WO2020149710A1 - Compound for organic electronic element, organic electronic element using same, and electronic device thereof - Google Patents

Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electronic element including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode; and an electronic device including the organic electronic element. The compound represented by chemical formula 1 is included in the organic layer so that the driving voltage of the organic electronic element can be lowered and the light-emitting efficiency and lifespan thereof can be improved.

Description

Compound for organic electric element, organic electric element using same, and electronic device thereof

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

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

The most important issues in organic electroluminescent devices are life and efficiency, and as the display becomes larger, this efficiency or life problem must be solved.

Efficiency, life, and driving voltage are related to each other, and when the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase the life.

However, simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the optimum combination of energy level, T1 value, and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

In addition, in order to solve the light emission problem in the hole transport layer in the recent organic electroluminescent device, there must be a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) It is time to develop the layer.

In general, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.

However, in the case of the material used for the hole transport layer, since it has to have a low HOMO value, most of them have a low T1 value, and as a result, exciton generated in the light emitting layer is transferred to the hole transport layer, resulting in charge unbalance in the light emitting layer. ) To emit light at the hole transport layer interface.

When emitting light at the interface of the hole transport layer, a problem arises in that the color purity and efficiency of the organic electric device decreases and the life is shortened. Therefore, the development of 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 is urgently required.

In order to fully exhibit the excellent characteristics of the organic electric device, materials constituting an organic material 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. It should be preceded by this, but the development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently achieved. Therefore, the development of new materials continues to be demanded, and in particular, the development of light-emitting auxiliary layer materials is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and lifetime of the device, an organic electrical device using the same, and an electronic device thereof.

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

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

By using the compound according to the embodiment of the present invention, not only can the driving voltage of the device be lowered, but also the luminous efficiency and lifetime of the device can be greatly improved.

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

2 shows a chemical formula according to an aspect of the present invention.

[Description of codes]

100: organic electrical element 110: substrate

120: first electrode 130: hole injection layer

140: hole transport layer 141: buffer layer

150: light emitting layer 151: light emitting auxiliary layer

160: electron transport layer 170: electron injection layer

180: second electrode

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified. In the present invention, an aryl group or an arylene group may include a monocyclic, ring aggregate, several conjugated ring systems, spiro compounds, and the like. In addition, unless otherwise specified herein, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R'and R" are both hydrogen in the following structures, unless otherwise specified. Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and R and R'are bonded to each other to form a bonded carbon. It includes the case where a compound was formed as a spy together. In the present invention, the fluorenyl group means a substituted or unsubstituted fluorenyl group, and the fluorenylene group means a substituted or unsubstituted fluorenylene group.

The term "spyro compound" as used in the present invention has a'spyro linkage', and a spiro linkage refers to a linkage formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called'spyro atoms', and these are'monospyro-','dispiro-', and'trispyro' depending on the number of spy atoms in a compound. It is called a compound.

The term "heterocyclic group" used in the present invention includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and carbon atoms each containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P or Si unless otherwise specified, and the heterocyclic group is a monocyclic, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like. In addition, the term "heterocyclic group" used in the present invention may include a compound containing a heteroatom group such as SO ₂ , P=O, and the like, instead of carbon forming a ring.

The term "aliphatic ring group" used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like, unless otherwise specified. It means a 3 to 60 ring, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it corresponds to the aliphatic ring.

In the present specification, the'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of a group reflecting a singer', but is described as a'parent compound name' You may. For example, in the case of'phenanthrene', which is a type of aryl group, the monovalent'group' is'phenanthryl' and the bivalent group is a singular such as'phenanthrylene', but the name of the group can be described. Regardless, the parent compound name may be described as'phenanthrene'. Similarly, in the case of pyrimidine, it can be described as'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidinylene, etc., as the'group name' of the corresponding singer. have.

In addition, in this specification, in describing the compound name or the substituent name, a number, an alphabet, or the like indicating the position may be omitted. For example, pyrido[4,3-d]pyrimidine is pyridopyrimidine, benzofuro[2,3-d]pyrimidine is benzofuropyrimidine, 9,9-dimethyl-9H-flu Oren can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless expressly stated, the formula used in the present invention is applied in the same manner as the definition of a substituent based on the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring. The formula or compound may be omitted. In addition, when a is an integer of 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, it binds to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different.

In addition, unless otherwise specified in the present specification, the rings formed by bonding with adjacent groups are C ₆ ~ C ₆₀ aromatic ring groups; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; And combinations thereof.

Hereinafter, a stacked structure of an organic electric device including the compound of the present invention will be described with reference to FIG. 1.

In describing the present invention, when it is determined that detailed descriptions of related known configurations or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

Also, if a component such as a layer, film, region, plate, etc. is said to be "on" or "on" another component, it is not only when the other component is "directly above", but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

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 an embodiment of the present invention includes a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110. Between the second electrode 180 includes an organic material layer containing the compound according to the present invention. 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 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 sequentially stacked on the first electrode 120. . At this time, at least one of these layers is omitted, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. It can also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface that does not contact the organic material layer on both sides of the first electrode or a surface that does not contact the organic material layer on both surfaces of the second electrode.

The compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), the host or dopant of the light emitting layer 150, or may be used as a material for the light efficiency improving layer, but preferably, the compound represented by Formula 1 of the present invention is used as a material for the light emitting auxiliary layer 151.

On the other hand, even in the case of the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is attached to which position, and thus, the selection of the core and the combination of sub-substituents coupled thereto. It is necessary to study, especially when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using the compound represented by the formula (1) as a material for the light-emitting auxiliary layer 151, the energy level and T ₁ value between each organic material layer, the material's intrinsic properties (mobility, interfacial properties, etc.) are optimized It is possible to simultaneously improve the life and efficiency of the organic electric device.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form an anode 120, and a hole injection layer 130 thereon , After forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 and the electron injection layer 170, can be prepared by depositing a material that can be used as the cathode 180 thereon have. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

In addition, the organic material layer is a solution process or a solvent process that is not 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, a doctor blade It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.

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

In addition, the organic electroluminescent device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

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

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

The compound according to an aspect of the present invention is represented by Formula 1 below.

<Formula 1> <Formula 1-1>

In the above formula, each symbol can be defined as follows.

Ar ¹ to Ar ⁴ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And Formula 1-1, provided that at least one of Ar ¹ to Ar ⁴ is Formula 1-1.

When Ar ¹ to Ar ⁴ are aryl groups, preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, etc. Can.

When Ar ¹ to Ar ⁴ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₂ heterocyclic groups, such as dibenzothiophene, benzonaphthothiophene, Dibenzofuran, benzonaphthofuran, carbazole, phenylcarbazole, naphthyl-carbazole, benzocarbazole, phenyl-benzocarbazole, and the like.

When Ar ¹ to Ar ⁴ are fluorenyl groups, 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorenyl group, 9,9'-spyrobifluorene, etc. Can.

L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof.

When L ¹ and L ² are arylene groups, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthalene, terphenyl, phenanthrene, etc. Can.

When L ¹ and L ² are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₂ heterocyclic groups, such as pyridine, dibenzofuran, dibenzothiophene, etc. Can.

L ¹ and L ² are fluorene case ylene group, 9,9-dimethyl -9 H - fluorene, 9,9-diphenyl -9 H - fluorenyl group, or the like as by-fluorene 9,9' spy Can.

R ¹ to R ⁶ are independently of each other hydrogen; Deuterium, tritium; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ), and adjacent groups may combine with each other to form a ring. At this time, the ring formed by bonding adjacent groups to each other is an aromatic ring group of C ₆ ~C ₆₀ ; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60. When adjacent groups are bonded to each other to form an aromatic ring, preferably an aromatic ring of C ₆ ~C ₃₀ , more preferably an aromatic ring of C ₆ ~C ₁₄ , such as benzene, naphthalene, phenanthrene, etc. Aromatic rings can be formed.

a, c, d, and f are each an integer from 0 to 4, b is an integer from 0 to 2, e is an integer from 0 to 3, and each of them is an integer of 2 or more, R ¹ each, R ² each, R Each of ^3, each of R ^4, each of R ^{5, and} each of R ⁶ is the same or different from each other.

When R ¹ to R ⁶ are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, biphenyl, naphthyl, terphenyl, and the like.

When R ¹ to R ⁶ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₂ heterocyclic groups, such as pyridine, pyrimidine, pyrazine, triazine, di Benzofuran, dibenzothiophene, and the like.

When R ¹ to R ⁶ are an alkyl group, preferably an alkyl group of C ₁ to C ₁₀ may be used, such as methyl, t-butyl, and the like. When R ¹ to R ⁶ are alkenyl groups, preferably C ₂ to C ₁₀ may be an alkenyl group, for example, ethene, propene, or the like. When R ¹ to R ⁶ are alkoxyl groups, preferably, they may be C ₁ to C ₁₀ alkoxyl groups, such as methoxy, t-butoxy, and the like.

X is C(R')(R"), N(R'), O or S.

R'and R" are independently of each other hydrogen; deuterium; tritium; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ heterocyclic group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; and C ₆ ~ C ₆₀ aryloxy group; is selected from the group consisting of, R'and R" may be bonded to each other to form a ring.

When R'and R" are aryl groups, it may be preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthyl, terphenyl, and the like.

When R'and R" are an alkyl group, it may preferably be a C ₁ to C ₁₀ alkyl group, such as methyl, t-butyl, and the like.

L'is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof.

R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; And C ₂ to C ₆₀ heterocyclic groups including at least one hetero atom among O, N, S, Si, and P.

Substituents indicated by each symbol may be further substituted. For example, the R ¹ ~ R ⁶ , L ¹ , L ² , Ar ¹ ~Ar ⁴ , R', R", L', R _a , R _b , rings formed by bonding adjacent groups to each other are deuterium; Halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a siloxane group; a boron group; a germanium group; a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group Phosphine oxide unsubstituted or substituted with a group; cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ the alkyl group; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; C ₂ -C ₂₀ alkenyl group of; C ₂ -C ₂₀ alkynyl of; an aryl group of C ₆ -C ₂₀ fluorenyl group; O, N , C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; and combinations thereof may be substituted with one or more substituents selected from the group consisting of.

Preferably, the Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 7.

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

<Formula 6> <Formula 7>

In Chemical Formulas 2 to 7, R ¹ to R ⁴ , L ¹ , L ² , Ar ¹ to Ar ⁴ , a, b, c, and d are as defined in Chemical Formula 1.

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

In another aspect of the present invention, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is represented by Chemical Formula 1 It contains one single compound or two or more compounds.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound is included in the light emitting auxiliary layer.

In another aspect of the present invention, the present invention provides an electronic device including a display device including the organic electric element represented by Chemical Formula 1 and a control unit driving the display device.

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

Synthetic example

The compound represented by Chemical Formula 1 according to the present invention (final product 1) may be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1> (Hal ² is Br or Cl)

Ⅰ. Sub1 Exemplary Compounds and Synthesis Examples

The compound belonging to Sub1 of Reaction Scheme 1 may be the following compound, but is not limited thereto.

The FD-MS (Field Desorption-Mass Spectrometry) value of the compound belonging to Sub1 is shown in Table 1 below.

[Table 1]

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

Scheme 2 (Hal ¹ is I, Br or Cl, Hal ² is Br or Cl)

1. Sub1-1 Synthesis Example

(1) Sub1-1-a synthesis example

2-bromo-1,1'-biphenyl (100 g, 431 mmol) was dissolved in THF (700 mL) under a nitrogen atmosphere, and then cooled to -78 °C. Then n- BuLi (172 mL) was slowly added dropwise and the mixture was stirred for 30 minutes. Then 4-bromo-2-chloro-9H-fluoren-9-one (126 g, 431 mmol) was dissolved in THF (700 mL) and then slowly added dropwise to the mixture. After stirring at -78°C for 1 hour, the temperature is gradually raised to room temperature. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and the organic layer was dried over MgSO ₄ and concentrated to separate the resulting compound using a silica gel column and recrystallized to obtain 163 g of product (yield: 85%).

(2) Sub1-1-b synthesis example

Sub1-1-a (163 g, 336 mmol), acetic acid (920 mL) and concentrated hydrochloric acid (150 mL) were added to a round-bottomed flask and stirred at 60-80° C. for 3 hours under a nitrogen atmosphere. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated to separate the resulting compound with a silica gel column and recrystallized to obtain 143 g of product (yield: 91%).

(3) Sub1-1 synthesis example

After dissolving Sub1-1-b (30.0 g, 70.1 mmol) with toluene (350 mL), Sub2-4 (17.2 g, 70.1 mmol), Pd ₂ (dba) ₃ (1.93 g, 2.10 mmol), P( t -Bu) ₃ (0.85 g, 4.21 mmol), NaO t -Bu (13.5 g, 140 mmol) was added and stirred at 90°C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated to separate the resulting compound with a silica gel column and recrystallized to obtain 32.8 g of product (yield: 79%).

2. Sub1-3 Synthesis Example

Sub1-1-b (30 g, 70.1 mmol), Sub2-35 (19.9 g, 70.1 mmol), Pd ₂ (dba) ₃ (1.93 g, 2.10 mmol), P( t -Bu) ₃ (0.85 g, 4.21 mmol), NaO t -Bu (13.5 g, 140 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 33.3 g of the product (yield: 75%).

3. Sub1-18 Synthesis Example

(1) Sub1-18-a synthesis example

The Sub1 was prepared using 2-bromo-1-phenylnaphthalene (100 g, 355 mmol), n-BuLi (142 mL), 4-bromo-2-chloro-9H-fluoren-9-one (103.5 g, 355 mmol). Proceeding in the same manner as in the synthesis of -1-a, 144 g of product (yield: 82%) was obtained.

(2) Sub1-18-b synthesis example

Sub1-18-a (144 g, 291 mmol), acetic acid (730 mL) and concentrated hydrochloric acid (120 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to give 129 g of product (yield: 93%). ).

(3) Sub1-18 Synthesis Example

Sub1-18-b (50 g, 105 mmol), Sub2-4 (25.6 g, 105 mmol), Pd ₂ (dba) ₃ (2.87 g, 3.14 mmol), P( t -Bu) ₃ (1.27 g, 6.28 mmol), NaO t -Bu (20.1 g, 209 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 52.5 g of product (yield: 78%).

4. Sub1-27 Synthesis Example

(1) Sub1-27-a synthesis example

2-bromo-1,1'-biphenyl (50.0 g, 216 mmol), n-BuLi (86 mL), 4-(4-bromophenyl)-2-(4-chlorophenyl)-9H-fluoren-9-one ( 95.7 g, 216 mmol) was carried out in the same manner as in the synthesis method of Sub1-1-a to obtain 103 g of product (yield: 80%).

(2) Sub1-27-b synthesis example

Sub1-27-a (103 g, 172 mmol) and acetic acid (430 mL) and concentrated hydrochloric acid (70 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to yield 89.0 g of product (yield: 89 %).

(3) Sub1-27 Synthesis Example

Sub1-27-b (50.0 g, 86.2 mmol), Sub2-24 (23.7 g, 86.2 mmol), Pd ₂ (dba) ₃ (2.37 g, 2.59 mmol), P( t -Bu) ₃ (1.05 g, 5.17 mmol), NaO t -Bu (16.6 g, 172 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 54.8 g of the product (yield: 82%).

5. Sub1-37 Synthesis Example

(1) Sub1-37-a synthesis example

2-bromo-1,1'-biphenyl (100 g, 431 mmol), n-BuLi (172 mL), 1-bromo-3-chloro-9H-fluoren-9-one (126 g, 431 mmol) By proceeding in the same manner as the synthesis method of Sub1-1-a, 142 g of product (yield: 74%) was obtained.

(2) Sub1-37-b synthesis example

Sub1-37-a (142 g, 319 mmol), acetic acid (800 mL) and concentrated hydrochloric acid (130 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to yield 113 g of product (yield: 83%). ).

(3) Sub1-37 Synthesis Example

Sub1-37-b (50 g, 117 mmol), Sub2-1 (19.8 g, 117 mmol), Pd ₂ (dba) ₃ (3.21 g, 3.50 mmol), P( t -Bu) ₃ (1.42 g, 7.01 mmol), NaO t -Bu (22.5 g, 234 mmol) was carried out in the same manner as in the synthesis method of Sub1-1 to obtain 44.1 g of the product (yield: 73%).

6. Sub1-39 Synthesis Example

Sub1-37-b (25.0 g, 58.4 mmol), Sub2-35 (16.7 g, 58.4 mmol), Pd ₂ (dba) ₃ (1.60 g, 1.75 mmol), P( t -Bu) ₃ (0.71 g, 3.50 mmol), NaO t -Bu (11.2 g, 117 mmol) was carried out in the same manner as in the synthesis method of Sub1-1 to obtain 26.3 g of the product (yield: 71%).

7. Sub1-57 Synthesis Example

(1) Sub1-57-a synthesis example

Sub1 using 2-bromo-3-phenylnaphthalene (50.0 g, 177 mmol), n-BuLi (71 mL), 1-bromo-3-chloro-9H-fluoren-9-one (51.8 g, 177 mmol) Proceeding in the same manner as in the synthesis of -1-a, 66.8 g of product (yield: 76%) was obtained.

(2) Sub1-57-b synthesis example

Sub1-57-a (66.8 g, 135 mmol) and acetic acid (340 mL) and concentrated hydrochloric acid (50 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to produce 52.2 g of product (yield: 81%). ).

(3) Sub1-57 synthesis example

Sub1-57-b (25.0 g, 52.3 mmol), Sub2-1 (8.8 g, 52.3 mmol), Pd ₂ (dba) ₃ (1.44 g, 1.57 mmol), P( t -Bu) ₃ (0.63 g, 3.14 mmol), NaO t -Bu (10.1 g, 105 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 22.8 g of the product (yield: 77%).

8. Sub1-72 Synthesis Example

(1) Sub1-72-a Synthesis Example

2-bromo-1,1'-biphenyl (100 g, 431 mmol), n-BuLi (172 mL), 3,4-dichloro-9H-fluoren-9-one (107 g, 431 mmol) Proceeding in the same manner as in the synthesis of Sub1-1-a, 147 g of product (yield: 85%) was obtained.

(2) Sub1-72-b synthesis example

Sub1-72-a (147 g, 366 mmol) and acetic acid (920 mL) and concentrated hydrochloric acid (150 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to give 127 g of product (yield: 90%). ).

(3) Sub1-72 synthesis example

Sub1-72-b (25.0 g, 65.1 mmol), Sub2-24 (17.9 g, 65.1 mmol), Pd ₂ (dba) ₃ (1.79 g, 1.95 mmol), P( t -Bu) ₃ (0.79 g, 3.91 mmol), NaO t -Bu (12.5 g, 130 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 27.6 g of the product (yield: 68%).

9. Sub1-80 Synthesis Example

(1) Sub1-80-a synthesis example

Sub1-1 using 2-bromo-1-phenylnaphthalene (50.0 g, 177 mmol), n-BuLi (71 mL), 3,4-dichloro-9H-fluoren-9-one (44.0 g, 177 mmol) Proceeding in the same manner as in the synthesis method of -a, product 67.3 g (yield: 84%) was obtained.

(2) Sub1-80-b synthesis example

Sub1-80-a (67.3 g, 149 mmol) and acetic acid (370 mL) and concentrated hydrochloric acid (60 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to yield 57.5 g of product (yield: 89%). ).

(3) Sub1-80 Synthesis Example

Sub1-80-b (25.0 g, 57.6 mmol), Sub2-1 (9.7 g, 57.6 mmol), Pd ₂ (dba) ₃ (1.58 g, 1.73 mmol), P( t -Bu) ₃ (0.70 g, 3.46 mmol), NaO t -Bu (11.1 g, 115 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 23.8 g of the product (yield: 73%).

10. Sub1-92 synthesis example

(1) Sub1-92-a synthesis example

2-bromo-1,1'-biphenyl (100 g, 431 mmol), n-BuLi (172 mL), 3-bromo-2-iodo-9H-fluoren-9-one (166 g, 431 mmol) By proceeding in the same manner as the synthesis method of Sub1-1-a, 197 g of product (yield: 85%) was obtained.

(2) Sub1-92-b synthesis example

Sub1-92-a (197 g, 366 mmol), acetic acid (920 mL) and concentrated hydrochloric acid (150 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to yield 179 g of product (yield: 94%). ).

(3) Sub1-92 Synthesis Example

Sub1-92-b (50.0 g, 96.2 mmol) was dissolved in 480 mL of toluene, Sub2-1 (16.3 g, 96.2 mmol), Pd ₂ (dba) ₃ (2.64 g, 2.89 mmol), P( t -Bu ) ₃ (1.17 g, 5.77 mmol), NaO t -Bu (18.5 g, 192 mmol) was added and stirred at 60°C. Subsequently, the same method as for the synthesis of Sub1-1 was carried out to obtain 41.0 g of product (yield: 76%).

11. Sub1-120 Synthesis Example

(1) Sub1-120-a synthesis example

2-bromo-1,1'-biphenyl (100 g, 431 mmol), n-BuLi (172 mL), 1,2-dichloro-9H-fluoren-9-one (107 g, 431 mmol) The same procedure as for the synthesis of Sub1-1-a was carried out to obtain 128 g of product (yield: 74%).

(2) Sub1-120-b synthesis example

Sub1-120-a (128 g, 319 mmol) and acetic acid (800 mL) and concentrated hydrochloric acid (130 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to give 96.8 g of product (yield: 79%). ).

(3) Sub1-120 Synthesis Example

Sub1-120-b (40.0 g, 104 mmol), Sub2-20 (27.0 g, 104 mmol), Pd ₂ (dba) ₃ (2.86 g, 3.12 mmol), P( t -Bu) ₃ (1.26 g, 6.25 mmol), NaO t -Bu (20.0 g, 208 mmol) was carried out in the same manner as the synthesis method of Sub1-1 to obtain 42.4 g of product (yield: 67%).

12. Synthesis of Sub1-122

(1) Sub1-122-a synthesis example

2-bromo-1,1'-biphenyl (100 g, 431 mmol), n-BuLi (172 mL), 4-bromo-1-chloro-9H-fluoren-9-one (126 g, 431 mmol) By proceeding in the same manner as the synthesis method of Sub1-1-a, 146 g of product (yield: 76%) was obtained.

(2) Sub1-122-b synthesis example

Sub1-122-a (146 g, 328 mmol) and acetic acid (820 mL) and concentrated hydrochloric acid (130 mL) were used to proceed in the same manner as in the synthesis of Sub1-1-b to produce 120 g of product (yield: 85%). ).

(3) Sub1-122 synthesis example

Sub1-122-b (25.0 g, 58.4 mmol), Sub2-1 (9.9 g, 58.4 mmol), Pd ₂ (dba) ₃ (1.60 g, 1.75 mmol), P( t -Bu) ₃ (0.71 g, 3.50 mmol), NaO t -Bu (11.2 g, 117 mmol) was carried out in the same manner as in the synthesis method of Sub1-1 to obtain 20.8 g of the product (yield: 69%).

II. Synthesis Examples and Illustrative Compounds of Sub 2

Sub 2 of Reaction Scheme 3 may be synthesized by the reaction route of Reaction Scheme 3 (disclosed in Korean Registered Patent No. 10-1251451 of the applicant (published on April 5, 2013)), but is not limited thereto.

<Scheme 3>

The compound belonging to Sub 2 may be the following compound, but is not limited thereto, and the FD-MS (Field Desorption-Mass Spectrometry) value of the following compound is shown in Table 2 below.

[Table 2]

III. Synthesis of final compounds

1. Synthesis example of P-1

After dissolving Sub1-1 (32.8 g, 55.3 mmol) with toluene (276 mL), Sub2-19 (14.3 g, 55.3 mmol), Pd ₂ (dba) ₃ (1.52 g, 1.66 mmol), P( t -Bu ) ₃ (0.67 g, 3.32 mmol), NaO t -Bu (10.6 g, 111 mmol) was added and refluxed. After the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ , concentrated, separated by a silica gel column, and recrystallized to obtain 33.4 g of product (yield: 74%).

2. Synthesis of P-3

Sub1-3 (33.3 g, 52.6 mmol), Sub2-4 (12.9 g, 52.6 mmol), Pd ₂ (dba) ₃ (1.44 g, 1.58 mmol), P( t -Bu) ₃ (0.64 g, 3.16 mmol) , NaO t -Bu (10.1 g, 105 mmol) was carried out in the same manner as in the synthesis method of P-1 to obtain 31.5 g of product (yield: 71%).

3. Synthesis of P-18

Sub1-18 (25.0 g, 38.9 mmol), Sub2-44 (15.9 g, 38.9 mmol), Pd ₂ (dba) ₃ (1.07 g, 1.17 mmol), P( t -Bu) ₃ (0.47 g, 2.33 mmol) , NaO t -Bu (7.5 g, 77.7 mmol) was carried out in the same manner as in the synthesis method of P-1 to obtain 26.9 g of the product (yield: 68%).

4. Synthesis Example of P-27

Sub1-27 (54.8 g, 70.7 mmol), Sub2-1 (12.0 g, 70.7 mmol), Pd ₂ (dba) ₃ (1.94 g, 2.12 mmol), P( t -Bu) ₃ (0.86 g, 4.24 mmol) , NaO t -Bu (13.6 g, 141 mmol) was carried out in the same manner as in the synthesis method of P-1 to obtain 47.5 g of product (yield: 74%).

5. Synthesis Example of P-37

Sub1-37 (20.0 g, 38.7 mmol), Sub2-21 (10.0 g, 38.7 mmol), Pd ₂ (dba) ₃ (1.06 g, 1.16 mmol), P( t -Bu) ₃ (0.47 g, 2.32 mmol) , NaO t -Bu (7.4 g, 77.3 mmol) was carried out in the same manner as in the synthesis method of P-1 to obtain 20.3 g of the product (yield: 71%).

6. Synthesis of P-40

Sub1-39 (26.3 g, 41.5 mmol), Sub2-1 (7.0 g, 41.5 mmol), Pd ₂ (dba) ₃ (1.14 g, 1.25 mmol), P( t -Bu) ₃ (0.50 g, 2.49 mmol) , NaO t -Bu (8.0 g, 83.1 mmol) was performed in the same manner as in the synthesis method of P-1 to obtain 24.2 g of the product (yield: 76%).

7. Synthesis Example of P-58

Sub1-57 (22.8 g, 40.2 mmol), Sub2-46 (14.1 g, 40.2 mmol), Pd ₂ (dba) ₃ (1.10 g, 1.21 mmol), P( t -Bu) ₃ (0.49 g, 2.41 mmol) , NaO t -Bu (7.7 g, 80.4 mmol) was carried out in the same manner as in the synthesis method of P-1 to obtain 24.8 g of the product (yield: 70%).

8. P-73 Synthesis Example

Sub1-72 (27.6 g, 44.3 mmol), Sub2-1 (7.5 g, 44.3 mmol), Pd ₂ (dba) ₃ (1.22 g, 1.33 mmol), P( t -Bu) ₃ (0.54 g, 2.66 mmol) , NaO t -Bu (8.5 g, 88.6 mmol) was performed in the same manner as in the synthesis method of P-1 to obtain 21.4 g of product (yield: 64%).

9. Synthesis Example of P-81

Sub1-80 (23.8 g, 42.0 mmol), Sub2-35 (12.0 g, 42.0 mmol), Pd ₂ (dba) ₃ (1.15 g, 1.26 mmol), P( t -Bu) ₃ (0.51 g, 2.52 mmol) , NaO t -Bu (8.1 g, 83.9 mmol) was carried out in the same manner as in the synthesis method of P-1 to obtain 21.2 g of the product (yield: 62%).

10. Synthesis Example of P-94

Sub1-92 (20.0 g, 35.6 mmol), Sub2-45 (13.7 g, 35.6 mmol), Pd ₂ (dba) ₃ (0.98 g, 1.07 mmol), P( t -Bu) ₃ (0.43 g, 2.14 mmol) , NaO t -Bu (6.9 g, 71.3 mmol) was carried out in the same manner as the synthesis method of P-1 to obtain 20.7 g of the product (yield: 67%).

11.P-124 Synthesis Example

Sub1-122 (20.8 g, 40.2 mmol), Sub2-20 (10.4 g, 40.2 mmol), Pd ₂ (dba) ₃ (1.10 g, 1.21 mmol), P( t -Bu) ₃ (0.49 g, 2.41 mmol) , NaO t -Bu (7.7 g, 80.4 mmol) was performed in the same manner as in the synthesis method of P-1 to obtain 18.5 g of product (yield: 62%).

The FD-MS values of the compounds P-1 to P-128 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[Example 1] Red organic light emitting device (light emitting auxiliary layer)

4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) on the ITO layer (anode) formed on a glass substrate is vacuum-deposited to a thickness of 60 nm to inject holes. After forming a layer, N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter, on the hole injection layer) , Abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Subsequently, the compound P-1 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light-emitting auxiliary layer, and then 4,4'-N,N'-dicarbazole-biphenyl ( Hereinafter, abbreviated as CBP) is used as a host material, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as (piq) ₂ Ir(acac)) is used as a dopant material, but in a 95:5 weight ratio To form a 30 nm thick light emitting layer by vacuum deposition.

Subsequently, a hole blocking layer is formed by vacuum-depositing (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) to a thickness of 10 nm on the light emitting layer. Then, on the hole blocking layer, tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as “Alq ₃ ”) was vacuum-deposited to a thickness of 40 nm to form an electron transport layer.

Subsequently, an organic electroluminescent device was manufactured by depositing LiF to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.

[Example 2] to [Example 30]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 below was used instead of the compound P-1 of the present invention as the light-emitting auxiliary layer material.

[Comparative Example 1]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the auxiliary light emitting layer was not formed.

[Comparative Example 2] and [Comparative Example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following Comparative Compound A or Comparative Compound B was used as the light-emitting auxiliary layer material.

<Comparative Compound A> <Comparative Compound B>

The electroluminescence (EL) characteristics of the organic electroluminescent devices of Examples 1 to 30 and Comparative Examples 1 to 3 manufactured as described above were measured by photoresearch's PR-650 by applying a direct bias DC voltage and measuring 2500 cd/m. ² T95 life was measured at a reference luminance through a life measurement equipment manufactured by Max Science. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results in Table 4, when a red organic electroluminescent device was manufactured using the material for an organic electroluminescent device of the present invention as a light-emitting auxiliary layer material, a light-emitting auxiliary layer was not used or Comparative Compound A or Comparative Compound The light emission efficiency and lifespan of the organic electroluminescent device were significantly improved than the comparative example using B.

That is, the device results of Comparative Example 2 or Comparative Example 3 in which the light-emitting auxiliary layer was formed using Comparative Compound A or Comparative Compound B were better than Comparative Example 1 without using the light-emitting auxiliary layer, and similar to Comparative Compound A, Examples 1 to 30 using the compounds of the present invention in which specific substituents such as dibenzofuran and dibenzothiophene were introduced as amino groups as the light emitting auxiliary layer material showed remarkably excellent results in efficiency and life.

When comparing the results of Comparative Example 2 and Examples 1 to 8, amino groups are substituted at positions 2 and 4 of fluorene in the same manner as Comparative Compound A, but specific substituents such as dibenzofuran, dibenzothiophene, etc. The result of the presently-introduced compound exhibits remarkably excellent results, since when a specific substituent such as dibenzofuran or dibenzothiophene is introduced, the refractive index is significantly higher than that of the general aryl group substituent and Tg is increased. The efficiency and thermal stability become excellent. Therefore, it appears that Examples 1 to 8 exhibit better device characteristics.

When comparing Examples 1 to 8 and Examples 9 to 30, since the physical properties of the compound or the interaction between molecules changes depending on the position of the amino group bound to fluorene, it can be confirmed that the performance of each substitution position is different in the device results. .

In the case of the light-emitting auxiliary layer, since it is necessary to grasp the relationship between the hole transport layer and the light-emitting layer (host), even if a similar core is used, it will be very difficult to infer the characteristics of the light-emitting auxiliary layer in which the compound of the present invention is used.

In addition, in the evaluation results of the above-mentioned device fabrication, the device characteristics in which the compound of the present invention is applied only to the light-emitting auxiliary layer were described, but the compound of the present invention may be used for both the hole transport layer and the hole transport layer and the light-emitting auxiliary layer.

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

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is filed in US Patent Law Nos. 10-2019-0006685 filed in Korea on January 18, 2019. ), and all contents are incorporated into this patent application as a reference. In addition, if this patent application claims priority to the countries other than the United States for the same reason as above, all the contents are incorporated into this patent application as a reference.

Claims (8)

1. Compound represented by the formula (1):

   <Formula 1> <Formula 1-1>

   

   

   In the above formula,

   Ar ¹ to Ar ⁴ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And it is selected from the group consisting of Formula 1-1, provided that at least one of Ar ¹ to Ar ⁴ is Formula 1-1,

   L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof,

   R ¹ to R ⁶ are independently of each other hydrogen; Deuterium, halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ), and adjacent groups may combine with each other to form a ring,

   a, c, d, and f are each an integer from 0 to 4, b is an integer from 0 to 2, e is an integer from 0 to 3, and each of them is an integer of 2 or more, R ¹ each, R ² each, R ³ each, R ⁴ each, R ⁵ each, R ⁶ each is the same or different from each other,

   X is C(R')(R"), N(R'), O or S,

   R'and R" are independently of each other hydrogen; deuterium; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ heterocyclic group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₆₀ Alkenyl group of; and C ₆ ~ C ₆₀ aryloxy group; is selected from the group consisting of, R'and R" may be bonded to each other to form a ring,

   L'is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof,

   R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C ₂ ~ C ₆₀ containing at least one hetero atom,

   The R ¹ ~ R ⁶ , L ¹ , L ² , Ar ¹ ~Ar ⁴ , R', R", L', R _a , R _b , and rings formed by bonding adjacent groups to each other are deuterium, halogen; Silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or C ₆ -C ₂₀ aryl group; siloxane group; C ₁ -C ₂₀ alkyl group or C ₆ -C ₂₀ aryl group substituted or unsubstituted phosphine Oxide; cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ the alkenyl group; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; C ₂ -C ₂₀ alkynyl of; an aryl group of C ₆ -C ₂₀ fluorenyl group; consisting of O, N, S, Si and P A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group; a C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of.
2. According to claim 1,

   Chemical Formula 1 is a compound characterized in that represented by one of the following Chemical Formulas 2 to 7:

   <Formula 2> <Formula 3>

   

   <Formula 4> <Formula 5>

   

   <Formula 6> <Formula 7>

   

   In the above formula, R ¹ ~R ⁴ , L ¹ , L ² , Ar ¹ ~Ar ⁴ , a, b, c, d are as defined in claim 1.
3. According to claim 1,

   The compound represented by Formula 1 is one of the following compounds:

   

   

   

   

   

   

   

   

   .
4. In the organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,

   The organic material layer is an organic electric device characterized in that it comprises a single compound or two or more compounds represented by the formula (1) of claim 1.
5. The method of claim 4,

   The organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer.
6. The method of claim 5,

   The compound is an organic electric device, characterized in that included in the light-emitting auxiliary layer.
7. A display device comprising the organic electric device of claim 4; And

   And a control unit driving the display device.
8. The method of claim 7,

   The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

Images