KR102767774B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric element including a compound represented by chemical formula 1, 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. By including the compound represented by chemical formula 1 in the organic layer, the driving voltage of the organic electric element can be lowered and the luminous efficiency and lifespan can be improved.

Description

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

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

In general, the organic 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, it is necessary to develop 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, materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must first be supported by stable and efficient materials, and in particular, development of host materials for the light-emitting layer is even more necessary.

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

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

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

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

Figures 1 to 3 are exemplary diagrams of organic electroluminescent devices according to the present invention.
Figure 4 shows a chemical formula according to one aspect of 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 monocyclic ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc. In addition, unless otherwise stated in the present specification, the aryl group may include a fluorenyl group, and the arylene group may include a fluorenylene group.

The terms "fluorenyl group", "fluorenylene group", and "fluorene triyl group" used in the present invention, unless otherwise stated, mean a monovalent, divalent, or trivalent functional group wherein R, R', and R" in the structures below are all hydrogen, and a "substituted fluorenyl group", a "substituted fluorenylene group", or a "substituted fluorene triyl group" mean that at least one of the substituents R, R', and 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. In the present specification, regardless of valence, a fluorenyl group, a fluorenylene group, and a fluorene triyl group may all be referred to as a fluorene group.

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. In addition, a compound containing a heteroatom group such as SO ₂ , P = O, etc. instead of carbon forming a ring, such as the following compounds, can also be included in the heterocyclic group.

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 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 name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the 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 monovalent and pyrimidinylene for divalent.

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 this specification, when indicating a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, and benzoquinazoline, can be expressed as a 3-condensed ring.

In addition, unless otherwise stated herein, when a ring is expressed in the form of a 'number-atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' represents the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-membered ring.

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; and a C ₃ to C ₆₀ aliphatic ring group.

Here, unless otherwise stated herein, the term 'neighboring groups' includes, using the following chemical formula as an example, not only R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , and R ₅ and R ₆ , but also R ₇ and R ₈ sharing a single carbon, and may also include substituents bonded to non-adjacent ring constituent elements (carbon, nitrogen, etc.) such as R ₁ and R ₇ , R ₁ and R ₈ , or R ₄ and R _5. That is, when there are substituents on ring constituent elements such as carbon or nitrogen that are immediately adjacent, they can be neighboring groups, but when no substituent is bonded to the ring constituent element at the immediately adjacent position, the substituent bonded to the next ring constituent element can be a neighboring group, and also substituents bonded to the same ring constituent carbon can be said to be neighboring groups.

In the chemical formula below, when substituents bonded to the same carbon, such as R ₇ and R ₈ , bond with each other to form a ring, a compound containing a spiro moiety can be formed.

,

Additionally, in this specification, the expression 'adjacent groups can form a ring by combining with each other' is used with the same meaning as 'adjacent groups selectively form a ring by combining with each other', and means a case where at least one pair of adjacent groups forms a ring by combining with each other.

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

When adding reference signs to components of each drawing, it should be noted that identical components are given the same signs as much as possible even if they are shown on different drawings. In addition, when describing the present invention, if it is determined that a specific description of a related known configuration or function may obscure the gist of the present invention, the detailed description is omitted.

In describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

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 to mean that there are no other parts in between.

Figures 1 to 3 are exemplary diagrams of organic electric devices according to embodiments 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 (110), a second electrode (170) formed on a substrate (not shown), and an organic layer formed between the first electrode (110) and the second electrode (170).

The above first electrode (110) may be an anode, and the second electrode (170) may be a cathode. In the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

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

Preferably, a light efficiency improvement layer (180) may be formed on one surface of the first electrode (110) or the second electrode (170) that is not in contact with the organic layer, and when the light efficiency improvement layer (180) is formed, the light efficiency of the organic electric element may be improved.

For example, a 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 formation of the light efficiency improvement layer (180) can reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode (170), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer (180) can perform a buffering role for the second electrode (170).

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

Referring to FIG. 2, an organic electric element (200) according to another embodiment of the present invention may include a hole injection layer (120), a hole transport layer (130), a buffer layer (210), 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) sequentially formed on a first electrode (110), and a light efficiency improvement layer (180) may be formed on the second electrode.

Although not shown in FIG. 2, an electron transport auxiliary layer may be additionally 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 layer may be formed in a form in which a plurality of stacks including a hole transport layer, a light-emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

Referring to FIG. 3, an organic electric element (300) according to another embodiment of the present invention may have two or more sets of stacks (ST1, ST2) of organic layers formed of multiple layers formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stacks of organic layers.

Specifically, an organic electric device according to one embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL: Charge Generation Layer), a second stack (ST2), a second electrode (170), and a light efficiency improvement layer (180).

The first stack (ST1) is an organic layer formed on the first electrode (110), which may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting 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 light-emitting layer (440), and a second electron transport layer (450). In this way, the first stack and the second stack may be organic layers having the same stacked structure, but may also be organic layers having different stacked 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 light-emitting layer (340) and the second light-emitting layer (440) to increase current efficiency generated in each light-emitting layer and to smoothly distribute charges.

The first light-emitting layer (340) may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer (440) may include a material in which a greenish yellow dopant and a red dopant are doped together in a green host; however, the materials of the first light-emitting layer (340) and the second light-emitting layer (440) according to the embodiment of the present invention are not limited thereto.

In FIG. 3, n can be an integer from 1 to 5, and when n is 2, a charge generation layer (CGL) and a third stack can be additionally stacked on the second stack (ST2).

When a plurality of light-emitting layers are formed by a multilayer stack structure as in Fig. 3, not only can an organic light-emitting device be manufactured that emits white light by the mixing effect of the light emitted from each light-emitting layer, but an organic light-emitting device that emits light of various colors can also be manufactured.

The compound represented by the chemical formula 1 of the present invention can be used as a material of a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light-emitting auxiliary layer (220), an electron transport layer (150, 350, 450), an electron injection layer (160), a light-emitting layer (140, 340, 440), or a light efficiency improvement layer (180), but can preferably be used as a material of the light-emitting layer (140, 340, 440) and/or the light efficiency improvement layer (180).

Even if the core is identical or similar, the band gap, electrical properties, interface properties, etc. can vary depending on which substituent is bonded at which position. Therefore, research is needed on the selection of the core and the combination of sub-substituents bonded to it. In particular, when the energy level and _T1 value between each organic layer, and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, both a long lifespan and high efficiency can be achieved.

Therefore, in the present invention, by using the compound represented by chemical formula 1 as a material of the light-emitting layer (140, 340, 440) and/or the light efficiency improvement layer (180), the energy level and T ₁ value between each organic layer, the intrinsic properties of the material (mobility, interface properties, etc.), etc., can be optimized, thereby simultaneously improving the lifespan and efficiency of the organic electric device.

An organic light emitting diode according to an 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 (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and then forming an organic layer including a hole injection layer (120), a hole transport layer (130), an emission layer (140), an electron transport layer (150), and an electron injection layer (160) thereon, and then depositing a material that can be used as a cathode (170) thereon. In addition, an emission auxiliary layer (220) may be further formed between the hole transport layer (130) and the emission layer (140), and an electron transport auxiliary layer (not shown) may be further formed between the emission layer (140) and the electron transport layer (150), or may be formed in a stack structure as described above.

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 photoconductor, 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, a compound according to one aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by the following chemical formula 1.

<Chemical Formula 1>

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

X ¹ to X ³ are independently O or S.

R ¹ to R ⁴ are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₆₀ aliphatic ring group; C ₁ to C ₃₀ alkyl group; C ₂ to C ₃₀ alkenyl group; C ₂ to C ₃₀ alkynyl group; C ₁ to C ₃₀ alkoxyl group; C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ), and adjacent groups can be bonded to each other to form a ring.

a to d are each integers from 0 to 4, and when they are integers greater than or equal to 2, each of R ¹ , each of R ² , each of R ³ , and each of R ⁴ are equal to or different from each other.

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; and a C ₃ to C ₆₀ aliphatic ring group.

When adjacent groups are bonded to each other to form an aromatic ring, preferably an aromatic ring of _C6 to _C20 , more preferably an aromatic ring of _C6 to _C14 , such as benzene, naphthalene, phenanthrene, etc., can be formed, or a ring containing a benzene moiety can be formed.

When R ¹ to R ⁴ 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, naphthyl, biphenyl, terphenyl, and the like.

L ¹ to L ⁴ 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; and a C ₃ to C ₆₀ aliphatic ring group.

When L ¹ to L ⁴ 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, naphthylene, biphenylene, terphenyl, and the like.

When L ¹ to L ⁴ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₈ heterocyclic groups, such as pyridine, pyrimidine, triazine, quinazoline, quinoxaline, dibenzothiophene, dibenzothiophene, carbazole, phenylcarbazole, and the like.

Y ¹ to Y ⁶ are each independently C(R') or N, at least one of Y ¹ to Y ³ comprises N, and at least one of Y ⁴ to Y ⁶ comprises N.

The above R' can be selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₆₀ aliphatic ring group; C ₁ to C ₃₀ alkyl group; C ₂ to C ₃₀ alkenyl group; C ₂ to C ₃₀ alkynyl group; C ₁ to C ₃₀ alkoxyl group; C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ).

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; and -L'-N(R _a )(R _b ).

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, naphthyl, biphenyl, terphenyl, 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 ₁₈ heterocyclic groups, such as pyridine, pyrimidine, triazine, quinazoline, quinoxaline, dibenzothiophene, dibenzothiophene, carbazole, phenylcarbazole, and the like.

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

A ring to D ring are independently selected from the group consisting of a C ₆ to C ₆₀ aromatic ring; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group, provided that at least one of A ring to D ring is a C ₁₀ to C ₆₀ aromatic ring, and A ring to D ring may each be further substituted with R ⁵ . Here, R ⁵ may be the same or different.

When the A ring to the D ring are aromatic rings, they are preferably aromatic rings having _C6 to _C20 , more preferably aromatic rings having _C6 to _C14 , such as benzene, naphthalene, phenanthrene, etc.

The above R ⁵ can be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; C ₃ to C ₆₀ aliphatic ring group; C ₁ to C ₃₀ alkyl group; C ₂ to C ₃₀ alkenyl group; C ₂ to C ₃₀ alkynyl group; C ₁ to C ₃₀ alkoxyl group; C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ).

i and j are integers 0 or 1, respectively, at least one of which is 1.

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 combinations thereof.

When L' is an arylene group, it may be preferably a C ₆ to C ₃₀ arylene group, more preferably a C ₆ to C ₁₈ arylene group, such as phenylene, naphthylene, biphenylene, terphenyl, etc.

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; and a C ₃ to C ₆₀ aliphatic ring group.

When R _a and R _b 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, naphthyl, biphenyl, terphenyl, and the like.

The rings formed by bonding the above R ¹ to R ⁵ , R', L ¹ to L ⁴ , Ar ¹ , Ar ² , and adjacent groups to each other 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 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 ₆ -C ₂₀ arylthio 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 comprising 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; a C ₈ -C ₂₀ arylalkenyl group; and -L'-N(R _a )(R _b ) may be further substituted with one or more substituents selected from the group consisting of, wherein L', R _a and R _b are as defined above.

Preferably, the chemical formula 1 can be represented by the following chemical formula 1-1 or chemical formula 1-2.

<Chemical Formula 1-1>

<Chemical Formula 1-2>

In the above chemical formulas 1-1 and 1-2, X ¹ to X ³ , R ¹ to R ⁴ , a to d, L ¹ to L ⁴ , Y ¹ to Y ⁶ , Ar ¹ , Ar ² , ring A to ring D are as defined in chemical formula 1, and c' and d' are integers of 0 to 3, respectively.

In addition, the chemical formula 1 can be represented by one of the following chemical formulas 1-3 to 1-10.

<Chemical Formula 1-3> <Chemical Formula 1-4>

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

<Chemical Formula 1-7> <Chemical Formula 1-8>

<Chemical Formula 1-9> <Chemical Formula 1-10>

In the chemical formulas 1-3 to 1-10, X ¹ to X ³ , R ¹ to R ⁴ , a to d, L ¹ to L ⁴ , Y ¹ to Y ⁶ , Ar ¹ , Ar ² , ring A to ring D are as defined in chemical formula 1, and c' and d' are integers of 0 to 3, respectively.

Preferably, at least one of the A to D rings may be naphthalene or phenanthrene, and may be specifically selected from the group consisting of the following chemical formulae A-1 to A-6.

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

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

In the above chemical formulas A-1 to A-6, * represents a condensation position with a five-membered ring containing X ² or a five-membered ring containing X ³ , R ⁵ is as defined in chemical formula 1, e is an integer from 0 to 5, and f is an integer from 0 to 7.

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

.

In another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, and an organic layer formed between the anode and the cathode, wherein the organic layer includes one single compound or two or more compounds represented by the chemical formula 1.

In another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, an organic layer formed between the anode and the cathode, and a light efficiency improvement layer. In this case, the light efficiency improvement layer is formed on one side of the anode or the cathode that is not in contact with the organic layer, and the organic layer or the light efficiency improvement layer includes a compound represented by the chemical formula 1.

The organic layer includes at least one layer from among a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound can be included in the light-emitting layer.

The above organic layer may include two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks.

In another aspect of the present invention, the present invention provides a display device including an organic electric element represented by the chemical formula 1, and an electronic device including a control unit for driving the display device.

Hereinafter, examples of synthesis of a compound represented by chemical formula 1 according to the present invention and examples of manufacturing an organic electric device are described in detail by way of examples, but the present invention is not limited to the following examples.

Synthetic example

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

<Reaction Scheme 1> (L _a = L ¹ or L ³ , L _b = L ² or L ⁴ , Ar = Ar ¹ or Ar ² , E ring = A ring or C ring, F ring = B ring or D ring, Hal = I, Br, Cl, X = X ² or X ³ , Y ₁ ~Y ₃ =Y ¹ ~Y ³ or Y ⁴ ~Y ⁶ )

I. Synthesis of Sub-1

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

(1) Sub-1-2 synthesis

Synthesis of Sub-1-2-a

(2-bromophenyl)(phenyl)sulfane (9.40 g, 35.45 mmol) was added to THF (100 ml), 2.5 M n-BuLi (14.18 ml, 35.45 mmol) was slowly added at -78°C, and stirred for 1 hour. 2-bromo-9H-fluoren-9-one (9.18 g, 35.45 mmol) dissolved in THF (50 ml) was added at -78°C, and slowly warmed to room temperature. When the reaction was complete, quenched with _NH4Cl and the solvent was removed. Acetic acid (AcOH) (100 ml) and HCl (20 ml) were added, and stirred at 80°C for 5 hours. When the reaction was complete, the temperature was cooled to room temperature, filtered, extracted with MC, and washed with water. Afterwards, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silica gel column to obtain 10.45 g (69%) of the product.

Synthesis of Sub-1-2

To Sub-1-2-a (8.60 g, 21.12 mmol), bis(pinacolato)diboron (8.46 g, 30.19 mmol), PdCl ₂ (dppf) ₂ (0.82 g, 1.01 mmol), KOAc (3.95 g, 40.25 mmol), and toluene (100 ml) were added and refluxed at 120°C for 6 hours. When the reaction was complete, the temperature of the reaction product was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic matter was separated through a silica gel column to obtain 7.64 g (80%) of the product.

(2) Sub-1-7 synthesis

Synthesis of Sub-1-7-a

Using 1-bromo-2-phenoxybenzene (11.00 g, 44.16 mmol), 2.5 M n-BuLi (17.66 ml, 44.16 mmol), 3-bromo-9H-fluoren-9-one (11.44 g, 44.16 mmol), THF (150 ml), AcOH (110 ml), HCl (20 ml), the same synthesis method as Sub-1-2-a was carried out to obtain 13.08 g (72%) of the product.

Synthesis of Sub-1-7

Using Sub-1-7-a (7.40 g, 17.99 mmol), bis(pinacolato)diboron (7.56 g, 26.99 mmol), PdCl ₂ (dppf) ₂ (0.73 g, 0.90 mmol), KOAc (3.53 g, 35.98 mmol), and toluene (100 ml), the same synthesis method as that of Sub-1-2 was carried out, and 6.68 g (81%) of the product was obtained.

(3) Sub-1-8 synthesis

Synthesis of Sub-1-8-a

Using 1-bromo-2-phenoxybenzene (14.50 g, 58.21 mmol), 2.5 M n-BuLi (23.28 ml, 58.21 mmol), 4-bromo-9H-fluoren-9-one (15.08 g, 58.21 mmol), THF (200 ml), AcOH (150 ml), HCl (25 ml), the same synthesis method as Sub-1-2-a was carried out, and 16.76 g (70%) of the product was obtained.

Synthesis of Sub-1-8

Using Sub-1-8-a (10.20 g, 24.80 mmol), bis(pinacolato)diboron (10.42 g, 37.20 mmol), PdCl ₂ (dppf) ₂ (1.01 g, 1.24 mmol), KOAc (4.87 g, 49.60 mmol), toluene (120 ml), the same synthesis method as that of Sub-1-2 was carried out, and 9.55 g (84%) of the product was obtained.

(4) Sub-1-9 synthesis

Synthesis of Sub-1-9-a

To 2-bromo-1,1'-biphenyl (8.70 g, 37.32 mmol) is added THF (100 ml), 2.5 M n-BuLi (14.93 ml, 37.32 mmol) is slowly added at -78°C, and stirred for 1 hour. 4-bromo-9H-thioxanthen-9-one (10.87 g, 37.32 mmol) dissolved in THF (50 ml) is added at -78°C, and slowly warmed to room temperature. When the reaction is complete, quench with NH ₄ Cl and remove the solvent. Add AcOH (90 ml) and HCl (15 ml) and stir at 80°C for 5 hours. When the reaction is complete, cool to room temperature, filter, extract with MC, and wash with water. Afterwards, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was separated using a silica gel column to obtain 7.02 g (44%) of the product.

Synthesis of Sub-1-9

Using Sub-1-9-a (4.40 g, 10.30 mmol), bis(pinacolato)diboron (4.33 g, 15.44 mmol), PdCl ₂ (dppf) ₂ (0.42 g, 0.51 mmol), KOAc (2.02 g, 20.59 mmol), and toluene (60 ml), the same synthesis method as that of Sub-1-2 was carried out, and 4.01 g (82%) of the product was obtained.

(5) Sub-1-14 synthesis

Synthesis of Sub-1-14-a

Using 2-bromo-1,1'-biphenyl (7.20 g, 30.89 mmol), 2.5 M n-BuLi (12.35 ml, 30.89 mmol), 3-bromo-9H-xanthen-9-one (8.50 g, 30.89 mmol), THF (100 ml), AcOH (70 ml), HCl (12 ml), the same synthesis method as Sub-1-9-a was carried out to obtain 6.10 g (48%) of the product.

Synthesis of Sub-1-14

Using Sub-1-14-a (9.50 g, 23.10 mmol), bis(pinacolato)diboron (9.71 g, 34.65 mmol), PdCl ₂ (dppf) ₂ (0.94 g, 1.15 mmol), KOAc (4.53 g, 46.19 mmol), and toluene (100 ml), the same synthesis method as that of Sub-1-2 was carried out, obtaining 9.42 g (89%) of the product.

(6) Sub-1-15 synthesis

Synthesis of Sub-1-15-a

Using 2-bromo-1,1'-biphenyl (12.10 g, 51.91 mmol), 2.5 M n-BuLi (20.76 ml, 51.91 mmol), 2-bromo-9H-xanthen-9-one (14.28 g, 51.91 mmol), THF (160 ml), AcOH (120 ml), HCl (25 ml), the same method as for the synthesis of Sub-1-9-a was carried out to obtain 9.18 g (43%) of the product.

Synthesis of Sub-1-15

Using Sub-1-15-a (5.20 g, 12.64 mmol), bis(pinacolato)diboron (5.31 g, 18.96 mmol), PdCl ₂ (dppf) ₂ (0.52 g, 0.63 mmol), KOAc (2.48 g, 25.29 mmol), and toluene (60 ml), the same synthesis method as that of Sub-1-2 was carried out, obtaining 5.04 g (87%) of the product.

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

[Table 1]

Ⅱ. Example of Sub-2

Sub-2-2's Synthetic example

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

2,4-dichloro-6-phenyl-1,3,5-triazine (15 g, 66.4 mmol) was added benzo[b]naphtho[2,1-d]thiophen-5-ylboronic acid (22.2 g, 79.6 mmol), Pd(PPh ₃ ) ₄ (3.8 g, 3.3 mmol), K ₂ CO ₃ (27.5 g, 199.1 mmol), toluene (200 ml), and H ₂ O (100 ml) and refluxed at 120°C for 3 hours. When the reaction is complete, the temperature of the reaction mass is cooled to room temperature. The resulting solid was filtered, dissolved in o -DCB, separated using a silica filter, and then recrystallized to obtain 23.6 g (84%) of the product.

Sub-2-36's Synthetic example

Using 2,4-dichloro-6-phenyl-1,3,5-triazine (10 g, 44.2 mmol), (2-(naphtho[2,3-b]benzofuran-1-yl)phenyl)boronic acid (17.9 g, 53.1 mmol), Pd(PPh ₃ ) ₄ (2.5 g, 2.2 mmol), K ₂ CO ₃ (18.3 g, 132.7 mmol), toluene (140 ml), and H ₂ O (60 ml), the same synthesis method as that of Sub-2-2 was carried out, and 17.3 g (81%) of the product was obtained.

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

[Table 2]

Ⅲ. Synthesis of the final compound

Synthesis of P-12

To Sub-1-2 (3.10 g, 6.53 mmol), add Sub-2-31 (2.67 g, 6.53 mmol), Pd(PPh ₃ ) ₄ (0.18 g, 0.20 mmol), NaOH (0.52 g, 13.07 mmol), toluene (65 ml), and H ₂ O (30 ml) and reflux at 120°C for 3 hours. When the reaction is complete, cool the reaction mass to room temperature. Filter the resulting solid and dissolve in o -DCB. After that, it was separated using a silica filter and recrystallized to obtain 3.86 g (82%) of the product.

Synthesis of P-27

Sub-2-8 (1.96 g, 4.80 mmol), Pd(PPh ₃ ) ₄ (0.13 g, 0.14 mmol), NaOH (0.38 g, 9.60 mmol), toluene (50 ml), and H ₂ O (25 ml) were added to Sub-1-7 (2.20 g, 4.80 mmol), and the reaction was carried out in the same manner as the synthesis of P-12, to obtain 2.67 g (79%) of the product.

Synthesis of P-39

Sub-2-33 (1.76 g, 4.15 mmol), Pd(PPh ₃ ) ₄ (0.11 g, 0.12 mmol), NaOH (0.33 g, 8.29 mmol), toluene (40 ml), and H ₂ O (20 ml) were added to Sub-1-8 (1.90 g, 4.15 mmol), and the reaction was carried out in the same manner as the synthesis of P-12, to obtain 2.42 g (81%) of the product.

Synthesis of P-56

Sub-2-8 (2.22 g, 5.45 mmol), Pd(PPh ₃ ) ₄ (0.15 g, 0.16 mmol), NaOH (0.44 g, 10.91 mmol), toluene (55 ml), and H ₂ O (25 ml) were added to Sub-1-15 (2.50 g, 5.45 mmol), and the reaction was carried out in the same manner as the synthesis of P-12, to obtain 3.22 g (84%) of the product.

Synthesis of P-70

Sub-2-26 (3.05 g, 7.20 mmol), Pd(PPh ₃ ) ₄ (0.20 g, 0.22 mmol), NaOH (0.58 g, 14.40 mmol), toluene (70 ml), and H ₂ O (30 ml) were added to Sub-1-14 (3.30 g, 7.20 mmol), and the reaction was carried out in the same manner as the synthesis method of P-12, to obtain 4.04 g (78%) of the product.

Synthesis of P-75

Sub-2-23 (2.41 g, 5.90 mmol), Pd(PPh ₃ ) ₄ (0.16 g, 0.18 mmol), NaOH (0.47 g, 11.80 mmol), toluene (60 ml), and H ₂ O (30 ml) were added to Sub-1-9 (2.80 g, 5.90 mmol), and the reaction was carried out in the same manner as the synthesis method of P-12, to obtain 3.40 g (80%) of the product.

The FD-MS values of compounds P-1 to P-85 of the present invention manufactured according to the above synthetic examples are as shown in Table 3 below.

[Table 3]

Manufacturing and Evaluation of Organic Electronics

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

A N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter abbreviated as "2-TNATA") film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer with a thickness of 60 nm, and then a N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as "NPB") film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Thereafter, a 30 nm thick light-emitting layer was deposited on the hole transport layer using the compound P-4 of the present invention as a host material and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as “(piq) ₂ Ir(acac”)) as a dopant material at a weight ratio of 94:6.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm on the light-emitting layer to form a hole-blocking layer, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm on the hole-blocking layer to form an electron-transport layer.

Thereafter, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 14]

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 below was used instead of the compound P-4 of the present invention as a host material.

[Comparative Example 1] and [Comparative Example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 was used instead of Compound P-4 of the present invention as a host material.

<Comparative compound 1> <Comparative compound 2>

A forward bias DC voltage was applied to the organic electroluminescence devices of Examples 1 to 14 of the present invention and Comparative Examples 1 and 2 manufactured as described above, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch, and the T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a standard luminance of 2500 cd/m ² . The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results in Table 4 above, when the compound of the present invention is used as a host material of the light-emitting layer, the driving voltage of the device is lowered and the efficiency and lifespan are significantly improved compared to when Comparative Compound 1 or Comparative Compound 2 is used.

Comparing Comparative Examples 1 and 2, the driving voltage was lower and the efficiency and lifespan were better in the case where Comparative Compound 1, in which a benzocarbazole moiety was bonded to a triazine, was used (Comparative Example 1) than in the case where Comparative Compound 2, in which a dibenzofuran moiety was bonded to a triazine (Comparative Example 2).

In addition, in the case of the example of the present invention using the compound of the present invention in which one more benzene ring is condensed on dibenzofuran or dibenzothiophene as a host material, the driving voltage was lowered and the efficiency and lifespan were significantly improved compared to Comparative Example 1.

This is because the compound of the present invention, in which a naphthobenzofuran moiety or a naphthobenzothiophene moiety is linked to a triazine, has a higher refractive index and Tg value than comparative compounds 1 and 2, and thus the device performance appears to be improved due to improved efficiency and thermal stability.

In addition, the compound of the present invention has a deeper T1 value than comparative compounds 1 and 2, which results in improved energy transfer to the dopant, and thus appears to maximize luminescence efficiency.

These results suggest that even if the basic skeleton is similar, the physical properties of the compound, such as light efficiency characteristics and energy level, change as the rings are further condensed as in the present invention, and this may cause changes in the performance of the device.

The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications, such as methods for improving performance by including other compounds in the light-emitting layer, 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 a scope equivalent thereto should be interpreted as being included in the scope of the rights of the present invention.

100, 200, 300: Organic electrochemical device 110: First electrode
120: Hole injection layer 130: Hole transport layer
140: Emitting layer 150: Electron transport layer
160: Electron injection layer 170: Second electrode
180: Light efficiency improvement layer 210: Buffer layer
220: Light-emitting auxiliary layer 320: First hole injection layer
330: First hole transport layer 340: First light emitting layer
350: 1st electron transport layer 360: 1st charge generation layer
361: Second charge generation layer 420: Second hole injection layer
430: Second hole transport layer 440: Second light emitting layer
450: Second electron transport layer CGL: Charge generation layer
ST1: 1st stack ST2: 2nd stack

Claims (13)

A compound represented by the following chemical formula 1:
<Chemical Formula 1>

In the above chemical formula 1,
X ¹ to X ³ are independently O or S,
R ¹ to R ⁴ are independently selected from the group consisting of hydrogen; deuterium; and C ₆ to C ₃₀ aryl groups, and adjacent groups may combine with each other to form a C ₆ to C ₁₄ aromatic ring.
a to d are each integers from 0 to 4, and when they are integers greater than or equal to 2, R ¹ each, R ² each, R ³ each, and R ⁴ each are equal to or different from each other.
L ¹ to L ⁴ 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 including at least one heteroatom selected from O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group.
Y ¹ to Y ⁶ are independently C(R') or N, at least one of Y ¹ to Y ³ comprises N, and at least one of Y ⁴ to Y ⁶ comprises N,
Ar ¹ and Ar ² 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 containing at least one heteroatom selected from O, N, S, Si and P; a C ₃ to C ₆₀ aliphatic ring group; and -L'-N(R _a )(R _b ).
A ring to D ring are independently selected from the group consisting of a C ₆ to C ₆₀ aromatic ring; a C ₂ to C ₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group, provided that at least one of A ring to D ring is a C ₁₀ to C ₆₀ aromatic ring, and A ring to D ring may be further substituted with R ⁵ which is the same or different from each other,
i and j are integers 0 or 1, respectively, and i+j is 1.
The above R' and R ⁵ are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group including at least one heteroatom among O, N, S, Si and P; C ₃ to C ₆₀ aliphatic ring group; C ₁ to C ₃₀ alkyl group; C ₂ to C ₃₀ alkenyl group; C ₂ to C ₃₀ alkynyl group; C ₁ to C ₃₀ alkoxyl group; C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ),
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 among O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group.
The aromatic ring formed by bonding the above R ¹ to R ⁵ , R', L ¹ to L ⁴ , Ar ¹ , Ar ² , and adjacent groups to each other is 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 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 ₆ -C ₂₀ arylthio 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 comprising 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; a C ₈ -C ₂₀ arylalkenyl group; and -L'-N(R _a )(R _b ) may be further substituted with one or more substituents selected from the group consisting of. In paragraph 1,
The above chemical formula 1 is a compound characterized by being represented by the following chemical formula 1-1 or chemical formula 1-2:
<Chemical Formula 1-1>

<Chemical Formula 1-2>

In the above chemical formulas 1-1 and 1-2, X ¹ to X ³ , R ¹ to R ⁴ , a to d, L ¹ to L ⁴ , Y ¹ to Y ⁶ , Ar ¹ , Ar ² , ring A to ring D are as defined in the first term, and c' and d' are integers of 0 to 3, respectively. In paragraph 1,
The above chemical formula 1 is a compound characterized by being represented by one of the following chemical formulas 1-3 to 1-10:
<Chemical Formula 1-3><Chemical Formula 1-4>

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

<Chemical Formula 1-7><Chemical Formula 1-8>

<Chemical Formula 1-9><Chemical Formula 1-10>

In the chemical formulas 1-3 to 1-10, X ¹ to X ³ , R ¹ to R ⁴ , a to d, L ¹ to L ⁴ , Y ¹ to Y ⁶ , Ar ¹ , Ar ² , ring A to ring D are as defined in the first term, and c' and d' are integers of 0 to 3, respectively. In paragraph 1,
A compound characterized in that at least one of the A ring and the D ring is naphthalene or phenanthrene. In paragraph 1,
A compound represented by the above chemical formula 1 is characterized in that it is one of the following compounds:


. In an organic electric device including an anode, a cathode, and an organic layer formed between the anode and the cathode,
An organic electric device characterized in that the organic layer comprises a single compound or two or more compounds represented by the chemical formula 1 of claim 1. In an organic electric device including an anode, a cathode, an organic layer formed between the anode and the cathode, and a light efficiency improvement layer,
The above light efficiency improvement layer is formed on one side of the anode or cathode that is not in contact with the organic layer.
An organic electric device, characterized in that the organic layer or the light efficiency improvement layer comprises a compound represented by the chemical formula 1 of claim 1. In clause 6 or 7,
An organic electric device, characterized in that the organic layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. In Article 8,
An organic electric device characterized in that the compound is included in at least one of the light-emitting layer and the light-emitting auxiliary layer. In clause 6 or 7,
An organic electric device characterized in that the organic layer includes two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode. In Article 10,
An organic electric device characterized in that the organic layer further includes a charge generation layer formed between two or more stacks. A display device including an organic electric element according to claim 6 or claim 7; and
An electronic device including a control unit that drives the above display device. In Article 12,
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.