KR102663761B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a compound represented by Formula 1, an organic electric device 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 device. do. By including the compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered and the luminous efficiency and lifespan can be improved.

Description

Compounds for organic electric devices, organic electric devices using the same, and their electronic devices {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic electric devices that utilize the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic electric device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as organic layers in organic electric devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. In addition, the light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. there is. In addition, light-emitting materials can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to realize better natural colors.

On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interactions, and color purity is reduced or the efficiency of the device is reduced due to the luminescence attenuation effect. This causes an increase in color purity and energy transfer. In order to increase luminous efficiency through , a host/dopant system can be used as a luminescent material. The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

Currently, the portable display market is increasing in size toward large-area displays, which requires greater power consumption than that required for existing portable displays. Therefore, power consumption has become a very important factor for portable displays that have a limited power source such as batteries, and issues of efficiency and lifespan must also be resolved.

Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined. .

Therefore, there is a need to develop a light-emitting material that has high thermal stability and can efficiently achieve charge balance within the light-emitting layer. In other words, in order to fully demonstrate the excellent characteristics of organic electric devices, the materials that make up the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials. However, the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently developed, and in particular, the development of host materials for the light-emitting layer is urgently needed.

The purpose of the present invention is to provide a compound that can lower the driving voltage of the device and improve 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 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, not only can the driving voltage of the device be lowered, but also the luminous efficiency and lifespan of the device can be greatly improved.

1 to 3 are exemplary diagrams of organic electroluminescent devices according to the present invention.
Figure 4 shows a chemical formula according to one aspect of the present invention.

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or arylene group may include a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc. Additionally, unless otherwise stated herein, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

As used in the present invention, the term "fluorenyl group" or "fluorenylene group" refers to a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structure, respectively, unless otherwise specified. Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other and the carbon to which they are bonded This includes cases where they form a spiro compound together.

The term "spiro compound" used in the present invention has a 'spiro connection', and the spiro connection means a connection made by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms in one compound, they are 'monospiro-', 'dispiro-', and 'trispiro-' respectively. 'It is 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, each carbon number containing one or more heteroatoms. It refers to a ring numbered from 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 refers to a single ring containing heteroatoms, a ring aggregate, a fused multiple ring system, or a ring group. refers to compounds, etc.

The term "heterocyclic group" used in the present invention refers to a ring containing heteroatoms such as N, O, S, P or Si instead of carbon forming the ring, and "heteroaryl group" or "heteroarylene group". It includes not only aromatic rings such as but also non-aromatic rings, and may also include compounds containing heteroatoms such as SO ₂ , P=O, etc., such as the compounds below, instead of carbon forming a ring.

The term "aliphatic ring" used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes single rings, ring aggregates, fused multiple ring systems, spiro compounds, etc., and has the number of carbon atoms unless otherwise specified. It means a ring of 3 to 60, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it is an aliphatic ring.

In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent, may be written as the 'name of the group reflecting the valence', but is written as the 'name of the parent compound' You may. For example, in the case of 'phenanthrene', a type of aryl group, the name of the group may be written by distinguishing the valence, such as the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be written as the parent compound name, ‘phenanthrene’. Similarly, in the case of pyrimidine, it can be written as 'pyrimidine' regardless of the valence, or it can be written as the 'name of the group' of the valence, such as pyrimidineyl group in the case of monovalent group, pyrimidineylene in the case of divalent group, etc. there is.

Additionally, in this specification, when describing compound names or substituent names, 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, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless explicitly stated otherwise, the chemical formula used in the present invention is applied identically to the substituent definition according to the exponent definition of the following chemical formula.

Here, when a is an integer of 0, it means that the substituent R ¹ is absent. That is, when a is 0, it means that hydrogen is bonded to all carbons forming the benzene ring. In this case, the hydrogen bonded to the carbon is indicated as You can omit it and write the chemical formula or compound. 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 can be bonded as follows, for example, and a is 4 to 6 Even when it is an integer, it is bonded to the carbon of the benzene ring in a similar way, and when a is an integer of 2 or more, R ¹ may be the same or different.

In addition, unless otherwise specified in the specification, the ring formed by combining adjacent groups is an aromatic ring group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and combinations thereof.

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

When adding reference numerals to components in each drawing, it should be noted that identical components are given the same reference numerals as much as possible even if they are shown in different drawings. Additionally, 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 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 used to distinguish the component from other components, and the nature, sequence, or order of the component is not limited by the term. When a component is described as being “connected,” “coupled,” or “connected” to another component, that component may be directly connected or connected to that other component, but there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

Additionally, when a component, such as a layer, membrane, region, plate, etc., is said to be "on" or "on" another component, it means not only that it is "directly above" the other component, but also that there is another component in between. It should be understood that it can also include cases. Conversely, when an element is said to be "right on top" of another part, it should be understood to mean that there is no other part in between.

1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.

Referring to FIG. 1, the 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, and the second electrode 170 may be a cathode. 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, 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 may be formed sequentially on the first electrode 110.

Preferably, the luminous efficiency improvement layer 180 may be formed on one side of the first electrode 110 or the second electrode 170 that is not in contact with the organic layer, and when the luminous efficiency improvement layer 180 is formed, The light efficiency of organic electric devices can be improved.

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

Meanwhile, 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, and a hole injection layer 120 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 improvement layer 180 is formed on the second electrode. It 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.

Additionally, according to another embodiment of the present invention, the organic material layer may be formed in a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer. This will be explained with reference to FIG. 3 .

Referring to Figure 3, the organic electric device 300 according to another embodiment of the present invention has two stacks (ST1, ST2) of multi-layered organic material layers between the first electrode 110 and the second electrode 170. More than a set may be formed, and a charge generation layer (CGL) may be formed between the stacks of the 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. It may include (170) and a light efficiency improvement layer (180).

The first stack (ST1) is an organic material layer formed on the first electrode 110, which includes a first hole injection layer 320, a first hole transport layer 330, a first light emitting layer 340, and a first electron transport layer 350. ) may include, and the second stack (ST2) may include a second hole injection layer 420, a second hole transport layer 430, a second light-emitting layer 440, and a second electron transport layer 450. . In this way, the first stack and the second stack may be organic material layers with the same stacked structure, or they may be organic material layers with 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. This charge generation layer (CGL) is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the current efficiency generated in each light emitting layer and serves 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 may include a material doped with a greenish yellow dopant and a red dopant in a green host. However, the materials of the first light emitting layer 340 and the second light emitting layer 440 according to the embodiment of the present invention are not limited thereto.

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

When a plurality of light-emitting layers are formed using a multi-layer stack structure as shown in Figure 3, it is possible to manufacture an organic electroluminescent device that not only emits white light due to the mixing effect of the light emitted from each light-emitting layer, but also emits light of various colors. Organic electroluminescent devices that emit light can also be manufactured.

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

Even if the core is identical, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so research on the selection of the core and the combination of sub-substituents attached to it is required, and in particular, when the energy level and T ₁ value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using the compound represented by Formula 1 as a material for the light emitting layer (140, 340, 440), the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interface properties, etc.) By optimizing it, the lifespan and efficiency of organic electric devices can be improved simultaneously.

An 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, an anode 110 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120 is formed thereon. , It can be manufactured by 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, and then depositing a material that can be used as the cathode 170 thereon. there is. In addition, a light-emitting auxiliary 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. As shown, it can also be formed in a stack structure.

In addition, the organic material layer uses a variety of polymer materials, such as a solution process or solvent process rather than a deposition method, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, and doctor bleed process. It can be manufactured with fewer layers by methods such as a printing process, screen printing process, or 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 front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

Additionally, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices.

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 that controls the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

Hereinafter, a 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 can be defined as follows.

R ¹ to R ⁴ are independently hydrogen; deuterium, tritium; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); It is selected from the group consisting of, and neighboring groups can combine with each other to form a ring.

The ring formed by combining adjacent R ¹ , R ² , R ³ , and/or R ⁴ is an aromatic ring having C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ . When adjacent groups bond to each other to form an aromatic ring, preferably an aromatic ring of C ₆ to C ₃₀ , more preferably an aromatic ring of C ₆ to C ₁₄ , such as benzene, naphthalene, phenanthrene, etc. Aromatic rings can be formed.

a, b, and d are each an integer from 0 to 4, c is an integer from 0 to 3, 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 equal to each other or Different.

When R ¹ to R ⁴ are an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, etc.

When R ¹ to R ⁴ are a heterocyclic group, preferably a heterocyclic group of C ₂ to C ₃₀ , more preferably a heterocyclic group of C ₂ to C ₁₈ , such as pyridine, pyrimidine, triazine, dibenzothy. Ofene, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, benzofuropyridine, benzothienopyridine, indole, quinoxaline, quinazoline, dibenzoquinazoline, benzothienopyrazine, benzoyl It may be furopyrazine, naphthothyenopyrazine, naphthofuropyrazine, carbazole, benzocarbazole, phenylcarbazole, indolopyridine, etc.

Formula 1-1 is fused to Formula 1, where two adjacent v of Formula 1-1 are bonded to two adjacent * of Formula 1.

In Formula 1-1, v that is not fused (condensed) in Formula 1 is C(R ^c ), and R ^c is hydrogen; deuterium, tritium; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b );

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

R' and R" are independently of each other hydrogen; C ₆ ~ C ₆ aryl group; fluorenyl group; C ₃ ~ C ₆₀ hetero atom containing at least one heteroatom among O, N, S, Si, and P. Ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; and C ₆ ~ C ₆₀ aryloxy group; and R' and R" are combined with each other to form a ring. can do. When R' and R" combine with each other to form a ring, a spiro compound can be formed together with C to which they are bonded.

When R' and R" are alkyl groups, they may be preferably C ₁ to C ₂₀ alkyl groups, more preferably C ₁ to C ₁₀ alkyl groups such as methyl, t-butyl, etc.

When R' and R" are aryl groups, they may be preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, naphthyl, biphenyl, terphenyl, etc.

When R' and R" are heterocyclic groups, preferably heterocyclic groups of C ₂ to C ₃₀ , more preferably heterocyclic groups of C ₂ to C ₁₈ , such as pyridine, pyrimidine, triazine, quinoline, quina. It may be zoline, benzoquinazoline, quinoxaline, dimethylbenzoindenopyrimidine, benzothienopyrimidine, dibenzothiophene, dibenzofuran, carbazole, phenylcarbazole, naphthofuropyrimidine, etc.

R ⁵ is hydrogen; deuterium, tritium; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); It is selected from the group consisting of, and neighboring groups can combine with each other to form a ring.

The ring formed by combining adjacent R ⁵ groups is an aromatic ring group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ . When adjacent groups bond to each other to form an aromatic ring, preferably an aromatic ring of C ₆ to C ₃₀ , more preferably an aromatic ring of C ₆ to C ₁₄ , such as benzene, naphthalene, phenanthrene, etc. Aromatic rings can be formed.

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

When R ⁵ is an aryl group, it is preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, etc.

When R ⁵ is a heterocycle, preferably a heterocyclic group of C ₂ to C ₃₀ , more preferably a heterocyclic group of C ₂ to C ₁₈ , such as triazine, pyrimidine, pyridine, dibenzothiophene, dibenzothiophene, It may be benzofuran, carbazole, phenylcarbazole, benzocarbazole, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzimidazole, etc.

L' is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

When L' is an arylene group, it is preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, naphthylene, biphenyl, terphenyl, etc.

R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.

When R _a and R _b are aryl groups, they may be preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, naphthyl, biphenyl, terphenyl, etc.

When R _a and R _b are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₃ heterocyclic groups such as pyridine, pyrimidine, triazine, benzimidazole. , dibenzothiophene, benzonaphthothiophene, dibenzofuran, benzofuropyridine, carbazole, phenylcarbazole, indolopyridine, quinazoline, benzoquinazoline, benzothienopyrimidine, diphenylindeno. It may be pyrimidine, etc.

When R _a and R _b are fluorenyl groups, they may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-bispirofluorene, etc.

The rings formed by combining R ¹ to R ⁵ , R ^c , L', R _a , R _b , R', R", adjacent groups, and rings formed by combining R' and R" are 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; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; and combinations thereof; and may be further substituted with one or more substituents selected from the group consisting of.

Formula 1 may be represented by one of Formulas 2 to 5 below.

<Formula 2> <Formula 3> <Formula 4> <Formula 5>

In Formulas 2 to 5, R ¹ to R ⁴ , a to d, and * are as defined in Formula 1.

Additionally, Formula 1 may be represented by one of Formulas 6 to 9 below.

<Formula 6> <Formula 7>

<Formula 8> <Formula 9>

In Formulas 6 to 9, R ¹ to R ⁴ , a to d, R _a , R _b , L', * are as defined in Formula 1.

Additionally, Formula 1 may be represented by one of the following Formulas (a-1) to (d-16).

<Formula a-1> <Formula a-2> <Formula a-3> <Formula a-4>

<Formula a-5> <Formula a-6> <Formula a-7> <Formula a-8>

<Formula a-9> <Formula a-10> <Formula a-11> <Formula a-12>

<Formula a-13> <Formula a-14> <Formula a-15>

<Formula b-1><Formula b-2><Formula b-3><Formula b-4><Formula b-5>

<Formula b-6> <Formula b-7> <Formula b-8> <Formula b-9>

<Formula b-10> <Formula b-11> <Formula b-12> <Formula b-13>

<Formula b-14> <Formula b-15> <Formula b-16> <Formula b-17>

<Formula c-1> <Formula c-2 <Formula c-3> <Formula c-4>

<Formula c-5> <Formula c-6> <Formula c-7> <Formula c-8>

<Formula c-9> <Formula c-10> <Formula c-11>

<Formula d-1> <Formula d-2> <Formula d-3> <Formula d-4>

<Formula d-5> <Formula d-6> <Formula d-7> <Formula d-8>

<Formula d-9> <Formula d-10> <Formula d-11> <Formula d-12>

<Formula d-13> <Formula d-14> <Formula d-15> <Formula d-16>

In Formulas a-1 to d-16, R ¹ to R ⁵ , a to e, and X are as defined in Formula 1.

Formula 1-1 may be represented by one of the following Formulas A to F.

<Formula A> <Formula B> <Formula C>

<Formula D> <Formula E> <Formula F>

In the ^above formulas A to F ^, R ⁵ , v, In the case of an integer of 2 or more, each of R ⁶ is the same or different from each other.

Specifically, 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 comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer is one type of single compound or two or more types of the compound represented by Formula 1 above. Contains compounds.

In another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer. At this time, the light efficiency improvement layer is formed on one side of both sides of the anode or cathode that is not in contact with the organic material layer, and the organic material layer or light efficiency improvement layer includes the compound represented by Chemical Formula 1.

The organic layer includes at least one of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an auxiliary electron transport layer, an electron transport layer, and an electron injection layer. Preferably, the compound may be included in the light emitting 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 anode, and may further include a charge generation layer formed between the two or more stacks.

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

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

Synthesis example

The compound (final product) represented by Chemical Formula 1 according to the present invention may be prepared by reacting as shown in Scheme 1 to Scheme 2 below, but is not limited thereto. (Hal = Br, I or Cl)

<Scheme 1> When X is N(-L ¹ -Ar ¹ )

Two adjacent * combine with two adjacent v.

<Scheme 2> When X= NR', S, O, C(R')(R")

In the following reaction formula, two adjacent * are combined with two adjacent v, which means that at least one of R ¹ to R ⁵ is substituted with a halogen (represented as Hal below) element.

I. Synthesis of Core

1. Synthesis example of Core 1-1

(1) Synthesis of Core 1-1a

Compound 1a (10.56g, 26.00mmol), Pd(PPh ₃ ) ₄ in 9-(2-iodophenyl) -9H- carbazole (8.0g, 21.67mmol) (0.65g, 0.75mmol), Na ₂ CO ₃ (5.74g, 54.17mmol) and THF (100mL) were added, distilled water (25mL) was added, and the mixture was stirred at 80°C for 4 hours. When the reaction was completed, extraction was performed with Ethyl Acetate and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was subjected to a silica gel column to obtain 10.99 g of Core 1-1a (yield: 84%).

(2) Synthesis of Core 1-1

Core 1-1a (10.99g, 18.22mmol), Pd(OAc) ₂ (0.20g, 0.91mmol), P( t -Bu) ₃ (0.37g, 1.82mmol), K ₂ CO ₃ (7.55g, 54.63mmol) ), DMA (360mL) was added and refluxed at 170°C for 12 hours. When the reaction is completed, it is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ . After concentration, the resulting organic material was subjected to a silica gel column to obtain 7.33 g of the product Core 1-1 (yield: 71%).

2. Synthesis example of Core 1-27

(1) Synthesis of Core 1-27a

Compound _27a (6.71g, 16.47mmol), Pd(PPh 3 ) ₄ (0.48g, 0.41mmol), Na ₂ CO ₃ (5.74g, 54.17mmol) and THF (90mL) were added, distilled water (22mL) was added and stirred at 80°C for 4 hours. When the reaction was completed, extraction was performed with ethyl acetate and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was subjected to a silica gel column to obtain 7.81 g (yield: 80%) of the product Core 1-27a.

(2) Synthesis of Core 1-27

Core 1-27a (7.81g, 10.99mmol), Pd(OAc) ₂ (0.12g, 0.55mmol), P( t -Bu) ₃ (0.22g, 1.10mmol), K ₂ CO ₃ (4.56g, 32.97mmol) ), DMA (220mL) was added and refluxed at 170°C for 12 hours. When the reaction is completed, it is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Afterwards, the concentrate was subjected to a silica gel column to obtain 5.11 g (yield: 69%) of the product Core 1-27.

3. Synthesis example of Core 2-3

(1) Synthesis of Core 2-3b

Compound 3b (11.60g, 23.29mmol), (2-chlorophenyl)boronic acid (4.37g, 27.94mmol), Pd(PPh ₃ ) ₄ (0.81g, 0.70mmol), Na ₂ CO ₃ (6.17g, 58.21mmol) and THF (160mL) were added, distilled water (40mL) was added and stirred at 80°C for 4 hours. When the reaction was completed, extraction was performed with ethyl acetate and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was subjected to a silica gel column to obtain 8.32 g of product Core 2-3b (yield: 74%).

(2) Synthesis of Core 2-3b'

After dissolving Core 2-3b (8.32g, 17.23mmol) in Toluene (170mL), 2-chloroaniline (2.47g, 17.23mmol), Pd ₂ (dba) ₃ (0.16g, 0.17mmol), P( t -Bu ) ₃ (0.10g, 0.52mmol) and NaO t -Bu (3.31g, 34.46mmol) were added and stirred at 100°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 6.20 g (yield: 68%) of the product Core 2-3b'.

(3) Synthesis of Core 2-3

Core 2-3b' (6.20g, 11.71mmol) with Pd(OAc) ₂ (0.26g, 1.17mmol), P( t -Bu) ₃ (0.47g, 2.34mmol), K ₂ CO ₃ (9.71g, 70.26 mmol), DMA (240mL) was added and refluxed at 170°C for 12 hours. When the reaction was completed, it was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 3.21 g of product Core 2-3 (yield: 60%).

4. Synthesis example of Core 2-14

(1) Synthesis of Core 2-14b

Compound 14b (18.62g, 43.59mmol), 4-bromo-3-chloroaniline (7.50g, 36.32mmol), Pd(PPh ₃ ) ₄ (1.26g, 1.09mmol), Na ₂ CO ₃ (9.63g, 90.81mmol), Toluene (250mL) and EtOH (60mL) were added, distilled water (60mL) was added and stirred at 120°C for 6 hours. When the reaction was completed, extraction was performed with ethyl acetate and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 12.39 g (yield: 67%) of the product Core 2-14b.

(2) Synthesis of Core 2-14b'

Core 2-14b (10.62g, 20.86mmol), Pd(OAc) ₂ (0.23g, 1.04mmol), P( t -Bu) ₃ (0.42g, 2.09mmol), K ₂ CO ₃ (8.65g, 62.59mmol) ), DMA (420mL) was added and refluxed at 170°C for 12 hours. When the reaction was completed, it was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 7.30 g (yield: 74%) of the product Core 2-14b'.

(3) Synthesis of Core 2-14

Core 2-14b' (7.30g, 15.45mmol) is added to Acetonitrile (300mL), and then p -Toluenesulfonic acid monohydrate (8.82g, 46.34mmol) is added at 0℃. After 10 minutes, NaNO ₂ (2.13g, 30.90mmol) and KI (6.41g, 38.62mmol) were dissolved in distilled water (200mL) and then slowly added dropwise to the mixture. After the dropwise addition, the reaction temperature was gradually raised to room temperature and stirred for an additional 4 hours. When the reaction is completed, sodium thiosulfate is added to the reaction solution to terminate the reaction, and the reaction is extracted with Ethyl Acetate and water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was subjected to a silica gel column to obtain 5.32 g (yield: 59%) of Core 2-14.

5. Core 3-8 Synthesis example

(1) Synthesis of Core 3-8c

Compound 8c (9.36g, 18.25mmol), (2-bromophenyl)boronic acid (4.40g, 21.90mmol), Pd(PPh ₃ ) ₄ (0.63g, 0.55mmol), Na ₂ CO ₃ (4.84g, 45.63mmol) and THF (100mL) were added, distilled water (25mL) was added, and the mixture was stirred at 80°C for 4 hours. When the reaction was completed, extraction was performed with ethyl acetate and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was subjected to a silica gel column to obtain 7.42 g of the product Core 3-8c (yield: 69%).

(2) Synthesis of Core 3-8

Core 3-8c (7.42g, 12.60mmol) Pd(OAc) ₂ (0.14g, 0.63mmol), P( t -Bu) ₃ (0.25g, 1.26mmol), K ₂ CO ₃ (5.22g, 37.80mmol) ), DMA (250mL) was added and refluxed at 170°C for 12 hours. When the reaction is completed, it is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Afterwards, the concentrate was subjected to a silica gel column to obtain 4.86 g of product Core 3-8 (yield: 76%).

6. Synthesis example of Core 4-15

(1) Synthesis of Core 4-15d

Compound 15d (8.74g, 16.72mmol), (2-bromophenyl)boronic acid (4.03g, 20.06mmol), Pd(PPh ₃ ) ₄ (0.58g, 0.50mmol), Na ₂ CO ₃ (4.43g, 41.79mmol) and THF (100mL) were added, distilled water (25mL) was added, and the mixture was stirred at 80°C for 4 hours. When the reaction was completed, extraction was performed with ethyl acetate and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was subjected to a silica gel column to obtain 7.31 g (yield: 73%) of the product Core 4-15d.

(2) Synthesis of Core 4-15

Core 4-15d (7.31g, 12.20mmol) with Pd(OAc) ₂ (0.14g, 0.61mmol), P( t -Bu) ₃ (0.25g, 1.22mmol), K ₂ CO ₃ (5.06g, 36.61mmol) ), DMA (240mL) was added and refluxed at 170°C for 12 hours. When the reaction was completed, it was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was subjected to a silica gel column to obtain 4.30 g of the product Core 4-15 (yield: 68%). .

Compounds belonging to the core may be, but are not limited to, the following compounds, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 1]

II. Synthesis of Sub 2

Sub of Schemes 1 to 2 may be synthesized through the reaction routes of Schemes 3 to 5 below, but is not limited thereto. (Hal = Br, I or Cl)

<Scheme 3>

<Scheme 4>

<Scheme 5>

Examples of synthesis of specific compounds belonging to Sub 1 to Sub 3 are as follows.

1. Sub 1-1 Synthesis Example

After dissolving 2,4,6-trichloro-1,3,5-triazine (13.71g, 74.35mmol) in 270mL of THF, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (30.35g, 148.70mmol), Pd(PPh ₃ ) ₄ (4.30g, 3.72mmol), K ₂ CO ₃ (30.83g, 223.05mmol), and water (135mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 12.74 g of product Sub 1-1 (yield: 64%).

2. Sub 2-7 synthesis example

After dissolving 2-(4-chlorophenyl)quinazoline (8.60g, 35.73mmol) in 170mL of DMF, Bis(pinacolato)diboron (11.80g, 46.45mmol), Pd(dppf)Cl ₂ (1.31g, 1.79mmol), KOAc (10.52g, 107.19mmol) was added and stirred at 90°C. When the reaction was completed, DMF was removed through distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was separated using a silica gel column and recrystallized to obtain 9.14 g of product Sub 2-7 (yield: 77%).

3. Sub 3-5 synthesis example

2-bromodibenzo[ b,d ]thiophene (11.25g, 42.75mmol), Aniline (4.58g, 49.16mmol), Pd ₂ (dba) ₃ (1.96g, 2.14mmol), P( t -Bu) ₃ (0.86g) , 4.28mmol), NaO t -Bu (12.33g, 128.25mmol), and 230mL of Toluene were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 7.89 g of product Sub 3-5 (yield: 67%).

Compounds belonging to Sub 1 to Sub 3 may be the following compounds, and Table 2 shows the FD-MS values of the following compounds.

[Table 2]

III. Synthesis of final compound

1. P1-1 synthesis example

After dissolving Core 1-1 (5.72g, 10.09mmol) in 120mL of THF, Sub 2-1 (3.62g, 10.09mmol), Pd(PPh ₃ ) ₄ (0.58g, 0.50mmol), K ₂ CO ₃ (4.18 g, 30.26 mmol), 60 mL of water was added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 5.09 g of product P1-1 (yield: 66%).

2. P1-35 synthesis example

Core 1-24 (6.65g, 13.09mmol), Sub 3-7 (6.03g, 15.05mmol), Pd ₂ (dba) ₃ (0.60g, 0.65mmol), P( t -Bu) ₃ (0.26g, 1.31 mmol), NaO t -Bu (3.77g, 39.27mmol), and 150mL of Toluene were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 8.10 g of product P1-35 (yield: 71%).

3. P2-3 synthesis example

Core 2-3 (9.14g, 20.02mmol), Sub 1-12 (7.33g, 22.02mmol), Pd ₂ (dba) ₃ (0.18g, 0.20mmol), P( t -Bu) ₃ (0.12g, 0.60) mmol), NaO t -Bu (2.89g, 30.03mmol), and 180mL of Toluene were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 11.21 g of product P2-3 (yield: 76%).

The FD-MS values of compounds P1-1 to P4-28 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[Example 1] Red organic electroluminescent device (phosphorescent host)

N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene on the ITO layer (anode) formed on the glass substrate. -1,4-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.

Thereafter, on the hole transport layer, compound P1-1 of the present invention was used as a host material, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter referred to as (piq) ₂ Ir(acac)) as a dopant was applied at a ratio of 95:5. A light emitting layer with a thickness of 30 nm was formed using the weight ratio.

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 emitting layer to form a hole blocking layer. Then, Bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) was deposited on the hole blocking layer to a thickness of 50 nm to form an electron transport layer. Afterwards, 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 17]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds of the present invention listed in Table 4 below were used as the phosphorescent host material instead of the compound P1-1 of the present invention.

[ Comparative example 1] and [ Comparative example 2]

An organic electroluminescent device was manufactured in the same manner as Example 1, except that Comparative Compounds 1 to 2 shown in Table 4 below were used as the phosphorescent host material instead of Compound P1-1 of the present invention.

<Comparative compound 1> <Comparative compound 2>

Electroluminescence (EL) characteristics were obtained using PR-650 from Photoresearch by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured in Examples 1 to 17, Comparative Examples 1, and 2 of the present invention. The T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience at a standard luminance of 5000 cd/m ² . The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results in Table 4, when a red organic light emitting device is manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, the driving of the organic light emitting device is lower than when comparative compounds 1 to 2 are used. Not only can the voltage be lowered, but efficiency and lifespan have been significantly improved.

In detail, the comparative compound and the compound of the present invention are similar in that they contain a dibenzo[4,5:6,7]azepino[3,2,1 -jk ]carbazole moiety, but the simple The performance of the device using Comparative Compound 2 with an indole ring condensed was more improved than Comparative Compound 1 with an aryl condensation, and the device had three or more rings such as carbazole, dibenzothiophene, and benzonaphthothiophene than Comparative Compound 2. It was confirmed that the device results of Examples 1 to 17 manufactured with the mutually condensed compounds of the present invention showed significantly excellent results in terms of driving voltage, efficiency, and lifespan.

These results can be explained by the energy band gap of the parent core structure of the comparative compound and the present invention compound. Referring to Table 5 below, the parent core structure of the compound of the present invention has an energy band gap compared to the parent core structure of Comparative Compound 1 and Comparative Compound 2. You can see that this is narrower. As a result, the dopant, which has a very narrow energy band gap compared to the host, and the compound of the present invention have the most appropriate energy level difference, and as a result, the charge balance increases, which appears to enable better light emission inside the light-emitting layer.

[Table 5]

The above description is merely an illustrative description of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

100, 200, 300: Organic electric element 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 (13)

Compound represented by the following formula 1:
<Formula 1><Formula1-1>

In Formula 1,
R ¹ to R ⁴ are independently hydrogen; deuterium, tritium; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); is selected from the group consisting of, and adjacent groups can combine with each other to form a ring,
a, b, and d are each an integer from 0 to 4, c is an integer from 0 to 3, 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 equal to each other or different,
Formula 1-1 is fused to Formula 1, wherein two adjacent v of Formula 1-1 are bonded to two adjacent * of Formula 1,
In Formula 1-1,
v that is not fused to Formula 1 is C(R ^c ),
R ^c is hydrogen; deuterium, tritium; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); is selected from the group consisting of,
X is C(R')(R"), N(R'), O or S,
R' and R" are independently of each other hydrogen; C ₆ ~ C ₆ aryl group; fluorenyl group; C ₃ ~ C ₆₀ hetero atom containing at least one heteroatom among O, N, S, Si, and P. Ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; and C ₆ ~ C ₆₀ aryloxy group; and R' and R" are combined with each other to form a ring. You can do it,
R ⁵ is hydrogen; deuterium, tritium; halogen; Cyano group; nitro group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); is selected from the group consisting of, and adjacent groups can combine with each other to form a ring,
e is an integer from 0 to 4, and when e is an integer of 2 or more, R ⁵ is the same as or different from each other,
Wherein L' is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P;
R _a and R _b are each independently an aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring; and a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.
The rings formed by combining R ¹ to R ⁵ , R ^c , L', R _a , R _b , R', R", adjacent groups, and rings formed by combining R' and R" are Deuterium, respectively; halogen; Silane group substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne group; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; and combinations thereof; and may be further substituted with one or more substituents selected from the group consisting of: According to clause 1,
The above Chemical Formula 1 is a compound characterized in that it is represented by one of the following Chemical Formulas 2 to 5:
<Formula 2><Formula3><Formula4><Formula5>

In Formulas 2 to 5, R ¹ to R ⁴ , a to d, and * are as defined in claim 1. According to clause 1,
The above Chemical Formula 1 is a compound characterized in that it is represented by one of the following Chemical Formulas 6 to 9:
<Formula 6><Formula7>

<Formula 8><Formula9>

In Formulas 6 to 9, R ¹ to R ⁴ , a to d, R _a , R _b , L', * are as defined in claim 1. According to clause 1,
The above Chemical Formula 1-1 is a compound characterized in that any one of the following Chemical Formulas A to F:
<Formula A><FormulaB><FormulaC>

<Formula D><FormulaE><FormulaF>

In ^the above formulas A to F ^, R ⁵ , v, If is an integer of 2 or more, each of R ⁶ is the same or different from each other. According to clause 1,
Formula 1 is a compound characterized in that it is one of the following compounds:





. In an organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode,
The organic material layer is an organic electric device characterized in that it contains a single compound or two or more compounds represented by the formula (1) of claim 1. In an organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer,
The light efficiency improvement layer is formed on one side of both sides of the anode or cathode that is not in contact with the organic layer,
The organic material layer or the light efficiency improvement layer is an organic electric device characterized in that it contains a compound represented by the formula 1 of claim 1. According to claim 6 or 7,
The organic material layer is an organic electric device characterized in that it 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. According to clause 8,
An organic electric device, characterized in that the light-emitting layer contains the compound. According to claim 6 or 7,
The organic material layer is an organic electric device characterized in that it includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode. According to clause 10,
The organic material layer is an organic electric device, characterized in that it further includes a charge generation layer formed between the two or more stacks. A display device including the organic electric element of claim 6 or 7; and
An electronic device comprising a control unit that drives the display device. According to clause 12,
The organic electric device is an electronic device characterized in that it is selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices.