KR102270525B1 - Organic electronic element using a compound for organic electronic element, and an electronic device thereof - Google Patents

Abstract

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

Description

An organic electric device using a compound for an organic electric device and an electronic device therefor {ORGANIC ELECTRONIC ELEMENT USING A COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, AND AN ELECTRONIC DEVICE THEREOF}

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

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

Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these problems of efficiency and lifespan must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and if the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage is decreased, crystallization of organic materials due to Joule heating generated during driving decreases, resulting in a decrease in the driving voltage. It shows a tendency to increase the lifespan.

However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time.

In addition, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and each light emitting layer (R, G, B) supports different light emission. It is time for layer development.

In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.

However, most of the materials used for the hole transport layer have a low T1 value because they must have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. This results in light emission at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened. Therefore, it is urgently required to develop a light emitting auxiliary layer having a high T1 value and having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer.

On the other hand, while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of the organic electric device, stable characteristics against Joule heating generated during device driving, that is, high glass transition There is a need for development of a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has a characteristic of lowering the uniformity of the thin film surface when driving the device, which is reported to have a significant effect on the device lifespan. In addition, OLED devices are mainly formed by a deposition method, and it is necessary to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance.

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

In addition, as a material of the light emitting auxiliary layer, a 2-fluorene compound is widely used for reasons of excellent charge mobility and thermal stability and excellent uniformity when forming a thin film, but the 2-fluorene compound has a small band gap and a T1 value. Since there is this low disadvantage, it is necessary to develop a material that can compensate for this.

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

In one aspect, the present invention provides an organic electric device and an electronic device using a compound represented by the following formula.

a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer includes a hole transport layer, a light emitting auxiliary layer and a light emitting layer, and the light emitting auxiliary layer includes the hole transport layer and the light emitting layer Formed between and including a compound represented by the following formula (1), the light emitting layer includes a host and a dopant, the host is an organic containing at least one of the compounds represented by the following formulas (2) to (6) provide electrical devices.

Formula (1)

Formula (2) Formula (3)

Chemical formula (4) Chemical formula (5) Chemical formula (6)

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

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

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

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

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

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

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

The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has a single bond having 1 to 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo means a radical of saturated aliphatic functional groups including alkyl groups, cycloalkyl-substituted alkyl groups.

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

As used herein, the term "heteroalkyl group" means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.

The term "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise specified, has a double or triple bond of 2 to 60 carbon atoms, respectively, and includes a straight or branched chain group, and is limited thereto it is not

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

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

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 has a carbon number of, but is not limited thereto.

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

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by a neighboring substituent joining or participating in a reaction. For example, the aryl group may be a phenyl group or a biphenyl group.

The prefix “aryl” or “ar” refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the number of carbon atoms described herein.

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

As used herein, the term "heteroalkyl" refers to an alkyl containing one or more heteroatoms, unless otherwise specified. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl group or arylene group having 2 to 60 carbon atoms each containing one or more heteroatoms, unless otherwise specified, No, it includes at least one of a single ring and a multiple ring, and may be formed by combining adjacent functional groups.

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes a heteroaliphatic ring and a heterocyclic group. aromatic rings. It may be formed by combining adjacent functional groups.

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

In addition, the "heterocyclic group" may include a ring including _{SO 2 instead of carbon forming the ring.} For example, "heterocyclic group" includes the following compounds.

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

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

Other heterocompounds or heteroradicals other than the above-mentioned heterocompounds include one or more heteroatoms, but are not limited thereto.

Unless otherwise specified, the term "carbonyl" used in the present invention is represented by -COR', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. of a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, as used herein, the term "ether" is represented by -RO-R', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 6 to 30 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.

In addition, unless otherwise explicitly stated, in the term "substituted or unsubstituted" used in the present invention, "substitution" means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ 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 It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ ~ C _{20 heterocyclic group, but is not limited to these substituents.}

In addition, unless there is an explicit explanation, the formula used in the present invention is the same as the definition of the substituent by the exponential definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3 Each is bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is omitted.

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

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

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

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on 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 layer is a host or dopant of the hole injection layer 130 , the hole transport layer 140 , the electron transport layer 160 , the electron injection layer 170 , the light emitting layer 150 or the light efficiency improvement layer. material could be used. Preferably, the compound of the present invention may be used as the emission layer 150 or the emission auxiliary layer 151 .

On the other hand, even with the same core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of the sub-substituents coupled thereto are also very In particular, when the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

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

Therefore, in the present invention, the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial property), by forming the light emitting layer or the light emission auxiliary layer using the compounds represented by Formulas (1) to (6) etc.) can be optimized to improve the lifespan and efficiency of the organic electric device at the same time.

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

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

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

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

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

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/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 control, a navigation system, a game machine, various TVs, and various computers.

Hereinafter, an organic electric device according to an aspect of the present invention will be described.

According to one embodiment of the present invention, the first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode,

The organic material layer includes a hole transport layer, a light emitting auxiliary layer and a light emitting layer, the light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer and contains a compound represented by the following formula (1), The light emitting layer is a host and a dopant Including, wherein the host provides an organic electric device comprising at least one of the compounds represented by the following formulas (2) to (6).

Formula (1)

Formula (2) Formula (3)

Chemical formula (4) Chemical formula (5) Chemical formula (6)

In the above formula (1),

m, n and o are each independently an integer from 0 to 4,

R ^{1 To} R ^{3 When} m, n, and o are 2 or more, each is the same as or different from each other as a plurality, and each independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^a -N(R ^a )(R ^b ); or (wherein L ^a is a single bond; C ₆ to C ₆₀ arylene group; fluorenylene group; C ₃ to C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring, and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from the group consisting of, wherein R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; a fluorenyl group; a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group And O, N, S, Si, and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of), or a plurality of R ^{1 To} R ^{3 Are} each bonded to these can form an aromatic ring with carbon bonded to

Ar ^{1 To} Ar ^{3 Are} each independently a C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; selected from the group consisting of a hydroxyl group and -L ^b -N(R ^c )(R ^{d ); wherein L b} , R ^c and R ^d are the same as the definitions of ^{L a} , R ^a and R ^{b , respectively.} , or Ar ¹ and Ar ² may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded,

L ¹ is C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And C ₆ ~ C ₆₀ A divalent functional group consisting of a combination _{of an arylene group and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from

L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; And C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring is selected from the group consisting of,

In the above formulas (2) and (3),

a and b are each an integer from 0 to 1, a+b is 1 or more,

X and Y are each independently a single bond; S; O; NR′;CR′R″; and SiR′R″; wherein R′ and R″ are each independently hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and _{A C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₁ ~ C _{50 It} is selected from the group consisting of an alkyl group,

p is an integer from 0 to 2, q and r are integers from 0 to 4,

R ^{4 To} R ^{6 When} p is 2, q, or r is an integer of 2 to 4, each of which is the same as or different from each other and is independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; And ^{-L c -N (R e) (} R f); or selected from the group consisting of (where as defined in the L ^c, R ^e and R ^f are the L ^a, R ^a and R ^b, respectively), Or a plurality of R ⁴ to R ⁶ may be bonded to each other to form an aromatic ring together with the carbon bonded thereto,

Ar ⁴ and Ar ⁵ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^d -N(R ^g )(R ^h ); wherein L ^d , R ^g and R ^h are the same as defined above for L ^a , R ^a and R ^{b , respectively;}

L ³ and L ⁴ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; and C ₁ ~ C ₆₀ A divalent aliphatic hydrocarbon; selected from the group consisting of,

Z ¹ to Z ¹⁶ are each independently CR ⁷ ; or N; with the proviso ^{that at least one of Z 5} to Z ⁸ and at least one of Z ⁹ to Z ¹² is CR ⁷ , wherein the C ^{of CR 7} in one of ^{Z 5} to Z ⁸ and Z ⁹ to Z ¹² is ^{bonded to L 4} instead of bonding to ^{R 7} ),

wherein R ⁷ is hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; fluorenyl group; and -L ^e -N(R ⁱ )(R ^j ); wherein L ^e , R ⁱ and R ^j are the same as the definitions of ^{L a} , R ^a and R ^{b , respectively.} or Z ¹ to Z ¹⁶ , when each of the neighboring Z is CR ⁷ , the neighboring groups and each other can be combined to form an aromatic ring with the carbon bonded to them,

W is NAr ⁶ ; O; And S; is selected from the group consisting of,

Here, Ar ⁶ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₁ ~ C ₅₀ Alkyl group; is selected from the group consisting of,

In the above formulas (4) to (6),

R ⁸ to R ³⁹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^f -N(R ^k )(R ¹ ); wherein L ^f , R ^k and R ¹ have the same definitions as ^{L a} , R ^a and R ^{b , respectively.} or i) R ⁸ and R ⁹ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , R ¹⁷ and R ¹⁸ , R ¹⁸ and R ¹⁹ or R ¹⁹ and R ⁸ are bonded to each other to form a ring, or ii) R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ , R ²³ and R ²⁴ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ or R ²⁹ and R ²⁰ are bonded to each other to form a ring or iii) R ³⁰ and R ³¹ , R ³¹ and R ³² , R ³² and R ³³ , R ³³ and R ³⁴ , R ³⁴ and R ³⁵ , R ³⁵ and R ³⁶ , R ³⁶ and R ³⁷ , R ³⁷ and R ³⁸ , R ³⁸ and R ³⁹ or R ³⁹ and R ³⁰ may be bonded to each other to form a ring,

wherein the aryl group, fluorenyl group, heterocyclic group, fused ring group, aliphatic hydrocarbon group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, and fluorenylene group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L ^g -N(R ^m )(R ⁿ ), wherein L ^g , R ^m and R ⁿ are the same as defined above for L ^a , R ^a and R ^{b , respectively;} C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ An alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ to C ₂₀ aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; It may be further substituted with one or more substituents selected from the group consisting of a C ₇ ~ C ₂₀ arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group, and these substituents may be bonded to each other to form a ring.}

In another embodiment of the present invention, the light emitting auxiliary layer contains the compound represented by the formula (1), and the host of the light emitting layer contains two different compounds from the compounds represented by the formulas (2) to (6). An organic electric device containing a mixed compound is provided.

In another embodiment of the present invention, L ¹ in Formula (1) may be one of those represented by the following Formula.

In the above formula,

Q ¹ is CR ⁴⁰ ; or N;

Q ² is C(R ⁴¹ )(R ⁴² ); NR ⁴³ ; S; Or O; is selected from the group consisting of,

where R ⁴⁰ , Ar ⁷ and Ar ⁸ are, independently of each other, hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And a fluorenyl group; is selected from the group consisting of,

R ^{41 To} R ⁴³ are each independently, C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; and a fluorenyl group; or R ⁴¹ and R ⁴² may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded.

In another embodiment of the present invention, the compound represented by the formula (1) may be one of those represented by the following formulas (7) to (10).

Chemical formula (7) Chemical formula (8) Chemical formula (9) Chemical formula (10)

In Formulas (7) to (10), L ¹ , L ² , Ar ¹ ~Ar ³ , R ² , R ³ , n and o are each L ¹ , L ² , Ar ¹ ~ Same as the definitions of Ar ³ , R ² , R ^{3 , n and o.}

In one example, in Formulas (7) to (10), L ¹ is a C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And C ₆ ~ C ₆₀ A divalent functional group consisting of a combination _{of an arylene group and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; can be selected from

In another embodiment of the present invention, the compound represented by Formula (1) may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula (2) may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula (3) may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula (4) may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula (5) may be one of the following compounds.

In another embodiment of the present invention, the compound represented by Formula (6) may be one of the following compounds.

In another embodiment of the present invention, a light efficiency improvement layer formed on at least one of one side opposite to the organic material layer on one side of the first electrode or one side opposite to the organic material layer among one side of the second electrode An organic electric device is provided.

In another embodiment of the present invention, 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. do.

In another embodiment of the present invention, the first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer includes a hole transport layer, a light emitting auxiliary layer and a light emitting layer, and the light emitting auxiliary layer includes the hole transport layer and the light emitting layer a display device including an organic electric device positioned between and including a compound represented by Formula (1), wherein the light emitting layer includes at least one of the compounds represented by Formulas (2) to (6); and a controller for driving the display device.

In another embodiment of the present invention, the organic electric device according to the present invention is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organophotoreceptor (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting. can be one

Hereinafter, the synthesis examples of the compounds represented by the formulas (1) to (6) contained in the organic electric device of the present invention and the preparation examples of the organic electric device of the present invention will be described in detail with reference to Examples, The invention is not limited to the following examples.

Synthesis example

The synthesis of the compound was carried out in the following way.

I. Synthesis of formula (1)

Illustratively, the compound (1) (Final Product) according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in the following <Scheme 1>.

<Scheme 1>

(Hal ³ = Br or Cl, R ¹ to R ³ , L ¹ , L ² , Ar ¹ to Ar ³ , m, n and o are the same as defined in Formula (1))

One. Sub Synthesis example of 1

Sub 1 of <Scheme 1> may be synthesized by the reaction route of <Scheme 2> below, but is not limited thereto.

<Scheme 2>

(Hal ¹ ~Hal ² = I or Br, Hal ³ = Br or Cl, and R1, R2, L1, m and n are the same as those defined in Formula (1) above)

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

(One) Sub 1-4 Synthesis example

<Scheme 3>

intermediate Sub 1-I-4 synthesis

After dissolving the starting material phenylboronic acid (16.52g, 135.5mmol) in THF in a round-bottom flask, 1-bromo-2-nitrobenzene (32.84g, 162.6mmol), Pd(PPh ₃ ) ₄ (7.83g, 6.8mmol) , K ₂ CO ₃ (56.18 g, 406.5 mmol), water were added and stirred at 80 °C. Upon completion of the reaction _{, the mixture was extracted with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 24.83 g (yield: 92%) of the product.

intermediate Sub One- II -4 synthesis

Sub 1-I-4 (24.83 g, 124.6 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene in a round-bottom flask, triphenylphosphine (81.73 g, 311.6 mmol) was added and stirred at 200 °C. When the reaction was completed, o- dichlorobenzene was removed through distillation and extracted with _{CH 2} Cl _{2 and water.} The organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized by silicagel column to obtain 16.46 g (yield: 79%) of the product.

Sub 1-4 synthesis

After dissolving Sub 1-II-4 (16.46 g, 98.4 mmol) obtained in the above synthesis with toluene in a round-bottom flask, 4-bromo-4'-iodo-1,1'-biphenyl (70.68 g, 196.9 mmol), Pd ₂ (dba) ₃ (2.7g, 3mmol), 50% P( t- Bu) ₃ (3.8ml, 7.9mmol), NaO t- Bu (28.38g, 295.3mmol) were added and stirred at 70°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 26.27 g (yield: 67%) of the product.

(2) Sub 1-5 Synthesis example

<Scheme 4>

intermediate Sub 1-I-5 synthesis

3-bromo-4-nitro-1,1'-biphenyl (28.36g, 102mmol), Pd(PPh ₃ ) ₄ (4.91g, 4.2mmol), K ₂ CO in phenylboronic acid (10.36 g, 85 mmol) as a starting material ₃ (35.23g, 254.9mmol), THF, and water were used for the above Sub 1-I-4 synthesis to obtain 21.05 g (yield: 90%) of the product.

intermediate Sub One- II -5 synthesis

Sub 1-I-5 (21.05 g, 76.5 mmol) obtained in the above synthesis was mixed with triphenylphosphine (50.14 g, 191.2 mmol) and o- dichlorobenzene using the above Sub 1-II-4 synthesis method to 13.95 g (yield: 75%) ) was obtained.

Sub 1-5 Synthesis

_{4-bromo-4'-iodo-1,1'-biphenyl (41.17g, 114.7mmol), Pd 2} (dba) ₃ (1.58g) to Sub 1-II-5 (13.95g, 57.3mmol) obtained in the above synthesis , 1.7mmol), 50% P( t- Bu) ₃ (2.2ml, 4.6mmol), NaO t- Bu (16.53g, 172mmol), and toluene using the above Sub 1-4 synthesis method to synthesize product 17.95g (yield: 66%) was obtained.

(3) Sub 1-24 Synthesis example

<Scheme 5>

Sub 1-II-4 (5.72g, 34.2mmol) obtained in the above synthesis to 3,7-dibromodibenzo[ b , d ]thiophene (23.4g, 68.4mmol), Pd ₂ (dba) ₃ (0.94g, 1mmol), 50% P( t -Bu) ₃ (1.3ml, 2.7mmol), NaO t -Bu (9.86g, 102.6mmol), and toluene were prepared using the above Sub 1-4 synthesis method to obtain 8.94g (yield: 61%) of the product. got it

On the other hand, examples of Sub 1 are as follows, but are not limited thereto, and their FD-MS is shown in [Table 1] below.

[Table 1]

2. Sub 2 synthesis

Sub 2 of <Scheme 1> can be synthesized by the reaction route of the following <Scheme 6>.

<Scheme 6>

(Hal ⁴ , Hal ⁶ = Br or Cl, Hal ⁵ = I or Br, and R ³ , o, Ar ¹ to Ar ³ and L ² are the same as defined in Formula (1) above)

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

(One) Sub 2-1 Synthesis example

<Scheme 7>

intermediate Sub 2-I-1 synthesis

The starting material, methyl 4-chloro-2-hydroxybenzoate (51.27g, 274.8mmol) _{was dissolved in a round bottom flask with CH 2} Cl ₂ , and triethylamine (57.9ml, 412.2mmol) was added thereto. The temperature of the reactant was lowered to -78°C, trifluoromethanesulfonic anhydride (50.8ml, 302.3mmol) was slowly added dropwise, and then the temperature was slowly raised to room temperature and stirred. Upon completion of the reaction, the reaction was _{extracted with CH 2} Cl ₂ and water, and the organic layer _{was dried over MgSO 4} and concentrated. The resulting compound was again dissolved in diethyl ether, filtered through silicagel to remove the dark color, and concentrated and vacuum dried. 84.93 g (yield: 97%) of the product was obtained as a colorless oil.

intermediate Sub 2- II -1 synthesis

After dissolving Sub 2-I-1 (84.93g, 266.5mmol) obtained in the above synthesis with DMF in a round-bottom flask, phenylboronic acid (32.5g, 266.5mmol), Pd(PPh ₃ ) ₄ (6.16g, 5.3mmol) , K ₂ CO ₃ (55.26 g, 399.8 mmol) was added and stirred at 110 °C. Upon completion of the reaction, the mixture was extracted with diethyl ether and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 53.92 g (yield: 82%) of the product as a colorless oil.

intermediate Sub 2- IV -1 synthesis

Sub 2-II-1 (33.19g, 134.5mmol) obtained in the above synthesis was dissolved in THF in a round bottom flask, methylmagnesium chloride 3.0M in THF (179.4ml, 538.2mmol) was slowly added dropwise, followed by stirring at room temperature. . Upon completion of the reaction, the mixture was extracted with diethyl ether and water, and the organic layer _{was dried over MgSO 4} and concentrated to obtain a product Sub 2-III-1. This Sub 2-III-1 was dissolved in an acetic acid solution (500ml), HCl (10ml) was added, and refluxed. When the reaction was completed, water was added and the resulting solid was filtered under reduced pressure after stirring, and then washed with water and methanol to obtain 25.85 g of the product as a white powder (yield: 84% over two steps).

Sub 2-1 Synthesis

After dissolving Sub 2-IV-1 (4.01 g, 17.5 mmol) obtained in the above synthesis with toluene in a round bottom flask, aniline (3.27 g, 35.1 mmol), Pd ₂ (dba) ₃ (0.48 g, 0.5 mmol), 50% P( t- Bu) ₃ (0.7ml, 1.4mmol) and NaO t- Bu (5.06g, 52.6mmol) were added and stirred at 40°C. Upon completion of the reaction _{, the mixture was extracted with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 4.25 g (yield: 85%) of the product.

(2) Sub 2-8 Synthesis example

<Scheme 8>

To Sub 2-IV-1 (5.82 g, 25.4 mmol) obtained in the above synthesis, isoquinolin-4-amine (7.34 g, 50.9 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.8 mmol), 50% P ( t -Bu) ₃ (1ml, 2mmol), NaO t -Bu (7.34g, 76.3mmol), and toluene were obtained by using the Sub 2-1 synthesis method above to obtain 6.33g (yield: 74%) of the product.

(3) Sub 2-13 Synthesis example

<Scheme 9>

_{[1,1'-biphenyl]-4-amine (12.46g, 73.6mmol), Pd 2} (dba) ₃ (1.01g, 1.1mmol) to Sub 2-IV-1 (8.42g, 36.8mmol) obtained in the above synthesis ), 50% P( t- Bu) ₃ ( 1.4ml, 2.9mmol), NaO t- Bu (10.61g, 110.4mmol), and toluene using the above Sub 2-1 synthesis method to synthesize 10.91g of the product (yield: 82%) ) was obtained.

(4) Sub 2-30 Synthesis example

<Scheme 10>

intermediate Sub 2-V-30 Synthesis

After dissolving Sub 2-IV-1 (6.98 g, 30.5 mmol) obtained in the above synthesis in DMF in a round-bottom flask, Bis (pinacolato) diboron (8.52 g, 33.6 mmol), Pd (dppf) Cl ₂ (0.75 g, 0.9 mmol), KOAc (8.99 g, 91.6 mmol) was added and stirred at 90 °C. When the reaction was completed, DMF was removed through distillation, and the 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 recrystallized by silicagel column to obtain 7.92 g (yield: 81%) of the product.

intermediate Sub 2- VI -30 Synthesis

After dissolving Sub 2-V-30 (7.92 g, 24.7 mmol) obtained in the above synthesis in THF in a round-bottom flask, 1-bromo-4-iodobenzene (10.5 g, 37.1 mmol), Pd(PPh ₃ ) ₄ (1.43) g, 1.2 mmol), K ₂ CO ₃ (10.25 g, 74.2 mmol), and water were added and stirred at 80° C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 6.56 g (yield: 76%) of the product.

Sub 2-30 Synthesis

_{[1,1'-biphenyl]-4-amine (6.36g, 37.6mmol), Pd 2} (dba) ₃ (0.52g, 0.6mmol) to Sub 2-VI-30 (6.56g, 18.8mmol) obtained in the above synthesis ), 50% P( t- Bu) ₃ ( 0.7ml, 1.5mmol), NaO t- Bu (5.42g, 56.3mmol), and toluene using the above Sub 2-1 synthesis method to synthesize 6.82g (yield: 83%) ) was obtained.

(5) Sub 2-42 Synthesis example

<Scheme 11>

intermediate Sub 2- IV -42 synthesis

To Sub 2-II-1 (15.02 g, 60.9 mmol) obtained in the above synthesis, phenylmagnesium chloride 2.0M in THF (121.8 ml, 243.5 mmol), THF was added to the product Sub 2-III using the Sub 2-III-1 synthesis method. -42 was obtained, and acetic acid solution (250ml) and HCl (5ml) were added to this Sub 2-III-42 using the above Sub 2-IV-1 synthesis method to obtain 17.4 g (yield: 81% over two steps) of the product. .

Sub 2-42 Synthesis

_{[1,1'-biphenyl]-4-amine (9.64 g, 57 mmol), Pd 2} (dba) ₃ (0.78 g, 0.9 mmol) in Sub 2-IV-42 (10.05 g, 28.5 mmol) obtained in the above synthesis , 50% P( t -Bu) ₃ (1.1ml, 2.3mmol), NaO t -Bu (8.21g, 85.4mmol), and toluene using the above Sub 2-1 synthesis method, 10.7g of the product (Yield: 78%) got

On the other hand, examples of Sub 2 are as follows, but are not limited thereto, and their FD-MS is shown in [Table 2] below.

[Table 2]

4. Final product ( Final Product ) synthesis

After dissolving Sub 2 (1 equivalent) with toluene in a round bottom flask, Sub 1 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO t -Bu (3 eq) was added and stirred at 100°C. Upon completion of the reaction, _{extraction was performed with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain a final product.

(One) Product 1-15 Synthesis

<Scheme 12>

After dissolving Sub 2-13 (5.48 g, 15.2 mmol) obtained in the above synthesis with toluene in a round-bottom flask, Sub 1-4 (6.64 g, 16.7 mmol), Pd ₂ (dba) ₃ (0.42 g, 0.5 mmol) , 50% P( t- Bu) ₃ (0.6ml, 1.2mmol), NaO t- Bu (4.37g, 45.5mmol) were added and stirred at 100°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 8.03 g (yield: 78%) of the product.

(2) Product 1-23 Synthesis

<Scheme 13>

Sub 2-8 (6.19g, 18.4mmol) obtained in the above synthesis, Sub 1-4 (8.06g, 20.2mmol), Pd ₂ (dba) ₃ (0.51g, 0.6mmol), 50% P( t- Bu) ₃ (0.7ml, 1.5mmol), NaO t -Bu (5.31g, 55.2mmol), and toluene were obtained by using the above Product 1-15 synthesis method to obtain 8.78g (yield: 73%) of the product.

(3) Product 1-27 Synthesis

<Scheme 14>

_{Sub 1-5 (7.53 g, 15.9 mmol), Pd 2} (dba) ₃ (0.4 g, 0.4 mmol), 50% P ( t -Bu) to Sub 2-1 (4.12 g, 14.4 mmol) obtained in the above synthesis ₃ (0.6ml, 1.2mmol), NaO t -Bu (4.16g, 43.3mmol), and toluene were obtained by using the above Product 1-15 synthesis method to obtain 7.94g (yield: 81%) of the product.

(4) Product 1-36 Synthesis

<Scheme 15>

To Sub 2-42 (6.32 g, 13 mmol) obtained in the above synthesis, Sub 1-5 (6.79 g, 14.3 mmol), Pd ₂ (dba) ₃ (0.36 g, 0.4 mmol), 50% P( t- Bu) ₃ (0.5ml, 1mmol), NaO t- Bu (3.75g, 39mmol), and toluene were obtained by using the above Product 1-15 synthesis method to obtain 8.47g (yield: 74%) of the product.

(5) Product 1-55 Synthesis

<Scheme 16>

Sub 2-13 (5.26 g, 14.6 mmol) obtained in the above synthesis, Sub 1-24 (6.86 g, 16 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), 50% P( t- Bu) ₃ (0.6ml, 1.2mmol), NaO t -Bu (4.2g, 43.7mmol), and toluene were obtained by using the above Product 1-15 synthesis method to obtain 7.94g (yield: 77%) of the product.

(6) Product 1-67 Synthesis

<Scheme 17>

Sub 2-30 (5.93 g, 13.6 mmol) obtained in the above synthesis, Sub 1-4 (5.94 g, 14.9 mmol), Pd ₂ (dba) ₃ (0.37 g, 0.4 mmol), 50% P( t- Bu) ₃ (0.5ml, 1.1mmol), NaO t -Bu (3.91g, 40.7mmol), and toluene were obtained by using the above Product 1-15 synthesis method to obtain 8.08g (yield: 79%) of the product.

Meanwhile, FD-MS values of compounds 1-1 to 1-95 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

II . Synthesis of formula (2)

Synthesis of final products 2-9

An example of the synthesis of Product 2-9 in Formula (2) according to the present invention is shown in <Scheme 18>.

<Scheme 18>

Intermediate M 2-I-9 synthesis

After dissolving the starting material dibenzo[ b , d ]thiophen-4-ylboronic acid (9.05g, 39.7mmol) in THF in a round-bottom flask, 1-bromo-2-nitrobenzene (9.62g, 47.6mmol), Pd(PPh) ₃ ) ₄ ( _{2.29g, 2mmol), K 2} CO ₃ (16.45g, 119mmol), water were added and stirred at 80°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 10.78 g (yield: 89%) of the product.

Intermediate M 2- II -9 synthesis

M 2-I-9 (10.78 g, 35.3 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene in a round-bottom flask, triphenylphosphine (23.15 g, 88.3 mmol) was added and stirred at 200 °C. When the reaction was completed, o- dichlorobenzene was removed through distillation and extracted with _{CH 2} Cl _{2 and water.} The organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 7.14 g (yield: 74%) of the product.

Sub 2-9 Synthesis

After dissolving M 2-II-9 (7.14 g, 26.1 mmol) obtained in the above synthesis with toluene in a round-bottom flask, 5-chloro-2,4-diphenylpyrimidine (7.66 g, 28.7 mmol), Pd ₂ (dba) ₃ (0.72g, 0.8mmol), 50% P( t- Bu) ₃ (1ml, 2.1mmol), NaO t- Bu (7.53g, 78.4mmol) were added and stirred at 100°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 8.29 g (yield: 63%) of the product.

On the other hand, FD-MS values of compounds 2-1 to 2-32 of the present invention prepared according to the above synthesis examples are shown in [Table 4] below.

[Table 4]

III . Synthesis of formula (3)

Synthesis of final product 3-1

An example of the synthesis of Product 3-1 in Formula (3) according to the present invention is shown in <Scheme 19>.

<Scheme 19>

Intermediate M 3-I-1 synthesis

Starting material (9-phenyl-9 H -carbazol -3-yl) boronic acid (7.32g, 25.5mmol) was dissolved in THF to a round bottom flask, 3-bromo-9 H -carbazole (7.53g, 30.6mmol ), Pd(PPh ₃ ) ₄ (1.47 g, 1.3 mmol), K ₂ CO ₃ (10.57 g, 76.5 mmol), and water were added and stirred at 80°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 8.85 g (yield: 85%) of the product.

Sub 3-1 Synthesis

After dissolving M 3-I-1 (8.85 g, 21.7 mmol) obtained in the above synthesis with toluene in a round-bottom flask, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.38 g, 23.8 mmol) ), Pd ₂ (dba) ₃ (0.6 g, 0.6 mmol), 50% P( t -Bu) ₃ (0.8 ml, 1.7 mmol), NaO t -Bu (6.25 g, 65 mmol) were added and stirred at 100° C. did. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 9.56 g (yield: 69%) of the product.

Meanwhile, FD-MS values of compounds 3-1 to 3-24 of the present invention prepared according to the above synthesis examples are shown in Table 5 below.

[Table 5]

IV . Synthesis of formula (4)

Synthesis of final products 4-6

An example of the synthesis of Product 4-6 in Formula (4) according to the present invention is shown in <Scheme 20>.

<Scheme 20>

After dissolving the starting material triphenylen-2-ylboronic acid (5.44 g, 20 mmol) in THF in a round-bottom flask, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.76 g, 20mmol), Pd(PPh ₃ ) ₄ (0.69g, 0.6mmol), K ₂ CO ₃ (8.29g, 60mmol), and water were added and stirred at 80°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 7.5 g (yield: 70%) of the product.

Meanwhile, the FD-MS values of the compounds 4-1 to 4-20 of the present invention prepared according to the above synthesis examples are shown in Table 6 below.

[Table 6]

V. Synthesis of formula (5) and formula (6)

1. Synthesis of final products 5-10

A synthesis example of Product 5-10 in Chemical Formula (5) according to the present invention is shown in <Scheme 21>.

<Scheme 21>

After dissolving the starting material 9,10-dibromoanthracene (6.71 g, 20 mmol) in THF in a round-bottom flask, naphthalen-2-ylboronic acid (7.56 g, 43.9 mmol), Pd(PPh ₃ ) ₄ (0.69 g, 0.6 mmol) ), K ₂ CO ₃ (8.28 g, 59.9 mmol), and water were added and stirred at 80° C. After completion of the reaction, the reaction was _{extracted with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 6.71 g (yield: 78%) of the product.

2. Synthesis of final products 6-5

An example of the synthesis of Product 6-5 in Chemical Formula 6 according to the present invention is shown in <Scheme 22>.

<Scheme 22>

After dissolving the starting material 1,6-dibromopyrene (7.69g, 21.4mmol) with Toluene in a round bottom flask, phenylboronic acid (5.73g, 47mmol), Pd(PPh ₃ ) ₄ (0.74g, 0.6mmol), K ₂ CO ₃ (8.86 g, 64.1 mmol), water was added and stirred at 100 °C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 7.91 g (yield: 86%) of the product.

3. Synthesis of final products 6-14

An example of the synthesis of Product 6-14 in Formula (6) according to the present invention is shown in <Scheme 23>.

<Scheme 23>

After dissolving the starting material 1,6-dibromopyrene (7.27g, 20.2mmol) with toluene in a round bottom flask, diphenylamine (8.2g, 48.5mmol), Pd ₂ (dba) ₃ (0.55g, 0.6mmol), 50% P( t -Bu) ₃ (0.8ml, 1.6mmol) and NaO t -Bu (5.82g, 60.6mmol) were added and stirred at 100°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 8.13 g (yield: 75%) of the product.

Meanwhile, FD-MS values of compounds 5-1 to 5-24 and 6-1 to 6-16 of the present invention prepared according to the above synthesis examples are shown in Table 7 below.

[Table 7]

Meanwhile, in the above, exemplary synthesis examples of the present invention represented by Chemical Formulas (1) to (6) have been described, but these are all Suzuki cross-coupling reaction, PPh _3- mediated reductive cyclization reaction ( J. Org . Chem . 2005 , 70 , 5014.), Buchwald-Hartwig cross coupling reaction, Triflatation reaction, Grignard reaction, Cyclic Dehydration reaction, Miyaura boration reaction, etc. Substituents defined in Formulas (1) to (6) in addition to the substituents specified in the specific synthesis examples (Ar ¹ ~Ar ⁵ , L ¹ ~L ⁴ , W, X, Y, Z ¹ ~Z ¹⁶ , R ¹ ~R ³⁹ ) It will be readily understood by those skilled in the art that the reaction proceeds even when combined. For example, starting material -> Sub 1-I reaction in <Scheme 2>, Sub 2-I -> Sub 2-II reaction and Sub 2-V -> Sub 2-VI reaction in <Scheme 6>, <Scheme 18> In the starting material -> M 2-I-9 reaction, in <Scheme 19> the starting material -> M 3-I-1 reaction, <Scheme 20> to <Scheme 22> are based on the Suzuki cross-coupling reaction, < Sub 1-I -> Sub 1-II reaction in Scheme 2>, and M 2-I-9 -> M 2-II-9 reaction in <Scheme 18> _{are based on PPh 3-} mediated reductive cyclization reaction, <Scheme 18> Sub 1-II -> Sub 1 reaction in 2>, Sub 2-VI -> Sub 2 reaction in <Scheme 6>, <Scheme 12> to <Scheme 19>, <Scheme 23> are related to the Buchwald-Hartwig cross coupling reaction. it is based Then, the starting material -> Sub 2-I reaction in Scheme (6) is based on the Triflatation reaction, and the Sub 2-II -> Sub 2-III reaction in Scheme (6) is based on the Grignard reaction, and in Scheme (6), Sub The 2-III -> Sub 2-IV reaction is based on the Cyclic Dehydration reaction, and the Sub 2-IV -> Sub 2-V reaction in Scheme (6) is based on the Miyaura boration reaction. Even if a substituent not specifically specified is bound to these, the reactions will proceed.

Manufacturing evaluation of organic electric devices

[ Experimental example I] Red organic electroluminescent device ( light emitting layer + light emitting layer host)

First, on the ITO layer (anode) formed on the glass substrate, 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm and hole injection After forming the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer did. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, on the light emitting auxiliary layer, the compound (2-5) of the present invention as a host material and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] as a dopant material were 95 A light emitting layer with a thickness of 30 nm was deposited by doping at a weight ratio of :5. Subsequently, (1,1'bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter _{abbreviated as Alq 3} ) was formed on the hole blocking layer to form an electron transport layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example One]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example I], except that the light-emitting auxiliary layer was not used.

By applying a forward bias DC voltage to the organic electroluminescent devices according to [Experimental Example I] (Experimental Example (1) to Experimental Example (68)) and [Comparative Example 1] prepared in this way, a PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at a luminance of 2500 cd/m2.

[Table 8] below shows the device fabrication and evaluation results for [Experimental Example I] (Experimental Example (1) to Experimental Example (68)) and [Comparative Example 1] to which the compound according to the invention is applied.

[Table 8]

[ Experimental example Ⅱ] Green organic electroluminescent device ( light emitting layer + light emitting layer host)

First, on the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then NPD was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, on the light emitting auxiliary layer, the compound (3-1) of the present invention as a host material and Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant material were doped at a weight ratio of 95:5 to 30 nm. A thick light emitting layer was deposited. Then, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to a thickness of 40 nm and an electron transport layer was formed. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example II], except that the light-emitting auxiliary layer was not used.

A forward bias DC voltage was applied to the organic electroluminescent devices according to [Experimental Example II] (Experimental Example (69) to Experimental Example (115)) and [Comparative Example 2] prepared in this way, and PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the lifetime of T95 was measured using a life measuring device manufactured by McScience at 5000 cd/m2 standard luminance.

The following [Table 9] shows the device fabrication and evaluation results for [Experimental Example II] (Experimental Examples (69) to (115)) and [Comparative Example 2] to which the compound according to the invention is applied.

[Table 9]

[ Experimental example Ⅲ] Green organic electroluminescent device ( light emitting layer + light emitting layer host)

First, on the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then NPD was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, on the light emitting auxiliary layer, the compound (2-7) of the present invention as a host material and Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] as a dopant material were doped at a weight ratio of 95:5 to 30 nm. A thick light emitting layer was deposited. Then, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to form an electron transport layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example Ⅲ], except that the light-emitting auxiliary layer was not used.

By applying a forward bias DC voltage to the organic electroluminescent devices according to [Experimental Example Ⅲ] (Experimental Examples 116 to 162) and [Comparative Example 3] prepared in this way, a PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the lifetime of T95 was measured using a life measuring device manufactured by McScience at 5000 cd/m2 standard luminance.

The following [Table 10] shows the device fabrication and evaluation results for [Experimental Example Ⅲ] (Experimental Examples 116 to 162) and [Comparative Example 3] to which the compound according to the invention is applied.

[Table 10]

[ Experimental example IV] Blue organic electroluminescent device ( light emitting layer + light emitting layer host)

First, on the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then NPD was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, on the light emitting auxiliary layer, the compound (5-10) of the present invention as a host material and BD-052X (Idemitsu Kosan) as a dopant material were doped at a weight ratio of 93:7 to deposit a light emitting layer with a thickness of 30 nm. Then, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to form an electron transport layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example IV], except that the light-emitting auxiliary layer was not used.

By applying a forward bias DC voltage to the organic electroluminescent devices according to [Experimental Example IV] (Experimental Examples 163 to 189) and [Comparative Example 4] prepared in this way, a PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the lifetime of T95 was measured using a life measuring device manufactured by McScience at a standard luminance of 500 cd/m2.

The following [Table 11] shows the device fabrication and evaluation results for [Experimental Example IV] (Experimental Examples (163) to (189)) and [Comparative Example 4] to which the compound according to the invention is applied.

[Table 11]

[ Experimental example V] Blue organic electroluminescent device ( light emitting layer + light emitting layer host)

First, 2-TNATA was vacuum-deposited to a thickness of 60 nm on the ITO layer (anode) formed on a glass substrate to form a hole injection layer, and then NPD was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, on the light emitting auxiliary layer, the compound (6-5) of the present invention as a host material and BD-052X (Idemitsu Kosan) as a dopant material were doped in a weight ratio of 93:7 to deposit a light emitting layer having a thickness of 30 nm. Then, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to form an electron transport layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example 5]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example V], except that the light-emitting auxiliary layer was not used.

By applying a forward bias DC voltage to the organic electroluminescent devices according to [Experimental Example V] (Experimental Examples 190 to 208) and [Comparative Example 5] prepared in this way, a PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the lifetime of T95 was measured using a life measuring device manufactured by McScience at a standard luminance of 500 cd/m2.

The following [Table 12] shows the device fabrication and evaluation results for [Experimental Example V] (Experimental Examples 190 to 208) and [Comparative Example 5] to which the compound according to the invention is applied.

[Table 12]

As can be seen from the results of [Table 8] to [Table 12], when an organic electroluminescent device (red, green, blue) is manufactured using the material for an organic electroluminescent device of the present invention as a light emitting auxiliary layer material, light emission Compared to Comparative Examples ([Comparative Example 1] to [Comparative Example 5]) in which the auxiliary layer is not used, the driving voltage of the organic light emitting diode can be lowered, and luminous efficiency and lifespan can be significantly improved.

This is because, when the compounds of the present invention are used as a light emitting auxiliary layer, the charge balance is maintained and the high T ₁ value is lowered to lower the driving voltage and effective blocking is performed so that the excitons stay well in the light emitting layer. As a result, both efficiency and lifespan are greatly increased. improvement can be seen. In other words, the compounds of the present invention used as the light emitting auxiliary layer have high T ₁ value and deep HOMO energy level, holes are more smoothly transported from the hole transport layer to the light emitting layer, and excitons are trapped in the light emitting layer to prevent light emission leakage. It becomes possible to implement an organic electroluminescent device.

[ Experimental example Ⅵ] Green organic electroluminescent device ( light emitting layer + light emitting layer mixed host)

First, 2-TNATA was vacuum-deposited to a thickness of 60 nm on the ITO layer (anode) formed on a glass substrate to form a hole injection layer, and then NPD was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole number VIVI transport layer. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, the compound (2-7) of the present invention and the compound (3-1) of the present invention are mixed (50:50 weight ratio) as a host material on the light emitting auxiliary layer, and Ir(ppy) ₃ [tris] as a dopant material (2-phenylpyridine)-iridium] was doped in a weight ratio of 95:5 to deposit a light emitting layer with a thickness of 30 nm. Then, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to form an electron transport layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example 6]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example VI], except that the light-emitting auxiliary layer was not used.

A forward bias DC voltage was applied to the organic electroluminescent devices according to [Experimental Example VI] (Experimental Example (209) to Experimental Example (235)) and [Comparative Example 6] prepared in this way, and PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the lifetime of T95 was measured using a life measuring device manufactured by McScience at 5000 cd/m2 standard luminance.

The following [Table 13] shows the device fabrication and evaluation results for [Experimental Example VI] (Experimental Examples (209) to (235)) and [Comparative Example 6] to which the compound according to the invention is applied.

[Table 13]

[ Experimental example VII] Green organic electroluminescent device ( light emitting layer + light emitting layer mixed host)

First, on the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then NPD was vacuum deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Next, the compound (one of 1-1 to 1-95) of the present invention (one of 1-1 to 1-95) was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer. Then, the compound (3-1) of the present invention and the compound (4-1) of the present invention are mixed (50:50 weight ratio) as a host material on the light emitting auxiliary layer, and Ir(ppy) ₃ [tris] as a dopant material (2-phenylpyridine)-iridium] was doped in a weight ratio of 95:5 to deposit a light emitting layer with a thickness of 30 nm. Then, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to form an electron transport layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ comparative example 7]

An organic electroluminescent device was manufactured in the same manner as in [Experimental Example VII], except that the light-emitting auxiliary layer was not used.

By applying a forward bias DC voltage to the organic electroluminescent devices according to [Experimental Example VII] (Experimental Example 236 to Experimental Example 262) and [Comparative Example 7] prepared in this way, a PR- Electroluminescence (EL) characteristics were measured with 650, and as a result of the measurement, the lifetime of T95 was measured using a life measuring device manufactured by McScience at 5000 cd/m2 standard luminance.

The following [Table 14] shows the device fabrication and evaluation results for [Experimental Example VII] (Experimental Examples (236) to (262)) and [Comparative Example 7] to which the compound according to the invention is applied.

[Table 14]

As can be seen from the results of [Table 13] to [Table 14], the organic electroluminescent device using the material for the organic electroluminescent device of the present invention as a light emitting auxiliary layer material is more mixed than when a single host material is used. When the host material (compound of formula (2) and formula (3), mixture of formula (3) and formula (4)) was used, it was confirmed that higher luminous efficiency, lower driving voltage and lifespan were significantly improved. can This is considered to be because it has a wider band gap than a single host material due to the two host materials mixed, and at the same time makes it easier to balance charges in the light emitting layer.

In particular, the compound used as the light emitting auxiliary layer of the present invention is a curved 3-fluorene compound, has a wider band gap than the conventionally used linear 2-fluorene compound, and has a high T1 value. Characteristics can be further improved, and the 3-fluorene compound has a lower deposition temperature than the 2-fluorene compound, even during mass production, so that the process time can be shortened.

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

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

Claims (21)

a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer includes a hole transport layer, a light emitting auxiliary layer and a light emitting layer, the light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer and contains a compound represented by the following formula (1), The light emitting layer is a host and a dopant Including, wherein the host is an organic electric device comprising at least one of the compounds represented by the following formulas (3) to (4).
Formula (1)

Formula (3)

Formula (4)

[In the formula (1),
m, n and o are each independently an integer from 0 to 4,
R ^{1 To} R ^{3 When} m, n, and o are 2 or more, each is the same as or different from each other as a plurality, and each independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^a -N(R ^a )(R ^b ); or (wherein L ^a is a single bond; C ₆ to C ₆₀ Arylene group; Fluorenylene group; C ₃ to C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring, and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from the group consisting of, wherein R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; a fluorenyl group; a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group And O, N, S, Si, and P including at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of), or a plurality of R ³ is each bonded to the carbon can form an aromatic ring with
Ar ^{1 To} Ar ^{3 Are} each independently a C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; selected from the group consisting of a hydroxyl group and -L ^b -N(R ^c )(R ^{d ); wherein L b} , R ^c and R ^d are the same as the definitions of ^{L a} , R ^a and R ^{b , respectively.} , or Ar ¹ and Ar ² may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded,
L ¹ is C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And C ₆ ~ C ₆₀ A divalent functional group consisting of a combination _{of an arylene group and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from
L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; And C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring is selected from the group consisting of,
In the above formula (3),
Ar ⁵ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^d -N(R ^g )(R ^h ); wherein L ^d , R ^g and R ^h are the same as defined above for L ^a , R ^a and R ^{b , respectively;}
L ⁴ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; and of C ₁ to C ₆₀ It is selected from the group consisting of divalent aliphatic hydrocarbons,
Z ¹ to Z ¹⁶ are each independently CR ⁷ ; or N; with the proviso ^{that at least one of Z 5} to Z ⁸ and at least one of Z ⁹ to Z ¹² is CR ⁷ , wherein C ^{of CR 7} in one of ^{Z 5} to Z ⁸ and Z ⁹ to Z ¹² is ^{bonded to L 4} instead of bonding to ^{R 7} ),
wherein R ⁷ is hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; fluorenyl group; and -L ^e -N(R ⁱ )(R ^j ); wherein L ^e , R ⁱ and R ^j are the same as the definitions of ^{L a} , R ^a and R ^{b , respectively.} or Z ¹ to Z ¹⁶ , when each of the neighboring Z is CR ⁷ , the neighboring groups and each other can be combined to form an aromatic ring with the carbon bonded to them,
W is NAr ⁶ ; O; And S; is selected from the group consisting of,
Here, Ar ⁶ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₁ ~ C ₅₀ Alkyl group; is selected from the group consisting of,
In the above formula (4),
R ⁸ to R ¹⁹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^f -N(R ^k )(R ¹ ); wherein L ^f , R ^k and R ¹ have the same definitions as ^{L a} , R ^a and R ^{b , respectively.} or R ⁸ and R ⁹ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , R ¹⁷ and R ¹⁸ , R ¹⁸ and R ¹⁹ or R ¹⁹ and R ⁸ may combine with each other to form a ring,
wherein the aryl group, fluorenyl group, heterocyclic group, fused ring group, aliphatic hydrocarbon group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, and fluorenylene group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L ^g -N(R ^m )(R ⁿ ), wherein L ^g , R ^m and R ⁿ are the same as defined above for L ^a , R ^a and R ^{b , respectively;} C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ An alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ to C ₂₀ aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; It may be further substituted with one or more substituents selected from the group consisting of a C ₇ ~ C ₂₀ arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group, and these substituents may be bonded to each other to form a ring]} The method of claim 1,
The light emitting auxiliary layer contains the compound represented by the formula (1), and the host of the light emitting layer contains a compound in which two different compounds of the compounds represented by the formulas (3) to (4) are mixed. organic electric device. The method of claim 1,
^{L 1} of Formula (1) is an organic electric device, characterized in that one of those represented by the following formula.

[In the above formula,
Q ¹ is CR ⁴⁰ ; or N;
Q ² is C(R ⁴¹ )(R ⁴² ); NR ⁴³ ; S; Or O; is selected from the group consisting of,
where R ⁴⁰ , Ar ⁷ and Ar ⁸ are, independently of each other, hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And a fluorenyl group; is selected from the group consisting of,
R ^{41 To} R ⁴³ are each independently, C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; and a fluorenyl group; or R ⁴¹ and R ⁴² may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded] delete The method of claim 1,
The compound represented by the formula (1) is an organic electric device, characterized in that one of the following compounds.

delete The method of claim 1,
The compound represented by the formula (3) is an organic electric device, characterized in that one of the following compounds.

The method of claim 1,
The compound represented by the formula (4) is an organic electric device, characterized in that one of the following compounds.

a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer includes a hole transport layer, an auxiliary light emitting layer and a light emitting layer, the light emission auxiliary layer is formed between the hole transport layer and the light emitting layer and contains at least one of the compounds represented by the following formulas (7) to (10), , wherein the emission layer includes a host and a green dopant, and the host includes at least one of compounds represented by the following Chemical Formulas (2) to (4).
Chemical formula (7) Chemical formula (8) Chemical formula (9) Chemical formula (10)

Formula (2) Formula (3)

Formula (4)

[In the above formulas (7) to (10),
m, n and o are each independently an integer from 0 to 4,
R ^{2 To} R ^{3 When} m, n, and o are 2 or more, each is the same as or different from each other as a plurality, and each independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^a -N(R ^a )(R ^b ); or (wherein L ^a is a single bond; C ₆ to C ₆₀ arylene group; fluorenylene group; C ₃ to C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring, and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from the group consisting of, wherein R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; a fluorenyl group; a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group And O, N, S, Si, and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of), or a plurality of R ^{1 To} R ^{3 Are} each bonded to these can form an aromatic ring with carbon bonded to
Ar ^{1 To} Ar ^{3 Are} each independently a C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; selected from the group consisting of a hydroxyl group and -L ^b -N(R ^c )(R ^{d ); wherein L b} , R ^c and R ^d are the same as the definitions of ^{L a} , R ^a and R ^{b , respectively.} , or Ar ¹ and Ar ² may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded,
L ¹ is C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And C ₆ ~ C ₆₀ A divalent functional group consisting of a combination _{of an arylene group and a C 2} ~ C ₆₀ divalent heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from
L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; And C ₃ ~ C ₆₀ A divalent fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring is selected from the group consisting of,
In the above formulas (2) and (3),
a and b are each an integer from 0 to 1, a+b is 1 or more,
X and Y are each independently a single bond; S; O; NR′;CR′R″; and SiR′R″; wherein R′ and R″ are each independently hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and _{A C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₁ ~ C _{50 It} is selected from the group consisting of an alkyl group,
p is an integer from 0 to 2, q and r are integers from 0 to 4,
R ^{4 To} R ^{6 When} p is 2, q, or r is an integer of 2 to 4, each of which is the same as or different from each other and is independently deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; And ^{-L c -N (R e) (} R f); or selected from the group consisting of (where as defined in the L ^c, R ^e and R ^f are the L ^a, R ^a and R ^b, respectively), Or a plurality of R ⁴ to R ⁶ may be bonded to each other to form an aromatic ring together with the carbon bonded thereto,
Ar ⁴ and Ar ⁵ are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^d -N(R ^g )(R ^h ); wherein L ^d , R ^g and R ^h are the same as defined above for L ^a , R ^a and R ^{b , respectively;}
L ³ and L ⁴ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A divalent heterocyclic group; fluorenylene group; and of C ₁ to C ₆₀ It is selected from the group consisting of divalent aliphatic hydrocarbons,
Z ¹ to Z ¹⁶ are each independently CR ⁷ ; or N; with the proviso ^{that at least one of Z 5} to Z ⁸ and at least one of Z ⁹ to Z ¹² is CR ⁷ , wherein C ^{of CR 7} in one of ^{Z 5} to Z ⁸ and Z ⁹ to Z ¹² is ^{bonded to L 4} instead of bonding to ^{R 7} ),
wherein R ⁷ is hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; fluorenyl group; and -L ^e -N(R ⁱ )(R ^j ); wherein L ^e , R ⁱ and R ^j are the same as the definitions of ^{L a} , R ^a and R ^{b , respectively.} or Z ¹ to Z ¹⁶ , when each of the neighboring Z is CR ⁷ , the neighboring groups and each other can be combined to form an aromatic ring with the carbon bonded to them,
W is NAr ⁶ ; O; And S; is selected from the group consisting of,
Here, Ar ⁶ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₁ ~ C ₅₀ Alkyl group; is selected from the group consisting of,
In the above formula (4),
R ⁸ to R ¹⁹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ^f -N(R ^k )(R ¹ ); wherein L ^f , R ^k and R ¹ have the same definitions as ^{L a} , R ^a and R ^{b , respectively.} or i) R ⁸ and R ⁹ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , R ¹⁷ and R ¹⁸ , R ¹⁸ and R ¹⁹ or R ¹⁹ and R ⁸ may be bonded to each other to form a ring,
wherein the aryl group, fluorenyl group, heterocyclic group, fused ring group, aliphatic hydrocarbon group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, and fluorenylene group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L ^g -N(R ^m )(R ⁿ ), wherein L ^g , R ^m and R ⁿ are the same as defined above for L ^a , R ^a and R ^{b , respectively;} C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ An alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ to C ₂₀ aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; It may be further substituted with one or more substituents selected from the group consisting of a C ₇ ~ C ₂₀ arylalkyl group and a C ₈ ~ C _{20 arylalkenyl group, and these substituents may be bonded to each other to form a ring]} 10. The method of claim 9,
The light emitting auxiliary layer contains at least one of the compounds represented by the formulas (7) to (10), and the host of the light emitting layer is a mixture of two different compounds represented by the formulas (2) to (4) Organic electric device, characterized in that it contains a compound. 10. The method of claim 9,
^{L 1} of Chemical Formulas (7) to (10) is an organic electric device, characterized in that one of those represented by the following Chemical Formulas.

[In the above formula,
Q ¹ is CR ⁴⁰ ; or N;
Q ² is C(R ⁴¹ )(R ⁴² ); NR ⁴³ ; S; or O; is selected from the group consisting of (provided that L ¹ is

When , Q ² is NR ⁴³ ; S; or O; selected from the group consisting of),
wherein R ⁴⁰ , Ar ⁷ and Ar ⁸ are each independently selected from hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And a fluorenyl group; is selected from the group consisting of,
R ^{41 To} R ⁴³ are each independently, C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; and a fluorenyl group; or R ⁴¹ and R ⁴² may be bonded to each other to form a spiro compound together with the fluorene to which they are bonded] 10. The method of claim 9,
The compound represented by the formulas (7) to (10) is an organic electric device, characterized in that one of the following compounds.

10. The method of claim 9,
The compound represented by the formula (2) is an organic electric device, characterized in that one of the following compounds.

10. The method of claim 9,
The compound represented by the formula (3) is an organic electric device, characterized in that one of the following compounds.

10. The method of claim 9,
The compound represented by the formula (4) is an organic electric device, characterized in that one of the following compounds.

delete delete 10. The method of any one of claims 1 and 9,
and a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. 10. The method of any one of claims 1 and 9,
The organic material layer is an organic electric device, characterized in that 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 comprising the organic electric device of any one of claims 1 and 9; and
An electronic device comprising a; a control unit for driving the display device. 21. The method of claim 20,
The organic electroluminescent device is an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), and an electronic device, characterized in that at least one of a single color or white lighting device.

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