KR20190001967A - Compound for organic electric element, organic electric element comprising the same and electronic device thereof - Google Patents

Abstract

The present invention relates to a compound for allowing high luminous efficiency and low driving voltage in an element and increasing a lifespan thereof, and an organic electric element using the same, and an electronic device thereof. The compound is represented by chemical formula (1) in which Y is one of C and Si, and X^1 and X^2 are each independently the same or different, and are each selected from the group consisting of N-L^1-Ar^1, S and O.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound for organic electroluminescent devices, an organic electroluminescent device using the same,

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.

The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption becomes a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, Indicating a tendency for the lifetime to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time. Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, However, the development of a stable and efficient organic material layer for an organic electric device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and development of a host material for a light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of maximizing the effect of improving the luminous efficiency and long life, while maintaining or slightly reducing the driving voltage of the device, and an organic electronic device using the same and an electronic device thereof.

In one aspect, the present invention provides a compound 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.

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

1 is a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.

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, terms such as first, second, A, B, (a), and (b) may 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."

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

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

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

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 " heteroalkyl group " as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

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 " used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

The term " alkenoyl group ", " alkenoyl group ", " alkenyloxy group ", or " alkenyloxy group " as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

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 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, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorene group, a spirobifluorene group, or a spirobifluorene group.

The prefix " aryl " or " ar " means a radical substituted with an aryl group. For example, the arylalkyl group is an alkyl group substituted with an aryl group, the arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described in the present specification.

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

The term " heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term " heteroaryl group " or " heteroarylene group " as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term " heterocyclic group ", as used herein, unless otherwise indicated, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings and includes a heteroaliphatic ring and hetero Aromatic rings. Adjacent functional groups may be combined and formed.

As used herein, the term " heteroatom " refers to N, O, S, P or Si unless otherwise stated.

The " heterocyclic group " may also include a ring including SO2 instead of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

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

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

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term " carbonyl " as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise indicated, the term " ether " used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group of 1-20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

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, the substituent R ¹ is absent. That is, when a is 0, it means that all of the carbons forming the benzene ring are bonded to hydrogen. In this case, And the chemical formula or compound may be described. When a is an integer of 1, one substituent R < 1 > is bonded to any carbon of the carbons forming the benzene ring. When a is an integer of 2 or 3, for example, In case of an integer, they are bonded to the carbon of the benzene ring in a similar manner. When a is an integer of 2 or more, R ¹ may be the same or different.

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

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a compound according to the present invention. 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, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include 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.

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

On the other hand, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T1 value and the intrinsic properties (mobility, interfacial characteristics, etc.) between the organic layers are achieved, it is possible to achieve long life and high efficiency at the same time.

Accordingly, in the present invention, by forming the light emitting layer using the compound represented by the general formula (1), it is possible to optimize the energy level and the Tl value between the respective organic layers, the mobility of the material, And efficiency can be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer. A light emitting auxiliary layer 151 may be further formed between the hole transporting layer 140 and the light emitting layer 150 and an electron transporting auxiliary layer may be further formed between the light emitting layer 150 and the electron transporting 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 the present invention may be of a top 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 white organic electronic devices mainly used as backlight devices 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 the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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).

In the above formula (1)

1) Y is any one of C and Si,

2) X ¹ and X ² are each independently the same or different and are each selected from the group consisting of NL ¹ -Ar ¹ , S and O,

3) R ¹ to R ³ are each independently of the other hydrogen; heavy hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₂₄ heteroaryl group; A fluorenyl group; -L ' -N (R ' ^a ) (R ' ^b ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group of C ₆ to C ₃₀ , and a plurality of R ^{1 s} , R ^{2 s} or a plurality of R ^{3 s may} be bonded to each other to form an aromatic ring or a heteroaromatic ring,

4) m, n and s are each independently an integer of 0 to 4,

When m, n and s are 2 or more, R ¹ , R ² and R ³ are the same as or different from each other,

5) Ar ¹ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; -L ' -N (R ' ^a ) (R ' ^b ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, a plurality of Ar ^{1 s} are the same or different from each other,

6) L 'and L ¹ are each independently the same or different and are a single bond, a C ₆ to C ₆₀ arylene group; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si, and P, and a plurality of L ^{1 s} are the same or different from each other,

7) R ^a and R ^b are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And an arylene group having ₆ to ₆₀ carbon atoms.

The aryl group, the fluorenyl group, the arylene group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group may be respectively 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; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group having ₇ to ₂₀ carbon atoms and an arylalkenyl group having ₈ to ₂₀ carbon atoms, and these substituents may be further bonded to each other to form a ring, Refers to a fused ring consisting of an aliphatic ring of C ₃ to C ₆₀ or a C ₆ to C ₆₀ aromatic ring or a C ₂ to C ₆₀ hetero ring or a combination thereof and includes saturated or unsaturated rings.

The aryl group may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and the heterocyclic group may have 2 to 60 carbon atoms, preferably 2 carbon atoms More preferably 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and in the case of the alkyl group, the number of carbon atoms is 1 to 50, preferably 1 to 30, more preferably 1 to 20, May be an alkyl group of 1 to 10 carbon atoms.

Specifically, when the aryl group or the arylene group is the aryl group or the arylene group, the aryl group or the arylene group may be independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group or a phenylene group, a biphenylene group, Phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene or phenylene.

More specifically, the compound represented by Formula 1 may be any one of the following compounds, but is not limited to the following compounds.

The formula (1) may be represented by one of the following formulas (1) -1 to (1) -6.

Y, R ¹ to R ³ , m, n, s, Ar ¹ and L ¹ described in the above Chemical Formulas (1) -1 to (1) -6 are Y, R ¹ to R ³ , m, n, s, Ar < ¹ > And L < ¹ >.

The formula (1) may be represented by the following formula (2).

In the above formula (2)

1) Y, X ¹ , X ² , R ³ and n are the same as Y, X ¹ , X ² , R ³ and n defined in the above formula (1)

2) R ⁴ is hydrogen; heavy hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₂₄ heteroaryl group; A fluorenyl group; -L ' -N (R ' ^a ) (R ' ^b ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group of C ₆ to C ₃₀ , and a plurality of R ^{4 s may} be bonded to each other to form an aromatic ring or a heteroaromatic ring,

3) o is an integer from 0 to 8,

When o is 2 or more, plural R ⁴ are the same or different from each other,

In particular, in the above formula (1), R ¹ to R ³ may be a C ₂ to C ₂₄ heteroaryl group. In the formula (1), when R ¹ to R ³ are C ₂ to C ₂₄ heteroaryl groups, R ¹ to R ³ may be represented by the following formula (3).

In Formula 3,

1) V is selected from the group consisting of NL ² -Ar ² , O and S,

2) Z ¹ to Z ⁸ are each independently selected from the group consisting of C (R '), C and N,

3) L ² is a single bond, an arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

4) R 'is hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₂₄ heteroaryl group; A fluorenyl group; -L'-N (R ^e ) (R ^f ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms,

5) R ^e and R ^f are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And an arylene group having ₆ to ₆₀ carbon atoms.

More specifically, the compound represented by the formula (1) may be any one of the following compounds, but is not limited to the following compounds.

As another embodiment, the present invention provides a compound for an organic electric device represented by the above 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. The organic material layer may include a compound represented by the formula (1), and the compound represented by the formula (1) Layer, a hole transporting layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transporting layer, and an electron injection layer. In particular, the compound represented by the formula (1) may be contained in the hole transporting layer or the light emitting layer.

That is, the compound represented by the 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 layer or the electron injecting layer. In particular, the compound represented by the formula (1) can be used as a host material for a hole transporting layer or a light emitting layer. Specifically, the organic electroluminescent device includes one of the compounds represented by the chemical formula (1) in the organic layer, and more specifically, the organic electroluminescent device comprising the compound represented by the individual chemical formulas (P-1 to P-120) And an organic electroluminescent device.

In still another embodiment, the compound is contained singly in at least one layer of the hole injection layer, the hole transport layer, the light emission assisting layer, the light emitting layer, the electron transport layer, and the electron injection layer of the organic material layer, Wherein the compound is contained in combination of two or more different compounds, or the compound is contained in combination with two or more kinds of other compounds. In other words, each of the layers may contain a compound corresponding to the formula (1) alone, and may include a mixture of two or more compounds of the formula (1), and the compound of the claims 1 to 5, And a compound that does not correspond to the compound of formula (I). Herein, the compound not corresponding to the present invention may be a single compound or may be two or more compounds. When the compound is contained in combination with two or more kinds of other compounds, the other compound may be a known compound of each organic layer or a compound to be developed in the future. At this time, the compound contained in the organic material layer may be composed of the same kind of compound, but it may be a mixture of two or more different kinds of compounds represented by the formula (1).

For example, the organic compound layer may be prepared by mixing two compounds having different structures from each other in a molar ratio of 99: 1 to 1:99.

In another embodiment of the present invention, the light efficiency improving layer is formed on at least one side of the one side of the first electrode opposite to the organic layer, or one side of the one side of the second electrode opposite to the organic layer, And an organic electroluminescent device.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production example 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

[Synthesis Example 1]

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

In the above Reaction Scheme 1, X ₁ is any one of NAr ² , S and O, and Hal ¹ is any one of Br and Cl.

, R¹ 및 R³ 중 어느 하나이다. 여기서, R¹ 및 R³ 은 상기 화학식 (1)에서 정의된 R¹ 및 R³ 과 동일하다.In the above scheme 2 C is any one of R1, Br and Cl, and D is R ^3, any one of Br and Cl, C 'and D' is

, R < ¹ > and R < ³ >. Here, R ¹ and R ³ are the same as R ¹ and R ³ defined in the above formula (1).

I. Synthesis of Sub 1

Sub 1 in the above Reaction Scheme 1 may be synthesized by a reaction route of the following Synthesis Examples, but is not limited thereto.

1. Sub 1-1 Synthetic example

(1) Sub 1-I-1 synthesis

Add a condenser and Dean-stark trap in a round flask, add benzene-1,2-diamine (10 g, 92 mmol), 9-fluorenone (16.5 g 92 mmol), EtOH (400 ml) and acetic acid (9 ml). And the mixture was refluxed and stirred under nitrogen at 120 캜. When the reaction was completed, the temperature was lowered, the solution was filtered, the obtained compound was dried and concentrated, and the resulting compound was recrystallized to obtain 16 g (65%) of sub 1-I-1.

(2) Sub 1-1 Synthesis

Pd (OAc) ₂ (0.4 g, 1.7 mmol) and P (t-Bu) ₃ (0.7 g, 3.7 mmol) were added to a round bottom flask with iodobenezne (11 g, 55 mmol), Sub 1-I- mmol), NaOt-Bu (15.4 g, 163.8 mmol) and toluene (250 ml). When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 1-1 (10.7 g, yield: 50%).

2. Sub 1-14 Synthetic example

(1) Sub 1-14 synthesis

The Sub 1-I-1 To a round bottom flask was placed (16g, 62mmol) 2- (3 -bromophenyl) -4,6-diphenyl-1,3,5-triazine (21g, 55mmol), Pd (OAc) 2 (0.4 g, 1.7 mmol), P (t-Bu) ₃ (0.7 g, 3.7 mmol), NaOt-Bu (15.4 g, 163.8 mmol) and toluene (250 ml). When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to give Sub 1-14 (9.5 g, yield: 30%).

3. Sub 1-36 Synthetic example

(1) Sub 1-36 Synthesis

(13 g, 55 mmol), Pd (OAc) ₂ (0.4 g, 1.7 mmol) and P (t-Bu) were placed in a round bottom flask, ₃ (0.7 g, 3.7 mmol), NaOt-Bu (15.4 g, 163.8 mmol) and toluene (250 ml). When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 1-36 (8.3 g, yield: 32%).

4. Sub 1-49 Synthetic example

(1) Sub 1-I-49 synthesis

A condenser and a Dean-stark trap were placed in a round flask and benzene-1,2-diamine (10 g, 92 mmol) and 4- (diphenylamino) -9H-fluoren-9-one (32 g 92 mmol) 9 ml). And the mixture was refluxed and stirred under nitrogen at 120 캜. When the reaction was completed, the temperature was lowered, the solution was filtered, and the obtained compound was dried and concentrated. The resulting compound was recrystallized to obtain 19 g (40%) of sub 1-I-49.

 (2) Sub 1-49 Synthesis

Pd (OAc) ₂ (0.4 g, 1.7 mmol) and P (t-Bu) ₃ (0.7 g, 3.7 mmol) were added to a round bottom flask with Sub 1-I-49 (19 g, 37 mmol) mmol), NaOt-Bu (15.4 g, 163.8 mmol) and toluene (250 ml). When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 1-49 (10.7 g, yield: 50%).

5. Sub 1-65 Synthetic example

(1) Sub 1-65 Synthesis

2-aminobenzenethiol (10 g, 80 mmol) and 9-fluorenone (14 g 80 mmol) CAS No. were added to a round flask . 109-63-7 (1 eq) is added to CHCl3 (400 ml). And the mixture was refluxed and stirred under nitrogen at 120 캜. When the reaction was completed, the temperature was lowered, the solution was filtered, the obtained compound was dried and concentrated, and the resulting compound was recrystallized to obtain 7g (30%) of sub 1-65.

6. Sub 1-89 Synthetic example

(1) Sub 1- 89 synthesis

1,2-dithiol (170 mg, 1.2 mmol), 2-bromo-9H-fluoren-9-one (259.1 mg, 1 mmol), trichloroacetic acid (0.16 g, 1 mmol) in a round bottom flask was treated with sodium dodecyl sulfate 25 mol%, 0.07 g) are added to water and stirred at 25 ° C. After the reaction was completed, K ₂ CO ₃ (0.07 g, 0.5 mmol) was added, extracted with EA, dried, concentrated and recrystallized from a silicagel column to obtain 191 mg of Sub 1-89 (50%).

On the other hand, the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.

II. Synthesis of Sub 2

Sub 2 in the above Reaction Scheme 1 may be synthesized by the following synthesis example, but is not limited thereto. Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

1. Sub 2-16 Synthetic example

Dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (18.92 g, 80.20 mmol) was added to 1,4-dibromobenzene 27.37 g, 88.22 mmol), Pd (PPh 3) 4 (3.71 g, 3.21 mmol), K ₂ CO ₃ (33.25 g, 240.61 mmol), THF (280 ml) and water (140 ml) were added and the mixture was refluxed at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride 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 2-16 (19.22 g, yield: 70%).

2. Sub 2-33 Synthetic example

To the starting material 2,4-dibromopyrimidine (25 g, 103 mmol) was added 4,4,5,5-tetramethyl-2- (naphthalen-1-yl-d7) -1,3,2-dioxaborolane (29.54 g, _{mmol), Pd (PPh 3)} 4 (5 g, 4.33 mmol), K ₂ CO ₃ (43.21 g, 307.47 mmol), THF (360 ml) and water (180 ml) were added and the mixture was refluxed at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to give Sub 2-33 (20g yield: 70%).

3. Sub 2-43 Synthetic example

(1) Sub 2-I-43 synthesis

The starting material 2-amino-1-naphthoic acid (75 g, 401 mmol) was added to a round bottom flask with urea (168.7 g, 2808.75 mmol) and stirred at 160 ° C. After confirming the reaction by TLC, the reaction mixture was cooled to 100 ° 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 dried to obtain 64 g of Sub 2-I-43 (yield: 76%).

(2) Sub 2-II-43 Synthesis

After the dropwise addition was dissolved to ₃ (200ml) POCl in the Sub 2-I-50 (63.86 g, 300.94 mmol) obtained in the above Synthesis round bottom flask at room temperature, N, N -Diisopropylethylamine (97.23 g , 752.36 mmol) slowly , And stirred at 90 [deg.] 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 68 g of Sub 2-II-43 (yield: 90%).

(3) Sub 2-43 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-43 (67.47 g, 270.86 mmol) ₃ ) ₄ (12.52 g, 10.83 mmol), K 2 CO 3 (112.30 g, 812.57 mmol), THF (950ml), water (475ml) was added to and use the Sub 2-43 synthesis product was 45 g (yield: 58%) .

4. Sub 2-59 Synthetic example

The starting material 1,3-dibromobenzene (20.10 g, 85.45 mmol) was dissolved in THF (300 ml) in a round-bottomed flask and then 4,4,5,5-tetramethyl-2- (triphenylen- 3,2-dioxaborolane (33.32 g, 94.05 mmol), Pd (PPh 3) 4 (3.95 g, 3.42 mmol), K 2 CO 3 (35.45 g, 256.51 mmol), in water was added (150ml) and 90 ° C Lt; / RTI > 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 obtain 19 g of Sub 2-59 (yield: 60%).

5. Sub 2-61 Synthetic example

The starting material, 2,4-dichlorobenzo [4,5] thieno [ 3,2- d] pyrimidine 4,4,5,5-tetramethyl-2- (naphthalen-2-yl) a (32 g, 125.6 mmol) - 1,3,2-dioxaborolane (35 g, 138 mmol), Pd (PPh 3) 4 (5.80 g, 5.02 mmol), K 2 CO 3 (52 g, 376.41 mmol), THF (440ml), water (220ml) And the mixture is heated under reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 2-61 (19.58 g, yield: 45%).

6. Sub 2-83 Synthetic example

The starting material, 1-bromo-3-fluorobenzene ( 45.3 g, 259.09 mmol) was dissolved in toluene (1360ml) in a round bottom flask, aniline (26.54 g, 285.00 mmol ), Pd 2 (dba) 3 (7.12 g, 7.77 mmol), 50% P ( t- Bu) ₃ (10.1 ml, 20.73 mmol) and NaO t- Bu (74.70 g, 777.28 mmol) 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 36.88 g (yield: 75%) of Sub 2-83.

7. Sub 2-85 Synthetic example

Aniline (19 g, 112 mmol), Pd ₂ (dba) ₃ (2.79 g, 3.00 mmol), 50% P ( t -butyldimethylsilane) were added to the starting material, 4-bromo-1,1'- 27.55 g (Yield: 85%) of Sub 2-85 was obtained by adding Bu ₃ (4.1 ml, 8.15 mmol), NaO t- Bu (29.25 g, 304.38 mmol) and toluene (710 ml) ).

8. Sub 2-92 Synthetic example

Aniline (16 g, 165.10 mmol), Pd ₂ (dba) ₃ (4.03 g, 4.34 mmol) and 50% P ( t- Bu) were added to the starting material, 2-bromodibenzo [b, d] thiophene 35 g (Yield: 85%) of Sub 2-92 was synthesized by using the Sub 2-92 synthesis method by adding ₃ (5.6 ml, 11.59 mmol), NaO t- Bu (41.76 g, 434.47 mmol) .

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.

III. Product synthesis

Sub 1 (1 eq.) Was dissolved in toluene in a round bottom flask and Sub 2 (1 eq.), Pd ₂ (dba) ₃ (0.03 eq.), (T- Bu 3P 0.0 > 100 C < / RTI > 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 subjected to silicagel column and recrystallization to obtain final product.

1. P1-1 Synthetic example

Sub 1-1 (11.6 g, 33.62 mmol), Sub 2-1 (5.27 g, 33.62 mmol), Pd ₂ (dba) ₃ (9 g, 0.1 mmol), (t-Bu) ₃ P (0.4 g, 0.002 mmol) and NaOt-Bu (9.61 g, 100 mmol) were dissolved in anhydrous toluene and refluxed for 3 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO _4. After filtration under reduced pressure, the organic solvent was concentrated, and the resulting product was purified by silicagel column and recrystallized to obtain 11.5 g of desired P 1-1. (Yield: 80%).

2. P1-6 Synthetic example

Sub 1-1 (10 g, 33.62 mmol), Sub 2-4 (9 g, 33.62 mmol), Pd ₂ (dba) ₃ (1 g, 0.1 mmol), (t-Bu) 3 P (0.4 g, 0.002 mmol), NaOt-Bu After dissolved (9.61 g, 100 mmol) in anhydrous Toluene, 1-1 in the same manner as the P 18.4 g of the desired P 1-6 was obtained. (Yield: 95%).

3. P1-7 Synthetic example

Sub 1-1 (10 g, 33.62 mmol), Sub 2-8 (10.5 g, 33.62 mmol), Pd ₂ (dba) ₃ (1 g, 0.1 mmol), (t-Bu) 3 P (0.4 g, 0.002 mmol), NaOt-Bu After dissolved (9.61 g, 100 mmol) in anhydrous Toluene, 1-1 in the same manner as the P 18.5 g of desired P 1-7 was obtained. (Yield: 92%)

4. P1-13 Synthetic example

Sub 1-1 (10 g, 33.62 mmol), Sub 2-29 (10 g, 33.62 mmol), Pd ₂ (dba) ₃ (1 g, 0.1 mmol), (t-Bu) 3 P (0.4 g, 0.002 mmol), after dissolved in the NaOt-Bu (11.2 g, 106 mmol) in anhydrous Toluene, 1-1 in the same manner as the P 18.3 g of desired P 1-13 was obtained. (Yield: 95%).

5. P1-80 Synthetic example

Sub 1-4 (24.5 g, 48.79 mmol), Sub 2-8 (15.1 g, 48.79 mmol), Pd ₂ (dba) ₃ (1.3 g, 0.1 mmol), (t-Bu) 3 P (0.5 g, 0.003 mmol), after dissolved in the NaOt-Bu (14 g, 146 mmol) in anhydrous Toluene, 1-1 in the same manner as the P 23.2 g of desired P 1-80 was obtained. (Yield: 65%).

6. P1-84 Synthetic example

Sub 1-30 (16.5 g, 34.8 mmol), Sub 2-77 (12 g, 34.8 mmol), Pd ₂ (dba) ₃ (1.1 g, 0.1 mmol), (t-Bu) 3 P (0.5 g, 0.003 mmol), NaOt-Bu (9 g, 94.42 mmol) and then I is dissolved in anhydrous Toluene, 1-1 in the same manner as the P 17.5 g of the desired P 1-84 was obtained. (Yield: 74%).

7. P1-86 Synthetic example

Sub 1-49 (7.7 g, 15.0 mmol), Sub 2-1 (2.3 g, 15.0 mmol), Pd ₂ (dba) ₃ A (0.6 g, 0.05 mmol), (t-Bu) 3 P (0.25 g, 0.0015 mmol), NaOt-Bu (5 g, 47 mmol) in the same manner as after dissolved in anhydrous Toluene, the P 1-1 8 g of desired P 1-86 was obtained. (Yield: 70%).

8. P1-27 Synthetic example

Sub 1-65 (7 g, 24.32 mmol), Sub 2-78 (9.3 g, 24.32 mmol), Pd ₂ (dba) ₃ (0.9 g, 0.09 mmol), (t-Bu) 3 P (0.3 g, 0.002 mmol), NaOt-Bu After dissolved (7 g, 72.96 mmol) in anhydrous Toluene, 1-1 in the same manner as the P 11.7 g of the desired P 1-27 was obtained. (Yield: 88%).

9. P1-29 Synthetic example

Sub 1-70 (5.1 g, 18.92 mmol), Sub 2-1 (2.9 g, 18.92 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.06 mmol), (t-Bu) 3 P (0.1 g, 0.001 mmol), NaOt-Bu (5.4 g, 56.76 mmol) and then I is dissolved in anhydrous Toluene, 1-1 in the same manner as the P 7.2 g of the desired P2-29 was obtained. (Yield: 90%).

10. P1-62 Synthetic example

Sub 1-114 (5.5 g, 18.42 mmol), Sub 2-41 (7.7 g, 18.42 mmol), Pd ₂ (dba) ₃ A (0.5 g, 0.05 mmol), (t-Bu) 3 P (0.1 g, 0.001 mmol), NaOt-Bu (4.8 g, 55.26 mmol) was dissolved in anhydrous Toluene as after, the same procedure as described in the P 1-1 11.1 g of the desired P 1-62 was obtained. (Yield: 88%).

The FD-MS values of the compounds P-1 to P-120 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

In the meantime, although an exemplary synthesis example of the present invention represented by the general formula (1) has been described above, all of them are exemplified by Buchwald-Hartwig cross coupling reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. 1999, 9, 2095.), Pd (II) -catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), Grignard reaction, Cyclic Dehydration reaction and PPh3-mediated reductive cyclization reaction (J. Org. , 70, 5014.), and it will be easily understood by those skilled in the art that the above reaction proceeds even when other substituents defined in the general formula (1) are bonded in addition to the substituent specified in the specific synthesis example.

Evaluation of manufacturing of organic electric device

[ Example  One] Green organic electroluminescent device (Phosphorescent host)

A 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, and then a hole transport layer was formed by vacuum deposition of NPD on the hole injection layer to a thickness of 60 nm.

Then, the compound P 1-1 of the present invention was doped with tris (2-phenylpyridine) -iridium (hereinafter referred to as " Ir (ppy) ₃ ") as a host material on a hole transport layer in a ratio of 95: To form a light emitting layer with a thickness of 30 nm.

Next, BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq ³ was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example  2] to [ Example  21] Green organic electroluminescent device

An organic electroluminescence 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 P1-1 as a host material in the light emitting layer.

[ Comparative Example  1] and [ Comparative Example  2]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 described in Table 4 was used instead of Compound P1-1 of the present invention as a host material in the light emitting layer.

A forward bias DC voltage was applied to the organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Examples 1 and 2 to measure electroluminescence (EL) characteristics with PR-650 of a photoresearch company And the T95 lifetime was measured by 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 4 below.

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 host material in the emissive layer is superior to the device using the comparative compounds 1 and 2 as the phosphorescent host material in the emissive layer. And it is confirmed that it is remarkably improved.

In other words, Comparative Example 2 using Comparative Compound 2 having the same skeleton as the compound of the present invention as a phosphorescent host showed better device results in terms of driving voltage, efficiency, and lifetime than Comparative Example 1 using CBP as a phosphorescent host, The device driving voltage, the luminous efficiency, and the lifetime of Examples 1 to 21 using the compound of the present invention in which the hetero atom was introduced into the skeleton were improved.

This is because the comparison of the compound of the present invention and the comparative compound 2 shows different results depending on the kind of atoms (S, O, N, C) introduced into the core even though the chemical structure has the same skeleton.

That is, the compounds of the present invention (Examples 1 to 21) have hetero atoms introduced at X ¹ and X ² positions to form Sp ³ Exhibits a higher thermal stability than comparative compound 2 made only of carbon.

Accordingly, the heat resistance against Joule's heat generated between the organic layer and the organic layer and between the organic layer and the metal electrode in the organic layer during the electroluminescence and the heat resistance under the high-temperature environment are increased, and the driving voltage and lifetime of the device can be improved Can be confirmed.

The increase in the luminous efficiency of the devices of Examples 1 to 21 of the present invention with respect to Comparative Example 2 can be explained by the ΔE _ST value, which is the energy difference value between the inter-molecular triplet (Host) have. The ΔE _ST value is a value less than 0.3 eV (see Chem comm J. name. 2016, p. 201) for easy reverse interstitial crossing (RISC) to convert all triplet excitons into mono-states in the molecule. 00, 1-4).

The compounds of Examples 15 to 17 of the present invention exhibit significantly lower ΔE _{ST values} than the compounds of Comparative Example 2 by referring to the following Table 5 showing ΔE _ST values of Comparative Example 2 and Examples 15 to 17, Value. Compared with the compound of Comparative Example 2, the compound of the present invention is more easily transferred in the molecule and has a thermally activated delayed fluorescence (TADF) effectively, and as the delayed fluorescence probability increases, It can be confirmed that the efficiency is improved.

On the other hand, the ΔE _ST value was only shown in Examples 15 to 17 having the same structure as in Comparative Example 2, but the above-mentioned effects can be attained by using the compounds of Examples 1 to 14 and Examples 18 to 21 As shown in FIG.

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.

Claims (13)

A compound represented by the following formula (1).

In the above formula (1)
1) Y is any one of C and Si,
2) X ¹ and X ² are each independently the same or different and are each selected from the group consisting of NL ¹ -Ar ¹ , S and O,
3) R ¹ to R ³ are each independently of the other hydrogen; heavy hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₂₄ heteroaryl group; A fluorenyl group; -L ' -N (R ' ^a ) (R ' ^b ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group of C ₆ to C ₃₀ , and a plurality of R ^{1 s} , R ^{2 s} or a plurality of R ^{3 s may} be bonded to each other to form an aromatic ring or a heteroaromatic ring,
4) m, n and s are each independently an integer of 0 to 4,
When m, n and s are 2 or more, R ¹ , R ² and R ³ are the same as or different from each other,
5) Ar ¹ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; -L ' -N (R ' ^a ) (R ' ^b ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms, a plurality of Ar ^{1 s} are the same or different from each other,
6) L 'and L ¹ are each independently the same or different and are a single bond, a C ₆ to C ₆₀ arylene group; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si, and P, and a plurality of L ^{1 s} are the same or different from each other,
7) R ^a and R ^b are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And an arylene group having ₆ to ₆₀ carbon atoms.
The aryl group, the fluorenyl group, the arylene group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group may be respectively 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; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group having ₇ to ₂₀ carbon atoms and an arylalkenyl group having ₈ to ₂₀ carbon atoms and these substituents may be further bonded to each other to form a ring, Refers to a fused ring consisting of an aliphatic ring of C ₃ to C ₆₀ or a C ₆ to C ₆₀ aromatic ring or a C ₂ to C ₆₀ hetero ring or a combination thereof and includes saturated or unsaturated rings. The method according to claim 1,
Wherein the formula (1) is represented by the following formulas (1) -1 to (1) -6.

Y, R ¹ to R ³ , m, n, s, Ar ¹ and L ¹ described in the above Chemical Formulas (1) -1 to (1) -6 are Y, R ¹ to R ³ , m, n, s, Ar < ¹ > And L < ¹ >. The method according to claim 1,
Wherein the formula (1) is represented by the following formula (2).

In the above formula (2)
1) Y, X ¹ , X ² , R ³ and n are the same as Y, X ¹ , X ² , R ³ and n defined in the above formula (1)
2) R ⁴ is hydrogen; heavy hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₂₄ heteroaryl group; A fluorenyl group; -L ' -N (R ' ^a ) (R ' ^b ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group of C ₆ to C ₃₀ , and a plurality of R ^{4 s may} be bonded to each other to form an aromatic ring or a heteroaromatic ring,
3) o is an integer from 0 to 8,
When o is 2 or more, plural R ⁴ are the same or different from each other. The method according to claim 1,
Wherein R ¹ to R ³ in the above formula (1) are C ₂ to C ₂₄ heteroaryl groups, 5. The method of claim 4,
Wherein R ¹ to R ³ are compounds represented by the following general formula (3).

In Formula 3,
1) V is selected from the group consisting of NL ² -Ar ² , O and S,
2) Z ¹ to Z ⁸ are each independently selected from the group consisting of C (R '), C and N,
3) L ² is a single bond, an arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;
4) R 'is hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₂₄ heteroaryl group; A fluorenyl group; -L'-N (R ^e ) (R ^f ); A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; And an aryloxy group having ₆ to ₃₀ carbon atoms,
5) R ^e and R ^f are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₂ to C ₂₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And an arylene group having ₆ to ₆₀ carbon atoms. The method according to claim 1,
Wherein the compound represented by the formula (1) is one of the following formulas.

A first electrode;
A second electrode; And
And an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a compound according to any one of claims 1 to 6. 8. The method of claim 7,
Wherein the organic material layer is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and an electron injecting layer, and the organic material layer comprises one or more of the above compounds. . 9. The method of claim 8,
Wherein the organic material layer is a host material of a hole transporting layer or a light emitting layer. 8. The method of claim 7,
Further comprising a light-efficiency-improvement layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the one side of the second electrode opposite to the organic material layer. 8. The method of claim 7,
Wherein the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and 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. 13. The method of claim 12,
Wherein the organic electroluminescent 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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