KR20220014504A - Compound for organic electric element, organic electric element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides: an organic electric element comprising a compound represented by chemical formula 1, a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode; and an electronic device including the organic electric element. By including the compound represented by chemical formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered, and the luminous efficiency and lifespan can be improved.

Description

A compound for an organic electric device, an organic electric device 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 light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function. In addition, the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. have. In addition, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is reduced due to the emission attenuation effect. A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through the The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is a large-area display, and the size thereof is increasing, so that power consumption greater than the power consumption required for the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and the problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan. However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T ₁ value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time. .

Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer. In other words, in order to sufficiently exhibit the excellent characteristics of an organic electric device, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. should be preceded, and in particular, development of a host material for the light emitting layer is required.

An object 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 formula.

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

By using the compound according to the embodiment of the present invention, it is possible to lower the driving voltage of the device and improve the luminous efficiency and lifespan of the device.

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

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like. In addition, unless otherwise specified in the present specification, the aryl group may include a fluorenyl group, and the arylene group may include a fluorenylene group.

As used herein, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, "fluorenylene group" refers to a substituted or unsubstituted fluorenyl group, and as used in the present invention, the fluorenyl group or The fluorenylene group includes spiro compounds formed by bonding R and R′ to each other in the following structure, and also includes compounds in which adjacent R″ are bonded to each other to form a ring.

"Substituted fluorenyl group", "substituted fluorenylene group" means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and R" in the following formula is 1 to 8 days can In the present specification, regardless of the valence, a fluorenyl group, a fluorenylene group, a fluorentriyl group, etc. may all be referred to as a fluorene group.

As used herein, the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

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 specified, the number of carbon atoms each containing one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to an element other than carbon, for example, N, O, S, P or Si, unless otherwise specified, and, instead of carbon forming a ring, SO ₂ , P= It may also contain a heteroatom group such as O. In the present specification, the heterocyclic group includes a monocyclic type including a heteroatom, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.

The term "aliphatic ring group" used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

In the present specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'. Similarly, in the case of pyrimidine, regardless of the valence, it can be described as 'pyrimidine' or as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent or pyrimidinylene in the case of divalent. have.

In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in the present invention applies the same as the definition of the substituent by the exponential definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring. It 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 is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same as or different from each other.

In addition, unless otherwise specified in the present specification, when representing 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, benzoquinazoline, etc., may be expressed as a 3-condensed ring.

In addition, unless otherwise specified in the present specification, when a ring is expressed in the form of a 'numeric atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates 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 is a C ₆ ~ C ₆₀ aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ An aliphatic ring group; may be selected from the group consisting of.

At this time, unless otherwise explained in the present specification, 'neighboring groups' refers to each other when describing the following chemical formula as an example, R ₁ and R ₂ each other, R ₂ and R _{3 each} other, R ₃ and R _{4 each} other, It includes not only R ₅ and R ₆ , but also R ₇ and R ₈ that share one carbon, R ₁ and R ₇ , R ₁ and R ₈ , or R ₄ and R ₅ that are not immediately adjacent Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included. That is, if there is a substituent on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.

In the following formula, when substituents bonded to the same carbon as R ₇ and R ₈ combine with each other to form a ring, a compound including a spiro moiety may be formed.

,

,

In addition, in the present specification, the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.

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

In adding reference numerals to the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the component from other components, and the essence, order, or order of the component is not limited by the term. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may be “connected,” “coupled,” or “connected.”

Further, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” another component, but also when another component is in between. It should be understood that cases may be included. Conversely, when it is said that an element is "on top of" another part, it should be understood to mean that there is no other part in the middle.

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

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). ) and an organic material layer formed between the second electrode 170 .

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

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

Preferably, the light efficiency improving layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the light efficiency improving layer 180 is formed Light efficiency of the organic electric device may be improved.

For example, the light efficiency improving layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the light efficiency improving layer 180 is formed to form the second electrode 170 . ) can reduce optical energy loss due to surface plasmon polaritons (SPPs), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.

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 .

2, the organic electric device 200 according to another embodiment of the present invention is a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, It may include 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 , and a light efficiency improving layer 180 is formed on the second electrode. can be

Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .

Referring to FIG. 3 , in the organic electric device 300 according to another embodiment of the present invention, there are two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, in the organic electric device according to an embodiment of the present invention, a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode 170 and the light efficiency improving layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 . ), and the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 . . As described above, the first stack and the second stack may be organic material layers having the same stacked structure or organic material 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 generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current 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 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.

In FIG. 3 , n may be an integer of 1 to 5. When n is 2, the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .

When a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3, an organic electroluminescent device that emits white light by the mixing effect of the light emitted from each light emitting layer can be manufactured, as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.

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

A study on the selection of a core and a combination of sub-substituents coupled thereto because the band gap, electrical properties, and interfacial properties, etc. may vary depending on which position and which substituent is bonded to the same and similar core. In particular, long lifespan and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.

Therefore, in the present invention, by using the compound represented by Chemical Formula 1 as a material for the light emitting layers 140, 340, 440 and/or the light efficiency improving layer 180, the energy level and T ₁ value between each organic material layer, the inherent properties of the material ( Mobility, interface characteristics, etc.) can be optimized to improve the lifetime and efficiency of the organic electric device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have. In addition, an auxiliary light emitting layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.

In addition, the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, 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, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

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

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

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.

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

The compound according to one aspect of the present invention is represented by the following formula (1).

<Formula 1> <Formula 1-A>

In the above formula, each symbol may be defined as follows.

In Formula 1, A is Formula 1-A.

X ¹ to X ³ are each independently N or C(R′), with the proviso that at least one of X ¹ to X ³ is N and Y is O or S.

Ar ¹ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ It is selected from the group consisting of an aryloxy group.

L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ It is selected from the group consisting of an aliphatic cyclic group.

Ar ² , R ¹ to R ⁴ , and R′ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ It is selected from the group consisting of an aryloxy group. In this case, one of R ³ and R ⁴ is combined with L ² . That is, one of R ³ and R ⁴ is a linking group of a single bond used to connect L ² and Formula 1-A.

a, b and c are each an integer of 0-4, d is an integer of 0-6, and when each of these is an integer of 2 or more, each of R ¹ , each of R ² , each of R ³ , and each of R ⁴ are the same or different

Neighboring groups may be bonded to each other to form a ring, for example, at least one pair of neighboring R ¹ or neighboring R ² may be bonded to each other to form a ring, and neighboring Ar ² and R' may be each other They can combine to form a ring. However, the case where neighboring L ² and R ³ or neighboring L ² and R ⁴ are bonded to each other to form a ring is excluded, and when neighboring R ³ or neighboring R ⁴ are bonded to each other to form a ring also excluded.

The case where adjacent Ar ² and R′ are bonded to each other to form a ring means that when X ¹ or X ² is CR′, R′ forms a ring with neighboring Ar ² .

A ring formed by bonding adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic ring group; fluorene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic cyclic group.

When adjacent groups are bonded to each other to form an aromatic ring group, the aromatic ring group is, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₀ , C ₆ ~ C ₁₆ , C ₆ ~ C ₁₄ , C ₆ ~ C ₁₀ , It may be C ₆ and the like, and specifically may be an aromatic ring such as benzene, naphthalene, and phenanthrene.

When adjacent groups are bonded to each other to form a heterocyclic group, the heterocyclic group is, for example, C ₂ ~ C ₃₀ , C ₃ ~ C ₃₀ , C ₄ ~ C ₃₀ , C ₄ ~ C ₂₅ , C ₄ ~ C ₂₄ , C ₄ ~C ₂₀ , C ₄ ~C ₁₈ , C ₄ ~C ₁₆ , C ₄ ~C ₁₂ , C ₄ ~C ₁₁ , C ₄ ~C ₁₀ , C ₄ ~C ₉ , C ₄ ~C ₈ , C ₄ ~C ₇ , C ₄ ~C ₆ , C ₄ ~ C ₅ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₂ , C ₁₆ It may be a heterocyclic group such as, Specifically, it may be a heterocyclic group such as furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene.

When at least one of Ar ¹ , Ar ² , R ¹ to R ⁴ , and R′ 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 ~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 ₁₅ , C ₁₆ , C ₁₇ , may be an aryl group such as C ₁₈ , and specifically, phenyl, biphenyl, naphthyl, terphenyl , phenanthrene, triphenylene, and the like.

When at least one of L ¹ and L ² is an arylene group, the arylene group 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 , It may be an arylene group such as C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, tri phenylene and the like.

When at least one of Ar ¹ , Ar ² , R ¹ to R ⁴ , R′, L ¹ , and L ² is a heterocyclic group, the heterocyclic group is, for example, C ₂ to C ₃₀ , C ₂ to 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 , C ₂₁ , C ₂₂ , C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , C ₂₉ may be a heterocyclic group such as, specifically, pyridine, Pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quina Zoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dynaphthofuran, thiophene, benzothiophene , dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole Sol, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole , benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyan Tren, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc. have.

When at least one of Ar ¹ , Ar ² , R ¹ to R ⁴ , R′ is a fluorenyl group, or at least one of L ¹ , L ² is a fluorenylene group, the fluorenyl group or the fluorenylene group is 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- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene, and the like.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, and neighboring Each of the rings formed by bonding the groups to each other is deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring When at least one of the rings formed by bonding 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 It may be an aryl group such as ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , or C ₁₈ .

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring When at least one of the rings formed by bonding between groups 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 a heterocyclic group.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring When at least one of the rings formed by bonding groups to each other is substituted with a fluorenyl group, the fluorenyl group is 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-11H-benzo[ b ]flu orene , 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, and the like.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring When at least one of the rings formed by bonding with each other is substituted with an alkyl group, the alkyl group is, for example, C ₁ ~C ₂₀ , C ₁ ~ C ₁₀ , C ₁ ~ C ₄ , C ₁ , C ₂ , C ₃ , C It may be an alkylyl group such as ₄ .

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring When at least one of the rings formed by bonding between groups is substituted with an alkenyl group, the alkenyl group is, for example, C ₂ ~ C ₂₀ , C ₂ ~ C ₁₀ , C ₂ ~ C ₄ , C ₂ , C ₃ , C ₄ It may be an alkenyl group, such as.

The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, fluorene group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring When at least one of the rings formed by bonding groups to each other is substituted with an alkoxy group, the alkoxy group is, for example, C ₁ ~C ₂₀ , C ₁ ~C ₁₀ , C ₁ ~ C ₄ , C ₁ , C ₂ , C ₃ , C It may be an alkoxy group such as ₄ .

Formula 1 may be represented by Formula 1-1 or Formula 1-2 below.

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

In Formulas 1-1 and 1-2, X ¹ to X ³ , Y, L ¹ , L ² , R ¹ to R ⁴ , Ar ¹ , Ar ² , a, b are the same as defined in Formula 1. In Formula 1-1, c is an integer of 0 to 3, d is an integer of 0 to 6, in Formula 1-2, c is an integer of 0 to 4, and d is an integer of 5.

In addition, Chemical Formula 1 may be represented by one of Chemical Formulas 1-3 to 1-8 below.

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

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

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

In Formulas 1-3 to Formula 1-8, X ¹ to X ³ , Y, L ¹ , L ² , R ¹ to R ⁴ , Ar ¹ , Ar ² , a to c are the same as defined in Formula 1, d is an integer from 0 to 5;

In the above formula, L ¹ or L ² may be selected from the group consisting of the following formulas b-1 to b-13.

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

<Formula b-4> <Formula b-5> <Formula b-6>

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

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

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

R ¹¹ to R ¹³ are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₂₀ selected from the group consisting of an aliphatic ring group, and adjacent groups may be bonded to each other to form a ring.

a', c', d' and e' are each an integer from 0 to 4, b' is an integer from 0 to 6, f' and g' are each an integer from 0 to 3, h' is an integer from 0 to 2 an integer, and when each of these is an integer of 2 or more, each of R ¹¹ , each of R ¹² , and each of R ¹³ is the same as or different from each other.

Y is NL ₁ -Ar ₁ , O, S or C(R ₁ )(R ₂ ), Z ⁵⁰ to Z ⁵⁴ are independently of each other C, C(R ₃ ) or N, one of which is C and at least One is N.

The Ar ₁ is a C ₆ -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It is selected from the group consisting of an aliphatic cyclic group.

The L ₁ is a single bond; C ₆ -C ₂₀ Arylene group; fluorenylene group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It is selected from the group consisting of an aliphatic cyclic group.

The R _One To R ₃ They are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₂₀ selected from the group consisting of an aliphatic cyclic group, R ₁ and R ₂ may be bonded to each other to form a ring, and adjacent R ₃ may be bonded to each other to form a ring.

Specifically, the compound represented by 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 material layer formed between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.

The organic material 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, and preferably, the compound is included in the light emitting layer.

The organic material 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 generating layer formed between the two or more stacks.

In another aspect of the present invention, there is provided an electronic device including a display device including the organic electric device represented by Formula 1, and a control unit for driving the display device.

Hereinafter, examples of the synthesis of the compound represented by Formula 1 and the preparation of an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[ Synthesis example ]

The compound represented by Formula 1 according to the present invention may be synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

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

Synthesis example of Sub 1

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

<Scheme 2>

1. Sub 1-2 Synthesis example

After dissolving Sub 1-2a (50 g, 221.2 mmol) in THF (1106 ml), Sub 1-2b (63.7 g, 176.9 mmol), Pd(PPh ₃ ) ₄ (15.3 g, 13.3 mmol), NaOH (26.5 g, 663.5 mmol) and water (553 ml) are added and reacted at 80°C. When the reaction is completed, extraction is performed with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 59.7 g of a product. (Yield: 63.7%)

2. Sub 1-8 Synthesis example

After dissolving Sub 1-8a (50.0 g, 181.1 mmol) in THF (905 ml), Sub 1-8b (49.9 g, 144.9 mmol), Pd(PPh ₃ ) ₄ (12.6 g, 10.9 mmol), NaOH (21.7) g, 543.2 mmol) and water (453 ml) were added, and the same procedure as in Sub 1-2 above was followed to obtain 53.5 g of the product. (Yield: 64.5%)

3. Sub 1-35 Synthesis example

After dissolving Sub 1-35a (50.0 g, 181.1 mmol) in THF (905 ml), Sub 1-35b (68.1 g, 144.9 mmol), Pd(PPh ₃ ) ₄ (12.6 g, 10.9 mmol), NaOH (21.7) g, 543.2 mmol) and water (453 ml) were added, and 64.7 g of the product was obtained in the same manner as in Sub 1-2. (Yield: 61.2%)

4. Sub 1-42 Synthesis example

After dissolving Sub 1-42a (50.0 g, 158.2 mmol) in THF (791 ml), Sub 1-42b (43.6 g, 126.5 mmol), Pd(PPh ₃ ) ₄ (11.0 g, 9.5 mmol), NaOH (19.0) g, 474.5 mmol) and water (395 ml) were added, and 46.3 g of the product was obtained in the same manner as in Sub 1-2. (Yield: 58.8%)

The compounds belonging to Sub 1 are the same as, but not limited to, the following compounds, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1.

[Table 1]

Sub 2's Synthesis example

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

<Scheme 3>

1. Sub 2-2 Synthesis example

After dissolving Sub 1-42a (50.0 g, 158.2 mmol) in THF (791 ml), Sub 1-42b (43.6 g, 126.5 mmol), Pd(PPh ₃ ) ₄ (11.0 g, 9.5 mmol), NaOH (19.0) g, 474.5 mmol) and water (395 ml) are added and reacted at 80°C. When the reaction is completed, extraction is performed with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 46.3 g of a product. (Yield: 58.8%)

2. Sub 2-19 Synthesis example

(1) Synthesis of Sub 2-19b

2-iodo-1,1'-biphenyl (50.0 g, 178.5 mmol) was dissolved in THF (300 mL) under a nitrogen atmosphere, and then cooled to -78°C. Then, n -BuLi (71 mL) is slowly titrated and the mixture is stirred for 30 minutes. After dissolving Sub 2-19a (35.5 g, 178.5 mmol) in THF (300 mL) and slowly titrating the mixture, the mixture was stirred at -78°C for 1 hour, and then the temperature was slowly raised to room temperature. When the reaction was completed, the organic layer was extracted with ethyl acetate and water, dried over MgSO ₄ , and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 50.7 g of a product. (Yield: 80.4%)

(2) Synthesis of Sub 2-19c

Sub 2-19b (50.7 g, 143.5 mmol), acetic acid (359 mL) and HCl (57 mL) were placed in a round-bottom flask and stirred at 60-80°C under nitrogen atmosphere for 3 hours. When the reaction is completed, extraction is performed with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 42.1 g (yield 87.6%) of the product.

(3) Synthesis of Sub 2-19

Sub 2-19c (42.1 g, 125.6 mmol) was dissolved in DMF (628 mL), bis(pinacolato)diboron (35.1 g, 138.1 mmol), KOAc (37.0 g, 376.7 mmol), PdCl ₂ (dppf) (2.8 g, 3.8 mmol) was added, and 34.1 g of the product was obtained in the same manner as in Sub 2-2. (Yield: 71.1%)

3. Sub 2-20 Synthesis example

(1) Synthesis of Sub 2-20b

Using 2-iodo-1,1'-biphenyl (50.0 g, 178.5 mmol) and Sub 2-20a (35.7 g, 178.5 mmol), 50.7 g of the product was obtained in the same manner as in the synthesis of Sub 2-19b. (Yield: 80.4%)

(2) Synthesis of Sub 2-20c

Using Sub 2-20b (49.0 g, 138.3 mmol), acetic acid (346 mL) and HCl (55 mL), the same procedure was followed for the synthesis of Sub 2-19c to obtain 39.1 g of a product. (Yield: 84.1%)

(3) Synthesis of Sub 2-20

Sub 2-20c (39.1 g, 116.3 mmol) was dissolved in DMF (581 mL), bis(pinacolato)diboron (32.5 g, 127.9 mmol), KOAc (34.2 g, 348.9 mmol), PdCl ₂ (dppf) (2.6 g, 3.5 mmol) was added, and 37.0 g of the product was obtained in the same manner as in the synthesis method of Sub 2-2. (Yield: 71.5%)

4. Sub 2-32 Synthesis example

(1) Synthesis of Sub 2-32b

Using 2-iodo-1,1'-biphenyl (50.0 g, 178.5 mmol) and Sub 2-32a (54.5 g, 178.5 mmol), the same procedure was followed for the synthesis of Sub 2-19b to obtain 56.5 g of the product. (Yield: 68.9%)

(2) Synthesis of Sub 2-32c

Sub 2-32b (56.5 g, 123.0 mmol), acetic acid (307 mL) and HCl (49 mL) were used in the same manner as in the synthesis method of Sub 2-19c to obtain 49.4 g of a product. (Yield: 79.8%)

(3) Synthesis of Sub 2-32

Sub 2-32c (98.1 g, 98.1 mmol) was dissolved in DMF (491 mL), bis(pinacolato)diboron (27.4 g, 107.9 mmol), KOAc (28.9 g, 294.4 mmol), PdCl ₂ (dppf) (2.2 g, 2.9 mmol) was added, and 38.0 g of the product was obtained in the same manner as in the synthesis method of Sub 2-2. (Yield: 70.3%)

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

[Table 2]

of the final compound Synthesis example

1. P-2 Synthesis example

After dissolving Sub 1-2 (20.0 g, 47.2 mmol) in THF (236 ml), Sub 2-2 (21.0 g, 47.2 mmol), Pd(PPh ₃ ) ₄ (3.3 g, 2.8 mmol), NaOH (5.7 g, 141.5 mmol) and water (118 ml) are added and reacted at 80°C. When the reaction is completed, extraction is performed with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 26.5 g of the product. (Yield: 79.6%)

2. P-8 Synthesis example

After dissolving Sub 1-8 (20.0 g, 43.7 mmol) in THF (218 ml), Sub 2-1 (19.4 g, 43.7 mmol), Pd(PPh ₃ ) ₄ (3.0 g, 2.6 mmol), NaOH (5.2 g, 131.0 mmol) and water (109 ml) were added, and the same procedure was followed for the synthesis of P-2 to obtain 25.8 g of the product. (Yield: 79.9%)

3. P-38 Synthesis example

After dissolving Sub 1-35 (20.0 g, 34.2 mmol) in THF (171 ml), Sub 2-19 (13.1 g, 34.2 mmol), Pd(PPh ₃ ) ₄ (2.4 g, 2.1 mmol), NaOH (4.1 g, 102.7 mmol) and water (86 ml) were added, and the same procedure was followed for the synthesis of P-2 to obtain 21.6 g of the product. (Yield: 78.6%)

4. P-39 Synthesis example

After dissolving Sub 1-32 (20.0 g, 47.3 mmol) in THF (236 ml), Sub 2-20 (21.1 g, 47.3 mmol), Pd(PPh ₃ ) ₄ (3.3 g, 2.8 mmol), NaOH (5.7 g, 141.9 mmol) and water (118 ml) were added, and the same procedure was followed for the synthesis of P-2 to obtain 26.2 g of the product. (Yield: 78.5%)

5. P-44 Synthesis example

After dissolving Sub 1-42 (20.0 g, 40.2 mmol) in THF (201 ml), Sub 2-24 (18.4 g, 40.2 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (4.8 g, 120.5 mmol) and water (100 ml) were added, and the same procedure was followed for the synthesis of P-2 to obtain 24.9 g of the product. (Yield: 78.1%)

6. P-59 Synthesis example

After dissolving Sub 1-52 (20.0 g, 42.2 mmol) in THF (211 ml), Sub 2-32 (23.2 g, 42.2 mmol), Pd(PPh ₃ ) ₄ (2.9 g, 2.5 mmol), NaOH (5.1 g, 126.6 mmol) and water (105 ml) were added, and the same procedure was followed for the synthesis of P-2 to obtain 28.3 g of the product. (Yield: 77.9%)

FD-MS values of compounds P-1 to P-80 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[ Example One] Red organic electroluminescent device (Phosphor Host)

4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a 60 nm-thick hole injection layer Then, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was A hole transport layer having a thickness of 60 nm was formed by vacuum deposition.

Next, using the compound P-2 of the present invention as a host and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as (piq) ₂ Ir(acac)) as a dopant, the host and the dopant A light emitting layer with a thickness of 30 nm was formed on the hole transport layer by doping with a dopant in a 95:5 weight ratio.

Next, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited on the light emitting layer to have a thickness of 10 nm. A hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq ₃ ) was vacuum-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 form an electron injection layer having a thickness of 0.2 nm, and then Al was deposited to form a cathode having a thickness of 150 nm.

[ Example 2] to [ Example 15]

An organic electroluminescent device was always prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-2 as the host material of the light emitting layer.

[ comparative example 1] to [ comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following comparative compounds A to C was used instead of the compound P-2 of the present invention as a host material for the light emitting layer.

<Comparative compound A> <Comparative compound B> <Comparative compound C>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 15 and Comparative Examples 1 to 3 of the present invention, the electroluminescence (EL) characteristics were obtained with PR-650 of Photoresearch. It was measured, and the T95 lifespan was measured using the life measuring equipment of McScience at 2500cd/m ² standard luminance. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results in Table 4, when the compound of the present invention was used as a host material, the driving voltage, luminous efficiency and lifespan of the organic electroluminescent device were improved compared to Comparative Examples using Comparative Compounds A to C.

Comparative compounds A and C are similar to the present invention in that they have a skeleton similar to the compound of the present invention and a triazine moiety is substituted at the 9th position of fluorene via a linker (phenyl), but in Formula 1- There is a difference in the fusion form of naphthobenzofuran or naphthobenzothiophene corresponding to A. That is, in the case of Formula 1-A of the compound of the present invention, benzene is fused to the (1, 2) position of dibenzothiophene or dibenzofuran moiety, whereas Comparative Compound A is (3) of dibenzothiophene , Benzene is fused at position 4), and Comparative Compound C has benzene fused at position (2, 3) of dibenzofuran.

Comparative Compound B is the same as in the present invention in that, in the case of a naphthobenzofuran moiety corresponding to Formula 1-A of the present invention, benzene is fused to the (1,2) positions of dibenzofuran, but a fluorenyl group The substitution positions of the substituted triazine moieties are different.

Comparative Compounds A to C have a skeleton similar to that of the compound of the present invention, but the characteristics of the device vary depending on the fusion form of naphthobenzofuran or naphthobenzothiophene and the position at which the azine moiety is bonded to the fluorenyl group. change can be seen. Even if it is a compound having a similar skeleton, hole characteristics, light efficiency characteristics, energy levels (HOMO, LUMO), hole injection and migration characteristics, hole and electron balance, etc. may vary depending on the type and substitution position of the substituent, etc. This suggests that the compound is more suitable for the red phosphorescent host than the comparative compound.

The above description is merely illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to limit the present invention, and the scope of the present invention is not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (11)

A compound represented by the following formula (1):
<Formula 1><Formula1-A>

In Formula 1,
A is Formula 1-A,
X ¹ to X ³ are each independently N or C(R′), provided that at least one of X ¹ to X ³ is N,
Y is O or S;
Ar ¹ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ It is selected from the group consisting of an aryloxy group,
L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ It is selected from the group consisting of an aliphatic cyclic group,
Ar ² , R ¹ to R ⁴ , and R′ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; And C ₆ ~ C ₃₀ selected from the group consisting of an aryloxy group, one of R ³ and R ⁴ is combined with L ² ,
Adjacent R ¹ or neighboring R ² may be bonded to each other to form a ring, and neighboring Ar ² and R' may be bonded to each other to form a ring,
a, b and c are each an integer of 0-4, d is an integer of 0-6, and when each of these is an integer of 2 or more, each of R ¹ , each of R ² , each of R ³ , and each of R ⁴ are the same or different,
The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group. The method of claim 1,
Formula 1 is a compound, characterized in that represented by Formula 1-1 or Formula 1-2:
<Formula 1-1><Formula1-2>

In Formulas 1-1 and 1-2, X ¹ to X ³ , Y, L ¹ , L ² , R ¹ to R ⁴ , Ar ¹ , Ar ² , a, b are the same as defined in claim 1 . And, in Formula 1-1, c is an integer of 0 to 3, d is an integer of 0 to 6, in Formula 1-2, c is an integer of 0 to 4, and d is an integer of 5. The method of claim 1,
L ¹ or L ² is a compound characterized in that it is selected from the group consisting of the following formulas b-1 to b-13:
<Formula b-1><Formulab-2><Formulab-3>

<Formula b-4><Formulab-5><Formulab-6>

<Formula b-7><Formulab-8><Formulab-9><Formulab-10>

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

In Formulas b-1 to b-13,
R ¹¹ to R ¹³ are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₂₀ selected from the group consisting of an aliphatic cyclic group, and adjacent groups may combine with each other to form a ring,
a', c', d' and e' are each an integer from 0 to 4, b' is an integer from 0 to 6, f' and g' are each an integer from 0 to 3, h' is an integer from 0 to 2 an integer, and when each of these is an integer of 2 or more, each of R ¹¹ , each of R ¹² , and each of R ¹³ are the same as or different from each other,
Y is NL ₁ -Ar ₁ , O, S or C(R ₁ )(R ₂ ),
Z ⁵⁰ to Z ⁵⁴ are each independently C, C(R ₃ ) or N, one of them is C and at least one is N,
The Ar ₁ is a C ₆ -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It is selected from the group consisting of an aliphatic cyclic group,
The L ₁ is a single bond; C ₆ -C ₂₀ Arylene group; fluorenylene group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It is selected from the group consisting of an aliphatic cyclic group,
The R _One To R ₃ They are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ Arylthio group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C ₃ -C ₂₀ selected from the group consisting of an aliphatic cyclic group, R ₁ and R ₂ may be bonded to each other to form a ring, and adjacent R ₃ may be bonded to each other to form a ring. The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:

. An organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising a compound represented by the formula (1) of claim 1. 6. The method of claim 5,
The organic material layer is an organic electric device comprising 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. 6. The method of claim 5,
The compound is an organic electric device, characterized in that contained in the light emitting layer. 6. The method of claim 5,
The organic material layer comprises at least two stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 9. The method of claim 8,
The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 5; and
An electronic device comprising a; a control unit for driving the display device. 11. The method of claim 10,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, an electronic device, characterized in that selected from the group consisting of a single color lighting device and a quantum dot display device.

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