KR20220054483A - Compound for organic electric element, organic electric element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electric element including 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, it is possible to lower driving voltage, and improve luminous efficiency and lifespan of the organic electric element.

Description

A compound for an organic electric device, an organic electric device 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 usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered 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 when the efficiency is increased, the driving voltage is relatively decreased. 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 of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

In addition, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer should exist between the hole transport layer and the light emitting layer, and different light emitting auxiliary layers according to each light emitting layer (R, G, B). development is 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 lifespan of the 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 comprising the compound represented by the above formula, and an electronic device thereof.

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

1 to 3 are exemplary views of an organic electroluminescent device according to 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, and 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.

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 spiro compounds formed by bonding R and R' in the following structure, and also includes compounds in which adjacent R" is bonded to each other to form a ring. "Substituted fluorenyl group", "substituted The fluorenylene group "means that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and R" in the formula below may be 1 to 8.

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 an element other than carbon, for example, N, O, S, P or Si, unless otherwise specified, and, instead of carbon forming a ring, SO ₂ , P= It may also contain a heteroatom group such as O. In the present specification, the heterocyclic group includes a monocyclic type including a heteroatom, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.

The term "aliphatic ring group" used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and 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 as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent or pyrimidinylene in the case of divalent. 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 applies 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. 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 carbon 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.

In the present specification, unless otherwise specified, the term 'neighboring groups' refers to the following chemical formulas as an example, R ₁ and R ₂ each other, R ₂ and R _{3 each} other, R ₃ and R _{4 each} other, R ₅ and R ₆ as well as R ₇ and R ₈ that share one carbon are included, and non-adjacent ring structures such as R ₁ and R ₇ , R ₁ and R ₈ , or R ₄ and R ₅ are not immediately adjacent. Substituents bonded to elements (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. In the following formula, when substituents bonded to the same carbon as R ₇ and R ₈ 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.

In addition, unless otherwise specified in the present specification, an 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 alkoxy group, an aryloxy group, and neighboring Each ring formed by bonding one group to each other is deuterium; halogen; an amino group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.

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 elements from other elements, and the essence, order, or order of the elements 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 also be “connected,” “coupled,” or “connected.”

Further, 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” another component, but also when another component is in between. It should be understood that cases may be included. Conversely, when it is said that an element is "on top of" another part, it should be understood to mean 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 that is not in contact with the organic material layer, and when the light efficiency improving layer 180 is formed 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 .

2, the organic electric device 200 according to another embodiment of the present invention is 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 , in the organic electric device 300 according to another embodiment of the present invention, there are 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, in the organic electric device according to an embodiment of the present invention, 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 described above, 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 to 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 the 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 that emits light.

The compound represented by 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 improving layer 180 may be used as a material, but preferably may be used as a material of the light emitting auxiliary layer 220 .

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, long lifespan and high efficiency can be achieved at the same time 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.

Therefore, in the present invention, by using the compound represented by Formula 1 as a material for the light emitting auxiliary layer 220, the energy level and T ₁ value between each organic material layer, the inherent properties of the material (mobility, interfacial properties, etc.), etc. are optimized. It is possible to simultaneously improve the lifespan 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 prepared 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 further 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 a 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> <Formula 1-1>

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

V ¹ and V ² are each independently C(R), wherein R is 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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N(R _a )(R _b ); And selected from the group consisting of Formula 1-1, at least one of R is Formula 1-1, and R may form a ring by bonding with neighboring R ¹ .

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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N(R _a )(R _b ); And it is selected from the group consisting of combinations thereof, adjacent groups may be bonded to each other to form a ring.

a is an integer of 0 to 2, b, c and d are each an integer of 0 to 4, and when these are integers 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.

Neighboring groups, for example, R and R ¹ , neighboring R ¹ , neighboring R ² , neighboring R ³ , and neighboring R ⁴ are bonded to each other to form a ring formed by bonding with each other, a C ₆ ~ C ₆₀ aromatic ring 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 may be selected from the group consisting of an aliphatic cyclic group.

When adjacent groups are bonded to each other to form an aromatic ring, the aromatic ring is, for example, C ₆ ~ C ₂₀ , C ₆ ~ C ₁₈ , C ₆ ~ C ₁₆ , C ₆ ~ C ₁₄ , C ₆ ~ C ₁₃ , C ₆ ~ C ₁₂ , C ₆ ~ C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₈ , etc. may be, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene etc.

When adjacent groups are bonded to each other to form a heterocycle, the heterocyclic group is, 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 , 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 It may be a heterocyclic group such as, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, benzoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, Benzoquinazoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naph Tobenzothiophene, phenanthrobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, benzofuropyridine , benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, and the like.

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.

L ¹ is a C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group, L ² Is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group.

The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group.

The 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.

When at least one of R ¹ -R ⁴ , Ar ¹ , Ar ² , R, R _a , and R _b is an aryl group, the aryl group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ ~C ₂₇ , 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 , C ₁₆ , C ₁₇ , may be an aryl group such as C ₁₈ , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, and the like.

When at least one of L ¹ , L ² , and L′ is an arylene group, the arylene group is, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₉ , C ₆ ~ C ₂₈ , C ₆ ~ C ₂₇ , 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 , It may be an arylene group such as C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenane. Tren, or the like.

When at least one of R ¹ -R ⁴ , Ar ¹ , Ar ² , R, R _a , R _b , L ¹ , L ² , and L' is a heterocyclic group, the heterocyclic group is, for example, C ₂ to C ₃₀ , C ₂ ~C ₂₉ , C ₂ ~C ₂₈ , C ₂ ~C ₂₇ , 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 to C ₄ , C ₂ to 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 , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ heterocyclic radical such as Can, 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, phenanthro Benzofuran, dynaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenanthrobenzothiophene, dynaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl- Benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, Benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxy Photo, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodioxin methylphenylacridine, spiro[fluorene-9,9'-xanthene], and the like.

When at least one of R ¹ -R ⁴ , Ar ¹ , Ar ² , R, R _a , R _b is a fluorenyl group, or at least one of L ¹ , L ² , and L′ is a fluorenylene group, the fluorene group A diyl or fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene -11,9' -fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11H-benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H- It may be fluorene or 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 alkoxy group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an aryl group, the aryl group is, 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 , C ₁₄ , C ₁₅ , C ₁₆ , It may be an aryl group such as C ₁₇ or C ₁₈ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a heterocyclic group, the heterocyclic group is, 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 , C ₈ , C ₉ , C ₁₀ , It may be a heterocyclic group such as C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alicyclic group, the alicyclic group is, for example, C ₃ ~ C ₂₀ , C ₃ ~ C ₁₉ , C ₃ ~ C ₁₈ , C ₃ ~ C ₁₇ , C ₃ ~ C ₁₆ , C ₃ ~ C ₁₅ , C ₃ ~C ₁₄ , C ₃ ~C ₁₃ , C ₃ ~C ₁₂ , C ₃ ~C ₁₁ , C ₃ ~C ₁₀ , C ₃ ~C ₆ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , may be an aliphatic ring group such as C ₁₈ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene , spiro [benzo [ b ] fluorene-11,9'-fluorene], benzo [ b ] fluorene, 11,11-diphenyl-11 H -benzo [ b ] fluorene, 9- (naphthalene-2) -yl)9-phenyl- 9H -fluorene and the like.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkyl group, the alkyl group may be a C ₁ -C ₁₀ alkyl group, specifically, a methyl group, an ethyl group, a propyl group, a t-butyl group, or the like.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkoxy group, the alkoxy group may be a C ₁ -C ₁₀ alkoxy group, specifically, a methoxy group, an ethoxy group, a butoxy group, and the like.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkenyl group, the alkenyl group may be a C ₂ -C ₁₀ alkenyl group, specifically, an ethenyl group, a propenyl group, or the like.

Formula 1 may be represented by Formula 2-1 or Formula 2-2 below.

<Formula 2-1> <Formula 2-2>

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

In addition, Chemical Formula 1 may be represented by one of Chemical Formulas 3-1 to 3-6 below.

<Formula 3-1> <Formula 3-2> <Formula 3-3>

<Formula 3-4> <Formula 3-5> <Formula 3-6>

In Formulas 3-1 to 3-6, each symbol may be defined as follows.

Ar ¹ , Ar ² , R ¹ to R ⁴ , L ² , and a to d are as defined in Formula 1.

R ⁵ is 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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, and adjacent groups may be bonded to each other to form a ring.

e is an integer of 0-4, and when e is an integer of 2 or more, each of R ⁵ is the same as or different from each other.

L ³ is a single bond; C ₆ -C ₂₀ Arylene group; fluorenylene 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.

In addition, Chemical Formula 1 may be represented by one of Chemical Formulas 4-1 to 4-4 below.

<Formula 4-1> <Formula 4-2>

<Formula 4-3> <Formula 4-4>

In Formulas 4-1 to 4-4, each symbol may be defined as follows.

Ar ¹ , Ar ² , R ¹ to R ⁴ , L ² , and a to d are as defined in Formula 1.

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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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, and adjacent groups may be bonded to each other to form a ring.

e and f are each an integer of 0-4, and when they are an integer of 2 or more, each of R ⁵ and R ⁶ are the same as or different from each other.

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

.

.

In another aspect, the present invention provides a first electrode; a second electrode; It provides an organic electric device including an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes the formula (1).

In another aspect, the present invention provides 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, wherein the organic material layer is a light emitting layer, and the light emitting layer and a light-emitting auxiliary layer formed between the first electrode and the light-emitting auxiliary layer, wherein the light-emitting auxiliary layer includes a compound represented by the following Chemical Formula 5, and the light emitting layer includes a compound represented by at least one of the following Chemical Formulas 6 to 8.

<Formula 5> <Formula 6>

<Formula 7> <Formula 8>

In Chemical Formulas 5 to 8, each symbol may be defined as follows.

R ¹ to R ⁴ , R ¹⁰ to R ⁴¹ 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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N(R _a )(R _b ); And it is selected from the group consisting of combinations thereof, adjacent groups may be bonded to each other to form a ring.

a is an integer of 0 to 2, b, c and d are each an integer of 0 to 4, and when these are integers 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.

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.

L ¹ is a C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group.

L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group.

The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group.

The 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 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 alkoxy group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.

When at least one of R ¹ to R ⁴ , R ¹¹ to R ⁴¹ , R _a , and R _b is an aryl group, the aryl group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ ~C ₂₇ , 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 , C ₁₆ , C ₁₇ , may be an aryl group such as C ₁₈ , and specifically, phenyl, biphenyl, naphthyl , terphenyl, phenanthrene, triphenylene, and the like.

When L ¹ , L ² , L' is an arylene group, the arylene group is, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₉ , C ₆ ~ C ₂₈ , C ₆ ~ C ₂₇ , 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 , It may be an arylene group such as C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, etc. there is.

When at least one of R ¹ to R ⁴ , R ¹¹ to R ⁴¹ , R _a , R _b , L ¹ , L ² , and L' is a heterocyclic group, the heterocyclic group is, for example, C ₂ to C ₃₀ , C ₂ ~C ₂₉ , C ₂ ~C ₂₈ , C ₂ ~C ₂₇ , 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 , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ may be a heterocyclic group such as , 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 , dynaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenanthrobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole Sol, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, Benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxy Photo, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodioxin methylphenylacridine, spiro[fluorene-9,9'-xanthene], and the like.

When at least one of R ¹ to R ⁴ , R ¹¹ to R ⁴¹ , R _a , R _b is a fluorenyl group, or at least one of L ¹ , L ² , and L′ is a fluorenylene group, the fluorenyl group or The fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11 ,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene etc.

The aryl group, the fluorenyl group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group and a ring 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; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an aryl group, the aryl group is, 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 , C ₁₄ , C ₁₅ , C ₁₆ , It may be an aryl group such as C ₁₇ or C ₁₈ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a heterocyclic group, the heterocyclic group is, 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 , C ₈ , C ₉ , C ₁₀ , It may be a heterocyclic group such as C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene , spiro [benzo [ b ] fluorene-11,9'-fluorene], benzo [ b ] fluorene, 11,11-diphenyl-11 H -benzo [ b ] fluorene, 9- (naphthalene-2) -yl)9-phenyl- 9H -fluorene and the like.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkyl group, the alkyl group may be a C ₁ -C ₁₀ alkyl group, specifically, a methyl group, an ethyl group, a propyl group, a t-butyl group, or the like.

The Chemical Formula 7 may be represented by the following Chemical Formula 7-1.

<Formula 7-1>

In Formula 7-1, each symbol may be defined as follows.

R ²² , R ²³ , R ²⁵ to R ²⁸ , R ³⁰ , and R ³¹ are as defined in Formula 7.

Ar is 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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; And C ₆ ~ C ₂₀ It is selected from the group consisting of an aryloxy group.

L is a single bond; C ₆ -C ₂₀ Arylene group; fluorenylene 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.

X is O or S.

R ^1′ and R ^2′ 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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, and adjacent groups may be bonded to each other to form a ring.

a' is an integer of 0-3, b' is an integer of 0-4, and when each of these is an integer of 2 or more, each of R ^1' and R ^2' is the same as or different from each other.

The aryl group, the fluorenyl group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group and a ring 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; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.

Formula 7 may be represented by Formula 7-2 or Formula 7-3.

<Formula 7-2> <Formula 7-3>

In Formulas 7-2 and 7-3, each symbol may be defined as follows.

R ²² , R ²³ , R ²⁵ to R ²⁸ , R ³⁰ to R ³² , Ar, L, X, R ^1′ , R ^2′ , a′, b′ are as defined in Formula 7, and c′ is a Same as ', and d' is the same as b'.

R ^3′ and R ^4′ may be the same as R ^1′ and R ^2′ of Formula 7, and preferably each independently represent hydrogen, deuterium, or a substituted or unsubstituted C ₆ -C ₆₀ aryl group.

In addition, at least one of Ar or Ar ^c , R ^1′ , and R ^2′ may be a C ₆ ~ C ₆₀ aryl group in which one or more deuterium is substituted.

Specifically, the compound represented by Formula 5 may be one of the compounds P-1 to P-110 and the following compounds P-111 to P-132, but is not limited thereto.

.

.

Specifically, the compound represented by Formula 6 may be one of the following compounds, but is not limited thereto.

.

.

Specifically, the compound represented by Formula 7 may be one of the following compounds, but is not limited thereto.

.

.

Specifically, the compound represented by Formula 8 may be one of the following compounds, but is not limited thereto.

.

.

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

In addition, the present invention includes a display device including an organic electric device represented by Formula 5 in a light emitting auxiliary layer, and a compound represented by at least one of Formulas 6 to 8 in a light emitting layer, and a control unit for driving the display device. It provides an electronic device comprising.

Hereinafter, a synthesis example of the compound represented by Formula 1 according to the present invention and a manufacturing example of an organic electric device 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 A1 or Sub A2 with Sub B as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

of Sub A Synthesis example

Sub A1 and Sub A2 of Scheme 1 may be synthesized by the reaction routes of Schemes 2-1 and 2-2, respectively, but are not limited thereto.

<Reaction Scheme 2-1>

<Reaction Scheme 2-2>

1. Sub A-1 Synthesis example

(1) Synthesis of Sub 3-1

After dissolving Sub1-1 (100 g, 598.05 mmol) in toluene (1000 ml), Sub 2-1 (147.19 g, 598.05 mmol), Pd ₂ (dba) ₃ (27.38 g, 29.90 mmol), NaO t -Bu (172.44 g, 1794.19 mmol), P( t -Bu) ₃ (12.10 g, 59.81 mmol) was added and stirred at 100°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 153.07 g (yield: 77%) of the product.

(2) Synthesis of Sub A-1

After dissolving Sub 3-1 (60 g, 180.50 mmol) in toluene (600 mL), Sub 4-1 (48.30 g, 180.50 mmol), Pd ₂ (dba) ₃ (8.26 g, 9.02 mmol), NaO t -Bu (52.04 g, 541.46 mmol) and P( t -Bu) ₃ (3.65 g, 18.04 mmol) were added, followed by stirring at 100°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 67.02 g (yield: 71%) of the product.

2. Sub A-21 Synthesis example

(1)Synthesis of Sub 3-3

After dissolving Sub1-1 (100 g, 598.05 mmol) in toluene (1000 ml), Sub 2-3 (192.70 g, 598.06 mmol), Pd ₂ (dba) ₃ (27.38 g, 29.90 mmol), NaO t -Bu (172.44g, 1794.19mmol), P( t -Bu) ₃ (12.10g, 59.81 mmol) was added, and the same procedure was followed for the synthesis of Sub 3-1 to obtain 178.34 g (yield: 73%) of the product.

(2) Synthesis of Sub A-21

After dissolving Sub 3-3 (110 g, 269.28 mmol) in toluene (1100 ml), Sub 4-3 (51.55 g, 269.26 mmol), Pd ₂ (dba) ₃ (12.33 g, 13.46 mmol), NaO t - Bu (77.64g, 807.82mmol), P( t -Bu) ₃ (5.45 g, 26.94 mmol) was added, and the same procedure was followed for the synthesis of Sub A-1 to obtain 92.76 g (yield: 66%) of the product. .

3. Sub A-25 Synthesis example

(1)Synthesis of Sub 3-4

After dissolving Sub1-1 (100 g, 598.05 mmol) in toluene (1000 ml), Sub 2-4 (192.70 g, 598.06 mmol), Pd ₂ (dba) ₃ (27.38 g, 29.90 mmol), NaO t -Bu (172.44g, 1794.19mmol), P( t -Bu) ₃ (12.10g, 59.81 mmol) was added, and the same procedure as in the synthesis of Sub 3-1 was carried out to obtain 168.57 g (yield: 69%) of the product.

(2) Synthesis of Sub A-25

After dissolving Sub 3-4 (100 g, 244.80 mmol) in toluene (1000 ml), Sub 4-4 (68.92 g, 244.80 mmol), Pd ₂ (dba) ₃ (11.21 g, 12.24 mmol), NaO t - Bu (70.58g, 734.37mmol), P( t -Bu) ₃ (4.95 g, 24.47 mmol) was added, and the same procedure was followed for the synthesis of Sub A-1 to obtain 95.43 g (yield: 64%) of the product. .

4. Sub A-30 Synthesis example

(1)Synthesis of Sub 3-5

After dissolving Sub1-1 (50 g, 299.03 mmol) in toluene (1000 ml), Sub 2-5 (73.60 g, 299.03 mmol), Pd ₂ (dba) ₃ (13.69 g, 14.95 mmol), NaO t -Bu (86.22g, 897.10mmol), P( t -Bu) ₃ (6.05 g, 29.91 mmol) was added, and the same procedure was followed for the synthesis of Sub 3-1 to obtain 74.56 g (yield: 75 %) of the product.

(2) Synthesis of Sub A-30

Sub 3-5 (35 g, 105.29 mmol) was dissolved in toluene (350 ml), Sub 4-5 (20.16 g, 105.29 mmol) was added, and Pd ₂ (dba) ₃ (4.82 g, 5.27 mmol), NaO t -Bu (30.36g, 315.89mmol), P( t -Bu) ₃ (4.26g, 10.53 mmol) was added, and then proceeded as in the synthesis method of Sub A-1 to obtain 33.58 g (yield: 72%) of the product got it

5. Sub A-58 Synthesis example

(1)Synthesis of Sub 3-6

After dissolving Sub1-2 (30 g, 138.08 mmol) in toluene (300 ml), Sub 2-6 (40.89 g, 138.08 mmol), Pd ₂ (dba) ₃ (6.32 g, 6.90 mmol), NaO t -Bu (39.81 g, 414.21 mmol), P( t -Bu) ₃ (2.79 g, 13.79 mmol) was added, and the same procedure as in the synthesis of Sub 3-1 was followed to obtain 38.23 g (yield: 64 %) of the product.

(2) Synthesis of Sub A-58

After dissolving Sub 3-6 (35 g, 80.92 mmol) in toluene (350 ml), Sub 4-3 (15.49 g, 80.92 mmol), Pd ₂ (dba) ₃ (3.71 g, 4.05 mmol), NaO t - Bu (23.33g, 242.74mmol), P( t -Bu) ₃ (1.64 g, 8.10 mmol) was added, and the same procedure was followed for the synthesis of Sub A-1 to obtain 30.32 g (yield: 69%) of the product. .

6. Sub A-63 Synthesis example

(1)Synthesis of Sub 3-7

After dissolving Sub1-3 (40 g, 164.40 mmol) in toluene (400 ml), Sub 2-5 (40.46 g, 164.40 mmol), Pd ₂ (dba) ₃ (7.53 g, 8.22 mmol), NaO t -Bu (47.4g, 493.20mmol), P( t -Bu) ₃ (3.33 g, 16.44 mmol) was added, and the same procedure was followed for the synthesis of Sub 3-1 to obtain 43.65 g (yield: 65%) of the product.

(2) Synthesis of Sub A-63

After dissolving Sub 3-7 (30 g, 73.44 mmol) in toluene (300 ml), Sub 4-3 (14.06 g, 73.44 mmol), Pd ₂ (dba) ₃ (3.36 g, 3.67 mmol), NaO t -Bu (21.17g, 220.32mmol), P( t -Bu) ₃ (1.49g, 7.34 mmol) was added, and the same procedure was followed for the synthesis of Sub A-1 to obtain 26.68 g (yield: 70%) of the product.

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

[Table 1]

Synthesis example of Sub B

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

<Scheme 3>

1. Sub B-1 Synthesis example

After dissolving Sub 2a-1 (50.0 g, 295.70 mmol) in toluene (500 ml), Sub 2b-1 (68.93 g, 295.70 mmol), Pd ₂ (dba) ₃ (13.54 g, 14.79 mmol), NaO t - Bu (85.26g, 887.11mmol) and P( t -Bu) ₃ (5.98g, 29.56 mmol) were added, followed by stirring at 100°C. When 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. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 66.38 g of a product (yield: 70%).

2. Sub B-3 Synthesis example

After dissolving Sub 2a-1 (50.0 g, 295.70 mmol) in toluene (500 ml), Sub 2b-3 (80.78 g, 295.71 mmol), Pd ₂ (dba) ₃ (13.54 g, 14.79 mmol), NaO t - Bu (85.26g, 887.11mmol) and P( t -Bu) ₃ (5.98g, 29.56 mmol) were added, followed by stirring at 100°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 72.62 g of a product (yield: 68%).

3. Sub B-4 Synthesis example

After dissolving Sub 2a-1 (50.0 g, 295.70 mmol) in toluene (500 ml), Sub 2b-4 (73.06 g, 295.70 mmol), Pd ₂ (dba) ₃ (13.54 g, 14.79 mmol), NaO t - Bu (85.26g, 887.11mmol) and P( t -Bu) ₃ (5.98g, 29.56 mmol) were added, followed by stirring at 100°C. When 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. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 64.47 g (yield: 65%) of the product.

The compound belonging to Sub B may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS values of the following compounds.

[Table 2]

Synthesis of final compound

1. of P-1 Synthesis example

After dissolving Sub A-1 (10 g, 19.26 mmol) in toluene (100 ml), Sub B-1 (6.19 g, 19.26 mmol), Pd ₂ (dba) ₃ (0.88 g, 0.96 mmol), NaO t - Bu (5.55 g, 57.75 mmol) and P( t -Bu) ₃ (0.39 g, 1.93 mmol) were added, followed by stirring at 100°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. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 9.51 g of a product (yield: 61%).

2. P-35's Synthesis example

After dissolving Sub A-25 (10 g, 16.42 mmol) in toluene (100 ml), Sub B-28 (5.74 g, 16.42 mmol), Pd ₂ (dba) ₃ (0.75 g, 0.82 mmol), NaO t -Bu (4.73g, 49.21mmol), P( t -Bu) ₃ (0.33g, 1.64 mmol) was added, and the mixture was stirred at 100°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. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 9.99 g (yield: 66%) of the product.

3. P-67 Synthesis example

After dissolving Sub A-47 (10 g, 19.27 mmol) in toluene (100 ml), Sub B-3 (6.96 g, 19.27 mmol), Pd ₂ (dba) ₃ (0.88 g, 0.96 mmol), NaO t - Bu (5.56 g, 57.85 mmol) and P( t -Bu) ₃ (0.39 g, 1.93 mmol) were added, followed by stirring at 100°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 10.57 g (yield: 65%) of the product.

4. P-99 Synthesis example

After dissolving Sub A-58 (10 g, 18.41 mmol) in toluene (100 ml), Sub B-1 (5.92 g, 18.41 mmol), Pd ₂ (dba) ₃ (0.84 g, 0.92 mmol), NaO t - Bu (5.31 g, 55.25 mmol) and P( t -Bu) ₃ (0.37 g, 1.83 mmol) were added, followed by stirring at 100°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 11.28 g of a product (yield: 74%).

FD-MS values of the compounds 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 One] Blue organic electroluminescent device ( light emitting 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 -diamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then N,N'-bis(1-naphthalenyl)-N,N'- bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Then, on the hole transport layer, the compound P-1 of the present invention was vacuum-deposited to a thickness of 20 nm to form a light emitting auxiliary layer, and then 4,10-di(naphthalen-2-yl) anthracene was deposited on the light emission auxiliary layer. As a host material, BD-052X (manufactured by Idemitsu kosan) was used as a dopant material, but the dopant was doped in a weight ratio of 96:4 to form a light emitting layer with a thickness of 30 nm.

Next, (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 was formed, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq ₃ ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

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

[ Example 2] to [ Example 16]

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 was used instead of the compound P-1 of the present invention as a light emitting auxiliary layer material.

[ comparative example 1] and [ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or 2 below was used instead of Compound P-1 of the present invention as a light emitting auxiliary layer material.

<Comparative compound 1> <Comparative compound 2>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 16, Comparative Example 1, and Comparative Example 2 of the present invention, the electroluminescence (EL) characteristics were measured with PR-650 of Photoresearch. It was measured, and the T95 lifespan was measured using the life measuring equipment of McScience at 500cd/m ² standard luminance. The measurement results are shown in Table 4 below.

[Table 4]

From Table 4, it can be seen that when the compound represented by Formula 1 of the present invention is used as a light emitting auxiliary layer material, the driving voltage can be lowered compared to Comparative Compound 1 or Comparative Compound 2, and the efficiency and lifespan are significantly improved. there is.

Comparative Compound 1 and Comparative Compound 2 are identical in that they contain two carbazole moieties and that one amine group is bonded to N of the carbazole, but differ in the position where N-carbazole is bonded to another carbazole. Do. That is, in the compound of the present invention, N-carbazole is bonded to the 1st or 4th position of the carbazole, Comparative Compound 2 is bonded to the 2nd position, and Comparative Compound 3 is bonded to the 3rd position.

When the compound of the present invention is used as a material for the light-emitting auxiliary layer, the device characteristics are improved because the HOMO values are different.

Table 5 below shows the HOMO values of Comparative Compound 1, Comparative Compound 2, and the compound of the present invention.

[Table 5]

As can be seen from Table 5, the HOMO values of the compounds of the present invention are greater than those of Comparative Compound 1 and Comparative Compound 2. As such, when the compound of the present invention having a large HOMO value is used as a material for the light-emitting auxiliary layer, it is considered that the hole mobility is improved because hole injection is performed smoothly compared to Comparative Compound 1 or Comparative Compound 2.

These results show that even if the core is the same compound, the physical properties of the compound, such as hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, electron blocking characteristics, etc., are different depending on the bonding position. This suggests that the difference in physical properties affects the device characteristics.

[Example 17] to [Example 26]

The compounds shown in Table 6 below were used for the light emitting auxiliary layer material and the host of the light emitting layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) was used instead of Alq ₃ as the electron transport layer material. Then, an organic electroluminescent device was manufactured in the same manner as in Example 1.

[Comparative Example 3]

The point of using bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) instead of Alq ₃ as the electron transport layer material is that compound 9-4 is used as the host of the light emitting layer without forming a light emitting auxiliary layer. An organic electroluminescent device was manufactured in the same manner as in Example 1, except that.

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 17 to 26 and Comparative Example 3 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, 500 cd /m ² Lifespan of T95 was measured using a life measuring device of McScience at standard luminance. The measurement results are shown in Table 6 below.

[Table 6]

From the results of Table 6, when the compound of the present invention represented by Formula 5 is used as a material for the light-emitting auxiliary layer and the compound represented by Formula 7 is used as a host, compared to Comparative Example 3 in which the light-emitting auxiliary layer is not formed It can be seen that the driving voltage is lowered, and the efficiency and lifespan are improved.

The compound of the present invention represented by the formula (5) has strong hole characteristics, and has increased stability to not only electrons but also holes, so that holes can be more efficiently transported in the hole transport layer.

Therefore, when the compound represented by Formula 5 is used as a material for the light emitting auxiliary layer and the compound represented by Formula 7 is used as a host, the combination of these materials is electrochemically synergistic, and it seems that the overall device is more improved.

In particular, referring to Examples 17 to 20, when a host is used in which a compound in which a tricyclic heterocycle such as dibenzofuran and/or deuterium is substituted, rather than a compound in which a simple aryl is substituted on both sides of the anthracene core, the driving voltage is not only However, it can be seen that the efficiency and lifespan are improved.

Therefore, when an organic electric device is manufactured by appropriately combining the compounds represented by Chemical Formulas 5 and 7, more holes move quickly and easily to the light emitting layer, thereby increasing the charge balance of holes and electrons in the light emitting layer. Light emission is well performed inside the light emitting layer rather than the hole transport layer interface, and thus deterioration at the HTL interface is also reduced, thereby lowering the driving voltage of the entire device, and improving efficiency and lifespan. That is, when the compound represented by Chemical Formula 5 and Chemical Formula 7 is properly combined, electrochemically synergistic effect appears to improve the performance of the entire device.

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 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 (18)

A compound represented by the following formula (1):
<Formula 1><Formula1-1>

In Formula 1,
V ¹ and V ² are each independently C(R),
wherein R is 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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N(R _a )(R _b ); And selected from the group consisting of Formula 1-1, at least one of R is Formula 1-1, R may combine with each other to form a ring with neighboring R ¹ ,
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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N(R _a )(R _b ); And selected from the group consisting of combinations thereof, adjacent groups may combine with each other to form a ring,
a is an integer of 0-2, b, c and d are each an integer of 0-4, and when these are integers 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,
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,
L ¹ is a C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group,
L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group,
The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group,
The 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 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 alkoxy group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group. The method of claim 1,
Formula 1 is a compound, characterized in that represented by Formula 2-1 or Formula 2-2:
<Formula 2-1><Formula2-2>

In Formulas 2-1 and 2-2, Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁴ , and a to d are the same as defined in claim 1. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 3-1 to 3-6:
<Formula 3-1><Formula3-2><Formula3-3>

<Formula 3-4><Formula3-5><Formula3-6>

In Formulas 3-1 to 3-6, Ar ¹ , Ar ² , R ¹ to R ⁴ , L ² , a to d are the same as defined in claim 1,
R ⁵ is 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 Alkoxy 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, and adjacent groups may combine with each other to form a ring,
e is an integer of 0-4, and when e is an integer of 2 or more, each of R ⁵ is the same as or different from each other,
L ³ is a single bond; C ₆ -C ₂₀ Arylene group; fluorenylene 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,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 4-1 to 4-4:
<Formula 4-1><Formula4-2>

<Formula 4-3><Formula4-4>

In Formulas 4-1 to 4-4, Ar ¹ , Ar ² , R ¹ to R ⁴ , L ² , a to d are the same as defined in claim 1,
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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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, and adjacent groups may combine with each other to form a ring,
e and f are each an integer of 0-4, and when they are an integer of 2 or more, each of R ⁵ and R ⁶ are the same as or different from each other. The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:

. a first electrode; a second electrode; An organic electric device including an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the formula (1) of claim 1. a first electrode; a second electrode; In the organic electric device comprising an organic material layer formed between the first electrode and the second electrode,
The organic material layer includes a light emitting layer, and a light emitting auxiliary layer formed between the light emitting layer and the first electrode,
The light emitting auxiliary layer includes a compound represented by the following formula (5),
The light emitting layer is an organic electric device comprising a compound represented by at least one of the following Chemical Formulas 6 to 8:
<Formula 5><Formula6>

<Formula 7><Formula8>

In Formulas 5 to 8,
R ¹ to R ⁴ , R ¹⁰ to R ⁴¹ 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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N(R _a )(R _b ); And selected from the group consisting of combinations thereof, adjacent groups may combine with each other to form a ring,
a is an integer of 0-2, b, c and d are each an integer of 0-4, and when these are integers 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,
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,
L ¹ is a C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group,
L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group,
The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And C ₂ ~ C ₆₀ It is selected from the group consisting of a heterocyclic group,
The 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 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 alkoxy group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; 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 Alkoxy 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group. 8. The method of claim 7,
The formula 7 is an organic electric device, characterized in that represented by the following formula 7-1:
<Formula 7-1>

In Formula 7-1, R ²² , R ²³ , R ²⁵ to R ²⁸ , R ³⁰ , R ³¹ are the same as defined in claim 7,
Ar is 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 An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; And C ₆ ~ C ₂₀ It is selected from the group consisting of an aryloxy group,
L is a single bond; C ₆ -C ₂₀ Arylene group; fluorenylene 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,
X is O or S;
R ^1′ and R ^2′ 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 Alkoxy 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, and adjacent groups may combine with each other to form a ring,
a' is an integer from 0 to 3, b' is an integer from 0 to 4, and when each of these is an integer of 2 or more, each of R ^1' and R ^2' are the same as or different from each other,
The aryl group, the fluorenyl group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, and a ring 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; 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 Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An 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 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group. 9. The method of claim 8,
The R ^1′ and R ^2′ are each independently hydrogen; heavy hydrogen; And C ₆ ~ C ₂₀ Organic electric device, characterized in that selected from the group consisting of an aryl group. 9. The method of claim 8,
At least one of Ar, R ^1' and R ^2' is a C ₆ ~ C ₆₀ aryl group in which one or more deuterium is substituted. 8. The method of claim 7,
The compound represented by Formula 5 is an organic electric device, characterized in that one of the following compounds:

8. The method of claim 7,
The compound represented by Formula 6 is an organic electric device, characterized in that one of the following compounds:

. 8. The method of claim 7,
The compound represented by Formula 7 is an organic electric device, characterized in that one of the following compounds:

. 8. The method of claim 7,
The compound represented by Formula 8 is an organic electric device, characterized in that one of the following compounds:

. 8. The method according to claim 6 or 7,
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. 16. The method of claim 15,
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 6 or 7; and
An electronic device comprising a; a control unit for driving the display device. 18. The method of claim 17,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, an electronic device, characterized in that selected from the group consisting of a single color lighting device and a quantum dot display device.

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