KR102768901B1 - 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.

In addition, a method of using a light-emitting auxiliary layer between the hole transport layer and the light-emitting layer is being studied to solve the light-emitting problem in the hole transport layer in recent organic light-emitting devices. Since the desired material properties are different for each light-emitting layer (R, G, B), development of a light-emitting auxiliary layer for each light-emitting layer is required.

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 an important factor for portable displays that have a limited power supply source called a battery, and efficiency and lifespan issues are also important factors that must 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 results in a tendency for the lifespan to increase.

However, simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved simultaneously 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. Therefore, it is necessary to develop a light-emitting layer material and a light-emitting auxiliary layer material that can improve both the efficiency and life of the device.

The present invention aims to provide a compound capable of lowering the operating voltage of a device and improving the luminous efficiency and lifespan of a device by using a compound having strong hole properties and thus having high stability for not only electrons but also holes, thereby enabling more efficient hole transport, in a light-emitting layer or a light-emitting auxiliary layer, and 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.

According to the present invention, by using a compound that has strong hole characteristics and thus has high stability for not only electrons but also holes, thereby enabling more efficient hole transport, in a light-emitting layer or a light-emitting auxiliary layer, not only can the driving voltage of the device be lowered, but also the light-emitting efficiency and lifespan of the device can be 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 term "fluorenyl group" used in the present invention means a substituted or unsubstituted fluorenyl group, and the term "fluorenylene group" means a substituted or unsubstituted fluorenyl group. The fluorenyl group or fluorenylene group used in the present invention includes a case where R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.

The terms “substituted fluorenyl group” and “substituted fluorenylene group” mean that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in this specification, regardless of the valence, a fluorenyl group, a fluorenylene group, a fluorenetriyl group, etc. 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, for example, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , and R ₅ and R ₆ , as well as 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 (210) or a light-emitting auxiliary layer (220) 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 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 a light-emitting layer (140, 340, 440), a light-emitting auxiliary layer (220) and/or a 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 for the light-emitting layer (140, 340, 440), the light-emitting auxiliary layer (220), 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 and Y are independently O or S.

Ring A and ring B are each independently a _C6 - _C60 aromatic ring or a _C2 - _C60 heterocyclic group, and at least one of ring A and ring B is a condensed ring of two or more rings. Ring A may be substituted with one or more ^R4s, which are the same or different, and ring B may be substituted with one or more ^R5s , which are the same or different.

When at least one of the above A ring and B ring is an aromatic ring, the aromatic ring is, for example, C ₆ ~C ₃₀ , C ₆ ~C ₂₉ , C ₆ ~C ₂₈ , C ₆ ~C ₂₇ , C ₆ ~C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₆ , etc., and specifically, it can be benzene, naphthalene, phenanthrene, etc.

When at least one of the above A ring and B ring is a heterocyclic group, the heterocyclic group is, for example, C ₂ ~C ₃₀ , C ₂ ~C ₂₉ , C ₂ ~C ₂₈ , C ₂ ~C ₂₇ , C ₂ ~C ₂₆ , C ₂ ~C ₂₅ , C ₂ ~C ₂₄ , C ₂ ~C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C _{20 ,} etc., and specifically, it can be a heterocyclic group such as pyridine, pyrimidine, pyrazine, trizine, quinoline, quinoxaline, quinazoline, etc.

If at least one of the A ring and the B ring is an aromatic ring of two or more rings, the aromatic ring may be an aromatic ring of _C10 to _C60 , _C10 to _C30 , _C10 to _C20 , _C10 to _C18 , _C10 to _C16 , _C10 to _C14, etc., and specifically, may be naphthalene, phenanthrene, etc. In addition, when at least one of the A ring and the B ring is a heterocycle having two or more rings, the heterocycle may be a heterocycle such as C ₂ -C ₆₀ , C ₂ -C ₃₀ , C ₂ -C ₁₈ , C ₂ -C ₁₄ , C ₂ -C ₁₂ , C ₂ -C ₁₀ , C ₂ -C ₉ , C ₂ -C ₈ , C ₂ -C ₇ , and specifically, may be quinoline, isoquinoline, quinazoline, quinoxaline, and the like.

R ¹ to 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 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.

The ring formed by bonding adjacent groups to each other may be an aromatic ring having C ₆ to C ₆₀ , a heterocycle having C ₂ to C ₆₀ containing at least one heteroatom selected from O, N, S, Si and P, or an aliphatic ring having C ₃ to C ₆₀ .

When at least one pair of adjacent R ¹ s, adjacent R ² s, and adjacent R ³ s are bonded to each other to form an aromatic ring, preferably a C ₆ to C ₂₀ aromatic ring, more preferably a C ₆ to C ₁₄ aromatic ring, such as benzene, naphthalene, or phenanthrene, can be formed.

a is an integer from 1 to 6, b is an integer from 1 to 2, c is an integer from 1 to 3, and when these are integers greater than or equal to 2, each of the plurality of R ^1s , each of the plurality of R ^2s , and each of the plurality of R ^3s 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 containing at least one heteroatom selected from O, N, S, Si and P; and a C ₃ to C ₆₀ aliphatic ring group.

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; a C ₁ to C ₃₀ alkyl group; a C ₂ to C ₃₀ alkenyl group; a C ₂ to C ₃₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; a C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ).

The above L' is 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.

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

When at least one of the above R ¹ to R ⁵ , Ar ¹ , Ar ² , R _a and R _b is an aryl group, the aryl group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ to C ₂₆ , C ₆ to C ₂₅ , C ₆ to C ₂₄ , C ₆ to C ₂₃ , C ₆ to C ₂₂ , C ₆ to C ₂₁ , C ₆ to C ₂₀ , C ₆ to C ₁₉ , C ₆ to C ₁₈ , C ₆ to C ₁₇ , C ₆ to C ₁₆ , C ₆ to C ₁₅ , C ₆ to C ₁₄ , C ₆ to C ₁₃ , C ₆ to C ₁₂ , C ₆ to C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C _{18 ,} etc., and specifically, it can be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, fluoranthene, etc.

When at least one of L ¹ to L ⁴ and L' is an arylene group, the arylene group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ to C ₂₆ , C ₆ to C ₂₅ , C ₆ to C ₂₄ , C ₆ to C ₂₃ , C ₆ to C ₂₂ , C ₆ to C ₂₁ , C ₆ to C ₂₀ , C ₆ to C ₁₉ , C ₆ to C ₁₈ , C ₆ to C ₁₇ , C ₆ to C ₁₆ , C ₆ to C ₁₅ , C ₆ to C ₁₄ , C ₆ to C ₁₃ , C ₆ to C ₁₂ , C ₆ to C ₁₁ , C ₆ to C ₁₀ , C ₆ , It can be an arylene group such as C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, it can be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, and the like.

When at least one of the above R ¹ to R ⁵ , Ar ¹ , Ar ² , R _a , R _b , L ¹ to L ⁴ , L' is a heterocyclic group, the heterocyclic group is, for example, C ₂ to C ₃₀ , C ₂ to C ₂₉ , C ₂ to C ₂₈ , C ₂ to C ₂₇ , C ₂ to C ₂₆ , C ₂ to C ₂₅ , C ₂ to C ₂₄ , C ₂ to C ₂₃ , C ₂ to C ₂₂ , C ₂ to C ₂₁ , C ₂ to C ₂₀ , C ₂ to C ₁₉ , C ₂ to C ₁₈ , C ₂ to C ₁₇ , C ₂ to C ₁₆ , C ₂ to C ₁₅ , C ₂ to C ₁₄ , C ₂ to C ₁₃ , C ₂ to C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ It may be a heterocyclic group such as, and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, phenanthrobenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenantrobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, Benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothiopyridine, benzofuropyridine, benzothiopyrimidine, benzofuropyrimidine, benzothiopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilole, phenanthroline, dihydro-phenylphenazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, thianthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, 9,9-diphenyl-9H-xanthene, spiro[fluorene-9,9'-xanthene], These may include benzo[kl]xanthene, benzo[b]naphtho[2,3-e][1,4]dioxin, etc.

When at least one of the above R ¹ to R ⁵ , Ar ¹ , Ar ² , R _a , R _b is a fluorenyl group or when at least one of L ¹ to L ⁴ , L' is a fluorenylene group, the fluorenyl group or fluorenylene group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl-9 H -fluorene, etc.

When at least one of the above R ¹ to R ⁵ , Ar ¹ , Ar ² , R _a , and R _b is an aliphatic ring group, the aliphatic ring group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ to C ₂₆ , C ₆ to C ₂₅ , C ₆ to C ₂₄ , C ₆ to C ₂₃ , C ₆ to C ₂₂ , C ₆ to C ₂₁ , C ₆ to C ₂₀ , C ₆ to C ₁₉ , C ₆ to C ₁₈ , C ₆ to C ₁₇ , C ₆ to C ₁₆ , C ₆ to C ₁₅ , C ₆ to C ₁₄ , C ₆ to C ₁₃ , C ₆ to C ₁₂ , C ₆ to C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C _{18 ,} etc., and specifically, it can be an aliphatic ring group such as cyclohexane, adamantane, etc.

When at least one of the above R ¹ to R ⁵ is an alkyl group, the alkyl group may be, for example, an alkyl group of C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , C _{4 ,} etc., and specifically, may be methyl, ethyl, propyl, t-butyl, etc.

When at least one of the above R ¹ to R ⁵ is an alkoxy group, the alkoxy group may be, for example, an alkoxy group such as C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , C ₄ , and the like, and specifically, may be methoxy, ethoxy, t-butoxy, and the like.

The above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, and rings formed by bonding adjacent groups to each other are each selected from 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 phosphine oxide substituted or unsubstituted 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 alkoxyl 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 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.

When at least one of the above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and rings formed by bonding adjacent groups to each other is substituted with an aryl group, the aryl group is, for example, C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C It can be an aryl group such as ₁₈ .

When at least one of the above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and a ring formed by bonding adjacent groups to each other is substituted with a heterocyclic group, the heterocyclic group is, for example, C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , etc. may be heterocyclic groups.

When at least one of the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and rings formed by bonding adjacent groups to each other is substituted with an alkyl group, the alkyl group may be an alkyl group of C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , C ₄ , or the like.

When at least one of the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and rings formed by bonding adjacent groups to each other is substituted with an alkoxy group, the alkoxy group may be an alkoxy group of C ₁ to C ₂₀ , C ₁ to C ₁₀ , C ₁ to C ₄ , C ₁ , C ₂ , C ₃ , C ₄ , or the like.

For example, at least one of the A ring and the B ring can be selected from the group consisting of the following chemical formulas a-1 to a-7.

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

<Chemical formula a-5> <Chemical formula a-6> <Chemical formula a-7>

In the above chemical formulas a-1 to a-7, * represents a condensation position, V ¹ to V ⁴⁸ are each independently C(R') or N, and R' is the same as R ⁴ or R ⁵ defined in chemical formula 1. That is, R' is 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 ), and adjacent groups can combine with each other to form a ring.

The above chemical formula 1 can be represented by one of the following chemical formulas 1-1 to 1-6.

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

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

In the above chemical formulas 1-1 to 1-6, R ¹ to R ⁵ , L ¹ to L ⁴ , X, Y, Ar ¹ , Ar ² , a to c are as defined in chemical formula 1, d is an integer from 1 to 3, e is an integer from 1 to 6, f is an integer from 1 to 5, and g is an integer from 1 to 4.

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 a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a compound represented by the chemical formula 1.

In another aspect of the present invention, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic layer and a light efficiency improvement layer formed between the first electrode and the second electrode. In this case, the light efficiency improvement layer is formed on one surface of both surfaces of the first electrode and both surfaces of the second electrode that is not in contact with the organic layer, and the organic layer or the light efficiency improvement layer may include a compound represented by the chemical formula 1.

The above organic layer includes at least one layer 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 auxiliary layer and/or 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 first electrode, 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 a reaction route as shown in the following reaction scheme 1, but is not limited thereto.

<Reaction Formula 1>

Sub 1's Synthetic example

Sub 1 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Scheme 2 below, but is not limited thereto.

<Reaction Formula 2>

1. Sub 1-2 Synthetic example

(1) Synthesis of Sub 1-b-2

Sub1-a-2 (100 g, 355.2 mmol), Sub 1-a'-1 (33.1 g, 355.2 mmol), Pd ₂ (dba) ₃ (9.8 g, 10.6 mmol), P( t -Bu) ₃ (8.6 mL, 21.3 mmol), and t -BuONa (68.3 g, 710.4 mmol) were placed in a round-bottomed flask, dissolved in toluene (200 mL), and stirred at 60 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 85.6 g of the product (yield: 82%).

(2) Synthesis of Sub 1-c-2

Sub 1-b-2 (85.6 g, 291.4 mmol) was placed in a round-bottomed flask and dissolved with toluene (970 mL). Sub 1-b'-1 (83.3 g, 291.4 mmol), Pd ₂ (dba) ₃ (8.0 g, 8.7 mmol), P( t -Bu) ₃ (7.1 mL, 17.5 mmol), and t -BuONa (56.0 g, 582.8 mmol) were added and stirred at 60 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 82.9 g of the product (yield: 57%).

(3) Synthesis of Sub 1-2

Sub 1-c-2 (82.9 g, 166.2 mmol) was placed in a round-bottomed flask and dissolved with DMA (550 mL). Pd(OAc) ₂ (0.7 g, 3.3 mmol) and P(Cy) ₃ HBF ₄ (6.1 g, 16.6 mmol) were added and stirred at 120°C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was then recrystallized to obtain 47.2 g of the product (yield: 68%).

2. Sub 1-9 Synthetic example

(1) Synthesis of Sub 1-b-9

In a round-bottomed flask, Sub 1-a-9 (100 g, 323.0 mmol), Sub 1-a'-1 (30.1 g, 323.0 mmol), Pd ₂ (dba) ₃ (8.9 g, 9.7 mmol), P( t -Bu) ₃ (7.8 mL, 19.4 mmol), and t -BuONa (62.1 g, 646.0 mmol) were placed and dissolved in toluene (1,080 mL), and the mixture was stirred for 10 min. The reaction was carried out in the same manner as for the synthesis of Sub 1-b-2, to obtain 81.1 g of the product (yield: 78%).

(2) Synthesis of Sub 1-c-9

After dissolving Sub 1-b-9 (81.1 g, 252.0 mmol) in toluene (840 mL), Sub 1-b'-1 (72.1 g, 252.0 mmol), Pd ₂ (dba) ₃ (6.9 g, 7.6 mmol), P( t -Bu) ₃ (6.1 mL, 15.1 mmol), and t -BuONa (48.4 g, 504.0 mmol) were added, and the synthesis was carried out in the same manner as for Sub 1-c-2, obtaining 74.4 g of the product (yield: 56%).

(3) Synthesis of Sub 1-9

After dissolving Sub 1-c-9 (74.4 g, 141.2 mmol) in DMA470 mL, Pd(OAc) ₂ (0.6 g, 2.8 mmol) and P(Cy) ₃ HBF ₄ (5.2 mL, 14.1 mmol) were added, and the synthesis method of Sub 1-2 was carried out as described above to obtain 39.0 g of the product (yield: 62%).

3. Sub 1-20 Synthetic example

(1) Synthesis of Sub 1-b-20

In a round-bottomed flask, Sub 1-a-20 (100 g, 336.0 mmol), Sub 1-a'-2 (48.1 g, 336.0 mmol), Pd ₂ (dba) ₃ (9.2 g, 10.1 mmol), P( t -Bu) ₃ (8.2 mL, 20.2 mmol), and t -BuONa (64.6 g, 672.1 mmol) were placed and dissolved in toluene (1,100 mL), and the mixture was stirred for 10 minutes under reduced pressure. The reaction was carried out in the same manner as for the synthesis of Sub 1-b-2, to obtain 95.5 g of the product (yield: 79%).

(2) Synthesis of Sub 1-c-20

After dissolving Sub 1-b-20 (95.5 g, 265.4 mmol) in toluene (880 mL), Sub 1-b'-1 (75.9 g, 265.4 mmol), Pd ₂ (dba) ₃ (7.3 g, 8.0 mmol), P( t -Bu) ₃ (6.4 mL, 15.9 mmol), and t -BuONa (51.0 g, 530.7 mmol) were added, and the synthesis was carried out in the same manner as for Sub 1-c-2, obtaining 79.4 g of the product (yield: 53%).

(3) Synthesis of Sub 1-20

After dissolving Sub 1-c-20 (79.4 g, 140.5 mmol) in DMA (470 mL), Pd(OAc) ₂ (0.6 g, 2.8 mmol) and P(Cy) ₃ HBF ₄ (5.2 mL, 14.1 mmol) were added, and the synthesis method of Sub 1-2 was carried out as described above to obtain 44.9 g of the product (yield: 66%).

4. Sub 1-31 Synthetic example

Sub 1-2 (4.2 g, 10.1 mmol) was placed in a round-bottom flask and dissolved in THF (25 mL) and water (8 mL). Sub 1'-1 (2.4 g, 15.1 mmol), Pd(PPh ₃ ) ₄ (0.3 g, 0.3 mmol) and NaOH (0.8 g, 20 mmol) were added and stirred at 75°C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 3.6 g of the product (yield: 72%).

5. Sub 1-32 Synthetic example

(1) Synthesis of Sub 1-c-32

In a round-bottomed flask were placed Sub 1-b-2 (30 g, 102.1 mmol), 1-b'-3 (34.3 g, 102.1 mmol), Pd ₂ (dba) ₃ (2.8 g, 3.1 mmol), P( t -Bu) ₃ (2.5 mL, 6.1 mmol), and t -BuONa (19.6 g, 204.3 mmol), dissolved in toluene (340 mL), and the synthesis was carried out in the same manner as for Sub 1-b-2, to obtain 30.8 g of the product (yield: 55%).

(2) Synthesis of Sub 1-32

Sub 1-c-32 (30 g, 54.7 mmol) was dissolved in DMA (180 mL), and Pd(OAc) ₂ (0.2 g, 1.1 mmol) and P(Cy) ₃ HBF ₄ (2.0 mL, 5.5 mmol) were added. The synthesis was carried out in the same manner as for Sub 1-2, obtaining 15.6 g of the product (yield: 61%).

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

[Table 1]

Synthesis example of Sub 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 Scheme 3> (Hal is Br or Cl)

1. Sub 2-4 Synthetic example

In a round-bottomed flask were added Sub 2-a-4 (30 g, 101.0 mmol), Sub 2-b-4 (17.1 g, 101 mmol), Pd ₂ (dba) ₃ (2.8 g, 3.0 mmol), P( t -Bu) ₃ (2.5 mL, 6.1 mmol), and t -BuONa (19.4 g, 201.9 mmol), dissolved in toluene (340 mL), and stirred at 60°C. When the reaction was complete, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 31.9 g of the product (yield: 82%).

2. Sub 2-39 Synthetic example

(1) Synthesis of Sub 2-a-39

In a round-bottomed flask were added Sub 2-a'-39 (31.3 g, 100.0 mmol), Sub 2-b'-39 (20.6 g, 100.0 mmol), Pd(PPh ₃ ) ₄ (3.5 g, 3.0 mmol), and NaOH (8.0 g, 199.9 mmol). THF (250 mL) and water (82 mL) were added to dissolve, and the mixture was stirred at 50°C. When the reaction was complete, the mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 30.8 g of the product (yield: 78%).

(2) Synthesis of Sub 2-39

In a round-bottomed flask, Sub 2-a-39 (30.8 g, 78.0 mmol), Sub 2-b-39 (11.2 g, 78.0 mmol), Pd ₂ (dba) ₃ (2.1 g, 2.3 mmol), P( t -Bu) ₃ (1.9 mL, 4.7 mmol), and t -BuONa (15.0 g, 156.0 mmol) were placed and dissolved in toluene (840 mL), and the mixture was stirred for 10 minutes according to the synthesis method of Sub 2-4, to obtain 27 g of the product (yield: 69%).

3. Sub 2-49 Synthetic example

In a round-bottomed flask, Sub 2-a-49 (31.3 g, 100.0 mmol), Sub 2-b-49 (17.0 g, 100.0 mmol), Pd ₂ (dba) ₃ (2.7 g, 3.0 mmol), P( t -Bu) ₃ (2.4 mL, 6.0 mmol), and t -BuONa (19.2 g, 199.9 mmol) were placed and dissolved in toluene (330 mL), and the mixture was stirred for 10 minutes according to the synthesis method of Sub 2-4, to obtain 30.2 g of the product (yield: 75%).

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

[Table 2]

Final products Synthetic example

1. P-1's Synthetic example

Sub 1-3 (10 g, 23.9 mmol) was dissolved in toluene (80 mL), and Sub 2-1 (7.4 g, 23.9 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.7 mmol), P( t -Bu) ₃ (0.6 mL, 1.4 mmol), and t -BuONa (4.6 g, 47.9 mmol) were added and stirred at 120 °C. When the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 10.6 g of the product (yield: 64%).

2. P-11's Synthetic example

After dissolving Sub 1-5 (10 g, 23.0 mmol) in toluene (80 mL), Sub 2-11 (10.9 g, 23.0 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), P( t -Bu) ₃ (0.6 mL, 1.4 mmol), and t -BuONa (4.4 g, 46.1 mmol) were added, and the synthesis was carried out in the same manner as for P-1, obtaining 10.7 g of the product (yield: 53%).

3. P-29's Synthetic example

Sub 1-16 (10 g, 20.2 mmol) was dissolved in toluene (70 mL), and Sub 2-27 (8.3 g, 20.2 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.6 mmol), P( t -Bu) ₃ (0.5 mL, 1.2 mmol), and t -BuONa (3.9 g, 40.5 mmol) were added. The synthesis was carried out in the same manner as for P-1, obtaining 10.9 g of the product (yield: 62%).

4. P-35's Synthetic example

Sub 1-31 (7.3 g, 14.8 mmol) was dissolved in toluene (70 mL), and Sub 2-33 (7.1 g, 14.8 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), and P( t -Bu) ₃ (0.4 mL, 0.9 mmol), t -BuONa (15.0 g, 156.0 mmol) were added. The synthesis was carried out in the same manner as for P-1, to obtain 7.5 g of the product (yield: 54%).

5. P- Example of synthesis of 41

Sub 1-9 (10 g, 22.4 mmol) was dissolved in toluene (75 mL), and Sub 2-39 (11.2 g, 22.4 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), P( t -Bu) ₃ (0.5 mL, 1.3 mmol), and t -BuONa (4.3 g, 44.8 mmol) were added. The synthesis was carried out in the same manner as for P-1, to obtain 11.6 g of the product (yield: 57%).

The FD-MS values of compounds P-1 to P-104 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 electroluminescent device ( Luminescent auxiliary layer )

A hole injection layer was formed by vacuum depositing N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate.

Next, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was vacuum-deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer.

Next, the compound P-1 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emitting auxiliary layer, and then 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) as a host and bis-(1-phenyl isoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as '(piq) ₂ Ir(acac)') as a dopant were doped at a weight ratio of 95:5 on the light-emitting auxiliary layer to deposit a light-emitting layer with a thickness of 30 nm.

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 19]

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-1 of the present invention as a light-emitting auxiliary layer 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-1 of the present invention as a light-emitting auxiliary layer material.

<Comparative compound 1> <Comparative compound 2>

A forward bias DC voltage was applied to the organic electroluminescence devices manufactured by Examples 1 to 19 and Comparative Examples 1 and 2, 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 for an organic electric device of the present invention is used as a material for a light-emitting auxiliary layer, the driving voltage of the device can be significantly lowered and the light-emitting efficiency and lifespan can be significantly improved compared to when Comparative Compound 1 or Comparative Compound 2 is used.

Comparing Comparative Examples 1 and 2, when Comparative Compound 2 was used as a light-emitting auxiliary layer material, the driving voltage, efficiency, and lifespan of the device were improved compared to Comparative Compound 1. This is because in the case of Comparative Compound 2, the overall Hall characteristics increase due to the amine group substituent, and since the distance between substances is maintained constant, smooth interaction with adjacent layers can occur, so the overall driving voltage is lowered while the efficiency and lifespan are improved at the same time.

Comparative Compound 1 is similar to the compound of the present invention in that it has a 6-condensed ring structure containing N and S, but differs in whether an amine group is bonded. In addition, Comparative Compound 2 includes a 6-condensed ring structure, but the condensation position of the benzothiophene moiety is different from that of the compound of the present invention. Due to these differences, when the compound of the present invention is used as a light-emitting auxiliary layer, the characteristics of the device are improved compared to Comparative Compound 1 or Comparative Compound 2.

In particular, the compound of the present invention has a specific heterocycle having four or more rings, such as naphthobenzofuran or naphthobenzothiophene, as one of the substituents of the amine group bonded to the core, and thus has a high refractive index and T _g value, so that not only the luminescence efficiency is improved, but also the thermal stability is improved, and the lifespan seems to be increased.

Therefore, it can be seen that even if the cores are similar or identical compounds, the physical properties of the compound, such as hole characteristics, luminous efficiency characteristics, energy levels (LUMO, HOMO levels, T1 levels), hole injection and mobility characteristics, and electron blocking characteristics, can differ depending on the substituents, and this can lead to completely different device results.

Meanwhile, the evaluation results of the aforementioned device fabrication described the device characteristics in which the compound of the present invention was applied to the light-emitting auxiliary layer, but the compound of the present invention can be used as a material for one or more layers among the light-emitting layer, the hole transport layer, and the light-emitting auxiliary layer.

The above description is merely an exemplary description 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 scope of the present invention is not limited by these embodiments. The protection scope 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 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 (12)

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

In the above chemical formula 1,
X and Y are independently O or S,
Ring A and ring B are independently a _C6 ~ _C60 aromatic ring or a _C2 ~ _C60 heterocyclic group, and at least one of ring A and ring B is a condensed ring of two or more rings, ring A may be substituted with one or more ^R4s which are the same or different, and ring B may be substituted with one or more ^R5s which are the same or different,
R ¹ to 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 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 is an integer from 1 to 6, b is an integer from 1 to 2, c is an integer from 1 to 3, and if they are integers greater than or equal to 2, each of the plurality of R ^1s , each of the plurality of R ^2s , and each of the plurality of R ^3s 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.
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; a C ₁ to C ₃₀ alkyl group; a C ₂ to C ₃₀ alkenyl group; a C ₂ to C ₃₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; a C ₆ to C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ),
The above L' is 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; and a C ₃ to C ₆₀ aliphatic ring group,
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 above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, and rings formed by bonding adjacent groups to each other are each selected from 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 phosphine oxide substituted or unsubstituted 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 alkoxyl 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 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. In paragraph 1,
A compound characterized in that at least one of the above A ring and B ring is selected from the group consisting of the following chemical formulas a-1 to a-7:
<Chemical formula a-1><Chemical formula a-2><Chemical formula a-3><Chemical formula a-4>

<Chemical formula a-5><Chemical formula a-6><Chemical formula a-7>

In the chemical formulas a-1 to a-7 above, * indicates a condensation position, V ¹ to V ⁴⁸ are each independently C(R') or N, and R' is the same as R ⁴ or R ⁵ in claim 1. In paragraph 1,
The above chemical formula 1 is a compound characterized by being represented by one of the following chemical formulas 1-1 to 1-6:
<Chemical Formula 1-1><Chemical Formula 1-2><Chemical Formula 1-3>

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

In the above chemical formulas 1-1 to 1-6, R ¹ to R ⁵ , L ¹ to L ⁴ , X, Y, Ar ¹ , Ar ² , a to c are as defined in the first clause, d is an integer from 1 to 3, e is an integer from 1 to 6, f is an integer from 1 to 5, and g is an integer from 1 to 4. In paragraph 1,
The compound represented by the above chemical formula 1 is a compound characterized by being one of the following compounds:




. 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 comprises a compound represented by the chemical formula 1 of claim 1. In an organic electric device including a first electrode, a second electrode, and an organic layer and a light efficiency improvement layer formed between the first electrode and the second electrode,
The above light efficiency improvement layer is formed on one side of the first electrode and the second electrode that does not come into 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 5 or 6,
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 7,
An organic electric device characterized in that the compound is included in the light-emitting auxiliary layer or the light-emitting layer. In clause 5 or 6,
An organic electric device characterized in that the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode. In Article 9,
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 5 or 6; and
An electronic device including a control unit that drives the display device. In Article 11,
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.