KR102712988B1 - 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 element including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and an electronic device including the organic electric element, wherein the organic layer includes compounds represented by chemical formulas 1 and 2, thereby lowering the driving voltage of the organic electric element and improving the luminous efficiency and lifespan.

Description

Organic electronic element comprising a compound for an organic electronic element 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 comprising a compound for an organic electric device and an electronic device thereof.

In general, the organic luminescence phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. An organic electric device utilizing the organic luminescence phenomenon usually has a structure including an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

Materials used as organic layers in organic electroluminescent devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions. In addition, the light-emitting materials can be classified into high molecular weight and low molecular weight types depending on their molecular weight, and can be classified into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons depending on their luminescence mechanisms. In addition, the light-emitting materials can be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials required to realize better natural colors depending on their luminescence colors.

Meanwhile, when only one substance is used as a light-emitting material, the maximum light-emitting wavelength shifts to a longer wavelength due to intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light-emitting attenuation effect. Therefore, a host/dopant system can be used as a light-emitting material to increase the color purity and the light-emitting efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, thereby emitting light with high efficiency. At this time, the wavelength of the host shifts to the wavelength of the dopant, so light of a desired wavelength can be obtained depending on the type of dopant used.

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

Efficiency, lifespan, and driving voltage are interrelated. As efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, the crystallization of organic substances due to Joule heating generated during operation decreases, which tends to increase the lifespan. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved simultaneously when the energy level and T ₁ value between each organic layer and the inherent properties of the material (mobility, interfacial properties, etc.) are optimally combined.

Therefore, there is a need for the development of a light-emitting material that has high thermal stability and can efficiently achieve charge balance within the light-emitting layer. In other words, in order to fully demonstrate the excellent characteristics of organic electric devices, it is necessary for the materials forming the organic layers within the devices, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, to be supported by stable and efficient materials. However, stable and efficient organic layer materials for organic electric devices have not yet been sufficiently developed, and among these, the development of host materials for the light-emitting layer is particularly urgently required.

The purpose of the present invention is to provide an organic electric element and an electronic device thereof capable of lowering the driving voltage of the element and improving the luminous efficiency and lifespan of the element.

In one aspect, the present invention provides an organic electric device including a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2 in a light-emitting layer.

<Chemical Formula 1> <Chemical Formula 2>

In another aspect, the present invention provides an electronic device including the organic electric element.

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

Figure 1 is an exemplary diagram of an organic light-emitting device according to the present invention.

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

The term "fluorenyl group" or "fluorenylene group" used in the present invention, unless otherwise stated, means a monovalent or divalent functional group wherein R, R' and R" in the following structures are all hydrogen, respectively, and a "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

The term "spiro compound" used in the present invention has a 'spiro linkage', and a spiro linkage means a link formed by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms contained in a compound, they are called 'monospiro-', 'dicepiro-', and 'trispiro-' compounds, respectively.

The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise stated means a ring having 2 to 60 carbon atoms each containing one or more heteroatoms, but is not limited thereto. The term "heteroatom" used herein represents N, O, S, P or Si unless otherwise stated, and a heterocyclic group means a monocyclic ring, ring aggregate, fused multiple ring system, spiro compound, etc. containing a heteroatom.

The term "heterocyclic group" used in the present invention means a ring that contains a heteroatom, such as N, O, S, P or Si, instead of a carbon forming the ring, and includes not only an aromatic ring, such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and may also include a compound that contains a heteroatom group, such as SO ₂ , P = O, instead of a carbon forming the ring, as in the following compounds.

The term "aliphatic ring" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise stated, means a ring having 3 to 60 carbon atoms, but is not limited thereto. For example, even if an aromatic ring, benzene, and a non-aromatic ring, cyclohexane, are fused, it is also considered an aliphatic ring.

In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', or may be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the group name may be described by distinguishing the valence, such as 'phenanthryl' for a monovalent 'group' and 'phenantrylene' for a divalent group, or it may be described as 'phenanthrene', the name of the parent compound, regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for a monovalent group and pyrimidinylene for a divalent group.

In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine may be described as benzofuropyrimidine, and 9,9-dimethyl-9H-fluorene may be described as dimethylfluorene. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

In addition, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

Here, when a is an integer of 0, it means that the substituent R ¹ is absent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring, and in this case, the indication of the hydrogen bonded to the carbon can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R ¹ bonds to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can bond as follows, for example, and when a is an integer of 4 to 6, it bonds to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or greater, R ¹ can be the same or different.

In addition, unless otherwise stated in the present specification, the ring formed by bonding adjacent groups to each other may be selected from the group consisting of a C ₆ to C ₆₀ aromatic ring group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si, and P; a C ₃ to C ₆₀ aliphatic ring group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; and combinations thereof.

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

In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

Also, when it is said that a component such as a layer, film, region, or plate is "on" or "over" another component, it should be understood that this includes not only the case where it is "directly on" the other component, but also the case where there are other components in between. Conversely, when it is said that a component is "directly on" another part, it should be understood that there are no other parts in between.

FIG. 1 is an exemplary diagram of an organic electric device according to one embodiment of the present invention.

Referring to FIG. 1, an organic electric element (100) according to one embodiment of the present invention includes a first electrode (120), a second electrode (180), and an organic layer including a compound according to the present invention between the first electrode (120) and the second electrode (180) formed on a substrate (110). At this time, the first electrode (120) may be an anode, the second electrode (180) may be a 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 layer may include a hole injection layer (130), a hole transport layer (140), an emission layer (150), an electron transport layer (160), an electron injection layer (170), etc., which are sequentially laminated on the first electrode (120). At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, an emission auxiliary layer (151), an electron transport auxiliary layer, a buffer layer (141), etc. may be further included, and the electron transport layer (160), etc., may play the role of a hole blocking layer.

In addition, although not shown, the organic electric element according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer. This light efficiency improvement layer may be formed on a surface of both sides of the first electrode that is not in contact with the organic layer or on a surface of both sides of the second electrode that is not in contact with the organic layer.

The compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (130), a hole transport layer (140), a light-emitting auxiliary layer (151), an electron transport auxiliary layer, an electron transport layer (160), an electron injection layer (170), a light-emitting layer (150), or a material of a light efficiency improvement layer. However, preferably, a mixture of a compound represented by the chemical formula 1 of the present invention and a compound represented by the chemical formula 2 is used as a host of the light-emitting layer.

Meanwhile, since even if the core is similar to the same core, the band gap, electrical properties, and interfacial properties may differ depending on which substituent is bonded at which position, research is needed on the selection of the core and the combination of sub-substituents bonded to it, and in particular, when the energy level and _T1 value between each organic layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, both a long lifespan and high efficiency can be achieved.

Therefore, in the present invention, by using a mixture of a compound represented by chemical formula 1 and a compound represented by chemical formula 2 as a host for a light-emitting layer, the energy level and T ₁ value between each organic layer, and the intrinsic properties of the material (mobility, interface properties, etc.) can be optimized, thereby simultaneously improving the lifespan and efficiency of the organic electric device.

An organic light emitting diode according to one embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD. For example, it may be manufactured by forming an anode (120) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer (130), a hole transport layer (140), an emission layer (150), an electron transport layer (160), and an electron injection layer (170) thereon, and then depositing a material that can be used as a cathode (180) thereon. In addition, an emission auxiliary layer (151) may be additionally formed between the hole transport layer (140) and the emission layer (150), and an electron transport auxiliary layer may be additionally formed between the emission layer (150) and the electron transport layer (160).

In addition, the organic layer can be manufactured with a smaller number of layers by using various polymer materials, rather than a deposition method, such as a solution process or a solvent process, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, a screen printing process, or a thermal transfer method. Since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

An organic electric device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

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

Another embodiment of the present invention may include a display device including the organic electric element 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 systems, game consoles, various TVs, and various computers.

Hereinafter, an organic electric device according to one aspect of the present invention will be described.

An organic electric device according to one aspect of the present invention comprises a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a phosphorescent emitting layer, and a host of the phosphorescent emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2.

<Chemical Formula 1> <Chemical Formula 2>

First, chemical formula 1 is explained.

In the above chemical formula 1, each symbol can be defined as follows.

X ₁ is O or S.

Ar ¹ and Ar ² can be independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxy group; and a C ₆ to C ₃₀ aryloxy group.

When Ar ¹ and Ar ² are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, pyrene, triphenylene, and the like. When Ar ¹ and Ar ² are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₆ heterocyclic groups, such as pyridine, quinoline, isoquinoline, carbazole, phenylcarbazole, dibenzothiophene, dibenzofuran, dibenzodioxin, and the like. When Ar ¹ and Ar ² are fluorenyl groups, they can be 9,9-diphenylfluorene, 9,9-dimethylfluorene, and the like. When Ar ¹ and Ar ² are an aliphatic ring, it is preferably a C ₃ to C ₃₀ aliphatic ring, more preferably a C ₃ to C ₁₂ aliphatic ring, such as cyclohexane, cyclohexylcyclohexane, etc. When Ar ¹ and Ar ² are an alkyl group, it is preferably a C ₂ to C ₁₀ alkynyl group, such as methyl, t-butyl, etc. When Ar ¹ and Ar ² are an alkenyl group, it is preferably a C ₂ to C ₁₀ alkenyl group, such as ethene, propene, etc.

L ¹ to L ³ may be independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring.

When L ¹ to L ³ are arylene groups, they are preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₁₈ arylene groups, such as phenyl, biphenyl, naphthyl, terphenyl, and the like. When L ¹ to L ³ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₆ heterocyclic groups, such as carbazole, phenylcarbazole, dibenzofuran, dibenzothiophene, and the like.

R ¹ is selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxy group; a C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b );, wherein adjacent groups can be bonded to each other to form a ring.

a is an integer from 0 to 9, and when a is an integer greater than or equal to 2, multiple R ¹ are equal to or different from each other.

The ring formed by the adjacent R ¹ groups bonding to each other may be a C ₆ to C ₆₀ aromatic ring group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P; a C ₃ to C ₆₀ aliphatic ring group; or a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring, etc. When the adjacent R ¹ groups bond to each other to form an aromatic ring, preferably a C ₆ to C ₃₀ aromatic ring, more preferably a C ₆ to C ₁₄ aromatic ring, such as benzene, naphthalene, phenanthrene, etc. can be formed.

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

The above L' can be independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring.

The above R _a and R _b can be independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si, and P; a C ₃ to C ₆₀ aliphatic ring group; and a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring.

Preferably, in the above chemical formula 1, a compound derived from the following chemical formula 1-1 may be excluded.

<Chemical Formula 1-1>

In the above chemical formula 1-1, each symbol is as defined in the above chemical formula 1. Preferably, Ar ¹ and Ar ² are independently selected from the group consisting of a C ₆ to C ₁₈ aryl group; a fluorenyl group; a C ₂ to C ₁₆ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxy group; and a C ₆ to C ₃₀ aryloxy group.

Preferably, the chemical formula 1 can be represented by one of the following chemical formulas 1-A to 1-E.

<Chemical Formula 1-A> <Chemical Formula 1-B>

<Formula 1-C> <Formula 1-D>

<Chemical Formula 1-E>

In the above chemical formulas 1-A to 1-E, each symbol can be defined as follows.

Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , a are as defined in chemical formula 1.

X ₂ and X ₃ are independently O or S.

R ₄ , R ⁸ and R ⁹ are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₂₀ aliphatic ring group; fused ring group of C ₃ to C ₂₀ aliphatic ring and C ₆ to C ₂₀ aromatic ring; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₁ to C ₂₀ alkoxy group; C ₆ to C ₃₀ aryloxy group; and -L ^a -N(R ^a )(R ^b );, and adjacent groups can combine with each other to form a ring.

d1 is an integer from 0 to 7, i and j are each an integer from 0 to 6, and when each of them is an integer greater than or equal to 2, each of the plurality of R _4s , each of the plurality of R ^8s , and each of the plurality of R ^9s are equal to or different from each other.

The above L ^a may be independently selected from the group consisting of a single bond; a C ₆ to C ₂₀ arylene group; a fluorenylene group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.

The above R ^a and R ^b can be independently selected from the group consisting of a C ₆ to C ₂₀ aryl group; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.

Preferably, the chemical formula 1-A can be represented by one of the following chemical formulas 1-A-1 to 1-A-6.

<Chemical Formula 1-A-1> <Chemical Formula 1-A-2> <Chemical Formula 1-A-3>

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

In the above chemical formulas 1-A-1 to 1-A-6, Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , and a are as defined in chemical formula 1-A.

In the above chemical formula 1, chemical formulas 1-A to 1-E, and chemical formulas 1-A-1 to 1-A-6, each symbol can be further substituted. For example, Ar ¹ , Ar ² , L ¹ to L ³ , L', L ^a , R ¹ , R ₄ , R ⁸ , R ⁹ , R _a , R _b , R ^a , R ^b , and rings formed by bonding adjacent groups, etc. are each independently 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 siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ -C ₂₀ alkylthio group; a C ₁ -C ₂₀ alkoxy group; a C ₆ -C ₂₀ aryloxy group; a C ₁ -C ₂₀ alkyl group; A C ₂ -C ₂₀ alkenyl group; a C ₂ -C ₂₀ alkynyl group; a C ₆ -C ₂₀ aryl group; a C ₆ -C ₂₀ aryl group substituted with deuterium; a fluorenyl group; a C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; a C ₃ -C ₂₀ aliphatic ring group; a C ₇ -C ₂₀ arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group.

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

.

Next, the following chemical formula 2 is explained.

<Chemical formula 2>

In the above chemical formula 2, each symbol can be defined as follows.

Ar ⁴ to Ar ⁶ can be independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si, and P; a C ₃ to C ₆₀ aliphatic ring group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxy group; and a C ₆ to C ₃₀ aryloxy group.

When Ar ⁴ to Ar ⁶ are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, etc.

When Ar ⁴ to Ar ⁶ are a heterocyclic group, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₀ heterocyclic group, for example, dibenzothiophene, dibenzofuran, benzothioenopyrimidine, carbazole, phenylcarbazole, benzonaphthothiophene, benzofurothiophene, dinaphthothiophene, dinaphthofuran, etc.

When Ar ⁴ to Ar ⁶ are fluorenyl groups, it can be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, etc.

L ⁴ to L ⁶ may be independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and combinations thereof.

When L ⁴ to L ⁶ are arylene groups, they are preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₁₈ arylene groups, such as phenylene, biphenyl, naphthyl, terphenyl, and the like.

When L ⁴ to L ⁶ are fluorenyl groups, it can be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, etc.

The above chemical formula 2 can be represented by one of the following chemical formulas 2-A to 2-L.

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

<Chemical Formula 2-C>

<Formula 2-D> <Formula 2-E> <Formula 2-F>

<Chemical Formula 2-G> <Chemical Formula 2-H> <Chemical Formula 2-I>

<Formula 2-J> <Formula 2-K> <Formula 2-L>

In the above chemical formulas 2-A to 2-L, Ar ⁵ , Ar ⁶ , L ⁴ to L ⁶ are as defined in chemical formula 2, and Y ₁ to Y ₃ are each independently O, S, C(R')(R").

R ¹¹ to R ¹⁶ , R' and R" are each independently selected from the group consisting of 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; a C ₁ -C ₂₀ alkoxy group; a C ₆ -C ₂₀ aryloxy group; _{a C 1 -C 20} alkyl group; a C ₂ -C ₂₀ alkenyl group; a C 2 -C ₂₀ alkynyl group; a C ₆ -C ₂₀ aryl group; a fluorenyl group; a C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; and a C ₃ -C ₂₀ aliphatic ring group; and adjacent groups can be bonded to each other to form a ring.

The ring formed by bonding adjacent groups to each other may be a C ₆ ~ C ₆₀ aromatic ring group; a fluorenyl group; a C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si, and P; a C ₃ ~ C ₆₀ aliphatic ring group; or a fused ring group of a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring. For example, when adjacent R ¹ s, adjacent R ¹² s, adjacent R ¹³ s, adjacent R ¹⁴ s, adjacent R ¹⁵ s, adjacent R ¹⁶ s, or R' and R" s 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 an aromatic ring such as benzene, naphthalene, or phenanthrene can be formed.

b is an integer from 0 to 4, and when b is an integer greater than or equal to 2, a plurality of R ^11s , a plurality of R ^13s , and a plurality of R ^15s are equal to or different from each other, and c is an integer from 0 to 3, and when c is an integer greater than or equal to 2, a plurality of R ^12s , a plurality of R ^14s , and a plurality of R ^16s are equal to or different from each other.

The rings formed by bonding the above Ar ⁴ to Ar ⁶ , L ⁴ to L ⁶ , R ¹¹ to R ¹⁶ , R', R" and adjacent groups are each independently selected from the group consisting of 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 siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ -C ₂₀ alkylthio group; a C ₁ -C ₂₀ alkoxy group; a C ₆ -C ₂₀ aryloxy group; a C _{1 -C 20} alkyl group; a C 2 -C ₂₀ alkenyl group; a C ₂ -C ₂₀ alkynyl group; a C ₆ -C ₂₀ aryl group; a C ₆ -C ₂₀ aryl group substituted with deuterium; A fluorenyl group; a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a C ₃ -C ₂₀ aliphatic ring group; a C ₇ -C ₂₀ arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group.

Specifically, the compound represented by the chemical formula 2 may be one of the following compounds, but is not limited thereto.

.

Preferably, in the above chemical formulas 1 and 2, L ¹ to L ⁶ can be independently one of the following chemical formulas b-1 to b-13.

<Chemical formula b-1> <Chemical formula b-2> <Chemical formula b-3> <Chemical formula b-4>

<Chemical formula b-5> <Chemical formula b-6> <Chemical formula b-7> <Chemical formula b-8>

<Chemical formula b-9> <Chemical formula b-10>

<chemical formula b-11> <chemical formula b-12> <chemical formula b-13>

In the above chemical formulas b-1 to b-13, each symbol can be defined as follows.

R ⁵ to R ⁷ are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₂₀ aliphatic ring group; fused ring group of C ₃ to C ₂₀ aliphatic ring and C ₆ to C ₂₀ aromatic ring; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₁ to C ₂₀ alkoxy group; C ₆ to C ₃₀ aryloxy group; and -L ^a -N(R ^a )(R ^b );, and adjacent groups can combine with each other to form a ring.

When adjacent R ⁵ s, adjacent R ⁶ s, or adjacent R ⁷ s 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, or phenanthrene, can be formed.

Y is N-(L ^a -Ar ^a ), O, S, or C(R')(R").

Z ¹ to Z ³ are independently C, C(R') or N, and at least one of Z ¹ to Z ³ is N.

f is an integer from 0 to 6, e, g, h, and i are each integers from 0 to 4, j and k are each integers from 0 to 3, l is an integer from 0 to 2, and m is an integer from 0 to 3, and when each of these is an integer greater than or equal to 2, a plurality of R ^5s , a plurality of R ^6s , and a plurality of R ^7s may be the same or different from each other.

The above R' and R" can be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; C ₃ to C ₂₀ aliphatic ring group; fused ring group of C ₃ to C ₂₀ aliphatic ring and C ₆ to C ₂₀ aromatic ring; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₁ to C ₂₀ alkoxy group; C ₆ to C ₃₀ aryloxy group; and -L ^a -N(R ^a )(R ^b );.

In C(R')(R"), R' and R" can combine with each other to form a ring, and in C(R'), adjacent R' can combine with each other to form a ring.

The above Ar ^a can be selected from the group consisting of a C ₆ to C ₂₀ aryl group; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si, and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.

The above L ^a may be independently selected from the group consisting of a single bond; a C ₆ to C ₂₀ arylene group; a fluorenylene group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.

The above R ^a and R ^b can be independently selected from the group consisting of a C ₆ to C ₂₀ aryl group; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.

The above R ⁵ to R ⁷ , L ^a , Ar ^a , R', R" , R ^a , R ^b , and rings formed by bonding adjacent groups are each independently selected from the group consisting of 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 siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ -C ₂₀ alkylthio group; a C ₁ -C ₂₀ alkoxy group; a C ₆ -C ₂₀ aryloxy group; a C ₁ -C ₂₀ alkyl group; a C ₂ -C ₂₀ alkenyl group; a C ₂ -C ₂₀ alkynyl group; a C ₆ -C ₂₀ aryl group; a C ₆ -C ₂₀ aryl group substituted with deuterium; a fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a C ₃ -C ₂₀ aliphatic ring group; a C ₇ -C ₂₀ arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group.

The weight ratio of the first compound and the second compound is 1:9 to 9:1, preferably 3:7 to 7:3, and more preferably 3:7 to 5:5.

Hereinafter, examples of synthesis of compounds represented by chemical formulas 1 and 2 according to the present invention and examples of manufacturing organic electric devices are described in detail by way of examples, but the present invention is not limited to the following examples.

[ Synthetic example 1] Chemical formula 1

The compound represented by chemical formula 1 according to the present invention (final product) can be produced by reacting Sub 1 and Sub 2 as in the following reaction scheme 1, but is not limited thereto.

<Reaction Formula 1>

1. Example compounds of Sub 1 and Synthetic example

Compounds belonging to Sub 1 of the above reaction scheme 1 may be compounds as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 1 are as shown in Table 1 below.

[Table 1]

Sub 1 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

<Reaction Formula 2>

Synthesis example of Sub 1-7

2-(9,9-diphenyl-9H-fluoren-2-yl)-4,4,5,5 in 2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol) -tetramethyl-1,3,2-dioxaborolane (70.77 g, 159.25 mmol), Pd(PPh ₃ ) ₄ (7.67 g, 6.64 mmol), K ₂ CO ₃ (55.02 g, 398.12 mmol), THF (600 ml), and water (300 ml) were added, stirred and refluxed. After the reaction was completed, extracted with ether and water. The organic layer was concentrated, dried over MgSO ₄ , and concentrated. The concentrate was then separated using a silica gel column and recrystallized to obtain 51.24 g of the product (yield: 76%).

Synthesis example of Sub 1-29

2,4-dichloro-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (20 g, 63.26 mmol) was placed in a round-bottom flask and dissolved in 450 mL of THF, followed by 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (28.11 g, 75.92 mmol), Pd(PPh ₃ ) ₄ (3.66 g, 3.16 mmol), K ₂ CO ₃ (26.23 g, 189.79 mmol), and 150 mL of water were added, and the same experimental method as Sub 1-7 was performed to obtain 69.7 g of the product (yield: 73%).

Synthesis example of Sub 1-39

2-([1,1':3',1''-terphenyl]-5'-yl)-4,6-dichloro-1,3,5-triazine (17 g, 44.94 mmol) was placed in a round-bottom flask and dissolved in 340 mL of THF, followed by 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16.73 g, 53.93 mmol), Pd(PPh ₃ ) ₄ (2.6 g, 2.25 mmol), K ₂ CO ₃ (18.63 g, 134.83 mmol), and 170 mL of water were added, and the same experimental method as Sub 1-7 was performed to obtain 69.7 g of the product (yield: 73%).

2. Example compounds of Sub 2 and Synthetic example

Compounds belonging to Sub 2 of the above reaction scheme 1 may be compounds as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 2 are as shown in Table 2 below.

[Table 2]

Sub 2 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 3, but is not limited thereto.

<Reaction Formula 3>

Sub 2-4 Synthesis Example

6-(4-bromonaphthalen-2-yl)naphtho[1,2-b]benzofuran (15 g, 35.44 mmol) to bis(pinacolato)diboron (CAS Registry Number: 73183-34-3) (11.7 g, 46.07 mmol) ), PdCl ₂ (dppf) (1.3 g, 1.77 mmol), KOAc (10.4 g, 106.31 mmol), DMF (300 ml) were added, and the mixture was stirred and refluxed. After the reaction was completed, the organic layer was extracted using CH ₂ Cl ₂ and water, Dry with MgSO ₄ and concentrate. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 12.83 g of the product (yield: 77%).

Sub 2-25 Synthesis Example

8-bromobenzo[b]naphtho[2,1-d]thiophene (25 g, 79.82 mmol), bis(pinacolato)diboron (CAS registry number, 73183-34-3) (26.35 g, 103.76 mmol), PdCl ₂ ( dppf) (3.08 g, 4.21 mmol), KOAc (24.77 g, 252.4 mmol), DMF (500 ml) were added, and stirred and refluxed. After the reaction was completed, the organic layer was extracted using CH ₂ Cl ₂ and water, Dry with MgSO ₄ and concentrate. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 24 g of the product (yield: 83%).

3. Final compound synthesis example

Synthesis example of 1-13

Sub 1-11 (34.7 g, 80 mmol), Sub 2-25 (30.9 g, 80 mmol), K ₂ CO ₃ (19.3 g, 140 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol) were placed in a round-bottomed flask, and THF and water were added to dissolve them, and refluxed at 80 ℃ for 12 hours. After the reaction was complete, the temperature of the reaction product was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic matter was separated through a silica gel column to obtain the product (37.4 g, 71%).

Synthesis example of 1-27

Sub 1-13 (44.6 g, 80 mmol) and Sub 2-43 (30.9 g, 80 mmol) were synthesized using the same method as for 1-13, to obtain the product (43.2 g, 69%).

Synthesis example of 1-34

Sub 1-34 (42.7 g, 80 mmol) and Sub 2-18 (34.9 g, 80 mmol) were synthesized using the synthetic method of 1-13 to obtain the product (42.7 g, 66%).

Synthesis example of 1-45

Sub 1-37 (40.8 g, 80 mmol) and Sub 2-49 (43.1 g, 80 mmol) were synthesized using the synthetic method of 1-13 to obtain the product (51.0 g, 72%).

Synthesis example of 1-53

Sub 1-1 (40.8 g, 80 mmol) and Sub 2-51 (37.0 g, 80 mmol) were synthesized using the synthetic method of 1-13 to obtain the product (45.4 g, 70%).

Synthesis example of 1-88

Sub 1-4 (44.0 g, 80 mmol) and Sub 2-16 (29.6 g, 80 mmol) were synthesized using the synthetic method of 1-13 to obtain the product (41.2 g, 68%).

The FD-MS values of compounds 1-1 to 1-124 of the present invention synthesized by the same method as the above synthetic example are as shown in Table 3 below.

[Table 3]

[ Synthetic example 2] Chemical formula 2

The compound represented by chemical formula 2 of the present invention (Final product 2) can be produced by reacting Sub 3 and Sub 4 as in the following reaction scheme 4, but is not limited thereto.

<Reaction Formula 4>

1. Example compounds of Sub 3

Sub 3 of the above reaction scheme 4 can be synthesized as in the following reaction scheme 5, but is not limited thereto.

<Reaction Formula 5>

Compounds belonging to Sub 3 of the above reaction scheme 4 are as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 3 are as shown in Table 4 below.

[Table 4]

2. Example compounds of Sub 4 and Synthetic example

The FD-MS values of the compounds belonging to Sub 4 are as shown in Table 5 below.

[Table 5]

<Reaction Formula 6>

Sub 4-1 Synthetic example

A round-bottomed flask was charged with aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd ₂ (dba) ₃ (7.37 g, 8.05 mmol), P(t-Bu) ₃ (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), and toluene (1690 mL), and the reaction was carried out at 100 ℃. 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. The resulting organic matter was separated through a silica gel column and recrystallized to obtain 25.4 g of Sub 4-1. (Yield: 72%)

Sub 4-30 Synthetic example

[1,1'-biphenyl]-4-amine (15 g, 88.6 mmol), 2-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd ₂ (dba) ₃ (4.06 g, 4.43 mmol), P(t-Bu) ₃ (1.8 g, 8.86 mmol), NaOt-Bu (28.1 g, 292.5 mmol), and toluene (931 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as the synthesis method of Sub 4-1, to obtain 34.9 g of Sub 4-30. (Yield: 70%)

Sub 4-46 Synthetic example

In a round-bottomed flask, naphthalen-1-amine (15 g, 104.8 mmol), 2-bromodibenzo[b,d]thiophene (30.3 g, 115.2 mmol), Pd ₂ (dba) ₃ (4.8 g, 5.24 mmol), P(t-Bu) ₃ (2.12 g, 10.48 mmol), NaOt-Bu (33.22 g, 345.7 mmol), and toluene (1100 mL) were added, and the reaction was carried out in the same manner as the synthesis method of Sub 4-1, to obtain 24.9 g of Sub 4-46. (Yield: 73%)

Sub 4-49 Synthetic example

[1,1'-biphenyl]-4-amine (15 g, 88.64 mmol), 2-bromodibenzo[b,d]thiophene (23.32 g, 88.64 mmol), Pd ₂ (dba) ₃ (2.43 g, 2.66 mmol), P(t-Bu) ₃ (17.93 g, 88.64 mmol), NaOt-Bu (17.04 g, 177.27 mmol), and toluene (886 mL) were added to a round-bottomed flask, and the mixture was stirred for 15 minutes. The reaction mixture was stirred for 15 minutes ...

Sub 4-56 Synthetic example

In a round-bottomed flask, 4-(dibenzo[b,d]furan-2-yl)aniline (15 g, 57.85 mmol), 2-bromodibenzo[b,d]furan (15.7 g, 63.63 mmol), Pd ₂ (dba) ₃ (2.65 g, 2.89 mmol), P(t-Bu) ₃ (1.17 g, 5.78 mmol), NaOt-Bu (18.35 g, 190.9 mmol), and toluene (607 mL) were added, and the reaction was carried out in the same manner as the synthesis method of Sub 4-1, to obtain 17.2 g of Sub 4-56. (Yield: 70%)

3. The final compound Synthetic example

2- 1 of Synthesis

In a round bottom flask, add sub 3-1 (10 g, 42.9 mmol), Sub 4-21 (13.79 g, 42.9 mmol), Pd ₂ (dba) ₃ (1.18 g, 1.29 mmol), P(t-Bu) ₃ (8.68 g, 42.9 mmol), NaOt-Bu (8.25 g, 85.80 mmol), and toluene (429 mL), and then react at 100°C. When the reaction is complete, extract with CH ₂ Cl ₂ and water, dry the organic layer with MgSO ₄ , concentrate, and separate the resulting organic matter through a silica gel column and recrystallize to obtain 15.6 g of product 2-1. (Yield: 77%)

2- 4 of Synthesis

Sub 3-2 (10 g, 35.3 mmol), Sub 4-27 (14.8 g, 35.31 mmol), Pd ₂ (dba) ₃ (0.97 g, 1.06 mmol), P(t-Bu) ₃ (7.14 g, 35.31 mmol), NaOt-Bu (6.79 g, 70.63 mmol), and toluene (353 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 16.9 g of product 2-4. (Yield: 78%)

Composite of 2-10

Sub 3-6 (10 g, 32.34 mmol), Sub 4-12 (12.86 g, 32.34 mmol), Pd ₂ (dba) ₃ (0.89 g, 0.97 mmol), P(t-Bu) ₃ (6.54 g, 32.34 mmol), NaOt-Bu (6.22 g, 64.68 mmol), and toluene (323 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1, to obtain 15.1 g of product 2-10. (Yield: 75%)

Synthesis of 2-19

Sub 3-10 (10 g, 38 mmol), Sub 4-16 (11.23 g, 38 mmol), Pd ₂ (dba) ₃ (1.04 g, 1.14 mmol), P(t-Bu) ₃ (7.69 g, 38 mmol), NaOt-Bu (7.3 g, 76 mmol), and toluene (380 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1, to obtain 13.7 g of product 2-19. (Yield: 76%)

Synthesis of 2-68

Sub 3-38 (10 g, 33.65 mmol), Sub 4-49 (11.83 g, 33.65 mmol), Pd ₂ (dba) ₃ (0.92 g, 1.01 mmol), P(t-Bu) ₃ (6.81 g, 33.65 mmol), NaOt-Bu (6.47 g, 67.31 mmol), and toluene (337 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 15.28 g of the product 2-68. (Yield: 80%)

2- 24 of Synthesis

Sub 3-10 (10 g, 38 mmol), Sub 4-33 (18.38 g, 38 mmol), Pd ₂ (dba) ₃ (1.04 g, 1.14 mmol), P(t-Bu) ₃ (7.69 g, 38 mmol), NaOt-Bu (7.3 g, 76 mmol), and toluene (380 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above, to obtain 18.72 g of the product. (Yield: 74%)

Synthesis of 2-29

Sub 3-11 (10 g, 29.48 mmol), Sub 4-46 (9.59 g, 29.48 mmol), Pd ₂ (dba) ₃ (0.81 g, 0.88 mmol), P(t-Bu) ₃ (5.96 g, 29.48 mmol), NaOt-Bu (5.67 g, 58.95 mmol), and toluene (295 mL) were added to a round-bottomed flask, and the mixture was stirred for 12.39 g to obtain 12.39 g of product 2-29 (yield: 72%).

Synthesis of 2-30

Sub 3-14 (10 g, 29.48 mmol), Sub 4-20 (9.47 g, 29.48 mmol), Pd ₂ (dba) ₃ (0.81 g, 0.88 mmol), P(t-Bu) ₃ (5.96 g, 29.48 mmol), NaOt-Bu (5.67 g, 58.95 mmol), and toluene (295 mL) were added to a round-bottomed flask, and the mixture was stirred for 12.13 g to obtain 12.13 g of product 2-30 (yield: 71%).

Synthesis of 2-36

Sub 3-10 (10 g, 38 mmol), Sub 4-51 (14.5 g, 38 mmol), Pd ₂ (dba) ₃ (1.04 g, 1.14 mmol), P(t-Bu) ₃ (7.69 g, 38 mmol), NaOt-Bu (7.30 g, 76 mmol), and toluene (380 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 16.5 g of product 2-36. (Yield: 77%)

Composite of 2-50

Sub 3-40 (10 g, 30.94 mmol), Sub 4-21 (9.95 g, 30.94 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), P(t-Bu) ₃ (6.26 g, 30.94 mmol), NaOt-Bu (5.95 g, 61.88 mmol), and toluene (309 mL) were added to a round-bottomed flask, and the mixture was stirred for 10 minutes in the same manner as in the synthetic method of 2-1 to obtain 13.26 g of the product 2-50. (Yield: 76%)

Synthesis of 2-52

Sub 3-33 (10 g, 22.76 mmol), Sub 4-9 (7.86 g, 22.76 mmol), Pd ₂ (dba) ₃ (0.63 g, 0.68 mmol), P(t-Bu) ₃ (4.60 g, 22.76 mmol), NaOt-Bu (4.38 g, 45.52 mmol), and toluene (228 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 11.38 g of product 2-52. (Yield: 71%)

Synthesis of 2-60

Sub 3-35 (10 g, 30.94 mmol), Sub 4-59 (10.94 g, 30.94 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), P(t-Bu) ₃ (6.26 g, 30.94 mmol), NaOt-Bu (5.95 g, 61.88 mmol), and toluene (309 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 13.46 g of the product 2-60. (Yield: 73%)

Synthesis of 2-85

Sub 3-49 (10 g, 21.21 mmol), Sub 4-21 (6.82 g, 21.21 mmol), Pd ₂ (dba) ₃ (0.58 g, 0.64 mmol), P(t-Bu) ₃ (4.29 g, 21.21 mmol), NaOt-Bu (4.08 g, 42.43 mmol), and toluene (212 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 10.57 g of product 2-85. (Yield: 70%)

2- 89 of Synthesis

Sub 3-50 (10 g, 25.17 mmol), Sub 4-30 (14.14 g, 25.17 mmol), Pd ₂ (dba) ₃ (0.69 g, 0.76 mmol), P(t-Bu) ₃ (5.09 g, 25.17 mmol), NaOt-Bu (4.84 g, 50.34 mmol), and toluene (252 mL) were added to a round-bottomed flask, and the reaction was carried out in the same manner as in the synthesis method of 2-1 above to obtain 15.91 g of product 2-89. (Yield: 72%)

The FD-MS values of compounds 2-1 to 2-96 manufactured according to the above synthetic examples are as shown in Table 6 below.

[Table 6]

Manufacturing and Evaluation of Organic Electronics

[ Example 1] to [ Example 90] Red organic light emitting diode ( luminescent layer Mixed phosphor host)

A 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as "2-TNATA") film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 60 nm thick hole injection layer, and then a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPD") film was vacuum-deposited to a 55 nm thick hole transport layer.

Next, a 30 nm thick light-emitting layer was formed on the hole transport layer. At this time, as shown in Table 5 below, a mixture of a compound represented by Chemical Formula 1 of the present invention (first host) and a compound represented by Chemical Formula 2 of the present invention (second host) was mixed at a weight ratio of 3:7 as a host, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as “(piq) ₂ Ir(acac”)) was used as a dopant. The host and dopant were used at 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 light-emitting layer to form a hole-blocking layer.

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

[Comparative Example 1] to [Comparative Example 4]

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound represented by the chemical formula 1 of the present invention was used alone as a host material of the light-emitting layer, as described in Table 5 below.

[Comparative Example 5] and [Comparative Example 6]

An organic light-emitting device was manufactured in the same manner as in Example 1, except that a mixture of Comparative Compound 1 and Comparative Compound 2 and a mixture of Comparative Compound 1 and Comparative Compound 3 were used as the host material of the light-emitting layer, as described in Table 5 below.

<Comparative Compound 1> <Comparative Compound 2> <Comparative Compound 3>

A forward bias DC voltage was applied to the organic electroluminescence devices manufactured by Examples 1 to 90 and Comparative Examples 1 to 6 of the present invention, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch. The T95 lifespan was measured using lifespan measuring equipment from Maxscience at a reference luminance of 2500 cd/m ^{2 .} The measurement results are shown in Table 7 below.

[Table 7]

As can be seen from the results in Table 7 above, when the compounds represented by Chemical Formula 1 and Chemical Formula 2 of the present invention are mixed and used as a phosphorescent host (Examples 1 to 90), it can be confirmed that the driving voltage, efficiency, and lifespan of the device are significantly improved compared to when the compound represented by Chemical Formula 1 is used alone (Comparative Examples 1 to 4) or when a comparative compound is mixed and used (Comparative Examples 5 to 6).

Comparing Comparative Examples 1 to 6, the device characteristics were further improved when two types of comparative compounds were mixed and used (Comparative Examples 5 to 6) than when the compound of the present invention was used alone (Comparative Examples 1 to 4).

In addition, when comparing Comparative Examples 5 to 6 with the examples of the present invention, when a host was used in which a compound according to Chemical Formula 1 of the present invention and a compound according to Chemical Formula 2 were mixed rather than a host in which two types of comparative compounds were mixed, the driving voltage was lowered and the efficiency and lifespan were significantly improved.

The inventors of the present invention judged from these results that a mixture of the substance of Chemical Formula 1 and the substance of Chemical Formula 2 has novel properties other than the properties of each substance, and measured the PL lifetime using each of these substances and the mixture. As a result, it was confirmed that a new PL wavelength was formed in the case of a mixture of Chemical Formula 1 and Chemical Formula 2 of the present invention, unlike when they are either compound alone.

It is judged that when the compound of the present invention is mixed and used, the efficiency and lifespan are increased due to the movement of electrons and holes or energy transfer by a new region (exciplex) having a new energy level formed by mixing, in addition to the movement of electrons and holes through the energy level of each substance. This can be said to be an important example in which a mixed thin film exhibits an exciplex energy transfer and light emission process when the mixture of the present invention is used.

In addition, when a compound represented by Chemical Formula 2 having strong hole properties is mixed with a polycyclic compound represented by Chemical Formula 1 having high stability against not only electrons but also holes and a high T1 value, the electron-blocking ability is improved due to the high T1 and high LUMO energy values, and more holes move quickly and easily to the emitting layer. When holes move faster to the emitting layer and the electron-blocking ability is improved in this way, the charge balance within the emitting layer increases, so that light emission occurs well inside the emitting layer rather than at the hole transport layer interface, and as a result, deterioration of the HTL interface is also reduced, thereby maximizing the driving voltage, efficiency, and lifespan of the entire device. Therefore, when the compounds represented by Chemical Formula 1 and Chemical Formula 2 were mixed and used as a host, the performance of the entire device was significantly improved due to the electrochemical synergy effect.

[Example 91] to [Example 94]

An organic light-emitting device was manufactured using the same method as in Example 1, except that the first host and the second host were mixed and used at a certain ratio as described in Table 7 below.

The electroluminescence (EL) characteristics were measured by applying a forward bias DC voltage to the organic electroluminescence devices manufactured by Examples 91 to 94 of the present invention using PR-650 from Photoresearch, and the T95 lifespan was measured using a lifespan measuring device from Maxscience at a reference luminance of 2500 cd/m ² . The results are shown in Table 8 below. Examples 3 and 80 are the results of measuring device characteristics when the first host and the second host were mixed and used in a ratio of 3:7, as in Table 6.

[Table 8]

Referring to Table 8 above, when the first host and the second host are mixed in a ratio of 3:7, the driving voltage, efficiency, and lifespan are the best, and it can be confirmed that the device characteristics deteriorate as the ratio of the first host increases. This is believed to be because the charge balance within the light-emitting layer is maximized as the amount of the compound represented by Chemical Formula 2, which has relatively stronger hole characteristics than the compound represented by Chemical Formula 1, increases.

The above description is merely an example of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are not intended to limit the present invention but to explain it, 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 techniques within the equivalent scope should be interpreted as being included in the scope of the rights of the present invention.

100: Organic electronic device 110: Substrate
120: First electrode 130: Hole injection layer
140: Hole transport layer 141: Buffer layer
150: Emitting layer 151: Emitting auxiliary layer
160: Electron transport layer 170: Electron injection layer
180: 2nd electrode

Claims (11)

In an organic electric device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode,
An organic electric device characterized in that the organic layer includes a phosphorescent emitting layer, and the host of the phosphorescent emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2:
<Chemical Formula 1><Chemical Formula 2>

In the above chemical formula,
X ₁ is O,
Ar ¹ , Ar ² , Ar ⁴ to Ar ⁶ are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxy group; and a C ₆ to C ₃₀ aryloxy group,
L ¹ to L ⁶ are independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and combinations thereof.
R ¹ is selected from the group consisting of hydrogen; deuterium; halogen; cyano group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; fused ring group of C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b );, and adjacent R ¹ groups can be bonded to each other to form a ring,
a is an integer from 0 to 9, and if a is an integer greater than or equal to 2, each of the multiple R ^1s is equal to or different from each other.
The above L' is independently selected from the group consisting of a single bond; a C ₆ to C ₆₀ arylene group; a fluorenylene group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and combinations thereof.
The above R _a and R _b are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and combinations thereof. delete In paragraph 1,
An organic electric device characterized in that the above L ¹ to L ⁶ are independently one of the following chemical formulas b-1 to b-13:
<Chemical formula b-1><Chemical formula b-2><Chemical formula b-3><Chemical formula b-4>

<Chemical formula b-5><Chemical formula b-6><Chemical formula b-7><Chemical formula b-8>

<Chemical formula b-9><Chemical formula b-10>

<chemical formula b-11><chemical formula b-12><chemical formula b-13>

In the above chemical formula,
R ⁵ to R ⁷ are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₂₀ aliphatic ring group; fused ring group of C ₃ to C ₂₀ aliphatic ring and C ₆ to C ₂₀ aromatic ring; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₁ to C ₂₀ alkoxy group; C ₆ to C ₃₀ aryloxy group; and -L ^a -N(R ^a )(R ^b ); is selected from the group consisting of, and adjacent groups can combine with each other to form a ring,
Y is N-(L ^a -Ar ^a ), O, S or C(R')(R"),
Z ¹ to Z ³ are independently C, C(R') or N, and at least one of Z ¹ to Z ³ is N,
f is an integer from 0 to 6, e, g, h, i are each an integer from 0 to 4, j, k are each an integer from 0 to 3, l is each an integer from 0 to 2, m is an integer from 0 to 3, and when each of these is an integer greater than or equal to 2, each of the plurality of R ^5s , each of the plurality of R ^6s , and each of the plurality of R ^7s are the same as or different from each other,
The above R' and R" are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; C ₃ to C ₂₀ aliphatic ring group; fused ring group of C ₃ to C ₂₀ aliphatic ring and C ₆ to C ₂₀ aromatic ring; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₁ to C ₂₀ alkoxy group; C ₆ to C ₃₀ aryloxy group; and -L ^a -N(R ^a )(R ^b );,
In C(R')(R"), R' and R" can combine with each other to form a ring, and in C(R'), adjacent R' can combine with each other to form a ring.
The above Ar ^a is selected from the group consisting of a C ₆ to C ₂₀ aryl group; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom among O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.
The above L ^a is independently selected from the group consisting of a single bond; a C ₆ to C ₂₀ arylene group; a fluorenylene group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof.
The above R ^a and R ^b are independently selected from the group consisting of a C ₆ to C ₂₀ aryl group; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof. In paragraph 1,
The above chemical formula 1 is an organic electric device characterized by being represented by one of the following chemical formulas 1-A to 1-E:
<Chemical Formula 1-A><Chemical Formula 1-B>

<Formula 1-C><Formula1-D>

<Chemical Formula 1-E>

In the above chemical formula,
Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , a are as defined in clause 1,
X ₂ and X ₃ are independently O or S,
R ₄ , R ⁸ and R ⁹ are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₂₀ aryl group; fluorenyl group; C ₂ to C ₂₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₂₀ aliphatic ring group; fused ring group of C ₃ to C ₂₀ aliphatic ring and C ₆ to C ₂₀ aromatic ring; C ₁ to C ₂₀ alkyl group; C ₂ to C ₂₀ alkenyl group; C ₂ to C ₂₀ alkynyl group; C ₁ to C ₂₀ alkoxy group; C ₆ to C ₃₀ aryloxy group; and -L ^a -N(R ^a )(R ^b ); is selected from the group consisting of, and adjacent groups can combine with each other to form a ring,
d1 is an integer from 0 to 7, i and j are each an integer from 0 to 6, and when each of them is an integer greater than or equal to 2, each of the plurality of R _4s , each of the plurality of R ^8s , and each of the plurality of R ^9s are equal to or different from each other,
The above L ^a is independently selected from the group consisting of a single bond; a C ₆ to C ₂₀ arylene group; a fluorenylene group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and a combination thereof.
The above R ^a and R ^b are independently selected from the group consisting of a C ₆ to C ₂₀ aryl group; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₂₀ aliphatic ring group; and combinations thereof. In paragraph 4,
The organic electric device characterized in that the chemical formula 1-A above can be represented by one of the following chemical formulas 1-A-1 to 1-A-6:
<Chemical Formula 1-A-1><Chemical Formula 1-A-2><Chemical Formula 1-A-3>

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

In the above chemical formula, Ar ¹ , Ar ² , L ¹ to L ³ , X ₁ , R ¹ , and a are as defined in clause 4. In paragraph 1,
The above chemical formula 2 is an organic electric device characterized by being represented by one of the following chemical formulas 2-A to 2-C:
<Chemical Formula 2-A><Chemical Formula 2-B>

<Chemical Formula 2-C>

In the above chemical formula, Ar ⁵ , Ar ⁶ , L ⁴ to L ⁶ are as defined in the first clause,
Y ₁ ~Y ₃ are independently O, S, C(R')(R"),
R ¹¹ ~R ¹⁶ , R' and R" are each independently selected from the group consisting of hydrogen; deuterium; halogen; a silane group substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a cyano group; a nitro group; a C ₁ -C ₂₀ alkoxy group; a C ₆ -C ₂₀ aryloxy group; _{a C 1 -C 20} alkyl group; a C ₂ -C ₂₀ alkenyl group; a C 2 -C ₂₀ alkynyl group; a C ₆ -C ₂₀ aryl group; a fluorenyl group; a C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; and a C ₃ -C ₂₀ aliphatic ring group; and adjacent groups can be bonded to each other to form a ring,
b is an integer from 0 to 4, and when b is an integer greater than or equal to 2, each of the plurality of R ^11s , each of the plurality of R ^13s , and each of the plurality of R ^15s are equal to or different from each other.
c is an integer from 0 to 3, and when c is an integer greater than or equal to 2, each of the plurality of R ^12s , each of the plurality of R ^14s , and each of the plurality of R ^16s are equal to or different from each other. In paragraph 1,
The above chemical formula 2 is an organic electric device characterized by being represented by one of the following chemical formulas 2-D to 2-L:
<Formula 2-D><Formula2-E><Formula2-F>

<Chemical Formula 2-G><Chemical Formula 2-H><Chemical Formula 2-I>

<Formula 2-J><Formula2-K><Formula2-L>

In the above chemical formula, Ar ⁵ , Ar ⁶ , L ⁴ to L ⁶ are as defined in the first clause,
Y ₁ is independently O, S, C(R')(R"),
R ¹¹ and R ¹² are independently selected from the group consisting of 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; a C ₁ -C ₂₀ alkoxy group; a C ₆ -C ₂₀ aryloxy group; a C ₁ -C ₂₀ alkyl group; a C ₂ -C ₂₀ alkenyl group; a C 2 -C 20 alkynyl group; a C ₆ -C ₂₀ aryl group; a fluorenyl group; a C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; and a C ₃ -C ₂₀ aliphatic ring group; and adjacent groups can be bonded to each other to form a ring,
b is an integer from 0 to 4, and when b is an integer greater than or equal to 2, each of the multiple R ^11s is equal to or different from each other.
c is an integer from 0 to 3, and when c is an integer greater than or equal to 2, each of the multiple R ^12s is equal to or different from each other. In paragraph 1,
An organic electric device characterized in that the compound represented by the chemical formula 1 is one of the following compounds:











. In paragraph 1,
An organic electric device characterized in that the compound represented by the chemical formula 2 is one of the following compounds:




. A display device including the organic electric element of claim 1; and
An electronic device including a control unit that drives the above display device. In Article 10,
An electronic device characterized in that the organic electroluminescent element is selected from the group consisting of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, a monochrome lighting element, and a quantum dot display element.