KR20200111313A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention relates to an organic electric device comprising: a compound represented by chemical formula 1; a first electrode; a second electrode; and an organic material layer between the first electrode and the second electrode, and to an electric device comprising the organic electric device. It is possible to lower the driving voltage of the organic electric device and improve luminous efficiency and service life by including the compound represented by chemical formula 1 in the organic material layer.

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 using an organic material. An organic electric device using an 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 multi-layered 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 and an electron injection layer.

Materials used as an organic material layer in an organic electric 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. In addition, the light-emitting material may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may 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 for realizing 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 emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the color purity increases 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, power consumption that is greater than the power consumption required by the existing portable display is required. Therefore, power consumption has become a very important factor for portable displays that have a limited power supply source such as a battery, and efficiency and life issues must also 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, the crystallization of organic substances caused by Joule heating during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize the efficiency. This is because 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 materials (mobility, interfacial properties, etc.) are optimally combined. .

Accordingly, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer. In other words, in order to sufficiently exhibit the excellent characteristics of an organic electric device, development of a material constituting an organic material layer in the device, particularly, a material for a hole transport layer and a light emitting layer, is urgently 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 exemplary embodiment of the present invention, not only can the driving voltage of the device be lowered, but also the luminous efficiency and lifetime of the device can be greatly improved.

1 is an exemplary diagram of an organic electroluminescent device according to the present invention.
2 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, and "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 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" as 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'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.

The term "heterocyclic group" as 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 containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.

The term "heterocyclic group" as used herein refers to a ring in which a heteroatom such as N, O, S, P, or Si is included instead of carbon forming the ring, and "heteroaryl group" or "heteroarylene group" A non-aromatic ring is included as well as an aromatic ring such as, and a compound including a heteroatom group such as SO ₂ , P=O and the like may be included instead of carbon forming the ring.

The term "aliphatic ring group" 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 means a ring of 3 to 60, but is not limited thereto. For example, benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.

In the present specification, the'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of the group reflecting the number', but it is described as the'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, even 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 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 letters 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 way as the definition of the substituent group defined by the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that the substituent R ¹ does not exist, 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 described in the 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; C ₃ ~ C ₆₀ aliphatic ring group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And it may be selected from the group consisting of a combination thereof.

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

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, if 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 only used to distinguish the component from other components, and the nature, order, 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 another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.

In addition, 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, as well as another component 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, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.

Preferably, the light efficiency improvement layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency 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 SPPs (surface plasmon polaritons) 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 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 formed 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 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 1-5. 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 emission layers are formed by the multilayer 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 emission layer, 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 hole transport layer 130, 330, 430, the light emitting layer 140, It may be used as a material for the 340 and 440 and/or the light efficiency improvement layer 180.

Since the band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position of 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 materials (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 hole transport layer 130, 330, 430, the light emitting layer 140, 340, 440 and/or the light efficiency improvement layer 180, the energy level between each organic material layer And by optimizing the T ₁ value and the intrinsic properties of the material (mobility, interfacial properties, etc.), it is possible to simultaneously improve the life and efficiency of the organic electric device.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, a metal or a conductive metal oxide or an alloy thereof is deposited 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 spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side 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. 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 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>

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

A ring, B ring, and C ring are each independently a C ₆ ~ C ₆₀ aromatic ring group; Fluorene 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.

X is O, S, N(R ^a ) or C(R ^b )(R ^c ).

R ¹ is hydrogen; heavy hydrogen; halogen; Cyano 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 ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And -L ¹ -N (L ² -Ar ¹ ) (L ³ -Ar ² ); It may be selected from the group consisting of.

a is an integer of 0 to 2, and when a is 2, each of R ¹ may be the same as or different from each other.

When R ¹ is an aryl group, it may be 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 ¹ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group such as quinazoline, quinoxaline, dibenzothiophene, dibenzofuran Etc.

When R ¹ is an alkyl group, preferably a C ₁ to C ₂₀ alkyl group, more preferably a C ₁ to C ₁₀ alkyl group, such as methyl, t-butyl, and the like.

R ^a 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; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group, and R ^a may be further substituted with R'.

When R ^a is an aryl group, it may be 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 is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group such as triazine, quinazoline, quinoxaline, dibenzothiophene, Dibenzofuran and the like.

R', R ^b and R ^c are each independently hydrogen; heavy hydrogen; halogen; Cyano 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 ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And -L ¹ -N(L ² -Ar ¹ )(L ³ -Ar ² ); and R ^b and R ^c may be bonded to each other to form a ring. When R ^b and R ^c are bonded to each other to form a ring, a spy compound may be formed together with C to which they are bonded.

When R ^b and R ^c are an alkyl group, preferably a C ₁ to C ₂₀ alkyl group, more preferably a C ₁ to C ₁₀ alkyl group, such as methyl, t-butyl, and the like.

When R ^b and R ^c 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 ^b and R ^c are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₂ heterocyclic group, such as quinazoline, quinoxaline, dizothiophene, Dibenzofuran and the like.

The A ring may be further substituted with R ₁ , the B ring may be further substituted with R ₂ , and the C ring may be further substituted with R ₃ .

R ₁ to R ₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano 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 ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And -L ¹ -N (L ² -Ar ¹ ) (L ³ -Ar ² ); It may be selected from the group consisting of.

When R ₁ to R ₃ 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 ₁ to R ₃ are a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as triazine, pyridine, pyrimidine, quinoxaline, Quinazoline, carbazole, phenylcarbazole, indole, indenopyrimidine, benzofuropyrazine, benzofuropyrimidine, benzoquinazoline, dibenzoquinazoline, dibenzoquinoline, dibenzothiophene, dibenzofuran, etc. I can.

When R ₁ to R ₃ are fluorenyl groups, they may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, and the like.

When R ₁ to R ₃ are an alkoxy group, preferably a C ₁ to C ₂₀ alkoxy group, more preferably a C ₁ to C ₁₀ alkoxy group, such as methoxy, t-butoxy, and the like.

When R ₁ to R ₃ is an alkenyl group, it may be preferably an alkenyl group of C ₂ to C ₂₀ , more preferably an alkenyl group of C ₁ to C ₁₀ , such as ethene and butene.

The R ₁ and R ₂ , the R'and R ₁ , or the R'and R ₃ may be bonded to each other to form a ring.

A ring formed by bonding of R ₁ and R _{2 to} each other, R'and R _{1 to} each other, or R'and R _{3 to} each other is an aromatic ring group of C ₆ to C ₆₀ ; 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; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

The L ¹ to L ³ are each independently 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; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

Ar ¹ and Ar ² 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 Ar ¹ and Ar ² 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 Ar ¹ and Ar ² are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as benzoxazole, benzothiazole, dibenzothiazole Offene, dibenzofuran, benzonaphthothiophene, carbazole, phenylcarbazole, and the like.

When Ar ¹ and Ar ² are fluorenyl groups, it may be 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorene, 9,9'-spirobifluorene, etc. have.

The R ¹ , R ₁ ~ R ₃ , R ^b , R ^c , R', L ¹ ~ L ³ , Ar ¹ , Ar ² , a ring formed by bonding of R ^b and R ^{c to} each other, R ₁ and R _{2 to} each other The ring formed by bonding, the ring formed by bonding of R′ and R _{1 to} each other, and the ring formed by bonding of R′ and R _{3 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; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy 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; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -L ¹ -N(L ² -Ar ¹ )(L ³ -Ar ² ; And combinations thereof may be further substituted with one or more substituents selected from the group consisting of.

The A ring and B ring may be each independently represented by one of the following formulas F-1 to F-6.

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

<Formula F-4> <Formula F-5> <Formula F-6>

In Formulas F-1 to F-6, R ² to R ⁵ are defined in the same manner as R ₁ or R ₂ in Formula 1, neighboring groups may be bonded to each other to form a ring, Y is O, S, N (R ^a ) or C (R ^b ) (R ^c ), and R ^a to R ^c are the same as defined in Formula 1.

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

The C ring may be represented by one of the following formulas F-7 to F-10.

<Formula F-7> <Formula F-8> <Formula F-9> <Formula F-10>

In Formulas F-7 to F-10, R ⁶ to R ⁹ are defined the same as R ₃ in Formula 1, and neighboring groups may be bonded to each other to form a ring, and Y is O, S, N (R ^a ) or C(R ^b )(R ^c ), and R ^a to R ^c are the same as defined in Formula 1.

f is an integer of 0 to 3, g is an integer of 0 to 5, h is an integer of 0 or 1, i is an integer of 0 to 4, each of which is an integer of 2 or more, each of R ⁶ and R ⁷ Each of R ^8, each of R ⁹ is the same as or different from each other.

Preferably, Formula 1 may be represented by one of Formulas 2 to 10 below.

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

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

<Formula 9> <Formula 10>

In Formulas 2 to 10, R ¹ , R ₁ to R ₃ , X, a are the same as defined in Formula 1, and Y is O, S, N (R ^a ) or C (R ^b ) (R ^c ) , R ^a to R ^c are as defined in Formula 1.

R ₁₀ to R ₁₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy 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; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of, neighboring groups may be bonded to each other to form a ring.

b is an integer of 0-4, c is an integer of 0-3, d is an integer of 0-6, e is an integer of 0-5, f is an integer of 0-2, g is an integer of 0-1, and these When each is an integer of 2 or more, each of R _1, each of R _2, each of R _3, each of R _10, each of R ₁₁ , R ₁₂ , and R ₁₃ is the same as or different from each other.

In addition, Formula 1 may be represented by one of Formulas 11 to 14 below.

<Formula 11> <Formula 12> <Formula 13> <Formula 14>

In Formulas 11 to 14, ring A, ring B, ring C, R ¹ , R ^a ~ R ^c , a are as defined in Formula 1.

In addition, Chemical Formula 1 may be represented by Chemical Formula 15 below. In the following formula (15), when k is 1, the formula corresponds to a case where R'which is ^a substituent of R a and R _{1 which} is a substituent of the ring A are bonded to each other to form a ring. In addition, the formula when l is 1 in the following formula (15) corresponds to a case in which the substituent R'of R ^a and the substituent R ₃ of the C ring are bonded to each other to form a ring.

<Formula 15>

In Formula 15, A ring, B ring, C ring, R ¹ , a are the same as defined in Formula 1, and Y'and Y" are each independently a single bond, O, S, N (R ^a ) or C (R ^b ) (R ^c ), k and l are each an integer of 0 or 1, and R ^a to R ^c are the same as defined in Formula 1.

D ring is a C ₆ ~ C ₆₀ aromatic ring group; Fluorene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ of the aliphatic ring group; may be selected from the group consisting of, D ring is deuterium; 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; A C ₆ -C ₂₀ arylalkoxy 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; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -L ¹ -N(L ² -Ar ¹ )(L ³ -Ar ² ; And combinations thereof may be further substituted with one or more substituents selected from the group consisting of.

In addition, Chemical Formula 1 may be represented by Chemical Formula 16 below. Chemical Formula 16 is a substituent R ₁ and A ring B ring substituents R ₂ in the formula (1) can be the case if a bond to one another to form a ring.

<Formula 16>

In Formula 16, A ring, B ring, C ring, X, R ¹ , a are the same as defined in Formula 1, and Y ^a is a single bond, O, S, N (R ^a ) or C (R ^b ) (R ^c ), and R ^a to R ^c are the same as defined in Formula 1.

Preferably, at least one of the R ₁ to R ₃ may be -L ¹ -N(L ² -Ar ¹ ) (L ³ -Ar ² ), or the following Formula A or Formula B.

<Formula A> <Formula B>

In Formulas A and B, Q ¹ to Q ⁴ are each independently N, C (R ^e ) or C, Q ⁵ to Q ⁹ are each independently N or C (R ^e ), wherein R ^e is hydrogen ; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy 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; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of, Z ring may be represented by one of the following Z-1 to Z-15.

<Z-1> <Z-2> <Z-3> <Z-4> <Z-5>

<Z-6> <Z-7> <Z-8> <Z-9> <Z-10>

<Z-11> <Z-12> <Z-13> <Z-14> <Z-15>

In the above Z-1 to Z-15, each symbol may be defined as follows.

* Is a moiety bonded to the ring containing Q ¹ to Q ⁴ .

V is independently of each other N, C(R ^f ) or C.

W ¹ and W ² are independently a single bond, -NL ⁴ -Ar ³ , S, O, C(R ^g ) or C(R ^g )(R ^h ), provided that both W ¹ and W ² are single Excluding the case of combination.

R ^f , R ^g and R ^h are each independently hydrogen; heavy hydrogen; C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; selected from the group consisting of, neighboring R ^f may be bonded to each other to form a ring, and R ^g and R ^h may be bonded to each other to form a ring.

L ⁴ is a single bond; C ₆ ~ C ₂₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₂₀ aliphatic ring group; And it is selected from the group consisting of a combination thereof.

Ar ³ is each independently a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; is selected from the group consisting of.

Preferably, Formula 1 may be represented by one of the following structural formulas E-1 to E-88.

In Formulas E-1 to E-88, symbols such as X, Y ^a , and Y are as defined in the above formulas. For example, X and Y are the same as defined in Formulas 2 to 8, and Y ^a is the same as defined in Formula 14. In Formulas E-1 to E-88, the rings corresponding to the A ring, B ring, and C ring of Formula 1 may be further substituted with R ₁ , R ₂ , R ₃ , respectively, as described in Formula 1, and D The ring corresponding to the ring may be further substituted with one or more substituents as described in Formula 15.

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 electrical 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 yet 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 hole transport layer and/or the light emitting layer. I can.

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 yet another aspect of the present invention, the present invention provides an electronic device including a display device including an organic electric element 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 will be described in detail, but the present invention is not limited to the following examples.

Synthesis example

The compounds represented by Formula 1 according to the present invention (Final Product 1, Final Product 2) may be synthesized according to the following Scheme 1, but the present invention is not limited thereto.

<Reaction Scheme 1>

I. Synthesis of Sub 1

Sub 1 of Scheme 1 may be exemplarily synthesized by the reaction route of Scheme 2 below, but is not limited thereto. Hal is I, Br or Cl.

<Reaction Scheme 2>

1. Sub1-1 synthesis example

(1) Sub 1-1a synthesis example

After dissolving 5-phenyl-5,10-dihydrophenazine (100 g, 387.1 mmol) with Xylene (774 mL) at room temperature under a nitrogen atmosphere, N-([1,1'-biphenyl]-4-yl)-N- (3-bromo-4-iodophenyl)-[1,1'-biphenyl]-4-amine (276.5 g, 425.8 mmol), CuI (47.9 g, 251.6 mmol), K ₂ CO ₃ (156.6 g, 774.23 mmol) And reflux while stirring for 1 hour. When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried with Na ₂ SO ₄ and concentrated. The resulting compound was separated with a silica gel column and recrystallized to obtain 241 g (yield: 80%) of the product. .

(2) Example of Sub 1-1b synthesis

After dissolving Sub1-1a (241 g, 309.1 mmol) with Triethylamine (773 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (33.4 g, 340.0 mmol), PdCl ₂ (PPh ₃ ) ₂ (17.39 g, 24.73 mmol), CuI (5.30 g, 27.82 mmol) was added, stirred for 24 hours, and heated to 80°C. When the reaction is complete, cool to room temperature and remove the solvent to obtain Sub 1-1b.

(3) Example of Sub 1-1 synthesis

After dissolving Sub 1-1b with THF (310 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 340.7ml, 340.7 mmol) was added and stirred at room temperature for 1 hour. When the reaction is complete, extraction is performed with water and Ethyl acetate, and the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 163.8 g (yield: 78%) of the product.

2. Sub1-6 Synthesis Example

(1) Example of Sub 1-6a synthesis

N-(3-(phenazin-5(10H)-yl)phenyl)-N-phenyldibenzo[b,d]furan-2-amine (100 g, 193.9 mmol) in Xylene (779 mL) at room temperature under nitrogen atmosphere. After dissolving, 1,2-diiodobenzene (70.4 g, 213.3 mmol), CuI (24.0 g, 126.1 mmol), K ₂ CO ₃ (78.5 g, 387.9 mmol) were added and proceeded in the same manner as in the synthesis method of Sub1-1a. Product 115.5 g (yield: 83%) was obtained.

(2) Example of Sub 1-6 synthesis

After dissolving Sub1-6a (115.5 g, 161.0 mmol) with Triethylamine (774 ml) at room temperature under a nitrogen atmosphere, ethynylbenzene (18.1 g, 177.0 mmol), PdCl ₂ (PPh ₃ ) ₂ (9.04 g, 12.9 mmol), CuI (2.76 g, 14.5 mmol) is dissolved, stirred for 24 hours, and heated to 80°C. When the reaction is complete, cool to room temperature, add 1N HCl (292.7 ml), extract with CH ₂ Cl ₂ , and dry the organic layer with Na ₂ SO ₄ and concentrate. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 88 g (yield: 79%) of the product.

3. Sub1-11 Synthesis Example

(1) Example of Sub 1-11a synthesis

N,N-di([1,1'-biphenyl]-4-yl)-12-phenyl-5,12-dihydrobenzo[b]phenazin-2-amine (100 g, 159.3 mmol) at room temperature under a nitrogen atmosphere After dissolving with Xylene (319 mL), 1,2-diiodobenzene (57.8 g, 175.2 mmol), CuI (19.72 g, 103.54 mmol), and K ₂ CO ₃ (64.5 g, 318.58 mmol) were added thereto, and the method for synthesizing Sub1-1a. Proceeding in the same manner as the product 108.4 g (yield: 82%) was obtained.

(2) Example of Sub 1-11b synthesis

Sub1-11-a (108.4 g, 130.6 mmol) was dissolved in Triethylamine (327 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (14.1 g, 143.7 mmol), PdCl ₂ (PPh ₃ ) ₂ (7.34 g, 10.5 mmol) , CuI (2.24 g, 11.76 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1-b to obtain Sub 1-11b.

(3) Example of Sub 1-11 synthesis

After dissolving Sub 1-11b in THF (131 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 143.7 ml, 143.7 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1, and the product 72.3 g ( Yield: 76%).

4. Sub1-90 synthesis example

(1) Example of Sub 1-90a synthesis

10H-spiro[acridine-9,9'-fluorene] (100 g, 331.4 mmol) was dissolved in Xylene (603 mL) at room temperature under a nitrogen atmosphere, and then N-(3-(2-bromo-3-iodo-9H) -carbazol-9-yl)phenyl)-N-phenylnaphthalen-2-amine (220.8 g, 331.9 mmol), CuI (37.4 g, 196.1 mmol), K ₂ CO ₃ (122.1 g, 603.5 mmol) was added and the Sub1- Proceeding in the same manner as in the synthesis method of 1a, 194.0 g of the product (yield: 74%) was obtained.

(2) Synthesis example of Sub 1-90b

After dissolving Sub1-90a (194.0 g, 223.3 mmol) with Triethylamine (558 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (24.1 g, 245.6 mmol), PdCl ₂ (PPh ₃ ) ₂ (12.5 g, 17.9 mmol), CuI (3.8 g, 20.1 mmol) was added and proceeded in the same manner as the synthesis method of Sub1-1b to obtain Sub 1-90b.

(3) Example of Sub 1-90 synthesis

After dissolving Sub 1-90b with THF (223 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 245.6 ml, 245.6 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1, and the product 149.0 g ( Yield: 82%).

5. Sub1-97 Synthesis Example

(1) Synthesis example of Sub 1-97a

N-([1,1'-biphenyl]-4-yl)-12,12-dimethyl-N-phenyl-5,12-dihydrobenzo[b]acridin-2-amine (100 g, mmol) under nitrogen atmosphere After dissolving with Xylene (398 mL) at room temperature, 1,2-diiodobenzene (72.2 g, 218.8 mmol), CuI (24.63 g, 129.31 mmol), K ₂ CO ₃ (80.5 g, 397.9 mmol) were added and the Sub1-1a Proceeding in the same manner as in the synthesis method of 120.6 g (yield: 86%) of the product was obtained.

(2) Example of Sub 1-97b synthesis

Sub1-97a (120.6 g, 171.1 mmol) was dissolved in Triethylamine (428 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (18.5 g, 188.3 mmol), PdCl ₂ (PPh ₃ ) ₂ (7.6 g, 13.7 mmol), CuI (2.9 g, 15.4 mmol) was added and proceeded in the same manner as for the synthesis of Sub1-1b to obtain Sub 1-97b.

(3) Example of Sub 1-97 synthesis

After dissolving Sub 1-97b with THF (171 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 188.3 ml, 188.3 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1, and the product 85.6 g ( Yield: 83%).

6. Sub1-164 synthesis example

(1) Synthesis example of Sub 1-164a

N,N-di([1,1'-biphenyl]-4-yl)-10H-phenoxazin-4-amine (100 g, 199.0 mmol) was dissolved in Xylene (398 mL) at room temperature under a nitrogen atmosphere, and then N -([1,1'-biphenyl]-4-yl)-N-(4-bromo-3-iodophenyl)-[1,1'-biphenyl]-4-amine (131.8 g, 218.9 mmol), CuI ( 24.6 g, 129.3 mmol), K ₂ CO ₃ (80.5 g, 397.9 mmol) was added and proceeded in the same manner as in the synthesis method of Sub1-1a to obtain 140 g (yield: 72%) of the product.

(2) Example of Sub 1-164 synthesis

Sub1-164a (140 g, 143.2 mmol) was dissolved in Triethylamine (358 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (15.5 g, 157.6 mmol), PdCl ₂ (PPh ₃ ) ₂ (8.1 g, 11.5 mmol), CuI (2.5 g, 12.9 mmol) was added and proceeded in the same manner as for the synthesis of Sub1-6 to obtain 98.7 g (yield: 69%) of the product.

7. Sub1-234 Synthesis Example

(1) Example of Sub 1-234a synthesis

After dissolving N-(naphthalen-2-yl)-N-phenyl-10H-phenothiazin-4-amine (100 g, 240.1 mmol) with Xylene (480 mL) at room temperature under a nitrogen atmosphere, N-(4-bromo- 3-iodophenyl)-N-phenylnaphthalen-2-amine (132.1 g, 264.1 mmol), CuI (29.7 g, 156.1 mmol), K ₂ CO ₃ (97.1 g, 480.1 mmol) was added and the same as the synthesis method of Sub1-1a. The method proceeded to give a product 128 g (yield: 68%).

(2) Synthesis example of Sub 1-234b

Sub1-234a (128 g, 163.2 mmol) was dissolved in Triethylamine (444 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (19.2 g, 195.2 mmol), PdCl ₂ (PPh ₃ ) ₂ (10.0 g, 14.2 mmol), CuI (3.0 g, 16.0 mmol) was added and proceeded in the same manner as for the synthesis of Sub1-1b to obtain Sub 1-234b.

(3) Example of Sub 1-234 synthesis

After dissolving Sub 1-234b with THF (177 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 195.2 ml, 195.2 mmol) was added and proceeded in the same manner as the synthesis method of Sub 1-1, and the product 100.3 g ( Yield: 77%).

8. Sub1-45 Synthesis Example

(1) Synthesis example of Sub 1-45a

After dissolving 5-phenyl-5,10-dihydrophenazine (100 g, 387.1 mmol) with Xylene (480 mL) at room temperature under a nitrogen atmosphere, 3-bromo-9-(4,6-diphenyl-1,3,5- triazin-2-yl)-2-iodo-9H-carbazole (256.9 g, 425.8 mmol), CuI (47.9 g, 251.6 mmol), K ₂ CO ₃ (156.6 g, 774.2 mmol) was added to the synthesis method of Sub1-1a Proceeding in the same manner as described above, the product 187.5 g (yield: 66%) was obtained.

(2) Example of Sub 1-45 synthesis

After dissolving Sub1-45a (187.5 g, 255.5 mmol) with Triethylamine (639 ml) at room temperature under a nitrogen atmosphere, ethynylbenzene (28.7 g, 281.1 mmol), PdCl ₂ (PPh ₃ ) ₂ (14.4 g, 20.5 mmol), CuI (4.4 g, 23.0 mmol)) was added, stirred for 24 hours, and heated to 80°C. When the reaction was completed, the mixture was cooled to room temperature, 1N HCl (465 ml) was added, extracted with CH ₂ Cl _2, and the organic layer was dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 138.9 g (yield: 72%) of the product.

9. Sub1-115 Synthesis Example

(1) Example of Sub 1-115a synthesis

After dissolving 10H-spiro[acridine-9,9'-fluorene] (100 g, mmol) with Xylene (603 mL) at room temperature under a nitrogen atmosphere, 2-(4-bromo-3-iodophenyl)-4-(dibenzo [b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (200.6 g, 331.9 mmol), CuI (37.4 g, 196.1 mmol), K ₂ CO ₃ (122.1 g, 603.5 mmol) ) And proceeded in the same manner as in the synthesis method of Sub1-1a to obtain 177.9 g (yield: 73%) of the product.

(2) Synthesis example of Sub 1-115b

Sub1-115a (177.9 g, 220.2 mmol) was dissolved in Triethylamine (551 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (23.8 g, 242.3 mmol), PdCl ₂ (PPh ₃ ) ₂ (12.4 g, 17.6 mmol), CuI (3.8 g, 19.8 mmol) was added and proceeded with the synthesis method of Sub1-1b to obtain Sub 1-b.

(3) Example of Sub 1-115 synthesis

After dissolving Sub 1-115b with THF (220 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 242.3 ml, 242.3 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1, and the product 126.0 g ( Yield: 76%).

10. Sub1-123 synthesis example

(1) Sub 1-123a synthesis example

13,13-diphenyl-7-(3-phenylquinoxalin-2-yl)-7,13-dihydro-5H-indolo[3,2-b]acridine (100 g, 159.6 mmol) was added to Xylene at room temperature under nitrogen atmosphere ( 319 mL), 1,2-diiodobenzene (57.9 g, mmol), CuI (19.8 g, 103.7 mmol), and K ₂ CO ₃ (64.6 g, 319.1 mmol) were added, and the same method as for the synthesis of Sub1-1a. To obtain 72.3 g (yield: 58%) of the product.

(2) Example of Sub 1-123b synthesis

Sub1-123a (72.3 g, 92.5 mmol) was dissolved in Triethylamine (231 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (10.0 g, 101.7 mmol), PdCl ₂ (PPh ₃ ) ₂ (5.2 g, 7.4 mmol), CuI (1.6 g, 8.3 mmol) was added and proceeded in the same manner as in the synthesis method of Sub1-1b to obtain Sub 1-123b.

(3) Example of Sub 1-123 synthesis

After dissolving Sub 1-123b with THF (92 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 101.7 ml, 101.7 mmol) was added and proceeded in the same manner as in the synthesis method of Sub 1-1, and the product 42.4 g ( Yield: 63%).

11. Sub1-191 synthesis example

(1) Synthesis example of Sub 1-191-a'

After dissolving 1-nitro-10H-phenoxazine (100 g, 438.2 mmol) with Xylene (876 mL) at room temperature under a nitrogen atmosphere, 1-bromo-2-iodobenzene (136.4 g, 482.0 mmol), CuI (54.2 g, 284.8 mmol), K ₂ CO ₃ (177.3 g, 876.4 mmol) was added and proceeded in the same manner as for the synthesis of Sub1-1a to obtain 142.7 g (yield: 85%) of the product.

(2) Synthesis example of Sub 1-191a"

Sub 1-191a' (142.7 g, 372.5 mmol) was dissolved in o -dichlorobenzene (1915 mL), triphenylphosphine (251.2 g, 957.7 mmol) was added and stirred for 24 hours to reflux. When the reaction was completed, the mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 107.6 g (yield: 80%) of the product.

(3) Synthesis example of Sub 1-191a

Sub 1-191a" (107.6 g, 306.5 mmol) was dissolved in Xylene (613 mL) at room temperature under a nitrogen atmosphere, and then 3-chloro-2-phenylbenzo[4,5]thieno[2,3-b]pyrazine (100 g, 337.0 mmol), CuI (37.9 g, 199.2 mmol), K ₂ CO ₃ (124.0 g, 612.8 mmol) was added and proceeded in the same manner as in the synthesis method of Sub1-1a to give 119.9 g of the product (yield: 64%) Got it.

(4) Synthesis example of Sub 1-191b

Sub1-191a (119.9 g, 196.1 mmol) was dissolved in Triethylamine (490 ml) at room temperature under a nitrogen atmosphere, and then ethynyltrimethylsilane (21.2 g, 215.7 mmol), PdCl ₂ (PPh ₃ ) ₂ (11.0 g, 15.7 mmol), CuI (3.4 g, 17.7 mmol) was added and proceeded in the same manner as for the synthesis of Sub1-1b to obtain Sub 1-191b.

(5) Synthesis example of Sub 1-191

After dissolving Sub 1-191b with THF (196 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 215.7 ml, 215.7 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1, and the product 61.1 g ( Yield: 56%).

12. Sub1-256 Synthesis Example

(1) Example of Sub 1-256a synthesis

3-(4-(dibenzo[b,d]furan-2-yl)-6-(7-phenyldibenzo[b,d]furan-4-yl)-1,3,5-triazin-2-yl)- 12H-benzo[b]phenothiazine (100 g, 438.2 mmol) was dissolved in Xylene (876 mL) at room temperature under a nitrogen atmosphere, and then 1,2-diiodobenzene (49.3 g, 149.3 mmol), CuI (16.8 g, 88.2 mmol) , K ₂ CO ₃ (54.9 g, 271.4 mmol) was added and proceeded in the same manner as the synthesis method of Sub1-1a to obtain 75.2 g (yield: 59%) of the product.

(2) Synthesis example of SSub 1-256b

After dissolving Sub1-256a (75.2 g, 80.1 mmol) with Triethylamine (200 ml) at room temperature under a nitrogen atmosphere, ethynyltrimethylsilane (8.7 g, 88.1 mmol), PdCl ₂ (PPh ₃ ) ₂ (4.5 g, 6.4 mmol), CuI (1.4 g, 7.2 mmol) was added and proceeded in the same manner as in the synthesis method of Sub1-1b to obtain Sub 1-256b.

(3) Example of Sub 1-256 synthesis

After dissolving Sub 1-256b with THF (80 ml) at 0°C, 1M in THF tetrabutylammonium fluoride (TBAF, 88.1 ml, 88.1 mmol) was added and proceeded in the same manner as for the synthesis of Sub 1-1, and the product 46.3 g ( Yield: 69%).

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

[Table 1]

II. Synthesis of the final compound

1. Synthesis Example of P-1

Sub 1-1 (50 g, 73.8 mmol) was dissolved in 1, 2-dichloroethane martial arts (738 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.7 g, 7.38 mmol), AgSbF ₆ (2.5 g) , 7.38 mmol) and reacted at 80° C. for 24 hours while stirring. When the reaction is complete, the mixture is cooled to room temperature, extracted with CH ₂ Cl ₂ and water, the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 44 g (yield: 88%) of the product.

2. Synthesis Example of P-6

(1) Inter 1-6 synthesis example

Sub 1-6 (50 g, 72.3 mmol) was dissolved in 1, 2-dichloroethane martial arts (723 ml) at room temperature under nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.6 g, 7.23 mmol), AgSbF ₆ (2.5 g , 7.23 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 43 g (yield: 86%) of the product.

(2) Synthesis example of Inter 1-6'

Inter 1-6 (43 g, 62.0 mmol) was dissolved in dichloromethane (311 ml), and N-bromosuccinimide (11.1 g, 62.0 mmol) was added thereto, followed by stirring at 80° C. for 24 hours to react. When the reaction was completed, the mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was recrystallized with dichloromethane and hexane to obtain 36.4 g (yield: 76%) of the product.

(3) Synthesis example of P-6

Inter 1-6' (36.4 g, 47.2 mmol) was dissolved in THF (236 ml)/H ₂ O (118 ml), and then phenylboronic acid (5.8 g, 47.2 mmol), Pd(PPh ₃ ) ₄ (3.27 g, 2.83 mmol) and NaOH (5.7 g, 141.7 mmol) were added and stirred at 80° C. for 24 hours to reflux. When the reaction was completed, the mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was recrystallized with dichloromethane and hexane to obtain 29.0 g (yield: 80%) of the product.

3. Synthesis Example of P-11

After dissolving Sub 1-11 (50 g, 68.7 mmol) with 1, 2-dichloroethane martial arts (687 ml) at room temperature under a nitrogen atmosphere, AuCl (PPh ₃ ) (3.4 g, 6.87 mmol), AgSbF ₆ (2.36 g) , 6.87 mmol) was added and proceeded in the same manner as in the synthesis method of P-1 to obtain 39.9 g (yield: 84%) of the product.

4. Synthesis Example of P-90

Sub 1-90 (50 g, 61.4 mmol) was dissolved in 1, 2-Dichloroethane martial arts (614 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.0 g, 6.14 mmol), AgSbF ₆ (2.1 g , 6.14 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 39.5 g (yield: 79%) of the product.

5. Synthesis Example of P-97

Sub 1-97 (50 g, 82.9 mmol) was dissolved in 1, 2-Dichloroethane martial arts (829 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (4.1 g, 8.29 mmol), AgSbF ₆ (2.9 g , 8.29 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 42.5 g (yield: 85%) of the product.

6. Synthesis Example of P-164

Sub 1-164 (50 g, 50.1 mmol) was dissolved in 1, 2-Dichloroethane martial arts (501 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (2.5 g, 5.01 mmol), AgSbF ₆ (1.7 g , 5.01 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 40.5 g (yield: 81%) of the product.

7. Synthesis Example of P-234

Sub 1-234 (50 g, 68.1 mmol) was dissolved in 1, 2-Dichloroethane martial arts (681 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.4 g, 6.81 mmol), AgSbF ₆ (2.3 g , 6.81 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 44.0 g (yield: 88%) of the product.

8. Synthesis Example of P-45

Sub 1-45 (50 g, 66.2 mmol) was dissolved in 1, 2-Dichloroethane martial arts (662 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.3 g, 6.62 mmol), AgSbF ₆ (2.3 g , 6.62 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 36.5 g (yield: 73%) of the product.

9. Synthesis Example of P-115

Sub 1-115 (50 g, 66.4 mmol) was dissolved in 1, 2-Dichloroethane martial arts (664 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.3 g, 6.64 mmol), AgSbF ₆ (2.3 g , 6.64 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 34.0 g (yield: 68%) of the product.

10. Synthesis Example of P-123

Sub 1-123 (50 g, 68.8 mmol) was dissolved in 1, 2-Dichloroethane martial arts (688 ml) at room temperature under nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.4 g, 6.88 mmol), AgSbF ₆ (2.4 g , 6.88 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 30.5 g (yield: 61%) of the product.

11. Synthesis Example of P-191

Sub 1-191 (50 g, 89.8 mmol) was dissolved in 1, 2-Dichloroethane martial arts (898 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (4.4 g, 8.98 mmol), AgSbF ₆ (3.1 g , 8.98 mmol) and proceeded in the same manner as in the synthesis method of P-1 to obtain 36.5 g (yield: 73%) of the product.

12. Synthesis Example of P-256

Sub 1-256 (50 g, 59.7 mmol) was dissolved in martial arts (597 ml) at room temperature under a nitrogen atmosphere, and then AuCl (PPh ₃ ) (3.0 g, 5.97 mmol), AgSbF ₆ (2.0 g, 5.97 mmol) was added. Put in and proceed in the same manner as the synthesis method of P-1 to obtain a product 32 g (yield: 64%).

The FD-MS values of the compounds P-1 to P-276 of the present invention prepared according to the synthesis example as described above are shown in Table 2 below.

[Table 2]

Manufacturing evaluation of organic electric devices

[ Example One] Green organic electroluminescent device ( Hole transport layer )

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) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then the compound P-1 of the present invention was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer. Formed.

Then, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") as a host on the hole transport layer, tris(2-phenylpyridine)-iridium (hereinafter, "Ir(ppy)) as a dopant. ₃ ) was used in a weight ratio of 90:10 to form a light emitting layer having a thickness of 30 nm.

Subsequently, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter, abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer. Then, 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 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 28]

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 3 was used instead of the compound P-1 of the present invention as a material for the hole transport layer.

[ Comparative example 1] to [ Comparative example 4]

As a hole transport layer material, instead of the compound P-1 of the present invention, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter Abbreviated as NPB), an organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following comparative compounds A to C was used.

<Comparative Compound A> <Comparative Compound B> <Comparative Compound C>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 28 and Comparative Examples 1 to 4 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. It was measured, and the T95 life was measured with a life measurement equipment manufactured by McScience at a reference luminance of 5000 cd/m ² . The measurement results are shown in Table 3 below.

[Table 3]

As can be seen from the results of Table 3, when a green organic electroluminescent device was manufactured using the material for an organic electroluminescent device of the present invention as a material for a hole transport layer, compared to a comparative example using NPB or comparative compounds A to C. The driving voltage of the organic electroluminescent device is lowered, and luminous efficiency and lifespan are remarkably improved.

Looking at Comparative Examples 1 to 4, when using Comparative Compound A to Comparative Compound C having a dibenzoazepine moiety as a hole transport layer material than NPB commonly used as a hole transport layer material, the driving voltage and efficiency of the organic electric device , Life, etc. have been improved. In particular, when comparative compound C, in which a substituent bonded to N of dibenzoazepine and a substituent of a benzene ring are bonded to each other to form a fused ring (a ring in which 6 rings are fused) is used as the material for the hole transport layer, the comparative compound A or the comparative compound Compared to the case of using B, the driving voltage, efficiency, and life were improved.

In the case of the compound of the present invention, in Examples 14 to 20 in which a compound containing O (oxygen) in the fused ring was used as the material for the hole transport layer, the lifespan was remarkably improved, and the compound containing S in the fused ring was In the case of Examples 21 to 28 used as the material for the hole transport layer, the efficiency was remarkably improved.

Meanwhile, the data measured using the DFT method (B3LYP/6-31g(D)) of the Gaussian program of Comparative Compound C and Compound P-86 of the present invention are shown in Table 4 below.

[Table 4]

Looking at Table 4, it can be seen that the compound P-86 of the present invention has a higher LUMO value than that of the comparative compound C. Accordingly, when the compound P-86 of the present invention is used as a material for a hole transport layer, electrons transferred from the emission layer are It can be effectively prevented, and as a result, the characteristics of the device are improved.

From these results, even if the compound has a similar basic skeleton like Comparative Compound C and the compound of the present invention, depending on whether R ¹ of Formula 1 of the present invention forms a ring, Hole characteristics, light efficiency characteristics, energy level (HOMO, LUMO), It can be seen that physical properties of the compound, such as hole injection and mobility characteristics, and charge balance between holes and electrons, may vary, and thus characteristics of the device may vary.

[ Example 29] Red organic electroluminescent device (Phosphorescent host)

Instead of compound P-1 of the present invention, NPB is used as the hole transport layer material, compound P-34 of the present invention is used instead of CBP as a host, and bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate (hereinafter, as a dopant) instead of Ir(ppy) ₃ An organic electroluminescent device was manufactured in the same manner as in Example 1, except that "(piq) ₂ Ir(acac)") was used in a weight ratio of 95:5.

[ Example 30] to [ Example 54]

An organic electroluminescent device was manufactured in the same manner as in Example 29, except that the compound of the present invention described in Table 5 was used instead of the compound P-34 of the present invention as a host material.

[Comparative Example 5] to [Comparative Example 7]

An organic electroluminescent device was manufactured in the same manner as in Example 29, except that one of the following comparative compounds D to F was used instead of the compound P-34 of the present invention as a host material.

<Comparative Compound D> <Comparative Compound E> <Comparative Compound F>

Electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 29 to 54 and Comparative Examples 5 to 7 of the present invention, and 2500 cd The T95 life was measured with a life measurement equipment manufactured by McScience at the luminance of /m ² . The measurement results are shown in Table 5 below.

[Table 5]

From Table 5, it can be seen that when the compound of the present invention is used as a phosphorescent host material, the driving voltage, efficiency, and lifespan are significantly improved compared to the case of using the comparative compounds D to F.

When using Comparative Compound E or Comparative Compound F having a dibenzoazepine moiety as a host than Comparative Compound D, which is generally used as a host, the driving voltage of the organic electroluminescent device was much lower, and the efficiency and lifespan were remarkably excellent. , When using the compound of the present invention as a host, which contains a dibenzoazepine moiety like Comparative Compounds E and F, but with a different skeleton, the device characteristics such as driving voltage, lifespan, and efficiency were the best.

This is because, when having the same fused ring skeleton as the compound of the present invention, the stability of not only electrons but also holes is increased than that of comparative compounds E or F, so that the life of the device is improved, and the charge balance between electrons and holes in the light emitting layer is increased. It seems that the driving voltage and efficiency are improved. In addition, it appears that the driving voltage, efficiency, and lifespan are maximized because the packing density is improved than that of the comparative compound during deposition using the compound of the present invention having a fusion ring formed thereon.

This suggests that the properties of the compound such as hole injection and mobility may change depending on whether or not an additional fused ring is formed in dibenzoazepine and the ring-forming atom, so that the result of the device may be significantly different so that it is difficult to predict.

The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. It should be interpreted by, and all technologies within the scope equivalent thereto should be interpreted 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 (18)

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

In the above formula,
A ring, B ring, and C ring are each independently a C ₆ ~ C ₆₀ aromatic ring group; Fluorene 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; is selected from the group consisting of,
X is O, S, N(R ^a ) or C(R ^b )(R ^c ),
R ¹ is hydrogen; heavy hydrogen; halogen; Cyano 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 ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And -L ¹ -N (L ² -Ar ¹ ) (L ³ -Ar ² ); is selected from the group consisting of,
a is an integer from 0 to 2, and when a is 2, each of R ¹ is the same as or different from each other,
R ^a 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; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group, R ^a may be further substituted with R',
R', R ^b and R ^c are each independently hydrogen; heavy hydrogen; halogen; Cyano 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 ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And -L ¹ -N (L ² -Ar ¹ ) (L ³ -Ar ² ); is selected from the group consisting of; R ^b and R ^c may be bonded to each other to form a ring,
The A ring may be further substituted with R ₁ , the B ring may be further substituted with R ₂ , and the C ring may be further substituted with R ₃ ,
R ₁ to R ₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano 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 ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; And -L ¹ -N (L ² -Ar ¹ ) (L ³ -Ar ² ); is selected from the group consisting of,
The R ₁ and R _{2 together} , the R'and R _{1 together} , or the R'and R ₃ may be bonded to each other to form a ring
The L ¹ to L ³ are each independently 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; And C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic ring group,
Ar ¹ and Ar ² 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 , R ₁ ~ R ₃ , R ^b , R ^c , R', L ¹ ~ L ³ , Ar ¹ , Ar ² , a ring formed by bonding of R ^b and R ^{c to} each other, R ₁ and R _{2 to} each other The ring formed by bonding, the ring formed by bonding of R′ and R _{1 to} each other, and the ring formed by bonding of R′ and R _{3 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; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy 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; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -L ¹ -N(L ² -Ar ¹ )(L ³ -Ar ² ; And combinations thereof may be further substituted with one or more substituents selected from the group consisting of. The method of claim 1,
The A ring and B ring are each independently a compound characterized in that one of the following formulas F-1 to F-6:
<Formula F-1><FormulaF-2><FormulaF-3>

<Formula F-4><FormulaF-5><FormulaF-6>

In the above formula,
R ² to R ⁵ are defined in the same manner as R ₁ or R ₂ of claim ₁ , and neighboring groups may be bonded to each other to form a ring,
b and e are each an integer of 0 to 4, c is an integer of 0 to 6, d is an integer of 0 to 2, and when each is an integer of 2 or more, each of R ^2, each of R ^3, each of R ⁴ , R ⁵ each is the same or different from each other,
Y is O, S, N(R ^a ) or C(R ^b )(R ^c ), and R ^a to R ^c are as defined in claim 1. The method of claim 1,
The C ring is a compound characterized in that one of the following formulas F-7 to F-10:
<Formula F-7><FormulaF-8><FormulaF-9><FormulaF-10>

In the above formula,
R ⁶ to R ⁹ are defined the same as R _{3 in} claim 1, and neighboring groups may be bonded to each other to form a ring,
f is an integer of 0 to 3, g is an integer of 0 to 5, h is an integer of 0 or 1, i is an integer of 0 to 4, each of which is an integer of 2 or more, each of R ⁶ and R ⁷ , Each of R ^8, each of R ⁹ is the same as or different from each other,
Y is O, S, N(R ^a ) or C(R ^b )(R ^c ), and R ^a to R ^c are 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 2 to 10:
<Formula 2><Formula3><Formula4><Formula5>

<Formula 6><Formula7><Formula8>

<Formula 9><Formula10>

In the above formula,
R ¹ , R ₁ to R ₃ , X, a are the same as defined in claim 1,
R ₁₀ to R ₁₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy 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; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ is selected from the group consisting of an aliphatic ring group; neighboring groups may be bonded to each other to form a ring,
b is an integer of 0-4, c is an integer of 0-3, d is an integer of 0-6, e is an integer of 0-5, f is an integer of 0-2, g is an integer of 0-1, and these When each is an integer of 2 or more, each of R _1, each of R _2, each of R _3, each of R _10, each of R ₁₁ , R _{12, and} each of R ₁₃ is the same as or different from each other,
Y is O, S, N(R ^a ) or C(R ^b )(R ^c ), and R ^a to R ^c are 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 11 to 14:
<Formula 11><Formula12><Formula13><Formula14>

In the above formula, A ring, B ring, C ring, R ¹ , R ^a ~ R ^c , a are as defined in claim 1. The method of claim 1,
Formula 1 is a compound characterized in that represented by the following formula 15:
<Formula 15>

In the above formula, ring A, ring B, ring C, R ¹ , a are the same as defined in claim 1,
D ring is a C ₆ ~ C ₆₀ aromatic ring group; Fluorene 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; is selected from the group consisting of,
The D ring is deuterium; 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; A C ₆ -C ₂₀ arylalkoxy 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; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -L ¹ -N(L ² -Ar ¹ )(L ³ -Ar ² ; And may be further substituted with one or more substituents selected from the group consisting of a combination thereof,
Y'and Y" are each independently a single bond, O, S, N (R ^a ) or C (R ^b ) (R ^c ),
k and l are each an integer of 0 or 1,
The R ^a to R ^c are as defined in claim 1. The method of claim 1,
Formula 1 is a compound characterized in that represented by the following formula 16:
<Formula 16>

In the above formula, A ring, B ring, C ring, X, R ¹ , a are the same as defined in claim 1, and Y ^a is a single bond, O, S, N (R ^a ) or C (R ^b ) (R ^c ), and R ^a to R ^c are as defined in claim 1. The method of claim 1,
At least one of the R ₁ to R ₃ is -L ¹ -N(L ² -Ar ¹ )(L ³ -Ar ² ). The method of claim 1,
At least one of the R ₁ to R ₃ is a compound characterized in that the formula A or B:
<Formula A><FormulaB>

In the above formula, Q ¹ to Q ⁹ are each independently N, C (R ^e ) or C,
R ^e is hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ arylalkoxy 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; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of,
Z ring is represented by one of the following Z-1 to Z-15,
<Z-1><Z-2><Z-3><Z-4><Z-5>

<Z-6><Z-7><Z-8><Z-9><Z-10>

<Z-11><Z-12><Z-13><Z-14><Z-15>

In the above Z-1 to Z-15,
* Is a moiety bonded to the ring containing Q ¹ to Q ⁴ ,
V is independently of each other N, C (R ^f ) or C,
W ¹ and W ² are independently of each other a single bond, -NL ⁴ -Ar ³ , S, O or C(R ^g )(R ^h ), except when both W ¹ and W ² are single bonds,
R ^f , R ^g and R ^h are each independently hydrogen; heavy hydrogen; C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; selected from the group consisting of, neighboring R ^f may be bonded to each other to form a ring, R ^g and R ^h may be bonded to each other to form a ring,
L ⁴ is a single bond; C ₆ ~ C ₂₀ arylene group; Fluorenylene group; O, N, S, Si, and C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₂₀ aliphatic ring group; And it is selected from the group consisting of a combination thereof,
Ar ³ is each independently a C ₆ -C ₂₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P; C ₃ -C ₂₀ aliphatic ring group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; is selected from the group consisting of. 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 comprising a single compound or two or more compounds represented by 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 the cathode that is not in contact with the organic material layer,
An organic electric device, characterized in that the organic material layer or the light efficiency improvement layer comprises a compound represented by Formula 1 of claim 1. The method of claim 11 or 12,
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 13,
The compound is an organic electric device, characterized in that included in the hole transport layer or the light emitting layer. The method of claim 11 or 12,
The organic material layer comprises at least two stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode. The method of claim 15,
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 11 or 12; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 17,
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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