KR20210023223A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

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

Description

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

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

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

Materials used as an organic material layer in an organic electronic device 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, according to their functions. And the light-emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and according to the light emitting mechanism, it can be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron. have. In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a long wavelength due to the interaction between molecules, and the color purity decreases or the efficiency of the device decreases due to the light-emitting attenuation effect.Therefore, the increase in color purity and energy transfer A host/dopant system may be used as a light-emitting material in order to increase the luminous efficiency through. The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light-emitting layer is mixed in the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is increasing in size as a large-area display, and for this reason, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for portable displays that have a limited power supply source, such as a battery, and efficiency and life issues are also important factors that must be solved.

Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan. However, the efficiency cannot be maximized simply by improving the organic material layer. This is because the long life and high efficiency can be achieved at the same time when the energy level and T1 value between the organic material layers, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.

In addition, in order to solve the problem of light emission in the hole transport layer in recent organic electroluminescent devices, a method of using a light emitting auxiliary layer between the hole transport layer and the light emitting layer is being studied. Since material properties are different, it is time to develop a light-emitting auxiliary layer for each light-emitting layer.

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

However, in the case of a material used in the hole transport layer, since it must have a low HOMO value, most have a low T ₁ value, and as a result, excitons generated in the light emitting layer pass to the hole transport layer interface or the hole transport layer, and as a result, the hole transport layer. It causes light emission at the interface or charge unbalance in the light emitting layer to emit light at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are deteriorated, and the lifespan is shortened. Therefore, it must be a material having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, has a high T1 value, and is within a suitable driving voltage range (within the driving voltage range of the blue device of the full device). Mobility) is required to develop a light-emitting auxiliary layer.

However, this cannot be achieved simply due to the structural characteristics of the core of the light-emitting auxiliary layer material, and the characteristics of the core and sub-substituent of the light-emitting auxiliary layer material, and a suitable combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer are made. When it is lost, a high-efficiency and high-life device can be implemented.

Meanwhile, development of materials for a light-emitting layer and a light-emitting auxiliary layer having stable properties, that is, a high glass transition temperature, against Joule heating generated when the device is driven is also required. The low glass transition temperature of the light emitting layer and the light emitting auxiliary layer material decreases the uniformity of the thin film surface when the device is driven, and the material may be deformed due to heat generated when the device is driven, which has been reported to have a great influence on the life of the device.

Therefore, it is necessary to develop a material that can withstand a long time during evaporation, that is, a material with strong heat resistance, and materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, and light emission, are required to fully exhibit the excellent characteristics of organic electronic devices. A material, an electron transport material, an electron injection material, a light-emitting auxiliary layer material, etc. must be supported by a stable and efficient material. In particular, development of materials used for a light-emitting auxiliary layer and a light-emitting layer is required.

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

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

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

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

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

The terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, 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 conjugated ring system, a spiro compound, and the like. In addition, unless otherwise stated in the specification, a fluorenyl group may be included in the aryl group, and a fluorenylene group may be included in the arylene group.

The terms "fluorenyl group", "fluorenylene group", and "fluorentriyl group" used in the present invention are monovalent, 2 in which R, R'and R" are all hydrogen in the following structures, respectively, unless otherwise specified. It means a valence or trivalent functional group, "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorentriyl group" means that at least one of the substituents R, R', R" is other than hydrogen It means that it is a substituent, and includes the case where R and R'are bonded to each other to form a spy compound together with the carbon to which they are bonded. In the present specification, a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of the valence.

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

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

The term "aliphatic ring group" as used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It refers to 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 is 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 substituent may describe'the name of the group reflecting the number', but is described as'parent compound name' You may. For example, in the case of'phenanthrene', which is a kind of aryl group, the monovalent'group' is'phenanthryl' and the divalent group can be labeled with the valence by dividing the valency such as'phenanthrylene'. Regardless, it may be described as the parent compound name'phenanthrene'. Similarly, in the case of pyrimidine, it may be described as'pyrimidine' regardless of the valence, or in the case of monovalent, it may be described as the'name of the group' of the corresponding valency, such as a pyrimidinyl group and in the case of divalent, pyrimidinylene. have.

In addition, in the present specification, when describing the name of the compound or the name of the substituent, 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 or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

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

Here, when a is an integer of 0, the substituent R ¹ means that the substituent R 1 is absent, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6 In the case of 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 or different from each other.

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

In addition, unless otherwise specified in the specification, when a ring is expressed in the form of a'numeric resource' such as a five-membered ring, a six-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 five-membered ring, and benzene or pyridine may correspond to a six-membered ring.

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

At this time, unless otherwise described in the specification, the term'neighboring groups' refers to the following formula as an example, _{between R 1} and R _2, between R ₂ and R _3, between R ₃ and R ₄ , Not only R ₅ and R _{6 but also R 7} and R ₈ sharing one carbon are included, and are not immediately adjacent, such as between _{R 1} and R ₇ , R ₁ and R _8, or R ₄ and R _5. Substituents bonded to ring elements (such as carbon or nitrogen) may also be included. In other words, if there are substituents on a ring element such as carbon or nitrogen immediately adjacent to each other, they may be neighboring groups, but if no substituent is bonded to the ring element at the immediately adjacent position, it is bonded to the next ring element. It may be a group adjacent to the substituted substituent, and also the substituents bonded to the carbon constituting the same ring may be referred to as neighboring groups.

In the following formula, _{when substituents bonded to the same carbon as R 7} and R ₈ are bonded to 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 can be bonded to each other to form a ring' is used in the same meaning as'neighboring groups are bonded to each other to selectively form a ring', and at least one pair of It refers to a case where neighboring groups are bonded to each other to form a ring.

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

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

In describing the constituent elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are for distinguishing the constituent element from other constituent elements, and the nature, order, or order of the constituent element 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 another component between each component It will be understood that elements may be “connected”, “coupled” or “connected”.

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

1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) And an organic material layer formed between the second electrode 170.

The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, a first electrode may be a cathode and a 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 sequentially formed on the first electrode 110.

Preferably, the light efficiency improvement 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 improvement layer 180 is formed The light efficiency of the organic electric device can be improved.

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

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

Referring to FIG. 2, an 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, which are sequentially formed on the first electrode 110. 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 may be included, and a light efficiency improvement 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, an emission layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

Referring to FIG. 3, in an organic electric device 300 according to another embodiment of the present invention, two stacks ST1 and ST2 formed of a multi-layered organic material layer are disposed between the first electrode 110 and the second electrode 170. A set or more 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 the embodiment of the present invention includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a light efficiency improvement 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 laminated structure, but may be organic material layers having different laminated 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 generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase current efficiency generated in each emission layer and smoothly distribute electric charges.

The first emission layer 340 may include a light emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first emission layer 340 and the second emission 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, 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 by the multi-layer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electroluminescent device in which white light is emitted by the mixing effect of light emitted from each of the light-emitting layers, as well as various colors of light. 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 emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material for the light efficiency improvement layer 180, but preferably, the light emitting layer 140, 340, 440, the light emitting auxiliary layer 220 ) And/or the light efficiency improvement layer 180 may be used as a material.

Since the band gap, electrical properties, and interfacial properties can vary depending on which substituent is bonded to any position even with the same and similar core, a study on the selection of the core and the combination of sub-substituents bonded thereto _{In particular, long life 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 layer 140, 340, 440, the light emitting auxiliary layer 220, and/or the light efficiency improving layer 180, the energy level and T _{1 between each organic material layer} By optimizing the value and intrinsic properties of the material (mobility, interfacial properties, etc.), it is possible to improve the life and efficiency of the organic electric device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate to form the anode 110, and a 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. have. In addition, a light emitting auxiliary layer 220 between the hole transport layer 130 and the light emitting layer 140, and an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 may be further formed. It can also be formed in a stack structure as shown.

In addition, the organic material layer is a solution process or a solvent process other than a vapor 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, and a doctor blaze. It can be manufactured with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

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

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

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired 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 an aspect of the present invention will be described.

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

<Formula 1> <Formula 2>

Symbols of Formulas 1 and 2 may be defined as follows.

The * part of Formula 1 and the * part of Formula 2 are condensed with each other. That is, at least a 9-condensed ring may be formed by bonding of * in Formula 2 to an adjacent pair of * in Formula 1.

X is O or S, and Y is O, S, C=O, C(R ⁶ )(R ⁷ ) or N(R ⁸ ).

R ¹ to R ⁷ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; Alkynyl group of C ₂ ~ C _30; An alkoxyl group of C ₁ to C _30; C ₆ ~ C ₃₀ aryloxy group; -LN(R _a ) (R _b ); And it is selected from the group consisting of a combination thereof, and neighboring groups may be bonded to each other to form a ring.

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

The ring formed by bonding of adjacent groups to each other is an aromatic ring group of _{C 6} ~ C _60; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ aliphatic ring group; may be selected from the group consisting of.

When adjacent groups are bonded to each other to form an aromatic ring, preferably a C ₆ ~ C ₂₀ aromatic ring, more preferably a C ₆ ~ C ₁₄ aromatic ring, such as benzene, naphthalene, phenanthrene, etc., or , May form a ring containing a benzene moiety.

When R ¹ to R ⁵ 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, triphenylene Etc.

When R ¹ to R ⁵ are heterocyclic _{groups, preferably a C 2} to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group such as pyridine, pyrimidine, triazine, quinoline, iso Quinoline, quinazoline, benzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, carbazole, phenylcarbazole, benzocarbazole, phenylbenzocarbazole, dibenzothiophene, dibenzofuran, naphthobenzothy Offene, naphthobenzofuran, benzothienopyrimidine, naphthofuropyridine, naphthofuropyrimidine, benzofuropyrimidine, naphthothienopyrimidine, pyridopyrazine, pyrimidoindole, phenylpyrimido It may be indole, pyrimidoindole, dimethyl indenopyrimidine, benzothienotriazine, benzothienothienopyrimidine, benzoxazole, cinnoline, spiro[fluorene indeno]pyrimidine, etc. .

When R ⁶ and R ⁷ 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, and the like.

When R ⁶ and R ⁷ are an alkyl group, preferably a C ₁ to C ₃₀ alkyl group, more preferably a C ₁ to C ₃₀ alkyl group, such as methyl, ethyl, propyl, and the like.

When R ⁶ and R ⁷ are bonded to each other to form a ring, a spy compound may be formed.

R ⁸ is a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; And -LN (R _a ) (R _b ) It may be selected from the group consisting of, neighboring groups may be bonded to each other to form a ring. When R ⁸ forms a ring with neighboring R ¹ , neighboring R ² , neighboring R ³ , neighboring R ^5, etc., a heterocycle containing N such as a pyrrole moiety, an indole moiety, etc. Can be formed.

When R ⁸ is 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, phenanthrene, and the like.

When R ⁸ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₆ heterocyclic group such as pyridine, pyrimidine, triazine, quinazoline, quinoxaline, Benzodioxinopyrazine, dibenzothiophene, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, naphthyridine, benzofuropyrimidine, benzothienopyrimidine, and the like.

L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; And it may be selected from the group consisting of a combination thereof.

When L is an arylene group, preferably a C ₆ to C ₃₀ arylene group, more preferably a C ₆ to C ₁₈ arylene group, such as phenylene, naphthylene, biphenylene, terphenyl, and the like.

R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

When R _a and R _b 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, and the like.

When R _a and R _b are heterocyclic _{groups, preferably a C 2} to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₅ heterocyclic group such as dibenzofuran, dibenzothiophene, naphtho Benzothiophene, naphthobenzofuran, spiro[fluorene-9,9'-xanthene], P-45, dibenzodioxin, phenoxatin, carbazole, phenylcarbazole, benzoxazole, spiroacridinflu It may be an orange, etc.

When R _a and R _b are fluorenyl groups, 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-(naphthalen-2-yl)9 -phenyl -9 H-fluorene, and the like.

The R ¹ to R ⁸ , and the rings formed by bonding of adjacent groups to each other, respectively, 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; A C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ arylthio group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; Alkynyl group of C ₂ -C _20; C ₆ -C ₂₀ aryl group; Fluorenyl group; _{A heterocyclic group of C 2} -C ₂₀ including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An aliphatic ring group of C ₃ -C _20; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -LN(R _a ) (R _b ); And it may be further substituted with one or more substituents selected from the group consisting of a combination thereof. Here, L, R _a and R _b are as defined above.

Illustratively, Formula 1 may be represented by one of Formulas 3 to 20 below.

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

<Formula 6> <Formula 7> <Formula 8>

<Formula 9> <Formula 10> <Formula 11>

<Formula 12> <Formula 13> <Formula 14>

<Formula 15> <Formula 16> <Formula 17>

<Formula 18> <Formula 19> <Formula 20>

In Formulas 3 to 20, X, Y, R ¹ to R ⁵ and a to e are the same as defined in Formula 1.

In addition, by way of example, Formula 1 may be represented by one of Formulas 21 to 36 below.

<Formula 21> <Formula 22> <Formula 23>

<Formula 24> <Formula 25> <Formula 26>

<Formula 27> <Formula 28> <Formula 29>

<Formula 30> <Formula 31> <Formula 32>

<Formula 33> <Formula 34>

<Formula 35> <Formula 36>

In Chemical Formulas 21 to 36, X, R ¹ to R ⁸ and a to e are the same as defined in Chemical Formula 1.

Preferably ^{, at least one of R 1} to R ⁵ may be represented by the following Formula 1-1 or 1-2.

<Formula 1-1>

<Formula 1-2>

In Formulas 1-1 and 1-2, L ² is the same as L in Formula 1, and Ar ² and Ar ³ are defined the same as _{R a} and R _b in Formula 1.

L ¹ is a single bond; C ₆ ~ C ₂₀ arylene group; Fluorenylene group; _{And a C 2} ~ C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; may be selected from the group consisting of, Ar ¹ is a C ₆ -C ₆₀ aryl group; Fluorenyl group; _{And a C 2} -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si, and P. It may be selected from the group consisting of.

In addition, preferably ^{, at least one of R 1} to R ⁵ may be represented by the following Formula 2-1 or Formula 2-2.

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

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

Z ¹ to Z ⁸ are each independently N or C(R ₁ ), ^{at least one of Z 1} to Z ⁵ is N, and at least one of Z ⁶ to Z ⁸ is N.

L ₁ is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si and P may be selected from the group consisting of _{a C 2} ~ C _{60 heterocyclic group containing at least one heteroatom.}

C ring is a C ₆ ~ C ₆₀ aromatic ring group; Or O, N, S, Si and P is a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom, the C ring may be further substituted with one or more of the same or different R _1.

R ₁ 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; A C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ arylthio group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; Alkynyl group of C ₂ -C _20; C ₆ -C ₂₀ aryl group; Fluorenyl group; _{A heterocyclic group of C 2} -C ₂₀ including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An aliphatic ring group of C ₃ -C _20; A C ₇ -C ₂₀ arylalkyl group; And it _{is selected from the group consisting of arylalkenyl group of C 8} -C ₂₀ , and neighboring groups may be bonded to each other to form a ring.

In Formula 2-2, the C ring may be selected from the group consisting of the following Formulas 3-1 to 3-6.

<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, Z ⁶ to Z ⁸ , R ₁ , L ₁ are the same as defined in Formula 2-2, o is an integer of 0 to 4, p is an integer of 0 to 6, q is an integer of 0 to 8, and when _{each of them is an integer of 2 or more, each of R 1} is the same as or different from each other, X ₁ and X ₂ are independently O or S, and e and f are each an integer of 0 or 1 And at least one of e and f is 1.

Specifically, the compound represented by Formula 1 may be one of the following compounds.

.

.

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 single compound or two or more 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. In this case, the light efficiency improvement layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improvement layer includes the compound represented by Formula 1 above.

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

The organic material layer may include two or more stacks including a hole transport layer, an emission 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 an electronic device including a display device including an organic electric device represented by Formula 1 and a control unit for driving the display device.

Hereinafter, examples for synthesizing the compound represented by Chemical Formula 1 according to the present invention and an example for preparing an organic electric device according to the present invention will be described in detail, 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 the following Scheme 1 or Scheme 2, but is not limited thereto.

<Reaction Scheme 1>

In Sub1, _one of R 1 to R ₄ is Cl or Br, and the others are the same as ^{R 1} to R ^4. When ^{at least one of R 1} to R ⁴ is an amine group, it may be synthesized according to a reaction path for reacting Sub1 and Sub3, and for other substituents, a reaction path for reacting Sub1 and Sub5.

Y is S, O, C(R ⁶ )(R ⁷ ) or N(R ⁸ ), and in Sub5, R is ^{a substituent R 1} to R bonded to the final compound instead of Cl in _{R 1} to R _{4 of Sub1} ^{It is 4} .

<Reaction Scheme 2>

When Y of the final compound is N (R ⁸ ), it can be synthesized by reacting Sub2 and Sub4 as shown in Scheme 2 above.

I. Sub1 And Sub2 Synthesis example

Sub1 and Sub2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but are not limited thereto.

<Reaction Scheme 3>

One. Sub1 - 1 Synthesis example

(1) Sub1-1b synthesis

3-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (20.9 g, 0.08 mol) in Sub1-1a (30 g, 0.08 mol), Pd (PPh ₃ ) ₄ (2.8 g, 0.002 mol), NaOH (9.8 g, 0.25 mol), THF (165 mL), and water (50 mL) were added and reacted for 6 hours. When the reaction is complete, the temperature of the reactant is cooled to room temperature, and THF and H ₂ O are removed. Then, after extraction with MC and washing with water, the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 30 g (79.9%) of the product Sub1-1b.

(2) Sub1-1 synthesis

_{Pd(OAc) 2} (0.44 g, 0.003 mol), 3-nitropyridine (0.24 g, 0.003 mol) was added to Sub1-1b (30 g, 0.07 mol) _{and C 6} F ₆ (100 ml), DMI (130 ml) After dissolving with, tert-butyl peroxybenzoate (38.2 g, 0.197 mol) was added and stirred at 90°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 25 g (83.7%) of the product Sub1-1.

2. Sub1-10 synthesis example

(1) Sub1-10b synthesis

Methyl 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (23.3 g, 0.08 mol) in Sub1-10a (30 g, 0.08 mol), After adding Pd(PPh ₃ ) ₄ (2.7 g, 0.002 mol), NaOH (9.4 g, 0.24 mol), THF (150 mL), and water (40 mL), proceed in the same manner as the synthesis method of Sub1-1b, the product Sub1- 10b 37 g (91.1%) was obtained.

(2) Sub1-10 synthesis

After adding phenylmagnesium bromide 1.0M in THF (36.8 g, 0.20 mol) and THF (135ml) to Sub 1-10b (35 g, 0.07 mol) to obtain an intermediate product, acetic acid solution (300ml) and HCl ( 5 ml) was added. Then, after stirring at room temperature for 24 hours, a pyridine aqueous solution (700ml, pyridine:H ₂ O = 1: 5) was slowly added dropwise and stirred under reflux for 30 minutes. 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 40 g (94.8%) of the product Sub1-10.

3. Sub1-15 Synthesis Example

(1) Sub1-15b synthesis

2-(5-chloro-2-(methylsulfinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23.6 g, 0.08 mol) in Sub1-15a (30 g, 0.08 mol) , Pd(PPh ₃ ) ₄ (2.7 g, 0.002 mol), NaOH (9.4 g, 0.24 mol), THF (160 mL), and water (50 mL) were added, and then proceeded as in the synthesis method of Sub1-1b, and the product Sub1 -15b 31 g (75.9%) was obtained.

(2) Sub1-15c synthesis

_{Add H 2} SO ₄ (100 ml) to Sub1-15b (31 g, 0.06 mol) and reflux for 6 hours. When the reaction was completed, it was slowly added to a 2M NaOH aqueous solution, and then cooled to room temperature. Thereafter, 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 28 g (96.4%) of the product Sub1-15c.

(3) Sub1-15 synthesis

2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in Sub1-15c (28 g, 0.06 mol) (18.1 g, 0.06 mol), Pd(PPh ₃ ) ₄ (2 g, 0.002 mol), NaOH (6.9 g, 0.17 mol), THF (120 mL), added to water (40 mL), and the synthesis method of Sub1-1b Proceeding in the same way, product Sub1-15 32 g (87.1%) was obtained.

4. Sub1-18 synthesis example

(1) Sub1-18b synthesis

4,4,5,5-tetramethyl-2-(3-(methylsulfinyl)-[1,1'-biphenyl]-4-yl)-1,3,2- in Sub1-18a (40 g, 0.09 mol) After adding dioxaborolane (29.7 g, 0.09 mol), Pd(PPh ₃ ) ₄ (3 g, 0.003 mol), NaOH (10.4 g, 0.26 mol), THF (180 mL), and water (60 mL), the Sub1-1b Proceeding according to the synthesis method of the product Sub1-18b 40 g (77.3%) was obtained.

(2) Sub1-18 synthesis

_{After adding H 2} SO ₄ (150 ml) to Sub1-18 (40 g, 0.07 mol) and refluxed for 6 hours, proceed in the same manner as the synthesis method of Sub1-15c to obtain 35 g (92.5%) of the product Sub1-18. Got it.

5. Sub1 -22 Synthesis example

(1) Sub1-22b synthesis

2-chloroaniline (26.3 g, 0.07 mol) in Sub1-22a (30 g, 0.07 mol), Pd ₂ (dba) ₃ (1.8 g, 0.002 mol), 50% P( t- Bu) ₃ (1.6 g, 0.004 mol), NaO t -Bu (18.8 g, 0.2 mol), toluene (130ml) was added and stirred at 90°C. Thereafter, 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 29 g (87.7) of the product Sub1-22b.

(2) Sub1-22c synthesis

_{Pd(OAc) 2} (0.4 g, 0.002 mol), P(t-Bu) ₃ (1.4 g, 0.004 mol), K ₂ CO ₃ (24.5 g, 0.18 mol) in Sub1-22b (29 g, 0.06 mol) , DMA (120 ml) was added and refluxed at 170° C. for 12 hours. 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 25 g (83.3%) of the product Sub1-22c.

(3) Sub1-22 synthesis

Sub1-22c (25 g, 0.05 mol) in iodobenzene (10.8 g, 0.05 mol), Pd ₂ (dba) ₃ (1.5 g, 0.002 mol), 50% P( t- Bu) ₃ (1.3 g, 0.004 mol) , NaO t -Bu (15.3 g, 0.16 mol), toluene (110ml) was added and stirred at 90°C. Thereafter, 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 25 g (86.1%) of the product Sub1-22.

6. Sub1 -49 Synthesis example

(1) Sub1-49b synthesis

22-bromo-3-iodo-9,9-dimethyl-9H-fluorene (45.4 g, 0.11 mol), Pd ₂ (dba) ₃ (3.1 g, 0.003 mol) in Sub1-49a (35 g, 0.11 mol), 50% P(t-Bu) ₃ (2.8 g, 0.006 mol), NaO t -Bu (32.8 g, 0.34 mol), and toluene (230 ml) were added and proceeded in the same manner as the synthesis method of Sub1-22, the product Sub1 -49b to give 55 g (83.7%)

(2) Sub1-49 synthesis

_{Pd(OAc) 2} (0.6 g, 0.003 mol), P(t-Bu) ₃ (2.1 g, 0.005 mol), K ₂ CO ₃ (35.8 g, 0.26 mol) in Sub1-49b (50 g, 0.09 mol) , DMA (180 ml) was added and then proceeded in the same manner as for the synthesis of Sub1-22c to obtain 38 g (88.2%) of the product Sub1-49.

7. Sub1-62 Synthesis Example

(1) Sub1-62b synthesis

1-bromo-6-(2-chlorophenyl)-2-iododibenzo[b,d]furan (53 g, 0.11 mol) in Sub1-62a (30 g, 0.11 mol), Pd ₂ (dba) ₃ (3.0 g, 0.003 mol), 50% P(t-Bu) ₃ (2.7 g, 0.006 mol), NaO t -Bu (31.7 g, 0.33 mol), toluene (220 ml) was added, and in the same manner as the synthesis method of Sub1-22. Proceeding to obtain the product Sub1-62b 50 g (72.5%)

(2) Sub1-62 synthesis

_{Pd(OAc) 2} (0.54 g, 0.002 mol), P(t-Bu) ₃ (1.9 g, 0.005 mol), K ₂ CO ₃ (33 g, 0.24 mol) in Sub1-62b (50 g, 0.08 mol) , DMA (160 ml) was added, followed by the same method as for the synthesis of Sub1-22c to obtain 39 g (89.4%) of the product Sub1-62.

8. Sub1-82 synthesis example

(1) Sub1-82b synthesis

3-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (20.9 g, 0.08 mol) in Sub1-82a (30 g, 0.08 mol), Pd (PPh ₃ ) ₄ (2.9 g, 0.002 mol), NaOH (9.9 g, 0.25 mol), THF (165 mL), and water (50 mL) were added, and then proceeded in the same manner as in the synthesis method of Sub1-1b, and the product Sub1 -82b 30 g (79.9%) was obtained.

(2) Sub1-82 synthesis

_{After adding Pd(OAc) 2} (0.44 g, 0.003 mol), 3-nitropyridine (0.24 g, 0.003 mol) to Sub1-82b (30 g, 0.07 mol) _{, C 6} F ₆ (100 ml), DMI ( 130 ml). Thereafter, tert-butyl peroxybenzoate (38.2 g, 0.197 mol) was added, followed by the same method as the synthesis method of Sub1-1 to obtain 27 g (90.4%) of the product Sub1-82.

9. Sub-116 Synthesis example

(1) Sub1-116b synthesis

Sub1-116a (40 g, 0.10 mol) in 3,6-dichloronaphthalen-2-amine (22 g, 0.10 mol), Pd ₂ (dba) ₃ (2.9 g, 0.003 mol), 50% P(t-Bu) ₃ (2.6 g, 0.006 mol), NaO t -Bu (30.2 g, 0.31 mol), and toluene (210 ml) were added and proceeded in the same manner as for the synthesis of Sub1-22b, and the product Sub1-116b 51 g (87.3%) was performed. Got

(2) Sub1-116c synthesis

Sub1-116b (51 g, 0.09 mol) in Pd(OAc) ₂ (0.62 g, 0.003 mol), P(t-Bu) ₃ (2.2 g, 0.006 mol), K ₂ CO ₃ (37.9 g, 0.27 mol) , DMA (185 ml) was added and proceeded in the same manner as for the synthesis of Sub1-22c to obtain 42 g (88.1%) of the product Sub1-116c.

(3) Sub1-116 synthesis

Sub1-116c (42 g, 0.08 mol) iodobenzene (16.4 g, 0.08 mol), Pd ₂ (dba) ₃ (2.2 g, 0.002 mol), 50% P(t-Bu) ₃ (2 g, 0.004 mol) , NaOt-Bu (23.3 g, 0.24 mol) was added toluene (160 ml) and proceeded in the same manner as the synthesis method of Sub1-22 to obtain 43 g (89.3%) of the product Sub1-116.

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

[Table 1]

II. Of Sub 2 Synthesis example

One. Sub2 -2 Synthesis example

(1) Sub2-2b synthesis

2-chloroaniline (26.9 g, 0.07 mol) in Sub2-2a (30 g, 0.07 mol), Pd ₂ (dba) ₃ (1.9 g, 0.002 mol), 50% P( t- Bu) ₃ (1.7 g, 0.004 mol), NaO t -Bu (20.3 g, 0.2 mol) and toluene (140ml) were added and stirred at 90°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 30 g (90.1%) of the product Sub2-2b.

(2) Sub2-2 synthesis

_{Pd(OAc) 2} (0.4 g, 0.002 mol), P(t-Bu) ₃ (1.4 g, 0.004 mol), K ₂ CO ₃ (24.5 g, 0.18 mol) in Sub2-2b (30 g, 0.06 mol) , DMA (125 ml) was added and refluxed at 170°C for 12 hours. 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 22 g (79.5%) of the product Sub2-2.

11. Sub2-12 synthesis example

(1) Sub2-12b synthesis

2-chloroaniline (28 g, 0.07 mol) in Sub2-12a (30 g, 0.07 mol), Pd ₂ (dba) ₃ (1.8 g, 0.002 mol), 50% P( t- Bu) ₃ (1.6 g, 0.004 mol), NaO t -Bu (18.8 g, 0.2 mol) was added toluene (145ml), and then proceeded in the same manner as for the synthesis of Sub2-2b to obtain 31 g (92.8%) of the product Sub2-12b.

(2) Sub2-12 synthesis

Sub2-12b (31 g, 0.07 mol) in Pd(OAc) ₂ (0.5 g, 0.002 mol), P(t-Bu) ₃ (1.6 g, 0.004 mol), K ₂ CO ₃ (28.1 g, 0.2 mol) , DMA (135 ml) was added, followed by the same method as for the synthesis of Sub2-2 to obtain 26 g (91.2%) of the product Sub2-12.

Compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 below shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 2]

Ⅲ. Sub 3 example

The compound belonging to Sub 3 of Scheme 1 may be a compound as follows, but is not limited thereto, and Table 3 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 3]

IV. Sub 4 example

The compound belonging to Sub 4 of Scheme 2 may be a compound as follows, but is not limited thereto, and Table 4 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 4]

Ⅴ. Sub 5 example

The compound belonging to Sub 5 of Scheme 1 may be the following compound, but is not limited thereto, and Table 5 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 5]

Ⅵ. Of the final compound Synthesis example

1. P-2 synthesis

Sub1-1 (10 g, 0.02 mol) to Sub3-2 (3.7 g, 0.02 mol), Pd ₂ (dba) ₃ (0.6 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.5 g, 0.0014 mol) mol), NaO t -Bu (6.3 g, 0.07 mol), and toluene (50ml) were added and stirred at 90°C. After the reaction was completed, the temperature of the reactant was cooled to room temperature, toluene was removed, extracted with MC, and washed with water. Thereafter, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting organic material was separated by a silica gel column and recrystallized to obtain 11 g (85.2%) of the product.

2. P-4 synthesis

Sub1-3 (10 g, 0.02 mol) to Sub5-1 (7.7 g, 0.02 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol), NaOH (8.3 g, 0.07 mol), THF (50 mL), After adding water (15 mL), it was reacted for 6 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, THF and H ₂ O were removed, extracted with MC, and washed with water. Thereafter, the organic layer _{was dried over MgSO 4} , concentrated, and the resulting organic material was separated by a silica gel column and recrystallized to obtain 13 g (91%) of the product.

3. P-9 synthesis

Sub2-3 (10 g, 0.02 mol) to Sub4-2 (4.6 g, 0.02 mol), Pd ₂ (dba) ₃ (0.6 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.5 g, 0.0014 mol), NaO t -Bu (6.3 g, 0.07 mol), and toluene (50ml) were added, followed by the same method as the synthesis method of P-2 to obtain 11 g (79.7%) of the product.

4. Synthesis Example of P-15

Sub1-18 (11 g, 0.02 mol) to Sub3-15 (5.6 g, 0.02 mol), Pd ₂ (dba) ₃ (0.5 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.5 g, 0.0014 mol) mol), NaO t -Bu (5.6 g, 0.07 mol), and toluene (40ml) were added, followed by the same method as the synthesis method of P-2 to obtain 13 g (82%) of the product.

5. Synthesis Example of P-38

Sub1-62 (13 g, 0.02 mol) to Sub3-14 (9.8 g, 0.02 mol), Pd ₂ (dba) ₃ (0.7 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.6 g, 0.0014 mol), NaO t -Bu (6.8 g, 0.07 mol), and toluene (50ml) were added, followed by the same method as the synthesis method of P-2 to obtain 18 g (82.2%) of the product.

6. Synthesis Example of P-49

Sub2-6 (11 g, 0.02 mol) to Sub4-13 (5.9 g, 0.02 mol), Pd ₂ (dba) ₃ (0.6 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.6 g, 0.0014 mol) mol), NaO t -Bu (6.8 g, 0.07 mol), and toluene (50 ml) were added, and then proceeded in the same manner as in the synthesis method of P-2 to obtain 15 g (93.4%) of the product.

7. Synthesis Example of P-59

Sub1-97 (11 g, 0.02 mol) to Sub3-19 (8.2 g, 0.02 mol), Pd ₂ (dba) ₃ (0.6 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.6 g, 0.0014 mol), NaO t -Bu (6.5 g, 0.07 mol) was added toluene (50ml), and then proceeded in the same manner as in the synthesis method of P-2 to obtain 15 g (81.8%) of the product.

8. Synthesis Example of P-73

Sub2-2 (10 g, 0.02 mol) to Sub4-24 (6.1 g, 0.02 mol), Pd ₂ (dba) ₃ (0.6 g, 0.0007 mol), 50% P( t- Bu) ₃ (0.6 g, 0.0014 mol), NaO t -Bu (6.6 g, 0.07 mol), and toluene (50ml) were added, followed by the same method as the synthesis method of P-2 to obtain 13 g (84.9%) of the product.

9. Synthesis Example of P-82

Sub1-14 (11 g, 0.02 mol) to Sub5-43 (8.3 g, 0.02 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.001 mol), NaOH (2.8 g, 0.07 mol), THF (50 mL), After adding water (15 mL), it was carried out in the same manner as in the synthesis method of P-4 to obtain 13 g (83.6%) of the product.

10. Synthesis Example of P-89

Sub1-28 (12 g, 0.02 mol) to Sub5-27 (9.5 g, 0.02 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.001 mol), NaOH (2.6 g, 0.07 mol), THF (50 mL), After adding water (15 mL), it was carried out in the same manner as in the synthesis method of P-4 to obtain 15 g (83.4%) of the product.

11. Synthesis Example of P-101

Sub1-50 (13 g, 0.02 mol) to Sub5-58 (9.4 g, 0.02 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.001 mol), NaOH (2.9 g, 0.07 mol), THF (50 mL), After adding water (15 mL), it proceeded in the same manner as in the synthesis method of P-4 to obtain 15 g (81.6%) of the product.

12. Synthesis Example of P-125

Sub2-8 (12 g, 0.02 mol) to Sub4-30 (13 g, 0.02 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.001 mol), NaOH (3.3 g, 0.08 mol), THF (60 mL), After adding water (18 mL), it proceeded in the same manner as in the synthesis method of P-2 to obtain 20 g (83.4%) of the product.

13. Synthesis Example of P-140

Sub1-115 (12 g, 0.02 mol) to Sub5-57 (8.4 g, 0.02 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol), NaOH (2.4 g, 0.006 mol), THF (50 mL), After adding water (12 mL), it was carried out in the same manner as in the synthesis method of P-4 to obtain 13 g (75.7%) of the product.

The FD-MS values of the compounds P-1 to P-144 of the present invention prepared according to the synthesis example as described above are shown in Table 6 below.

[Table 6]

Manufacturing evaluation of organic electric devices

[Example 1] Red organic light emitting device (phosphorescent host)

On the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 -Diamine (hereinafter abbreviated as "2-TNATA") film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, 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, the compound P-73 of the present invention as a host material on the hole transport layer, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, _{abbreviated as "(piq) 2} Ir(acac)") as a dopant Although used as a material, a light emitting layer having a thickness of 30 nm was deposited by doping with a dopant so that the weight ratio was 95:5.

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. And tris(8-quinolinol)aluminum (hereinafter _{abbreviated as Alq 3} ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer 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 17]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 7 was used instead of the compound P-73 of the present invention as a host 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 A or Comparative Compound B was used instead of Compound P-73 of the present invention as a host material.

<Comparative Compound A> <Comparative Compound B>

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples 1 to 42 and Comparative Examples 1 and 2 of the present invention prepared as described above, electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, and , T95 life was measured with a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m ^2. The measurement results are shown in Table 7 below.

[Table 7]

As can be seen from the results of Table 7, when the compound of the present invention is used as the host material of the light emitting layer, the driving voltage of the device is lowered and the efficiency and lifespan are significantly improved compared to the case of using Comparative Compound A or Comparative Compound B.

Compared to the case of using Comparative Compound A as a host material (Comparative Example 1), when Comparative Compound B having a similar basic skeleton to that of Formula 1 of the present invention is used as the host material (Comparative Example 2), the driving voltage, efficiency, and lifespan of the device are improved. The driving voltage, efficiency, and life were significantly improved when the compound of the present invention was used as a host rather than when Comparative Compound B was used (Comparative Example 2).

In more detail, the compound of the present invention differs from Comparative Compound B in that it contains S or O because X is S or O in Chemical Formula 1, and is a 9-condensed cyclic structure by condensation of Chemical Formula 2 to Chemical Formula 1. . Due to this difference, the compound of the present invention has a higher refractive index and Tg value than that of Comparative Compound B, and has an LUMO level that maximizes the energy transfer effect, resulting in improved luminous efficiency and high thermal stability. As a result, the lifespan seems to be significantly improved.

In addition, due to the difference as described above, the planarity of the compound of the present invention is increased compared to the comparative compound B containing the element N in the core, thereby improving the packing density, and as a result, it seems that the performance of the device is improved.

In the case of the exemplary embodiment of the present invention, it can be seen that in the compound represented by Formula 2, the driving voltage and efficiency characteristics differ depending on the type of Y. This means that even for similar compounds, the energy level or thin film characteristics of the compound vary depending on the type of hetero element or specific substituent, and this difference acts as a major factor (e.g., energy balance, stability, etc.) in improving device performance during device deposition. This suggests that different device results can be derived.

[ Example 43] to [ Example 81] Red organic electroluminescent device ( Light-emitting auxiliary layer )

A 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer with a thickness of 60 nm, and then NPB was vacuum evaporated to form a hole transport layer having a thickness of 60 nm.

Subsequently, after vacuum deposition of the compound of the present invention shown in Table 8 to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer, 4,4'-N,N'- as a host on the light emission auxiliary layer. Dicarbazole-biphenyl (hereinafter, abbreviated as CBP) was used as a dopant (piq) ₂ Ir (acac), but a dopant was doped so that the weight ratio was 95:5 to form a light emitting layer having a thickness of 30 nm.

Next, BAlq was vacuum deposited on the emission layer to a thickness of 10 nm to form a hole blocking layer, and Alq ₃ was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer 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.

[ Comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 43, except that the light emission auxiliary layer was not formed.

[Comparative Example 4] and [Comparative Example 5]

An organic electroluminescent device was manufactured in the same manner as in Example 43, except that the following Comparative Compound C or Comparative Compound D was used instead of the compound of the present invention as the light emitting auxiliary layer material.

<Comparative Compound C> <Comparative Compound D>

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples 43 to 81 and Comparative Examples 3 to 5 of the present invention prepared as described above, electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, and , T95 life was measured with a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m ^2. The measurement results are shown in Table 8 below.

[Table 8]

As can be seen from the results of Table 8, when the compound of the present invention is used as a material for a light-emitting auxiliary layer, no light-emitting auxiliary layer is formed (Comparative Example 3), or Comparative Compound C (Comparative Example 4) or Comparative Compound D (Comparative Example 5) Compared to the case of using, the driving voltage, efficiency, and life of the device were all significantly improved.

That is, in the case of Comparative Examples 4 to 5 using Comparative Compound C or Comparative Compound D than Comparative Example 3 in which the light-emitting auxiliary layer was not used, the device characteristics were superior, and the 9-condensed ring core was compared to Comparative Example 4 or Comparative Example 5 The device result of the Example using the compound of the present compound containing the element of S or O was better.

Comparative Compound C or Comparative Compound D contains N in the 7-condensed ring, whereas in the case of the present invention, X in Formula 1 is a 9-condensed ring structure in which X is O or S. In the 7-condensed ring moiety, it is similar to Comparative Compound C or Comparative Compound D, but differs in that it is O or S, not N.

Due to this difference, the compound of the present invention has a higher refractive index and Tg value than that of Comparative Compounds C or D, and the entire structure forms a plate shape to increase planarity, thereby increasing hole movement characteristics. As a result, when the compound of the present invention is used, luminous efficiency and thermal stability are increased to improve lifespan, and the HOMO and LUMO energy levels have an appropriate value between the hole transport layer and the emission layer, thereby balancing the charge between holes and electrons in the emission layer. As the (charge balance) increases, light emission is well performed inside the light-emitting layer rather than the interface of the hole transport layer, maximizing efficiency and lifespan.

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

The device characteristics in which the compound of the present invention was applied to only one of the light-emitting auxiliary layers were described in the evaluation results of the device fabrication described above, but it is also applied when the hole transport layer or both the hole transport layer and the light-emitting auxiliary layer are formed using the compound of the present invention. I will be able to.

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 within the scope not departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be 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 emission auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first emission 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 emission layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (15)

Compound represented by the following formula (1):
<Formula 1><Formula2>

In Formulas 1 and 2, * represents a condensation position, and Formula 2 is condensed in Formula 1,
X is O or S,
Y is O, S, C=O, C(R ⁶ )(R ⁷ ) or N(R ⁸ ),
R ¹ to R ⁷ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; Alkynyl group of C ₂ ~ C _30; An alkoxyl group of C ₁ to C _30; C ₆ ~ C ₃₀ aryloxy group; -LN(R _a ) (R _b ); And it is selected from the group consisting of a combination thereof, and neighboring groups can be bonded to each other to form a ring,
a is an integer of 0 to 3, b, c and e are each an integer of 0 to 4, d is an integer of 0 to 2, and when each is an integer of 2 or more, R ¹ each, R ² each, R ³ each, R ^{Each of 4 and} each of R ⁵ is the same as or different from each other,
R ⁸ is a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; And -LN (R _a ) (R _b ) is selected from the group consisting of,
L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; And it is selected from the group consisting of a combination thereof,
R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group,
The R ¹ to R ⁸ , and the rings formed by bonding of adjacent groups to each other, respectively, 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; A C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ arylthio group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; Alkynyl group of C ₂ -C _20; C ₆ -C ₂₀ aryl group; Fluorenyl group; _{A heterocyclic group of C 2} -C ₂₀ including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An aliphatic ring group of C ₃ -C _20; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -LN(R _a ) (R _b ); And it may be further substituted with one or more substituents selected from the group consisting of a combination thereof. The method of claim 1
Formula 1 is a compound characterized in that represented by one of the following formulas 3 to 20:
<Formula 3><Formula4><Formula5>

<Formula 6><Formula7><Formula8>

<Formula 9><Formula10><Formula11>

<Formula 12><Formula13><Formula14>

<Formula 15><Formula16><Formula17>

<Formula 18><Formula19><Formula20>

In Formulas 3 to 20, X, Y, R ¹ to R ⁵ and a to e are the same as defined in claim 1. The method of claim 1
Formula 1 is a compound characterized in that represented by one of the following formulas 21 to 36:
<Formula 21><Formula22><Formula23>

<Formula 24><Formula25><Formula26>

<Formula 27><Formula28><Formula29>

<Formula 30><Formula31><Formula32>

<Formula 33><Formula34>

<Formula 35><Formula36>

In Formulas 21 to 36, X, R ¹ to R ⁸ and a to e are the same as defined in claim 1. In claim 1
At least one of the R ¹ to R ⁵ is a compound, characterized in that represented by the following formula 1-1 or 1-2:
<Formula 1-1>

<Formula 1-2>

In Formulas 1-1 and 1-2, L ² is the same as L of claim 1, and Ar ² and Ar ³ are defined the same as _{R a} and R _{b of claim 1,}
L ¹ is a single bond; C ₆ ~ C ₂₀ arylene group; Fluorenylene group; And O, N, S, Si and P containing at least one heteroatom of C ₂ ~ C ₂₀ A heterocyclic group; is selected from the group consisting of,
Ar ¹ is a C ₆ -C ₆₀ aryl group; Fluorenyl group; _{And a C 2} -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P. The method of claim 1
At least one of the R ¹ to R ⁵ is a compound characterized in that it is represented by the following formula 2-1 or formula 2-2:
<Formula 2-1><Formula2-2>

In Chemical Formulas 2 and 3,
Z ¹ to Z ⁸ are each independently N or C (R ₁ ), ^{at least one of Z 1} to Z ⁵ is N, and at least one of Z ⁶ to Z ⁸ is N,
L ₁ is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of _{C 2} ~ C _{60 containing at least one heteroatom,}
C ring is a C ₆ ~ C ₆₀ aromatic ring group; Or O, N, S, Si and P is a heterocyclic group of C ₂ ~ C ₆₀ containing at least one heteroatom, the C ring may be further substituted with one or more of the same or different R _1,
R ₁ 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; A C ₆ -C ₂₀ aryloxy group; C ₆ -C ₂₀ arylthio group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; Alkynyl group of C ₂ -C _20; C ₆ -C ₂₀ aryl group; Fluorenyl group; _{A heterocyclic group of C 2} -C ₂₀ including at least one heteroatom selected from the group consisting of O, N, S, Si and P; An aliphatic ring group of C ₃ -C _20; A C ₇ -C ₂₀ arylalkyl group; And it _{is selected from the group consisting of arylalkenyl group of C 8} -C ₂₀ , and neighboring groups may be bonded to each other to form a ring. The method of claim 5,
In Formula 2-2, the C ring is a compound characterized in that it is selected from the group consisting 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, Z ⁶ to Z ⁸ , R ₁ , L ₁ are the same as defined in claim 3, o is an integer of 0 to 4, p is an integer of 0 to 6, q Is an integer of 0 to 8, and when _{each of them is an integer of 2 or more, each of R 1} is the same as or different from each other, X ₁ and X ₂ are each independently O or S, and e and f are each an integer of 0 or 1 At least one of e and f is 1. The method of claim 1,
The compound represented by Formula 1 is a compound characterized in that one of the following compounds:

. In an organic electric device comprising 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 surface of both surfaces of the anode or the cathode that is not in contact with the organic material layer,
An organic electric device, wherein the organic material layer or the light efficiency improvement layer comprises a compound represented by Formula 1 of claim 1. The method of claim 8 or 9,
The organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. The method of claim 10,
The compound is an organic electric device, characterized in that included in at least one of the light-emitting layer and the light-emitting auxiliary layer. The method of claim 8 or 9,
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 anode. The method of claim 12,
The organic material layer further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 8 or 9; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 14,
The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

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