer material.

&Lt; Comparative Compound 6 >

Electroluminescence (EL) characteristics were measured by PR-650 of a photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 56 to 82 and Comparative Example 7 of the present invention , And the T95 lifetime was measured using a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 5000 cd / m ² as a measurement result. 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 the hole transporting layer material significantly improved the luminescence efficiency and lifetime than the comparative compound 6.

These results show that since the compound has a deep HOMO energy level and a high T 1 value, which are intrinsic properties of the compound of the present invention, the blocking ability of electrons is improved and the hole is smoothly transported to the light emitting layer, And the efficiency is improved. Also, it can be confirmed that the lifetime is increased due to high thermal stability.

(-L ^a -N (R ^e ) (R ^f )) in the same 8-ring heterocyclic ring as the compound of the present invention can be obtained by combining the above-described characteristics of deep HOMO energy level, high T 1 value and high thermal stability It can be seen that the bandgap, electrical characteristics, and interface characteristics can be greatly changed with the introduction, which is a major factor in improving the performance of the device. Further, in the case of the hole transporting layer, the correlation with the light emitting layer (host) must be grasped. Even if similar cores are used, it is very difficult for the ordinary artisan to deduce the characteristics of the compound of the present invention in the hole transporting layer used.

The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are for the purpose of limiting the present invention and are not to be construed as limiting the spirit and scope of the present invention. The scope of protection of the present invention should be construed according to the claims, and all the techniques within the scope of the same 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 (12)

A compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
The A ring and the B ring are C ₆ aromatic rings,
X is selected from the group consisting of NL ² -Ar ² , S, O and C (R ^a ) (R ^b )
Y is selected from the group consisting of NL ³ -Ar ³ , S, O and C (R ^c ) (R ^d )
Ar ¹ And Ar ³ are independently of each other: i) a C ₆ -C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; -L ^a -N (R ^e ) (R ^f ); A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group,
R ¹ to R ⁵ independently of one another are deuterium; Tritium; halogen; Cyano; A nitro group; An aryl group of C ₆ -C ₆₀ ; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; -L ^a -N (R ^e ) (R ^f ); A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group; or ii) adjacent groups may be bonded to each other to form a ring, wherein R ¹ to R ⁵ which do not form a ring are the same as defined above &Lt; / RTI &gt;
m and q are independently an integer of 0 to 4, and when m and q are each an integer of 2 or more, a plurality of R ¹ and R ⁵ are the same or different,
o is an integer of 0 to 2, and when o is 2, plural R ³ are the same or different, n and p are integers of 0 or 1,
L ¹ to L ³ , and L ^a independently of one another are a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And aliphatic hydrocarbon groups; L ¹ to L ³ , and L ^a are each selected from the group consisting of deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A 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; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; -L ^a -N (R ^e ) (R ^f ); And an arylalkenyl group having from _{8 to 20} carbon atoms, which may be substituted with at least one substituent selected from the group consisting of
Aryl group of R ^a to R ^f are independently i) C ₆ -C ₆₀ with each other; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group, or ii) R ^a and R ^b or R ^c and R ^d may combine with each other to form a spiro compound together with the carbon (C) to which they are bonded, or R ^e and R ^f may combine with each other to form a ring,
The aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group and the aryloxy group may each be substituted with deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A 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; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; And an arylalkenyl group having from _{8 to 20} carbon atoms. The method according to claim 1,
(1) is represented by one of the following formulas (2) to (11):
&Lt; Formula 2 >< EMI ID =

&Lt; Formula 5 &gt;&lt; EMI ID =

&Lt; Formula 8 >< EMI ID =

&Lt; Formula 11 &gt;

In the above Chemical Formulas 2 to 11,
X, Y, R ¹ to R ⁵ , L ¹ , Ar ¹ , m, n, o, p and q are as defined in claim 1. The method according to claim 1,
Ar ¹ of Formula ¹ Or Ar < ³ > is represented by the following formula (A-1) or (A-2):
&Lt; Formula A-1 >&lt; Formula A-2 &

In the above formula (A-1), Q ¹ to Q ⁴ are each independently N (nitrogen), C (R ⁱ ) or C (carbon), provided that when they are bonded to one of L ¹ to L ³ , Lt;
In the above formula (A-2), Q ⁵ to Q ⁹ are each independently N (nitrogen) or C (R ¹ )
In the formula A-1) and (A-2, R ⁱ is hydrogen; heavy hydrogen; halogen; A silane group substituted or unsubstituted with an alkyl group having _{1 to 20} carbon atoms or an aryl group having _{6 to 20} carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₆ -C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A 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; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; And C ₈ may be selected from the group consisting of aryl alkenyl group of -C _20,
The Z ring of the formula (A-1) is one of the following formulas (Z-1) to (Z-15)

In the above formulas (Z-1) to (Z-15), the symbol (*) is a bonding moiety to form a fused ring by bonding to a ring including Q ¹ to Q ⁴ of the above formula (A-
V is independently N, or C (R &^lt; ¹ &gt;),
W ¹ and W ² are independently selected from the group consisting of a single bond, NL ⁴ -Ar ⁴ , S, O, and C (R ^j ) (R ^k )
L ⁴ is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And an aliphatic hydrocarbon group,
Ar ⁴ , R ^j and R ^k are each independently a C ₆ -C ₆₀ aryl group; A fluorenyl group; Heterocyclic group of _{O, N, S, C 2} -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And an aryloxy group of C ₆ -C ₃₀ ,
R ^j And R &lt; ^k &gt; may combine with each other to form a spiro compound together with C (carbon) to which they are bonded,
R ⁱ is the same as defined in the above formulas A-1 and A-2. The method of claim 3,
Wherein at least one of Q ¹ to Q ⁴ in the formula (A-1) is N (nitrogen). The method according to claim 1,
At least one of R &^lt; ¹ > to R &^lt; ⁵ &^gt; in the formula (1)
&Lt; Formula B &gt;

Wherein R ^e , R ^f , and L ^a are the same as defined in claim 1. The compound according to claim 1, wherein the compound of formula (1) is one of the following compounds:

. A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode,
Wherein the organic material layer contains the compound of any one of claims 1 to 6. 8. The method of claim 7,
The compound is characterized in that the compound is contained in at least one of the hole injection layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting auxiliary layer, the electron transporting layer and the electron injection layer of the organic material layer as a single compound or a mixture of two or more compounds . 9. The method of claim 8,
Wherein the compound is used as a phosphorescent host material in the light emitting layer. 8. The method of claim 7,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device including the organic electroluminescent device of claim 7; And
And a control unit for driving the display device. 12. The electronic device according to claim 11, wherein the organic electronic device is at least one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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