KR20200119039A - An organic electronic element comprising compound for organic electronic element and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electronic element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the same. Since a mixture of compounds respectively expressed in a chemical formula 1 and a chemical formula 2 of the present invention are included in a light emitting layer of an organic material layer, a driving voltage of the organic electronic element can be lowered and luminous efficiency and life can be improved.

Description

An organic electric device including a compound for an organic electric device, and an electronic device thereof {AN ORGANIC ELECTRONIC ELEMENT COMPRISING COMPOUND FOR ORGANIC ELECTRONIC ELEMENT AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to an organic electric device including a compound for an organic electric device 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 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 in 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 fully exhibit the excellent characteristics of organic electronic devices, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. Although this should be preceded, development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently developed, and among them, development of a host material for a light emitting layer is urgently required.

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

In one aspect, the present invention provides an organic electric device including a compound represented by the following formula (1) and formula (2), respectively, in a light emitting layer.

<Formula 1> <Formula 2>

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 a mixture of the compound represented by Formula 1 and the compound represented by Formula 2 of the present invention as a material for the light emitting layer, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan of the device can be improved.

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

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 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 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; And C ₃ ~ C ₆₀ aliphatic ring group; may be selected from the group consisting of.

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, 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), electron injection layer 160, light emitting layer (140, 340, 440), or may be used as a material for the light efficiency improvement layer 180, but is preferably represented by the compound represented by Formula 1 and Formula 2 of the present invention. A mixture of the compound may be used as a host of the emission layers 140, 340, and 440.

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 a mixture of the compound represented by Formula 1 and the compound represented by Formula 2 as a host of the emission layer, the energy level and T ₁ value between each organic material layer, and the inherent properties of the material (mobility, interfacial properties Etc.) can be optimized to improve the life and efficiency of organic electric devices 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, 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, an organic electric device according to an aspect of the present invention will be described.

An organic electronic device according to an aspect of the present invention includes an anode, a cathode, and an organic material layer formed between the anode and the cathode, the organic material layer includes a phosphorescent emission layer, and the host of the phosphorescent emission layer is represented by the following Formula 1 It includes a first compound and a second compound represented by the following formula (2).

<Formula 1> <Formula 2>

First, Formula 1 will be described.

Each symbol in Formula 1 may be defined as follows.

Ar ¹ to Ar ³ are each independently a C ₆ to 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 to Ar 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, biphenyl, naphthyl, terphenyl, phenanthrene Etc.

When Ar ¹ to Ar ³ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₆ heterocyclic group such as pyridine, quinoline, quinazoline, dibenzothio Offene, dibenzofuran, benzonaphthothiophene, benzonaphthofuran, carbazole, phenylcarbazole, benzocarbazole, phenyl-benzocarbazole, dibenzocarbazole, benzofuropyridine, benzothienopyridine, And indolocarbazole.

When Ar ¹ to Ar ³ are fluorenyl groups, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, 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 - may be a fluorene.

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

When L ¹ to L ³ 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, biphenyl, naphthalene, terphenyl, etc. have.

When L ¹ to L ³ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as dibenzothiophene, dibenzofuran, carba Sol, phenylcarbazole, and the like.

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

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

<Formula 1-A> <Formula 1-B> <Formula 1-C>

<Formula 1-D> <Formula 1-E> <Formula 1-F>

<Formula 1-G> <Formula 1-H> <Formula 1-I>

In Formula 1-A to Formula 1-I, the definition of each symbol is as follows.

L ¹ ~ L ³ , Ar ² , Ar ³ are the same as defined in Formula 1.

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

The R'and R" are independently of each other hydrogen; deuterium, tritium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; at least one of O, N, S, Si and P C ₂ ~ C ₆₀ heterocyclic group containing a hetero atom of; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne Diary; C ₁ ~ C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ aryloxy group; is selected from the group consisting of, R'and R" may be bonded to each other to form a ring. When R'and R" form a ring, a spy compound may be formed with C to which they are attached.

Preferably, R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; at least one selected from the group consisting of O, N, S, Si and P It may be selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group including a hetero atom; And a C ₃ -C ₂₀ aliphatic ring group.

Wherein R _c is a C ₆ ~C ₆₀ aryl group; Fluorenyl 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.

Preferably, R _c is a C ₆ ~C ₂₀ aryl group; Fluorenyl group; C ₃ ~ C ₂₀ aliphatic ring group; And O, N, S, Si and P may be selected from the group consisting of a heterocyclic group of C ₂ ~ C ₂₀ containing at least one heteroatom.

L ⁵ is a 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.

R ⁴ and R ⁵ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ aryloxy 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, and neighboring groups may be bonded to each other to form a ring.

a'is an integer of 0 to 4, b'is an integer of 0 to 3, and when each of them is an integer of 2 or more, each of R ^{4 and} each of R ⁵ are the same or different from each other.

In addition, Formula 1 may be represented by one of the following Formulas 1-J to 1-ZA.

<Formula 1-J> <Formula 1-K> <Formula 1-L>

<Formula 1-M> <Formula 1-N> <Formula 1-O>

<Formula 1-P> <Formula 1-Q> <Formula 1-R>

<Formula 1-S> <Formula 1-T> <Formula 1-U>

<Formula 1-V> <Formula 1-W> <Formula 1-X>

<Formula 1-Y> <Formula 1-Z> <Formula 1-ZA>

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

L ¹ ~ L ³ , Ar ² , Ar ³ are the same as defined in Formula 1, Y'is C(R')(R"), N(R _c ), O or S, and R', R" , R _c is the same as defined in Formula 1-A to Formula 1-I.

L ⁵ is a 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.

R ⁴ to R ⁷ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ aryloxy 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, and neighboring groups may be bonded to each other to form a ring.

a'is an integer of 0 to 4, b'is an integer of 0 to 3, c'is an integer of 0 to 6, d'is an integer of 0 to 8, and when each of these is an integer of 2 or more, each of R ⁴ and R ⁵ Respectively, each of R ^{6 and} each of R ⁷ are the same as or different from each other.

The Ar ¹ to Ar ³ , L ¹ to L ³ , L', R _a , R _b , R _c , R', R", a ring formed by bonding neighboring groups to each other, and R'and R" are each Each ring formed by bonding 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; And C ₈ -C ₂₀ arylalkenyl group; It may be further substituted with one or more substituents selected from the group consisting of.

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

Next, the following Chemical Formula 2 will be described.

<Formula 2>

Each symbol in Formula 2 may be defined as follows.

Ar ⁴ 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 It may be selected from the group consisting of an aliphatic ring group.

When Ar ⁴ 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, biphenyl, naphthyl, terphenyl, phenanthrene, triphenyl It may be Len, etc.

When Ar ⁴ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₅ heterocyclic group such as pyridine, pyrimidine, triazine, quinazoline, benzoquina Zoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuropyrimidine, benzothienopyrimidine, dibenzoquinoxaline, dibenzothiophene, dibenzofuran, phenanthroline, Acenaphthopyrimidine, Acenaphthopyrazine, benzofuroquinazoline, benzofuroquinoxaline, benzothioquinazoline, benzothioquinoxaline, benzonaphthofuran, benzonaphthothiophene, carbazole, phenyl It may be carbazole and the like.

When Ar ⁴ is this fluorenyl group, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, 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.

L ⁴ 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 a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; It may be selected from the group consisting of.

When L ⁴ 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 phenyl, biphenyl, naphthalene, terphenyl, phenanthrene, etc. .

When L ⁴ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as pyridine, pyrimidine, triazine, quinazoline, quinoxaline, Benzothienopyrimidine, benzofuropyrimidine, benzoquinazoline, benzoquinoxaline, dibenzoquinazoline, dibenzoquinoxaline, indolopyrimidine, phenyl-indolopyrimidine, dibenzothiophene, dibenzo It may be furan or the like.

When L ⁴ is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, and the like.

R ¹ to R ³ are each independently hydrogen; Deuterium, tritium; 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 to C ₃₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N(R _a ) (R _b ); It is selected from the group consisting of, and neighboring groups can be bonded to each other to form a ring.

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

Ring group of a neighboring each other R ^1, is formed in combination with each other between the adjacent R ^2, or R ³ adjacent to each other a ring is C ₆ ~ C _60; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Or C ₃ ~ C ₆₀ aliphatic ring group; Etc.

L'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 a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; It may be selected from the group consisting of.

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

이고, B환은

이다.A-hwan

And ring B is

to be.

X and Y are each independently C (R') (R"), N (R _c ), O or S.

The R'and R" are independently of each other hydrogen; deuterium, tritium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; at least one of O, N, S, Si and P C ₂ ~ C ₆₀ heterocyclic group containing a hetero atom of; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne Diary; C ₁ ~ C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ aryloxy group; is selected from the group consisting of, R'and R" may be bonded to each other to form a ring. When R'and R" form a ring, a spiro compound may be formed with the C to which they are attached. When R'and R" combine with each other to form a ring with the C to which they are attached, the spyro compound is Can be formed.

When R'and R" are an alkyl group, it may be preferably a C ₁ -C ₁₀ alkyl group, such as a methyl group, t-butyl, or the like.

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

When R _c 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, biphenyl, naphthyl, terphenyl, phenanthrene, triphenyl It may be Len, etc.

When R _c is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₅ heterocyclic group such as pyridine, pyrimidine, triazine, quinazoline, quinoxaline , Triazine, benzofuropyrimidine, benzothienopyrimidine, dibenzoquinazoline, benzoquinazoline, benzoquinoxaline, dibenzoquinoxaline, benzothienoquinazoline, benzofuroquinazoline, etc. .

The Ar ⁴ , L ⁴ , R ¹ to R ³ , A ring, B ring, L', R _a , R _b , R _c , R', R", a ring formed by bonding neighboring groups to each other, and R The ring formed by bonding of'and R'to each other 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; And C ₈ -C ₂₀ arylalkenyl group; It may be further substituted with one or more substituents selected from the group consisting of.

Preferably, Formula 2 may be represented by one of the following Formulas 2-A to 2-D.

<Formula 2-A> <Formula 2-B>

<Formula 2-C> <Formula 2-D>

In Formulas 2-A to 2-D, Ar ⁴ , L ⁴ , R ¹ to R ³ , X, Y, a to c are as defined in Formula 2.

Preferably, Ar ⁴ may be represented by the following Formula A or Formula B.

<Formula A> <Formula B>

In Formulas A and B, each symbol may be defined as follows.

Q ¹ to Q ⁴ are each independently N, C, or C(R _d ), and Q ⁵ to Q ⁹ are each independently N or C(R _d ).

The Z ring may be selected from the following structures.

<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 structure, * represents a condensation position with a ring including Q ¹ to Q ⁴ , and W ¹ and W ² are each independently a single bond, N-(L ₁ -Ar ₁ ), S, O, C or C(R _e )(R _f ), and V is independently of each other N, C or C(R _g ).

R _d , R _e , R _f , R _g and Ar ₁ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro 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 ; 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; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And a C ₈ -C ₂₀ arylalkenyl group, and neighboring groups may be bonded to each other to form a ring, and R _e and R _f may be bonded to each other to form a ring. When R _e and R _f are bonded to each other to form a ring, a spy compound may be formed together with C to which they are bonded.

L ₁ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

Preferably, L ₁ is a single bond; C ₆ -C ₂₀ arylene group; Fluorenylene group; A C ₂ -C ₂₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₂₀ It may be selected from the group consisting of an aliphatic ring group.

Specifically, the compound represented by Formula 2 may be one of the following compounds.

.

.

In Formulas 1 and 2, L ¹ to L ⁴ may be each independently represented by one of Formulas b-1 to b-13 below.

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

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

<Formula b-9> <Formula b-10>

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

In Formulas b-1 to b-13, each symbol may be defined as follows.

Y ¹ is N-(L ^a -Ar ^a ), O, S or C(R _d )(R _e ) and Z ¹ to Z ³ are each independently C, C(R _f ) or N, and Z ¹ to At least one of Z ³ is N.

R ⁵ to R ⁷ , R _d , R _e and R _f are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl 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; A fused ring group of an aliphatic ring of C ₃ to C ₂₀ and an aromatic ring of C ₆ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₂₀ alkoxy group; And C ₆ ~ C ₃₀ aryloxy group; selected from the group consisting of, neighboring groups may be bonded to each other to form a ring, and R _d and R _e may be bonded to each other to form a ring, and C ( In R _f ), neighboring R _f may be bonded to each other to form a ring. When R _d and R _e are bonded to each other to form a ring, a spy compound may be formed together with C to which they are bonded.

f is an integer of 0 to 6, e, g, h, and i are each an integer of 0 to 4, j and k are each an integer of 0 to 3, l is an integer of 0 to 2, and m is 0 It is an integer of 3, and when each of these is an integer of 2 or more, each of a plurality of R ^5, each of a plurality of R ^{6, and} each of a plurality of R ⁷ are the same or different from each other.

Ar ^a is 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 of P; C ₃ ~ C ₂₀ aliphatic ring group; And it may be selected from the group consisting of a combination thereof.

L ^a is each independently 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 may be selected from the group consisting of a combination thereof.

In one embodiment of the present invention, the compound represented by Formula 1 and the compound represented by Formula 2 are preferably mixed in a weight ratio of 2:8 to 8:2 and used as a host material.

Hereinafter, examples for synthesis of the compounds represented by Formulas 1 and 2 according to the present invention and examples for manufacturing an organic electric device will be described, but the present invention is not limited to the following examples.

[ Synthesis example 1] Formula 1

The compound represented by Formula 1 according to the present invention (Final product 1) can be synthesized by the reaction route of Reaction Scheme 1 below. The compound represented by Formula 1 is the applicant's Korean Patent Registration No. 10-1786749 (registered on Oct. 11, 2017), Korean Patent Application No. 2014-0152779 (filed on Nov. 5, 2014), and Korean Patent Application No. 2014-0161275 (2014.11. .19 filed) and the like.

<Reaction Scheme 1>

I. Sub 1-1 Synthesis example

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

<Scheme 2> (Hal is Br, I or Cl)

1.Sub 1-1-76 Synthesis example

In a round bottom flask, Aniline (50 g, 536.9 mmol), 3-bromonaphtho[2,3-b]benzofuran (158.9 g, 536.9 mmol), Pd ₂ (dba) ₃ (14.75 g, 16.1 mmol), P(t- Bu) ₃ (6.52 g, 32.2 mmol), NaOt-Bu (103.2 g, 1073.8 mmol), and toluene (2684 mL) were added, followed by reaction at 100°C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 129.5 g of a product. (Yield: 78%)

2. Sub 1-1-110 synthesis example

In a round bottom flask, [1,1'-biphenyl]-4-amine (50 g, 295.5 mmol), 2-bromo-11,11-dimethyl-11H-benzo[b]fluorene (95.5 g, 295.5 mmol), Pd ₂ (dba) ₃ (8.12 g, 8.9 mmol), P(t-Bu) ₃ (3.59 g, 17.7 mmol), NaOt-Bu (56.8 g, 590.9 mmol), toluene (1477 mL) was added and the Sub 1- It proceeded in the same manner as in the synthesis method of 1-76 to obtain 87.5 g of a product. (Yield: 72%)

II. Of Sub 1-2 Synthesis example

Sub 1-2 of Reaction Scheme 1 may be synthesized by a reaction route as shown in Scheme 3 below, but is not limited thereto.

<Scheme 3> (Hal ¹ is I, Br or Cl, and Hal ² is Br or Cl)

III. Of the final compound Synthesis example

1. Synthesis of 1-76

In a round bottom flask, Sub 1-2-76 (142.0 g, 418.6 mmol), Sub 1-1-76 (129.5 g, 418.6 mmol), Pd ₂ (dba) ₃ (11.5 g, 12.6 mmol), P(t- Bu) ₃ (5.1 g, 25.1 mmol), NaOt-Bu (80.5 g, 837.2 mmol), and toluene (2093 mL) were added, followed by reaction at 100 °C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 173.5 g of a product. (Yield: 73%)

2. Synthesis of 1-110

Sub 1-2-110 (52.5 g, 212.6 mmol), Sub 1-1-110 (87.5 g, 212.6 mmol), Pd ₂ (dba) ₃ (5.8 g, 6.4 mmol), P(t-Bu) ₃ ( 2.6 g, 12.8 mmol), NaOt-Bu (40.9 g, 425.2 mmol), and toluene (1063 mL) were carried out in the same manner as in the synthesis method of 1-76 to obtain 92.1 g of the product. (Yield: 75%)

The FD-MS (Field Desorption-Mass Spectrometry) values of the compounds 1-1 to 1-130 of the present invention prepared according to the synthesis example as described above are shown in Table 1 below.

[Table 1]

[Synthesis Example 2] Chemical Formula 2

The compound represented by Chemical Formula 2 of the present invention (Final product 2) may be prepared by reacting Sub2-1 and Sub2-2 as shown in Scheme 4 below, but is not limited thereto.

<Scheme 4> (Hal is Br, I or Cl)

I. Sub 2-1 Synthesis example

Sub 2-1 of Scheme 4 may be synthesized by Scheme 5 below, but is not limited thereto.

<Reaction Scheme 5>

1. Sub 2-1-1 synthesis example

(1) Sub 2-1 ^a' -1 synthesis

Sub 2-1 ^a -1 (50.0 g, 135.4 mmol) was dissolved in Toluene (677 mml), 2-chloroaniline (17.3 g, 182.3 mmol), Pd ₂ (dba) ₃ (3.7 g, 4.1 mmol), P ( t -Bu) ₃ (1.6 g, 8.1 mmol), NaO t -Bu (26.0 g, 364.5 mmol) was added and stirred at 100°C. When the reaction is complete, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the resulting compound was separated by a silica gel column and recrystallized to obtain 41.1 g (yield: 73%) of the product.

(2) Sub 2-1-1 synthesis

Sub 2-1 ^{a '-1} after a (41.1 g, 98.8 mmol) was dissolved in DMA (494 mL), Pd ( OAc) 2 (0.67 g, 3.0 mmol), K 2 CO 3 (41.0 g, 296.4 mmol), P(t-Bu) ₃ HBF ₄ (7.4 g, 5.9 mmol) was added and stirred at 90°C. When the reaction is complete, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 27.0 g (yield: 72%) of the product.

2. Sub 2-1-2 synthesis example

(1) Sub 2-1 ^a' -2 synthesis

Sub 2-1 ^a -2 (50.0 g, 141.6 mmol) was dissolved in Toluene (708 mml), and then 2-chloroaniline (18.1 g, 141.6 mmol), Pd ₂ (dba) ₃ (3.9 g, 4.3 mmol), P _{(t -Bu) 3 (1.7 g} , 8.5 mmol), NaO t -Bu (27.2 g, 283.1 mmol) were dissolved the Sub 2-1 ^{a 'by} proceeding in the same way as the synthesis of -1 to give the product 34.6 g. (Yield: 72%)

(2) Sub 2-1-2 synthesis

^{Sub 2-1 a '-2 (34.6 g} , 101.9 mmol) was dissolved in DMA (509 mL), Pd ( OAc) 2 (0.7 g, 3.1 mmol), K 2 CO 3 (42.2 g, 305.4 mmol), P(t-Bu) ₃ HBF ₄ (7.6 g, 6.1 mmol) was added and proceeded in the same manner as for the synthesis of Sub 2-1-1 to obtain 27.7 g of the product. (Yield: 75%)

3. Sub 2-1-11 synthesis example

(1) Sub 2-1 ^a' -11 synthesis

Sub 2-1 ^a -11 (50.0 g, 121.3 mmol) was dissolved in Toluene (606 mml), and then 2-chloroaniline (15.5 g, 121.3 mmol), Pd ₂ (dba) ₃ (3.3 g, 3.6 mmol), P _{(t -Bu) 3 (1.5 g} , 7.3 mmol), NaO t -Bu (23.3 g, 242.5 mmol) were dissolved the Sub 2-1 ^{a '-1} by proceeding in the same way as the synthesis significance obtain the product 42.3 g. (Yield: 76%)

(2) Sub 2-1-11 synthesis

^{Sub 2-1 a '-11 (42.3 g} , 92.2 mmol) with _{Pd (OAc) 2 (0.62 g} , 2.8 mmol), K 2 CO 3 (38.2 g, 276.5 mmol) was dissolved in DMA (461 mL), P (t-Bu) ₃ HBF ₄ (6.9 g, 5.5 mmol) was added and proceeded in the same manner as for the synthesis of Sub 2-1-1 to obtain 29.6 g of the product. (Yield: 76%)

4. Sub 2-1-18 synthesis example

(1) Sub 2-1 ^a' -18 synthesis

Sub 2-1 ^a -18 (50.0 g, 137.6 mmol) was dissolved in Toluene (688 mml), and then 2-chloroaniline (17.6 g, 137.6 mmol), Pd ₂ (dba) ₃ (3.8 g, 4.1 mmol), P _{(t -Bu) 3 (1.7 g} , 8.3 mmol), NaO t -Bu (26.5 g, 275.3 mmol) were dissolved the Sub 2-1 ^{a 'by} proceeding in the same way as the synthesis of -1 to give the product 44.0 g. (Yield: 78%)

(2) Sub 2-1-18 synthesis

^{Sub 2-1 a '-18 (44.0 g} , 107.3 mmol) of _{Pd (OAc) 2 (0.72 g} , 3.2 mmol) was dissolved in _{DMA (537 mL), K 2} CO 3 (44.5 g, 322.0 mmol), P (t-Bu) ₃ HBF ₄ (8.1 g, 6.4 mmol) was added and proceeded in the same manner as for the synthesis of Sub 2-1-1 to obtain 29.3 g of the product. (Yield: 73%)

5. Sub 2-1-23 synthesis example

(1) Sub 2-1 ^a' -23 synthesis

Sub 2-1 ^a -23 (50.0 g, 102.6 mmol) was dissolved in Toluene (513 mml), and then 2-chloroaniline (13.1 g, 102.6 mmol), Pd ₂ (dba) ₃ (2.8 g, 3.1 mmol), P _{(t -Bu) 3 (1.3 g} , 6.2 mmol), NaO t -Bu (19.7 g, 205.2 mmol) were dissolved the Sub 2-1 ^{a 'by} proceeding in the same way as the synthesis of -1 to give the product 38.9 g. (Yield: 71%)

(2) Sub 2-1-23 synthesis

^{Sub 2-1 a '-23 (38.9 g} , 72.8 mmol) was dissolved in DMA (364 mL), Pd ( OAc) 2 (0.49 g, 2.2 mmol), K 2 CO 3 (30.2 g, 218.5 mmol), P(t-Bu) ₃ HBF ₄ (5.5 g, 4.4 mmol) was added and proceeded in the same manner as for the synthesis of Sub 2-1-1 to obtain 25.0 g of the product. (Yield: 69%)

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

[Table 2]

II. Sub 2-2

The compounds belonging to Sub 2-2 may be the following compounds, but are not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 3.

[Table 3]

III. Of the final compound Synthesis example

1. Synthesis of 2-6

After dissolving Sub 2-1-1 (27.0 g, 71.1 mmol) with toluene (371 mL), Sub 2-2-6 (19.0 g, 71.1 mmol), Pd ₂ (dba) ₃ (2.0 g, 2.1 mmol), P( t -Bu) ₃ (0.9 g, 4.3 mmol), NaO t -Bu (13.7 g, 142.3 mmol) was added and stirred at 120°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 28.1 g of the product. (Yield: 74%)

2. Synthesis of 2-13

After dissolving Sub 2-1-2 (27.7 g, 76.2 mmol) with toluene (381mL), Sub 2-2-1 (18.3 g, 76.2 mmol), Pd ₂ (dba) ₃ (2.1 g, 2.3 mmol), P( t -Bu) ₃ (0.9 g, 4.6 mmol), NaO t -Bu (14.7 g, 152.4 mmol) was added and proceeded in the same manner as in the synthesis method of 2-6 to obtain 31.6 g of the product. (Yield: 73%)

3. Synthesis of 2-18

After dissolving Sub 2-1-2 (27.7 g, 76.2 mmol) with toluene (381mL), Sub 2-2-17 (24.2 g, 76.2 mmol), Pd ₂ (dba) ₃ (2.1 g, 2.3 mmol), P( t -Bu) ₃ (0.9 g, 4.6 mmol), NaO t -Bu (14.7 g, 152.4 mmol) was added and proceeded in the same manner as in the synthesis method of 2-6 to obtain 34.9 g of the product. (Yield: 71%)

4. Synthesis of 2-93

After dissolving Sub 2-1-11 (29.6 g, 70.1 mmol) with toluene (350mL), Sub 2-2-54 (20.8 g, 70.1 mmol), Pd ₂ (dba) ₃ (1.9 g, 2.1 mmol), P( t -Bu) ₃ (0.9 g, 4.2 mmol), NaO t -Bu (13.5 g, 140.1 mmol) was added and proceeded in the same manner as in the synthesis method of 2-6 to obtain 27.0 g of the product. (Yield: 68%)

5. Synthesis of 2-102

Sub 2-1-18 (29.3 g, 78.5 mmol) was dissolved in toluene (392 mL), and then Sub 2-2-6 (21.0 g, 78.5 mmol), Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol) , P( t- Bu) ₃ (1.0 g, 4.7 mmol), NaO t -Bu (15.1 g, 156.9 mmol) was added and proceeded in the same manner as in the synthesis method of 2-6 to obtain 34.2 g of the product. (Yield: 72%)

6. Synthesis of 2-109

After dissolving Sub 2-1-23 (25.0 g, 50.2 mmol) with toluene (251 mL), Sub 2-2-1 (12.1 g, 50.2 mmol), Pd ₂ (dba) ₃ (1.4 g, 1.5 mmol) , P( t- Bu) ₃ (0.6 g, 3.0 mmol), NaO t -Bu (9.7 g, 100.5 mmol) was added and proceeded in the same manner as in the synthesis method of 2-6 to obtain 24.7 g of the product. (Yield: 70%)

The FD-MS values of the compounds 2-1 to 2-120 of the present invention prepared according to the synthesis example as described above are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example 1] to [ Example 12] Red organic light emitting device ( Emitting layer Mixed phosphorescent host)

Holes with a thickness of 60 nm by vacuum depositing a 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as "2-TNATA") film on the ITO layer (anode) formed on the glass substrate After forming the injection layer, a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPD") film was vacuum deposited to a thickness of 55 nm to form a hole transport layer.

Next, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer. In this case, as shown in Table 5 below, the compound represented by Chemical Formula 1 (first host) and the compound represented by Chemical Formula 2 of the present invention (second Host) mixed in a weight ratio of 5:5 as a host, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir(acac)") as a dopant, The dopant was doped so that the host and the dopant had a weight ratio of 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 emission layer to form a hole blocking layer. Formed.

Subsequently, tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as "Alq ₃ ") and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) are 1:1 on the hole blocking layer. And formed to a thickness of 45 nm to form an electron transport layer. Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Comparative example 1] to [ Comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula 2 of the present invention was used alone as the host material of the emission layer as shown in Table 5 below.

[ Comparative example 4] to [ Comparative example 7]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that a mixture of Comparative Compound 1 and the compound represented by Formula 2 of the present invention was used as the host material of the emission layer as shown in Table 5 below.

[ Comparative example 8] and [ Comparative example 9]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that a mixture of the compound represented by Chemical Formula 1 and Comparative Compound 2 of the present invention was used as the host material of the emission layer as shown in Table 5 below.

<Comparative compound 1> <Comparative compound 2>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 12 and Comparative Examples 1 to 9 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. It was measured, and the T95 life was measured through a life measurement equipment of McScience at a reference brightness of 2500 cd/m ² , and the measurement results are shown in Table 7 below.

[Table 5]

[ Example 13] to [ Example 18] Green organic light emitting device ( Emitting layer Mixed phosphorescent host)

Using tris(2-phenylpyridine)-iridium (hereinafter referred to as "Ir(ppy) ₃ ) instead of (piq) ₂ Ir(acac) as a dopant, and represented by Chemical Formulas 1 and 2 as shown in Table 6 below as a host mixture. An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound was used.

[ Comparative example 10] and [ Comparative example 11]

An organic electroluminescent device was manufactured in the same manner as in Example 13, except that Comparative Compound 1 and the compound represented by Formula 2 of the present invention were mixed and used as a host.

[ Comparative example 12] and [ Comparative example 13]

An organic electroluminescent device was manufactured in the same manner as in Example 13, except that the compound represented by Formula 1 of the present invention and Comparative Compound 2 were mixed and used as a host.

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 13 to 18 and Comparative Examples 10 to 13 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. It was measured, and the T95 life was measured through a life measurement equipment of McScience at 5000 cd/m ² reference luminance, and the measurement results are shown in Table 6 below.

[Table 6]

From Tables 5 and 6, when the material for an organic electroluminescent device of the present invention represented by Formula 1 and Formula 2 is mixed and used as a phosphorescent host, when the compound contained in Formula 2 is used alone (Comparative Examples 1 to 3 ), when a mixture of Comparative Compound 1 and a compound represented by Formula 2 of the present invention (Comparative Examples 4 to 7), and a mixture of Comparative Compound 2 and a compound represented by Formula 1 of the present invention (Comparative Examples 8 and 9 ), it can be seen that the driving voltage is lowered and the efficiency and lifespan are remarkably improved.

Comparing Comparative Examples 1 to 9, compared to the case where the compound represented by Formula 2 was used alone, when the compound represented by Comparative Compound 1 and the compound represented by Formula 2 of the present invention were mixed and used as a host, the device characteristics were improved when the compound was used. When the compound 2 and the compound represented by Formula 1 of the present invention were mixed and used, the device characteristics were most improved.

However, compared to the case where the compound represented by Formula 1 and Comparative Compound 2 of the present invention were mixed and used as a host (Comparative Examples 8 and 9), the compound represented by Formula 1 and the compound represented by Formula 2 were mixed. When used as a phosphorescent host material, the device characteristics were the best.

This is because the compound of the present invention has stronger electron properties in the tertiary amine compound represented by Formula 1, which has superior stability to holes and quick hole injection properties than biscarbazole (moiety included in Comparative Compound 1). When the displayed compounds are mixed, the electron blocking ability is improved due to the high LUMO energy value of Formula 1, and more holes can move quickly and easily in the emission layer, and accordingly, the charge balance of holes and electrons in the emission layer is increased. This is because light is well emitted inside the light emitting layer rather than the transport layer interface, and thus deterioration at the HTL interface is also reduced, maximizing the driving voltage and efficiency of the entire device.

In addition, the compound represented by Formula 2 has a skeleton similar to that of Comparative Compound 2, but as a ring containing a heteroatom is additionally formed, the region of the HOMO orbital in the molecule is relatively increased, thereby increasing the stability of the hole. Life seems to have improved significantly.

Accordingly, the present invention seems to improve the performance of the entire device by electrochemically synergizing the combination of the compounds represented by Chemical Formulas 1 and 2 respectively.

[ Example 19] to [ Example 24] By mixing ratio Red organic light emitting device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the first host and the second host were mixed and used in a predetermined ratio as shown in Table 7 below.

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 19 to 24 of the present invention, based on 2500 cd/m ² In the luminance, the T95 life was measured through the life measurement equipment of McScience. The results are shown in Table 7 below. Example 19 and Example 22 are the result of measuring device characteristics when the first host and the second host are mixed at 3:7 as in Table 7 below.

[Table 7]

[ Example 25] to [ Example 30] By mixing ratio Green organic light emitting device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the first host and the second host were mixed and used in a predetermined ratio as shown in Table 8 below.

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 25 to 30 of the present invention, based on 5000 cd/m ² In the luminance, the T95 life was measured through the life measurement equipment of McScience. The results are shown in Table 8 below. Example 25 and Example 28 are the results of measuring device characteristics when the first host and the second host are mixed at 3:7 as in Table 8 below.

[Table 8]

From Tables 7 and 8, when the compound represented by Formula 1 and the compound represented by Formula 2 of the present invention are used as a mixed host at different mixing ratios (3:7, 5:5, 7:3) You can see that it can vary slightly.

From Table 7, it can be seen that in the case of the red organic light emitting device, as the ratio of the second host increases, the driving voltage decreases and the lifespan slightly increases.

On the other hand, from Table 8, in the case of the green organic light emitting device, it can be seen that the driving voltage slightly decreases as the ratio of the second host decreases, but the efficiency and lifespan are slightly improved.

Therefore, in the case of a mixture, since the amount of the mixing ratio affects the characteristics, it may be important to derive a mixing ratio that maximizes the charge balance in the light emitting layer.

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. The scope of protection of the present invention should be interpreted 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 (13)

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 includes a phosphorescent emission layer, and the host of the phosphorescent emission layer includes a first compound represented by Formula 1 below and a second compound represented by Formula 2 below:
<Formula 1><Formula2>

In Formulas 1 and 2,
Ar ¹ to Ar ⁴ are each independently a C ₆ to 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,
L ¹ to L ⁴ are each independently 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,
R ¹ to R ³ are each independently hydrogen; Deuterium, tritium; 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 to C ₃₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And it is selected from the group consisting of -L'-N (R _a ) (R _b ), and neighboring groups can be bonded to each other to form a ring,
a to c are each an integer of 0 to 4, and when each of them is an integer of 2 or more, each of R ^1, each of R ^{2, and} each of R ³ is the same or different from each other,
A-hwan

And ring B is

Is,
The X and Y are independently of each other C (R') (R"), N (R _c ), O or S,
L'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,
R _a , R _b , and R _c are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl 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,
The R'and R" are independently of each other hydrogen; deuterium, tritium; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; at least one of O, N, S, Si and P C ₂ ~ C ₆₀ heterocyclic group containing a hetero atom of; C ₃ ~ C ₆₀ aliphatic ring group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne Diary; C ₁ ~ C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ aryloxy group; is selected from the group consisting of, R'and R" can be bonded to each other to form a ring,
The Ar ¹ to Ar ⁴ , L ¹ to L ⁴ , R ¹ to R ³ , A ring, B ring, L', R _a , R _b , R _c , R', R", adjacent groups are bonded to each other The formed ring and the ring formed by bonding of R'and R" to each other are deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; 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; And C ₈ -C ₂₀ arylalkenyl group; It may be further substituted with one or more substituents selected from the group consisting of. The method of claim 1,
Formula 1 is an organic electric device, characterized in that represented by one of the following formulas 1-A to 1-I:
<Formula 1-A><Formula1-B><Formula1-C>

<Formula 1-D><Formula1-E><Formula1-F>

<Formula 1-G><Formula1-H><Formula1-I>

In Formula 1-A to Formula 1-I, L ¹ to L ³ , Ar ² , Ar ³ are the same as defined in claim 1,
Z is C(R')(R"), N(R _c ), O or S, wherein R', R", R _c are the same as defined in claim 1,
L ⁵ is a 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 ⁴ and R ⁵ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ aryloxy 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, and neighboring groups may be bonded to each other to form a ring,
a'is an integer of 0 to 4, b'is an integer of 0 to 3, and when each of them is an integer of 2 or more, each of R ^{4 and} each of R ⁵ are the same or different from each other. The method of claim 1,
Formula 1 is an organic electric device, characterized in that represented by one of the following formulas 1-J to 1-ZA:
<Formula 1-J><Formula1-K><Formula1-L>

<Formula 1-M><Formula1-N><Formula1-O>

<Formula 1-P><Formula1-Q><Formula1-R>

<Formula 1-S><Formula1-T><Formula1-U>

<Formula 1-V><Formula1-W><Formula1-X>

<Formula 1-Y><Formula1-Z><Formula1-ZA>

In Formula 1-J to 1-ZA, L ¹ to L ³ , Ar ² , Ar ³ are the same as defined in claim 1,
Y'is C(R')(R"), N(R _c ), O or S, wherein R', R", R _c are the same as defined in claim 1,
L ⁵ is a 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 ⁴ to R ⁷ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ aryloxy 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, and neighboring groups may be bonded to each other to form a ring,
a'is an integer of 0 to 4, b'is an integer of 0 to 3, c'is an integer of 0 to 6, d'is an integer of 0 to 8, and when each of these is an integer of 2 or more, each of R ⁴ and R ⁵ Respectively, each of R ^{6 and} each of R ⁷ are the same as or different from each other. The method of claim 1,
The L ¹ to L ⁴ are each independently an organic electric device, characterized in that one of the following Formulas b-1 to b-13:
<Formula b-1><Formulab-2><Formulab-3><Formulab-4>

<Formula b-5><Formulab-6><Formulab-7><Formulab-8>

<Formula b-9><Formulab-10>

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

In Formulas b-1 to b-13,
Y ¹ is N-(L ^a -Ar ^a ), O, S or C(R _d )(R _e ),
Z ¹ to Z ³ are each independently C, C (R _f ) or N, and at least one of Z ¹ to Z ³ is N,
R ⁵ to R ⁷ , R _d , R _e and R _f are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl 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; A fused ring group of an aliphatic ring of C ₃ to C ₂₀ and an aromatic ring of C ₆ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; C ₁ ~ C ₂₀ alkoxy group; And C ₆ ~ C ₃₀ aryloxy group; selected from the group consisting of, neighboring groups may be bonded to each other to form a ring, and R _d and R _e may be bonded to each other to form a ring, and C ( In R _f ), neighboring R _f can be bonded to each other to form a ring,
f is an integer of 0 to 6, e, g, h, and i are each an integer of 0 to 4, j and k are each an integer of 0 to 3, l is an integer of 0 to 2, and m is 0 It is an integer of 3, and when each of them is an integer of 2 or more, each of a plurality of R ^5, each of a plurality of R ^{6, and} each of a plurality of R ⁷ are the same or different from each other,
Ar ^a is 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 of P; C ₃ ~ C ₂₀ aliphatic ring group; And it is selected from the group consisting of a combination thereof,
L ^a is each independently 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. The method of claim 1,
An organic electric device, characterized in that the compound represented by Formula 1 is one of the following compounds:

. The method of claim 1,
Formula 2 is an organic electric device, characterized in that represented by one of the following formulas 2-A to 2-D:
<Formula 2-A><Formula2-B>

<Formula 2-C><Formula2-D>

In Formulas 2-A to 2-D, Ar ⁴ , L ⁴ , R ¹ to R ³ , X, Y, a to c are as defined in claim 1. The method of claim 1,
Ar ⁴ is an organic electric device, characterized in that represented by the following formula A or formula B:
<Formula A><FormulaB>

In the above formulas A and B,
Q ¹ to Q ⁴ are each independently N, C or C (R _d ), Q ⁵ to Q ⁹ are each independently N or C (R _d ),
Z ring is selected from the following structures,
<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 structure, * represents a condensation position with a ring including Q ¹ to Q ⁴ ,
W ¹ and W ² are independently of each other a single bond, N-(L ₁ -Ar ₁ ), S, O, C or C(R _e )(R _f ),
V is independently of each other N, C or C (R _g ),
R _d , R _e , R _f , R _g and Ar ₁ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro 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 ; 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; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ is selected from the group consisting of an arylalkenyl group, and neighboring groups may be bonded to each other to form a ring, and R _e and R _f may be bonded to each other to form a ring,
L ₁ is a single bond; C ₆ -C ₆₀ arylene group; Fluorenylene group; A C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₃ -C ₆₀ is selected from the group consisting of an aliphatic ring group. The method of claim 1,
An organic electric device, characterized in that the compound represented by Formula 2 is one of the following compounds:

. The method of claim 1,
An organic electric device, characterized in that the compound represented by Formula 1 and the compound represented by Formula 2 are included in a weight ratio of 2:8 to 8:2. The method of claim 1,
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 10,
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 1; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 12,
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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