KR20200136072A - An organic electronic element comprising compound for organic electronic element and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric device including an anode, a cathode, and an organic material layer between the anode and the cathode, and the electronic device including the organic electric device. By including a mixture of compounds represented by chemical formulas 1 and 2 of the present invention in a light emitting layer of the organic material layer, it is possible to lower the driving voltage of the organic electric device and improve luminous efficiency and a lifespan.

Description

An organic electric device including a compound for an organic electric device, and an electronic device therefor

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 can be classified into a high-molecular type and a low-molecular type according to the molecular weight, and according to the light-emitting mechanism, it can be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron. I can. In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors 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 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, it is necessary to develop a host material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer, and in particular, a phosphorescent host material is 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 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" used in the present invention has a'spyro linkage', and a 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 refers to 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 Means a compound, etc.

The term "heterocyclic group" as used in the present invention 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 refers to 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 compound name 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, it means that the substituent R ¹ is absent, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6 In the case of an integer of, it is bonded to carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different from each other.

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

In addition, unless otherwise specified in the specification, when a ring is expressed in the form of a'numeric resource' such as a five-membered ring or a six-membered ring, the number in'number-atomic' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a five-membered ring, and benzene or pyridine may correspond to a six-membered ring.

In addition, unless otherwise described in the 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 an 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 light-emitting layers are formed by the multi-layer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light-emitting layer, as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350, 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or the light efficiency improvement layer 180 may be used as a material, but preferably, the compound represented by Formula 1 and the compound represented by Formula 2 of the present invention A mixture of compounds is used as a host of the emission layer (140, 340, 440) or / is used, and the compound represented by Formula 1 is used as the hole transport layer (130, 330, 430) and / or the light emission auxiliary layer 220 It can be used as a material for the transport band.

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.

Accordingly, in the present invention, a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 is used as a host of the light emitting layers 140, 340, and 440, and/or the compound represented by Formula 1 is used as a hole transport layer ( 130, 330, 430) and/or light-emitting auxiliary layer 220, by using it as a material for the hole transport band layer, the energy level and T ₁ value between each organic material layer, intrinsic properties of the material (mobility, interfacial properties, etc.) By optimizing, it is possible to improve the life and efficiency of the organic electronic device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, 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 may be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

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

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

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. 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.

The Ar ¹ ~Ar ³ , L ¹ ~L ³ are each 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 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; 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 may be further substituted with one or more substituents selected from the group consisting of an arylalkenyl group.

Formula 1 may be represented by one of Formulas 1-1 to 1-18 below.

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

<Formula 1-4> <Formula 1-5> <Formula 1-6>

<Formula 1-7> <Formula 1-8> <Formula 1-9>

<Formula 1-10> <Formula 1-11> <Formula 1-12>

<Formula 1-13> <Formula 1-14> <Formula 1-15>

<Formula 1-16> <Formula 1-17> <Formula 1-18>

In Formulas 1-1 to 1-18, Ar ² , Ar ³ , and L ¹ to L ³ are the same as defined in Formula 1.

Y ₁ to Y ₃ are each independently O, S, N(R _c ) or C(R')(R").

R ³ to R ⁸ , R ¹² to R ¹⁸ , R'and R" are independently of each other hydrogen; deuterium; 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; C ₆ -C ₂₀ aryloxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkyne Diary; C ₆ -C ₂₀ Aryl group; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic ring group; selected from the group consisting of, neighboring groups may be bonded to each other to form a ring.

c, e, h, p, q, s, u, v are each an integer of 0-4, and if they are an integer of 2 or more, each of R ^3, each of R ^5, each of R ^8, each of R ^12, each of R ¹³ , R Each of ^15, each of R ^{17 and} each of R ¹⁸ is the same as or different from each other.

d, f, g, r, and t are each an integer of 0 to 3, and when these are integers of 2 or more, each of R ^4, each of R ^6, each of R ^7, each of R ^{14, and} each of R ¹⁶ is the same or different from each other.

R _c 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 selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of.

L ⁶ is a 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.

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

X is O or S.

Ar ⁴ and Ar ⁵ 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 ⁴ and Ar ⁵ are an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, etc. I can.

When Ar ⁴ and Ar ⁵ are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group such as pyridine, pyrimidine, triazine, quinoline, iso Quinoline, quinazoline, quinoxaline, benzothienopyrazine, benzofuropyrazine, benzothienopyrimidine, benzofuropyrimidine, benzoquinazoline, benzoquinoxaline, benzoxazole, dibenzothiophene, di Benzofuran, naphthofuropyrimidine, naphthothienopyrimidine, carbazole, phenylcarbazole, and the like.

When Ar ⁴ and Ar ⁵ are fluoroyl groups, they may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, and the like.

L ⁴ and L ⁵ 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 may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom.

When L ⁴ and L ⁵ are 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, biphenylene, naphthalene, terphenyl, etc. have.

When L ⁴ and L ⁵ are heterocyclic groups, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₄ heterocyclic group such as pyridine, pyrimidine, triazine, quinoline, iso Quinoline, quinazoline, quinoxaline, benzothienopyrazine, benzofuropyrazine, benzothienopyrimidine, benzofuropyrimidine, benzoquinazoline, benzoquinoxaline, dibenzothiophene, dibenzofuran, naph Topuropyrimidine, naphthothiopyrimidine, and the like.

R ¹ is 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 ); may be selected from the group consisting of.

The ring formed by bonding of adjacent R ^{1 to} each other is an aromatic ring group of C ₆ ~ C ₆₀ ; Fluorene group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Alternatively, it may be a C ₃ ~ C ₆₀ aliphatic ring group. When adjacent R ^1s are bonded to each other to form an aromatic ring, preferably an aromatic ring of C ₆ to C ₃₀ , more preferably an aromatic ring of C ₆ to C ₁₄ , such as benzene, naphthalene, phenanthrene, etc. Can form a ring.

a is an integer of 0 to 4, and when a is an integer of 2 or more, each of R ¹ is the same 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, biphenyl, naphthyl, 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 ₁₈ heterocyclic group such as pyridine, dibenzothiophene, carbazole, phenylcarbazole, It may be quinazoline, quinoline, isoquinoline, quinoxaline, and the like.

When R ¹ is an aliphatic ring group, preferably a C ₃ to C ₃₀ aliphatic ring group, more preferably a C ₃ to C ₁₂ aliphatic ring group, such as cyclohexane, cyclohexylcyclohexane, or the like.

When R ¹ is a 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.

When R ¹ is an alkyl group, it may be preferably a C ₂ to C ₂₀ alkyl group, more preferably a C ₂ to C ₁₀ alkyl group, such as methyl or t-butyl.

When R ¹ is an alkoxy group, it may be preferably a C ₁ to C ₂₀ alkoxyl group, more preferably a C ₁ to C ₁₀ alkoxyl group such as methoxy or ethoxy.

L'is 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; C ₃ ~ C ₆₀ aliphatic ring group; And it may be selected from the group consisting of a combination thereof.

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

The Ar ⁴ , Ar ⁵ , L ⁴ , L ⁵ , R ¹ , and the rings formed by bonding of adjacent groups to each other are deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group.

Preferably, Formula 2 may be represented by one of the following Formulas 2-1 to 2-4.

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

In Formulas 2-1 to 2-4, X, R ¹ , L ⁴ , L ⁵ , Ar ⁴ , Ar ⁵ , and a are as defined in Formula 2.

a ¹ to a ⁵ are each independently C(R _d ) or N, and at least one of a ¹ to a ⁵ is N.

R _d is independently of each other 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 alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ is selected from the group consisting of arylalkenyl group, neighboring groups may be bonded to each other to form a ring.

The L ¹ to L ⁵ may be each independently selected from the group consisting of the following Formulas a-1 to a-13.

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

<Formula a-4> <Formula a-5> <Formula a-6>

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

<Formula a-11> <Formula a-12> <Formula a-13>

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

R ⁹ to R ¹¹ 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 alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ is selected from the group consisting of arylalkenyl group, neighboring groups may be bonded to each other to form a ring.

i is an integer from 0 to 4, j is an integer from 0 to 6, m is an integer from 0 to 3, o is an integer from 0 to 2, and each of R ⁹ is the same as each other when each is an integer of 2 or more Different.

k is an integer of 0 to 4, n is an integer of 0 to 3, and when each of these is an integer of 2 or more, each of R ¹⁰ is the same as or different from each other.

l is an integer of 0-4, and when l is an integer of 2 or more, each of R ¹¹ is the same as or different from each other.

Z is N(L ^a -Ar ^a ), O, S or C(R ₁ )(R ₂ ), Z ¹ to Z ³ are each independently C, C(R ₃ ) or N, and Z ¹ to Z At least one of ³ is N.

R ₁ to R ₃ 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 alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ is selected from the group consisting of an arylalkenyl group, and R ₁ and R ₂ may be bonded to each other to form a ring, and adjacent R ₃ may be bonded to each other to form a ring.

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 Formula 2, at least one of Ar ⁴ and Ar ⁵ may be one of Formulas b-1 to b-3 below.

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

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

a ₆ to a ₁₆ are independently of each other C, C(R ₄ ) or N, at least one of a ₆ to a ₈ is N, at least one of a ₉ to a ₁₂ is N, and a ₁₃ to a ₁₆ of At least one is N, and X ₁ is O, S, C(R ₅ )(R ₆ ) or N(R ₇ ).

Ar ⁵ , Ar ⁶ and R ₄ to R ₆ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; It is selected from the group consisting of, and neighboring groups may be bonded to each other to form a ring, and R ₅ and R ₆ may be bonded to each other to form a ring.

R ₇ 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 selected from the group consisting of 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 the following compound, but is not limited thereto.

.

.

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.

In another embodiment of the present invention, the organic material layer further includes at least one hole transport band layer formed between the light emitting layer and the anode, and the hole transport band layer includes at least one of a hole transport layer and a light emission auxiliary layer, , It includes a compound represented by Formula 1.

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

[Synthesis Example 1] Chemical 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.

<Scheme 1> (Hal ¹ is I, Br or Cl)

Synthesis example of Sub 1

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

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

1. Sub 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. 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 129.5 g of a product. (Yield: 78%)

2. Sub 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 like the synthesis method of 76, and the product 87.5g was obtained. (Yield: 72%)

Synthesis example of Sub 2

Sub 2 of Scheme 1 may be synthesized by Scheme 3 below, but is not limited thereto.

<Scheme 3> (Hal ¹ And Hal ² are independently of each other I, Br or Cl)

Synthesis of final compound (final product 1)

1. 1-76 Synthesis Example

In a round bottom flask, Sub 2-76 (142.0 g, 418.6 mmol), Sub 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. 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 173.5 g of a product. (Yield: 73%)

2. Synthesis of 1-110

Sub 2-110 (52.5 g, 212.6 mmol), Sub 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 used in the same manner as in the synthesis method of 1-76 to obtain 92.1 g of the product. (Yield: 75%)

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] Formula 2

The compound represented by Formula 2 according to the present invention (final product 2) may be prepared by reacting Sub 3 and Sub 4 as shown in Scheme 4 below, but is not limited thereto.

<Reaction Scheme 4>

Sub 3 synthesis example

Sub 3 of Scheme 4 may be synthesized by the following Scheme 5, but is not limited thereto.

<Reaction Scheme 5>

1.Sub 3-1 Synthesis example

2-chloro-4,6-diphenyl-1,3,5-triazine (50 g, 186.8 mmol) bis(pinacolato)diboron (52.2 g, 205.4 mmol), Pd(dppf)Cl ₂ (4.1 g, 5.6 mmol) ), KOAc (55 g, 560.3 mmol) and toluene (900 ml) were added, followed by stirring at 120°C. When the reaction was completed, the temperature of the reaction product was cooled to room temperature, extracted with MC, and washed with 1N HCl. Thereafter, the organic layer was dried with MgSO ₄ and then concentrated to separate the resulting organic material with a silica gel filter to obtain 49.6 g (yield: 74%) of the product Sub 3-1.

2.Sub 3-38 Synthesis example

(1) Sub 3-38a synthesis

2-bromo-4-(naphthalen-1-yl)quinazoline (50 g, 149.2 mmol), 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (35.6 g , 149.2 mmol), Pd(PPh ₃ ) ₄ (10.34 g, 8.95 mmol), K ₂ CO ₃ (61.8 g, 447.5 mmol) was dissolved in THF (750 ml), and then water (350 ml) was added and 90°C Stirred at. Thereafter, when the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and then concentrated and the resulting organic material was separated with a silica gel filter to obtain 44.3 g (yield: 81%) of the product Sub 3-38a.

(2) Sub 3-38 synthesis

Sub 3-38a (44.3 g, 120.8 mmol) bis(pinacolato)diboron (33.7 g, 132.8 mmol), Pd(dppf)Cl ₂ (2.65 g, 3.62 mmol), KOAc (35.6 g, 362.3 mmol), toluene ( 600 ml) was added and then proceeded in the same manner as for the synthesis of Sub 3-1 to obtain 38.7 g (yield: 70%) of the product Sub 3-38.

3.Sub 3-63 Synthesis example

(1) Sub 3-63a synthesis

2-chloro-3-phenylquinoxaline (50 g, 207.7 mmol) in bis(pinacolato)diboron (58 g, 228.5 mmol), Pd(dppf)Cl ₂ (4.56 g, 6.23 mmol), KOAc (61.2 g, 623.2 mmol) , Toluene (1000 ml) was added and then proceeded in the same manner as the synthesis method of Sub 3-1 to obtain 49 g (yield: 71%) of the product Sub 3-63a.

(2) Sub 3-63b synthesis

Sub 3-63a (49 g, 147.5 mmol), 3-bromo-4'-chloro-1,1'-biphenyl (39.5 g, 147.5 mmol), Pd(PPh ₃ ) ₄ (10.23 g, 8.95 mmol), K ₂ CO ₃ (61.2 g, 442.5 mmol) was dissolved in THF (700 ml), then water (350 ml) was added and proceeded in the same manner as in the synthesis method of Sub 3-38a to add 47.5 g of Sub 3-63b (yield : 82%).

(3) Sub 3-63 synthesis

Sub 3-63b (47.5 g, 120.9 mmol) bis(pinacolato)diboron (33.8 g, 133 mmol), Pd(dppf)Cl ₂ (2.65 g, 3.63 mmol), KOAc (35.6 g, 362.7 mmol), toluene ( 600 ml) was added and then proceeded in the same manner as for the synthesis of Sub 3-1 to obtain 42.2 g (yield: 72%) of the product Sub 3-63.

Compounds corresponding to Sub 3 are as follows, but are not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 2]

Synthesis example of Sub 4

Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 6 below, but is not limited thereto.

<Reaction Scheme 6>

1.Sub 4-1 Synthesis example

2,4-dichlorobenzofuro[3,2-d]pyrimidine (50 g, 209.2 mmol), Sub 3-1 (75.1 g, 209.2 mmol), Pd(PPh ₃ ) ₄ (14.5 g, 12.55 mmol), K ₂ CO After dissolving THF (1000 ml) in ₃ (86.7 g, 627.5 mmol), water (500 ml) was added and stirred at 90°C. Thereafter, when the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated through a silica gel filter to obtain 51.1 g (yield: 56%) of the product Sub 4-1.

2.Sub 4-34 Synthesis example

2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (50 g, 196 mmol), Sub 3-24 (80 g, 196 mmol), Pd(PPh ₃ ) ₄ (13.59 g, 11.76 mmol), K ₂ CO ₃ (81.3 g, 588 mmol) was dissolved in THF (1000 ml), then water (500 ml) was added and proceeded in the same manner as for the synthesis of Sub 4-1, and the product Sub 4-34 54 g (yield: 55%) was obtained.

3.Sub 4-72 Synthesis example

2,4-dichlorobenzofuro[2,3-d]pyrimidine (50 g, 209.2 mmol), Sub 3-56 (107 g, 209.2 mmol), Pd(PPh ₃ ) ₄ (14.5 g, 12.55 mmol), K ₂ CO ₃ (86.7 g, 627.5 mmol) was dissolved in THF (1000 ml), then water (500 ml) was added and proceeded in the same manner as for the synthesis of Sub 4-1, and the product Sub 4-72 was 63.9 g (yield: 52%).

The compounds belonging to Sub 4 are as follows, but are not limited thereto, and Table 3 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 3]

Synthesis of the final compound of Formula 2

1.2-1 Synthesis example

Sub 4-1 (20 g, 45.9 mmol), Sub 3-12 (9.4 g, 45.9 mmol), Pd(PPh ₃ ) ₄ (3.18 g, 2.75 mmol), K ₂ CO ₃ (19 g, 137.7 mmol) THF (200 ml) was added and dissolved, then water (100 ml) was added and stirred at 90°C. Thereafter, when the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated through a silica gel filter to obtain 18.2 g (yield: 83%) of the product 2-1.

2. 2-8 Synthesis example

Sub 4-3 (20 g, 48.9 mmol), Sub 3-21 (17.4 g, 48.9 mmol), Pd(PPh ₃ ) ₄ (3.39 g, 2.94 mmol), K ₂ CO ₃ (20.3 g, 146.8 mmol) After adding and dissolving THF (200 ml), water (100 ml) was added and proceeded in the same manner as in the synthesis method of 2-1 to obtain 24.2 g (yield: 82%) of product 2-8.

3. 2-58 Synthesis example

Sub 4-53 (20 g, 36.3 mmol), Sub 3-12 (7.4 g, 36.3 mmol), Pd(PPh ₃ ) ₄ (2.52 g, 2.18 mmol), K ₂ CO ₃ (15 g, 108.9 mmol) After adding and dissolving THF (200 ml), water (100 ml) was added and proceeded in the same manner as in the synthesis method of 2-1 to obtain 17.2 g (yield: 80%) of product 2-58.

4. 2-86 Synthesis example

Sub 4-17 (20 g, 71.2 mmol), Sub 3-51 (36.4 g, 71.2 mmol), Pd(PPh ₃ ) ₄ (4.94 g, 4.27 mmol), K ₂ CO ₃ (29.5 g, 213.7 mmol) After adding and dissolving THF (300 ml), water (150 ml) was added and proceeded in the same manner as in the synthesis method of 2-1 to obtain 36.8 g (yield: 82%) of product 2-86.

5. 2-114 Synthesis example

Sub 4-74 (20 g, 34.7 mmol), Sub 3-89 (10.2 g, 34.7 mmol), Pd(PPh ₃ ) ₄ (2.4 g, 2.08 mmol), K ₂ CO ₃ (14.4 g, 104.0 mmol) After adding and dissolving THF (150 ml), water (75 ml) was added and proceeded in the same manner as in the synthesis method of 2-1 to obtain 20.6 g (yield: 84%) of the product 2-114.

The FD-MS values of the compounds 2-1 to 2-128 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 18] Green organic electroluminescent 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 "NPB") film was vacuum deposited to a thickness of 60 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, and at this time, as shown in Table 5 below, the first compound (first host) represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 of the present invention Use a mixture of the compound (second host) in a weight ratio of 5:5 as a host, and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as "Ir(ppy) ₃ ") as a dopant, but the host and the dopant Dopant was doped so that the weight ratio of was 95:5.

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

Thereafter, tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer, 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 was used alone as a host as shown in Table 5 below.

[ Comparative example 4] and [ Comparative example 5]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 was used as a host as shown in Table 5 below.

[ Comparative example 6]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compounds 1 and 2 were mixed and used as a host as shown in Table 5 below.

[ Comparative example 7] to [ Comparative example 10]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one type of comparative compound and one type of compound represented by Formula 1 or 2 of the present invention were mixed and used as a host 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 18 and Comparative Examples 1 to 10 of the present invention, electroluminescence (EL) characteristics were obtained by using PR-650 of photoresearch. It was measured, and the T95 life was measured using a life measurement equipment of McScience at 5000 cd/m ² reference luminance, and the measurement results are shown in Table 5 below.

[Table 5]

From Table 5, 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 (Examples 1 to 18), devices using a single material (Comparative Examples 1 to 5) , Compared to a device using a mixture of the comparative compound (Comparative Example 6) and a device using a mixture of the comparative compound and the compound represented by the formula of the present invention (Comparative Examples 7 to 10), the driving voltage, efficiency, and life were significantly improved I can confirm.

Looking at the comparative examples, when the compound of the present invention represented by Formula 2 is used as a single host (Comparative Examples 1 to 3), or when Comparative Compound 1 or Comparative Compound 2 is used as a single host (Comparative Examples 4 and 5) In comparison, driving voltage, efficiency, and life were improved when a host in which two types of compounds were mixed (Comparative Examples 6 to 10) was used.

And comparing the case of using as a host by mixing two types of compounds, compared to Comparative Examples 6-10, in the case of the embodiment of the present invention using a mixture of the compounds represented by Formulas 1 and 2 of the present invention, the driving voltage, efficiency, and The lifespan has improved.

This means that when a tertiary amine compound represented by Formula 1 with stability for holes and fast hole injection properties is mixed with a compound represented by Formula 2 with strong electron properties, more holes can move quickly and easily in the light emitting layer. It seems that this is because the electron blocking ability is improved due to the high LUMO energy value of 1, and the charge balance between holes and electrons in the emission layer is improved, so that light emission occurs well inside the emission layer rather than the hole transport layer interface. As a result, deterioration at the HTL interface is also reduced, and the driving voltage, efficiency, and lifespan of the entire device appear to be maximized.

That is, when the combination of the compounds represented by Chemical Formula 1 and Chemical Formula 2 is used as the phosphorescent host of the light-emitting layer, the combination electrochemically synergizes, thereby improving the overall performance of the device.

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

An organic electroluminescent device in the same manner as in Example 1, except that the first host compound and the second host compound were used in a weight ratio of 4:6, 3:7 and 2:8, as shown in Table 6 below. Was produced.

[Table 6]

From Table 6, it can be seen that the driving voltage, efficiency, and lifespan vary according to the mixing ratio of the first host and the second host. In terms of efficiency and lifespan, it can be seen that Example 19 and Example 22 are improved compared to other cases, and it can be seen that the efficiency and lifespan can be improved as the content of the first host is increased.

These results suggest that in the case of a mixture, since the amount of the mixing ratio affects the device characteristics, it is important to derive the mixing ratio in which the charge balance in the light emitting layer is maximized.

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 explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention is in the scope of the following claims. 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 (15)

In an organic electric device comprising an anode, a negative station, and an organic material layer formed between the anode and the cathode,
The organic material layer includes an emission layer, and the emission layer includes a first host compound represented by the following Formula 1 and a second host compound represented by the following Formula 2 as a phosphorescent emission layer:
<Formula 1><Formula2>

In Formulas 1 and 2,
Ar ¹ to Ar ⁵ 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 ⁵ 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,
X is O or S,
R ¹ is 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, neighboring groups can be bonded to each other to form a ring,
a is an integer of 0 to 4, and when a is an integer of 2 or more, each of R ¹ is the same as or different from each other,
L'is 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; C ₃ ~ C ₆₀ aliphatic ring group; And it is selected from the group consisting of a combination thereof,
R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; C ₃ ~ C ₆₀ aliphatic ring group; And it is selected from the group consisting of a combination thereof,
The Ar ¹ to Ar ⁵ , L ¹ to L ⁵ , R ¹ , and the rings formed by bonding of adjacent groups to each other are deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; 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 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; 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 1-1 to 1-3:
<Formula 1-1><Formula1-2><Formula1-3>

In Formulas 1-1 to 1-3, Ar ² , Ar ³ , L ¹ to L ³ are the same as defined in claim 1,
Y ₁ to Y ₃ are each independently O, S, N(R _c ) or C(R')(R"),
R ³ to R ⁸ , R'and R" are each independently hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a 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; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic It is selected from the group consisting of a cyclic group, and neighboring groups may be bonded to each other to form a ring,
c, e, and h are each an integer of 0-4, and when they are an integer of 2 or more, each of R ^3, each of R ^{5, and} each of R ⁸ is the same or different from each other,
d, f and g are each an integer of 0 to 3, and when they are an integer of 2 or more, each of R ^4, each of R ^{6, and} each of R ⁷ are the same or different from each other,
R _c 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 selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is 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 1-4 to 1-12:
<Formula 1-4><Formula1-5><Formula1-6>

<Formula 1-7><Formula1-8><Formula1-9>

<Formula 1-10><Formula1-11><Formula1-12>

In Formulas 1-4 to 1-12, Ar ² , Ar ³ , L ¹ to L ³ are the same as defined in claim 1,
Y ₁ is independently of each other O, S, N(R _c ) or C(R')(R"),
R ³ and R ⁴ , wherein R'and R" are independently of each other hydrogen; deuterium; halogen; silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or C ₆ -C ₂₀ aryl group; 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; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic It is selected from the group consisting of a cyclic group, and neighboring groups may be bonded to each other to form a ring,
c is an integer of 0-4, and when c is an integer of 2 or more, each of R ³ is the same as or different from each other,
d is an integer of 0-3, and when d is an integer of 2 or more, each of R ⁴ is the same as or different from each other,
R _c 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 selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is 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 1-13 to 1-18:
<Formula 1-13><Formula1-14><Formula1-15>

<Formula 1-16><Formula1-17><Formula1-18>

In Formulas 1-13 to 1-18, Ar ² , Ar ³ , L ¹ to L ³ are the same as defined in claim 1,
Y ₁ and Y ₂ are each independently O, S, N(R _c ) or C(R')(R"),
R ¹² to R ¹⁸ , R'and R" are each independently hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a cyano group; a 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; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic ring It is selected from the group consisting of groups, and neighboring groups may be bonded to each other to form a ring.
p, q, s, u, v are each an integer of 0-4, and when these are integers of 2 or more, each of R ^12, each of R ^13, each of R ^15, each of R ^{17, and} each of R ¹⁸ is the same or different from each other,
r and t are each an integer of 0-3, and when they are an integer of 2 or more, each of R ^{14 and} each of R ¹⁶ are the same as or different from each other,
R _c 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 selected from the group consisting of P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of,
L ⁶ is a 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. The method of claim 1,
Wherein L ¹ to L ⁵ are each independently an organic electric device, characterized in that selected from the group consisting of the following formulas a-1 to a-13:
<Formula a-1><Formulaa-2><Formulaa-3>

<Formula a-4><Formulaa-5><Formulaa-6>

<Formula a-7><Formulaa-8><Formulaa-9><Formulaa-10>

<Formula a-11><Formulaa-12><Formulaa-13>

In Formulas a-1 to a-13,
R ⁹ to R ¹¹ 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 alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ selected from the group consisting of arylalkenyl groups, and neighboring groups may be bonded to each other to form a ring,
i is an integer from 0 to 4, j is an integer from 0 to 6, m is an integer from 0 to 3, o is an integer from 0 to 2, and each of R ⁹ is the same as each other when each is an integer of 2 or more Different,
k is an integer of 0-4, n is an integer of 0-3, and when each of these is an integer of 2 or more, each of R ¹⁰ is the same or different from each other,
l is an integer of 0-4, and when l is an integer of 2 or more, each of R ¹¹ is the same as or different from each other,
Z is N(L ^a -Ar ^a ), O, S or C(R ₁ )(R ₂ ),
Z ¹ to Z ³ are each independently C, C (R ₃ ) or N, at least one of Z ¹ to Z ³ is N,
R ₁ to R ₃ 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 alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And it is selected from the group consisting of an arylalkenyl group of C ₈ -C ₂₀ , R ₁ and R ₂ may be bonded to each other to form a ring, and neighboring R ₃ may be bonded to each other to form a ring,
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,
The method of claim 1,
Formula 2 is an organic electric device, characterized in that represented by one of the following Formulas 2-1 to 2-4:
<Formula 2-1><Formula2-2><Formula2-3><Formula2-4>

In Formulas 2-1 to 2-4, X, R ¹ , L ⁴ , L ⁵ , Ar ⁴ , Ar ⁵ , a are the same as defined in claim 1,
a ¹ to a ⁵ are each independently C (R _d ) or N, at least one of a ¹ to a ⁵ is N,
R _d is independently of each other 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 alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ is selected from the group consisting of arylalkenyl group, neighboring groups may be bonded to each other to form a ring. The method of claim 1,
At least one of Ar ⁴ and Ar ⁵ is one of the following Formulas b-1 to b-3:
<Formula b-1><Formulab-2><Formulab-3>

In Formulas b-1 to b-3,
a ₆ to a ₁₆ are independently of each other C, C(R ₄ ) or N, at least one of a ₆ to a ₈ is N, at least one of a ₉ to a ₁₂ is N, and a ₁₃ to a ₁₆ of At least one is N,
X ₁ is O, S, C(R ₅ )(R ₆ ) or N(R ₇ ),
Ar ⁵ , Ar ⁶ and R ₄ to R ₆ are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio 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; C ₃ -C ₂₀ aliphatic ring group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; selected from the group consisting of, and neighboring groups may be bonded to each other to form a ring, and R ₅ and R ₆ may be bonded to each other to form a ring,
R ₇ 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 selected from the group consisting of P; And C ₃ -C ₂₀ 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 1 is one of the following compounds:

. 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 11,
The organic electroluminescent device further comprises a charge generation layer formed between the two or more stacks. The method of claim 1,
The organic material layer further includes at least one hole transport band layer formed between the light emitting layer and the anode,
The hole transport band layer includes at least one of a hole transport layer and an emission auxiliary layer, and includes a compound represented by Chemical Formula 1. A display device comprising the organic electric device of claim 1; And
Electronic device including; a control unit for driving the display device. The method of claim 14,
The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

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