KR20210090782A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides: an organic electric element comprising a compound represented by chemical formula 1, a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode; and an electronic device including the organic electric element. By including the compound represented by chemical formula 1 in the organic material layer, the luminous efficiency and lifespan of the organic electric element can be improved.

Description

A compound for an organic electric device, an organic electric device using the same, and an electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

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

In general, the organic light emitting phenomenon refers to a phenomenon in which 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.

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, it is preferable that a light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer, and different light emission according to each light emitting layer (R, G, B) is preferable. Development of the auxiliary layer is necessary.

An object of the present invention is to provide a compound capable of improving luminous efficiency and lifespan of a device, an organic electric 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 and an electronic device using the compound represented by the above formula.

By using the compound according to the embodiment of the present invention, both the luminous efficiency and lifespan of the device can be improved.

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
4 shows a chemical formula according to an aspect of the present invention.

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, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like. In addition, unless otherwise specified in the present specification, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

As used herein, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, "fluorenylene group" refers to a substituted or unsubstituted fluorenyl group, and as used in the present invention, the fluorenyl group or The fluorenylene group includes a case in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.

"Substituted fluorenyl group", "substituted fluorenylene group" means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, etc. may all be called a fluorene group.

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

The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like. _{In addition, a compound including a heteroatom group such as SO 2} , P=O, etc. may be included in the heterocyclic group, such as the following compounds instead of carbon forming a ring.

The term "aliphatic ring group" used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

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

In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

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 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded 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 as or different from each other.

In addition, unless otherwise specified in the present specification, when representing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.

In addition, unless otherwise specified in the present specification, when a ring is expressed in the form of a 'numeric atom' such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-membered ring.

In addition, unless otherwise stated in the present specification, the ring formed by bonding adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ An aliphatic ring group; may be selected from the group consisting of.

At this time, unless otherwise specified in the present specification, 'neighboring groups' refers to each other when describing the following chemical formula as an example, R ₁ and R _{2 each other} , R ₂ and R _{3 each other} , R ₃ and R _{4 each other} , Not only R ₅ and R _{6 but also R 7} and R ₈ sharing one carbon are included, and not immediately adjacent, such as _{R 1} and R ₇ , R ₁ and R _{8 ,} or R ₄ and R _{5 , etc.} Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included. That is, if there is a substituent on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.

_{When substituents bonded to the same carbon as R 7} and R ₈ in the following formula combine with each other to form a ring, a compound including a spiro moiety may be formed.

,

,

In addition, in the present specification, the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.

Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .

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 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 it is described that a component is “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.”

Also, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” the other component, but also when there is another component in between. It should be understood that cases may be included. Conversely, it should be understood that when an element is said to be "on top of" another part, it means that there is no other part in the middle.

1 to 3 are exemplary views 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 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). ) and an organic material layer formed between the second electrode 170 .

The first electrode 110 may be an anode (anode), the second electrode 170 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 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 . Specifically, the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .

Preferably, the light efficiency improving layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency improving layer 180 is formed The light efficiency of the organic electric device may be improved.

For example, the light efficiency improving layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the light efficiency improving layer 180 is formed to form the second electrode 170 . ) can reduce optical energy loss due to surface plasmon polaritons (SPPs), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.

A buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .

Referring to FIG. 2 , the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120 , a hole transport layer 130 , a buffer layer 210 sequentially formed on the first electrode 110 , It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode. can be

Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .

Referring to FIG. 3 , an organic electric device 300 according to another embodiment of the present invention includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, the organic electric device according to an embodiment of the present invention includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and the light efficiency improving layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 . ), and the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 . . As such, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.

A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 . The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 . The charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.

The first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.

In FIG. 3 , n may be an integer of 1 to 5. When n is 2, the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .

When a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3 , an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device emitting light.

The compound represented by Chemical Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer 210, a light emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layers 140, 340, 440 or the light efficiency improvement layer 180 may be used as a material, preferably, the light emission auxiliary layer 220 and / or the light efficiency improvement layer 180 ) can be used as a material for

A study on the selection of a core and a combination of sub-substituents bonded thereto because the band gap, electrical properties, and interfacial properties, etc. may vary depending on which position and which substituent is bonded even for the same and similar core In particular, when the energy level and T ₁ 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.

Therefore, in the present invention, by using the compound represented by Chemical Formula 1 as a material for the light emission auxiliary layer 220 and/or the light efficiency improving layer 180 , the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility) , interface characteristics, etc.) can be optimized to simultaneously improve the lifetime 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 can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be manufactured by depositing a material that can be used as the cathode 170 thereon. there is. In addition, an auxiliary light emitting layer 220 may be formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.

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 an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

In addition, the organic electric 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 device for monochromatic lighting, and a device for a quantum dot display.

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

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

<Formula 1>

In Formula 1, each symbol may be defined as follows.

X is O, S, N(R ₁ ), or C(R ₂ )(R ₃ ) am.

R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; 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 aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ), and adjacent groups may be bonded to each other to form a ring.

A ring formed by bonding adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic ring, O, N, S, Si and P including at least one heteroatom of at least one C ₂ ~ C ₆₀ heterocyclic ring, or C ₃ ~ It may be a _{C 60 aliphatic ring.}

When neighboring R ¹ , neighboring R ² , neighboring R ³ , or neighboring R ⁴ combine with each other to form an aromatic ring, preferably a C ₆ ~ C ₂₀ aromatic ring, more preferably A C ₆ ~ C ₁₄ aromatic ring, such as benzene, naphthalene, phenanthrene, and the like may be formed.

a to c are each an integer of 0 to 4, d is an integer from 0 to 5, and when each of these is an integer of 2 or more, each of R ^{1 ,} each of R ^{2 ,} each of R ^{3 , and} each of R ⁴ are the same as or different from each other .

L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

Ar ¹ and Ar ² 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; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

The R ₁ , R _a and R _b 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; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

The R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; 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 aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group, R ₂ And R ₃ may be bonded to each other to form a ring. When R ₂ and R ₃ combine with each other to form a ring, a spiro compound is formed.

The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

When each of R ¹ to R ⁴ , R ₁ to R ₃ , Ar ¹ , Ar ² , R _a , and R _b is an aryl group, each of these is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₈ , C ₆ to C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , _{may be an aryl group such as C 18} , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, tri phenylene, dihydrotetramethylanthracene, and the like.

When L ¹ and L' are each an arylene group, each of these is, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₈ , C ₆ ~ C ₂₆ , C ₆ ~ C ₂₅ , C ₆ ~ C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , It _{may be an arylene group such as C 16} , C ₁₇ , C ₁₈ , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenylene, and the like.

When each of R ¹ to R ⁴ , R ₁ to R ₃ , Ar ¹ , Ar ² , R _a , R _b , L ¹ , and L' is a heterocyclic group, each of these is, for example, C ₂ to C ₃₀ , C ₂ ~C ₂₆ , C ₂ ~C ₂₅ , C ₂ ~C ₂₄ , C ₂ ~C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , C ₂₃ , _{may be a heterocyclic group such as C 24} , and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, indole, phenyl-indole, benzoindole , phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline , benzofuran, naphthobenzofuran, dibenzofuran, phenanthrobenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenanthrobenzothiophene, dynaphthothiophene , carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuro Pyridine, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphena gin, 1 0-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H- Tioxanthrene, dihydrodimethylphenyl acridine, spiro [fluorene-9,9'-xanthene], spiro [fluorene-9,9'-thioxanthene], spiro [benzo [c] xanthene] -7,9'-fluorene], spiro[chromeno[2,3-c]pyridine-5,9'-fluorene], 10,10-dimethyl-10H-spiro[anthracene-9,9 '-fluorene], 10-phenyl-10H-spiro [acridine-9,9'-fluorene], spiro [benzo [c] fluorene-7,9'-thioxanthene], etc. .

When each of R ¹ to R ⁴ , R ₁ to R ₃ , Ar ¹ , Ar ² , R _a , R _b is a fluorenyl group or L ¹ , L′ each is a fluorenylene group, each of these is 9,9 -Dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b ]fluorene-11,9'-fluorene] , benzo [b] fluorene, diphenyl-11,11- -11 H - may be a fluorene-benzo [b] fluorene, 9- (naphthalen-2-yl) -9 H 9-phenyl.

When each of R ¹ to R ⁴ , R ₂ , and R ₃ is an alkyl group, each of these is preferably C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , _{may be an alkyl group such as C 4} , specifically methyl, ethyl, propyl, t-butyl, and the like.

When each of R ¹ to R ⁴ , R ₂ , and R ₃ is an alkenyl group, each of these is preferably C ₂ to C ₂₀ , C ₂ to C ₁₀ , C ₂ to C ₄ , C ₂ , C ₃ , C _It may be an alkenyl group such as 4, specifically methylene, ethylene, propylene, t-butylene, and the like.

The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and R ₂ and R ₃ are bonded to each other to form a ring and the like are each deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ An alkoxyl group; C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ Arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; and -L′-N(R _a )(R _b ) may be substituted with one or more substituents selected from the group consisting of. Here, L', R _a and R _b are as defined above.

The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and When _{at least one of the rings formed by combining R 2} and R ₃ is substituted with an aryl group, for example, C ₆ ~ C ₂₀ , C ₆ ~ C ₁₉ , C ₆ ~ C ₁₈ , C ₆ ~ C ₁₇ , C ₆ ~ C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , It may be substituted with an aryl group such as C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C _{18 .}

The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and When _{at least one of the rings formed by combining R 2} and R ₃ is substituted with a heterocyclic group, for example, C ₂ ~ C ₂₀ , C ₂ ~ C ₁₉ , C ₂ ~ C ₁₈ , C ₂ ~ C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , It may be substituted with a heterocyclic group such as C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C _{20 .}

The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and When _{at least one of the rings formed by combining R 2} and R ₃ is substituted with an alkyl group, for example, C ₁ ~C ₂₀ , C ₁ ~C ₁₀ , C ₁ ~ C ₄ , C ₁ , C ₂ , C ₃ , It may be substituted with an alkyl group such as C _{4 .}

In one embodiment, Chemical Formula 1 may be represented by Chemical Formula 2 below.

<Formula 2>

In Formula 2, X, R ¹ to R ⁴ , a to d, L ¹ , Ar ¹ , Ar ² are the same as defined in Formula 1.

In another embodiment, Chemical Formula 1 may be represented by Chemical Formula 3 below.

<Formula 3>

In Formula 3, each symbol may be defined as follows.

X, R ¹ to R ⁴ , a to d, L ¹ , Ar ² are the same as defined in Formula 1 above.

L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

Y is O, S, N(R ₄ ) or C(R ₅ )(R ₆ ).

R ⁸ , R ⁹ , R ₅ and R ₆ are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ An alkoxyl group; C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ Arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₂₀ selected from the group consisting of an aliphatic cyclic group, adjacent groups may be bonded to each other to form a ring, and R ₅ and R ₆ may be bonded to each other to form a ring.

e is an integer of 0-3, f is an integer of 0-4, and when each of these is an integer of 2 or more, each R ⁸ , each R ⁹ is the same as or different from each other.

wherein R ₄ is a C ₆ -C ₂₀ aryl group; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C _{20 It} is selected from the group consisting of an aliphatic cyclic group.

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 1 represented by Formula 1 a single compound or two or more compounds.

In another aspect of the present invention, the present invention provides an organic electric device including a first electrode, a second electrode, an organic material layer formed between the first electrode and the second electrode, and a light efficiency improving layer. In this case, the light efficiency improving layer is formed on one side of both surfaces of the first electrode or both sides of the second electrode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improving layer contains the compound represented by Formula 1 above.

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 may be included in the light emission auxiliary layer.

The organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode, and may further include a charge generating layer formed between the two or more stacks.

In another aspect of the present invention, the present invention provides an electronic device including a display device including the organic electric device represented by the formula (1), and a control unit for driving the display device.

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

Synthesis example

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

<Scheme 1>

I. Synthesis example of Sub 1

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

<Scheme 2>

1. Synthesis example of Sub 1-3

Add Mg (3.6 g, 149.4 mmol) to a round-bottom flask and heat sufficiently. After dissolving 9-bromo-9-phenyl-9H-fluorene (40.0 g, 124.5 mmol) in THF (90 mL) under a nitrogen stream, it was slowly added dropwise to the round bottom flask and stirred at 85° C. for 2 hours to prepare solution 1. did. In another round-bottom flask, 1-bromo-3-chlorodibenzo[b,d]furan (35.1 g, 124.5 mmol) was added, dissolved in 200 mL of THF, the solution 1 was slowly added at 0°C, and the mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction was terminated with 2M HCl, _{extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 29.2 g (yield: 53%) of the product.

2. Synthesis example of Sub 1-7

Add Mg (2.4 g, 97.0 mmol) to a round-bottom flask and heat sufficiently. After dissolving 7-bromo-7-phenyl-7H-benzo[c]fluorene (30.0 g, 80.8 mmol) in THF (80 mL) under a nitrogen stream, it was slowly added dropwise to the round bottom flask and stirred at 85°C for 2 hours. Solution 1 was prepared. In another round-bottom flask, 1-bromo-4-chlorodibenzo[b,d]thiophene (24.1 g, 80.8 mmol) was added, dissolved in 200 mL of THF, the solution 1 was slowly added at 0°C, and the mixture was stirred at 85°C for 4 hours. . Upon completion of the reaction, the reaction was terminated with 2M HCl, _{extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 20.2 g of a product (yield: 49%).

3. Sub 1-21 Synthesis example

Add Mg (1.9 g, 80.8 mmol) to a round-bottom flask and heat sufficiently. After dissolving 9-bromo-9-(naphthalen-1-yl)-9H-fluorene (25.0 g, 67.3 mmol) in THF (75 mL) under a nitrogen stream, it was slowly added dropwise to the round-bottom flask and heated at 85° C. for 2 hours. Solution 1 was prepared by stirring. In another round-bottom flask, add 9-bromo-7-chloro-11,11-dimethyl-11H-benzo[a]fluorene (24.1 g, 67.3 mmol), dissolve in 200 mL of THF, and then slowly add solution 1 at 0°C. and stirred at 85°C for 4 hours. Upon completion of the reaction, the reaction was terminated with 2M HCl, _{extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 17.6 g (yield: 46%) of the product.

4. Synthesis example of Sub 1-40

Add Mg (4.1 g, 168.1 mmol) to a round-bottom flask and heat sufficiently. After dissolving 7-bromo-7-phenyl-7H-benzo[c]fluorene (45.0 g, 140.1 mmol) in THF (90 mL) under a nitrogen stream, it was slowly added dropwise to the round bottom flask and stirred at 85°C for 2 hours. Solution 1 was prepared. In another round-bottom flask, 2-bromo-4-chlorodibenzo[b,d]thiophene (60.6 g, 140.1 mmol) was added, dissolved in 200 mL of THF, the solution 1 was slowly added at 0°C, and the mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction was terminated with 2M HCl, _{extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 50.7 g of a product (yield: 61%).

The compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 1]

II. Sub 2's Synthesis example

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

<Scheme 3>

1. Synthesis example of Sub 2-29

After dissolving 9,9-dimethyl-9H-fluoren-2-amine (20.0 g, 95.6 mmol) in toluene (200 mL), 2-bromo-9,9-dimethyl-9H-xanthene (27.6 g, 95.6 mmol) , Pd ₂ (dba) ₃ (2.6 g, 2.9 mmol), P( t -Bu) ₃ (1.2 g, 5.7 mmol), NaO t -Bu (27.5 g, 286.7 mmol) were added and stirred at 45°C. 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, and the resulting compound was separated and recrystallized using a silica gel column to obtain 31.1 g (yield: 78%) of the product.

2. Synthesis example of Sub 2-64

After dissolving 9,9-dimethyl-9H-fluoren-2-amine (15.0 g, 71.7 mmol) in toluene (150 mL), 1-bromodibenzo[b,d]furan (17.7 g, 71.7 mmol), Pd ₂ ( dba) ₃ (2.0 g, 2.2 mmol), P( t -Bu) ₃ (0.9 g, 4.3 mmol), NaO t -Bu (20.6 g, 215.0 mmol) were added and stirred at 45°C. After completion of the reaction, _{extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} , and concentrated, and the resulting compound was separated and recrystallized using a silica gel column to obtain 19.1 g (yield: 71%) of the product.

The compound belonging to Sub 2 of Scheme 1 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 2]

Ⅲ. of the final compound Synthesis example

1. P-1 Synthesis Example

After dissolving Sub 1-1 (10.0 g, 22.6 mmol) in toluene (100 mL), Sub 2-1 (8.2 g, 22.6 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), P( t -Bu) ₃ (0.3 g, 1.4 mmol) and NaO t -Bu (6.5 g, 67.7 mmol) were added and stirred at 130°C. Upon completion of the reaction _{, the mixture was extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 13.4 g of a product (yield: 77%).

2. P-25 Synthesis Example

After dissolving Sub 1-65 (9.0 g, 17.3 mmol) in toluene (100 mL), Sub 2-3 (8.7 g, 17.3 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P( t -Bu) ₃ (0.2 g, 1.0 mmol) and NaO t -Bu (5.0 g, 52.0 mmol) were added and the same method was followed for the synthesis of P-1 to obtain 11.8 g (yield: 69%) of the product.

3. P-56 Synthesis Example

After dissolving Sub 1-34 (8.8 g, 17.3 mmol) in toluene (100 mL), Sub 2-29 (7.2 g, 17.3 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P( t -Bu) ₃ (0.2 g, 1.0 mmol) and NaO t -Bu (5.0 g, 51.9 mmol) were added and the same method was followed for the synthesis of P-1 to obtain 12.9 g (yield: 84%) of the product.

4. P-129 Synthesis Example

After dissolving Sub 1-43 (6.5 g, 9.2 mmol) in toluene (100 mL), Sub 2-1 (3.3 g, 9.2 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), P( t -Bu) ₃ (0.1 g, 0.5 mmol) and NaO t -Bu (2.6 g, 27.5 mmol) were added and the same method was followed for the synthesis of P-1 to obtain 6.2 g (yield: 65 %) of the product.

FD-MS values of compounds P-1 to P-129 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] Green organic electroluminescent device (light emitting auxiliary layer)

N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate After vacuum deposition of a -diamine (hereinafter abbreviated as '2-TNATA') film to form a hole injection layer with a thickness of 60 nm, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- A (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as 'NPB') film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Then, after vacuum deposition of the compound P-3 of the present invention to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as 'CBP' about Flag), tris(2-phenylpyridine)-iridium (hereinafter abbreviated as 'Ir(ppy) ₃ ') was used as a dopant material, but the dopant was doped in a weight ratio of 95:5 to form a light emitting layer with a thickness of 30 nm.

Subsequently, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)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. Then, tris-(8-hydroxyquinoline)aluminum (hereinafter _{abbreviated as 'Alq 3} ') was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.

Then, LiF was deposited 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.

[ Example 2] to [ Example 18]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-3 of the present invention as a light emitting auxiliary layer material.

[Comparative Example 1]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 below was used instead of Compound P-3 of the present invention as a light emitting auxiliary layer material.

<Comparative compound 1>

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples 1 to 18 and Comparative Example 1 of the present invention prepared as described above, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, and 5000 cd /m ² Lifespan of T95 was measured with a life measuring device manufactured by McScience at standard luminance. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, when an organic light emitting device is manufactured using the material for an organic light emitting device of the present invention as a light emitting auxiliary layer material, the organic light emitting device emits light more than Comparative Example 1 using Comparative Compound 1 Efficiency and lifespan can be significantly improved.

The compound of the present invention and Comparative Compound 1 are similar in that they have a structure in which a heteroaryl group such as dibenzofuran is bonded to the 9th position of the fluorene group, but the bonding position of the amine group is different from each other.

In the benzene ring inside of Comparative Compound 1 in which an amine group is substituted on the outer benzene ring of the dibenzofuran bonded to the 9th position of the fluorene group, that is, in the same benzene ring of a heterocyclic compound such as dibenzofuran, dibenzothiophene, etc. When the compound of the present invention in which a fluorene group and an amine group are combined is used as a light emitting auxiliary layer material, the luminous efficiency and lifespan of the organic light emitting device are significantly improved.

Even if it is a compound having a similar core, the physical properties of the compound such as hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, and electron blocking characteristics vary depending on the bonding position of the substituent, This suggests that completely different device results may be derived.

In the case of the light emitting auxiliary layer, it is necessary to understand the correlation between the hole transport layer and the light emitting layer (host). It will be very difficult.

In addition, in the evaluation results of the above-described device fabrication, the device characteristics in which the compound of the present invention is applied only to the light emission auxiliary layer has been described, but the compound of the present invention may be applied to the hole transport layer or both the hole transport layer and the light emission auxiliary layer.

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 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 herein are for illustrative purposes rather than limiting the present invention, and the scope of the present invention is 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, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (12)

A compound represented by the following formula (1):
<Formula 1>

In Formula 1,
X is O, S, N(R ₁ ), or C(R ₂ )(R ₃ ) ego,
R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; 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 aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a ) (R _b ) is selected from the group consisting of, adjacent groups may combine with each other to form a ring,
a to c are each an integer of 0 to 4, d is an integer from 0 to 5, and when each of these is an integer of 2 or more, each of R ^{1 ,} each of R ^{2 ,} each of R ^{3 , and} each of R ⁴ are the same as or different from each other, ,
L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
Ar ¹ and Ar ² 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; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The R ₁ , R _a and R _b 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; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; 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 aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ is selected from the group consisting of an aryloxy group, R ₂ and R ₃ may be bonded to each other to form a ring,
The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and Rings formed by bonding R ₂ and R _{3 to} each other are each deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ An alkoxyl group; C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ Arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; and -L′-N(R _a )(R _b ) may be substituted with one or more substituents selected from the group consisting of. 2. The method of claim 1
Formula 1 is a compound, characterized in that represented by the following formula 2:
<Formula 2>

In Formula 2, X, R ¹ to R ⁴ , a to d, L ¹ , Ar ¹ , Ar ² are the same as defined in claim 1. 2. The method of claim 1
Formula 1 is a compound, characterized in that represented by the following formula 3:
<Formula 3>

In Formula 3, X, R ¹ to R ⁴ , a to d, L ¹ , Ar ² are the same as defined in claim 1,
L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
Y is O, S, N(R ₄ ) or C(R ₅ )(R ₆ ),
R ⁸ , R ⁹ , R ₅ and R ₆ are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ An alkoxyl group; C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ Arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₂₀ selected from the group consisting of an aliphatic ring group, adjacent groups may be bonded to each other to form a ring, and R ₅ and R ₆ may be bonded to each other to form a ring,
e is an integer from 0 to 3, f is an integer from 0 to 4, and when each of these is an integer of 2 or more, each R ⁸ , each R ⁹ is the same as or different from each other,
wherein R ₄ is a C ₆ -C ₂₀ aryl group; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C _{20 It} is selected from the group consisting of an aliphatic cyclic group. The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:

. In an organic electric device comprising 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 comprising a single compound or two or more compounds represented by the formula (1) of claim 1. In an organic electric device comprising a first electrode, a second electrode, an organic material layer formed between the first electrode and the second electrode, and a light efficiency improving layer,
The light efficiency improving layer is formed on one surface of both surfaces of the first electrode or both surfaces of the second electrode that does not come into contact with the organic material layer,
The organic material layer or the light efficiency improving layer is an organic electric device, characterized in that it comprises a compound represented by the formula (1) of claim 1. 7. The method of claim 5 or 6,
The organic material layer is an organic electric device comprising 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. 8. The method of claim 7,
The compound is an organic electric device, characterized in that included in the light emitting auxiliary layer. 7. The method of claim 5 or 6,
The organic material layer comprises at least two stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 10. The method of claim 9,
The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 5 or claim 6; and
An electronic device comprising a; a control unit for driving the display device. 12. The method of claim 11,
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 device for monochromatic lighting, and a device for a quantum dot display.

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