KR102344800B1 - 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 device comprising a compound represented by 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 thereof. 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 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 shifts 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 decreased 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, and thus, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for a portable display having a limited power supply such as a battery, and efficiency and lifespan problems are also important factors that must 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 by simply improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

In addition, recently, in order to solve the problem of light emission in the hole transport layer in organic electroluminescent devices, a method of using a light emitting auxiliary layer between the hole transport layer and the light emitting layer is being studied. Since the material properties are different, it is necessary to develop a light emitting auxiliary layer according to each light emitting layer.

In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.

However, since the material used for the hole transport layer should have a low HOMO value, most have a low T ₁ value. As a result, excitons generated in the light emitting layer are passed to the hole transport layer interface or the hole transport layer. As a result, the hole transport layer It causes light emission at the interface or charge unbalance in the light emitting layer to emit light at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened. Therefore, it should be a material having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, have a high T1 value, and within an appropriate driving voltage range (within the blue device driving voltage range of a full device) hole mobility (hole The development of a light emitting auxiliary layer having mobility) is urgently required.

However, this cannot be achieved simply with the structural characteristics of the core of the light-emitting auxiliary layer material, and the characteristics of the core and sub-substituents of the light-emitting auxiliary layer material, and an appropriate combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer are achieved. It is possible to realize high-efficiency and long-lived devices.

Meanwhile, development of materials for the light emitting layer and the light emitting auxiliary layer having stable characteristics against Joule heating generated during device driving, that is, a high glass transition temperature, is also required. The low glass transition temperature of the light emitting layer and the light emitting auxiliary layer material lowers the uniformity of the thin film surface when driving the device, and the material may be deformed due to the heat generated during device driving, which is reported to have a great influence on the device lifespan.

Therefore, it is necessary to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance, and in order to fully exhibit the excellent characteristics of an organic electric device, a material constituting an organic layer in the device, such as a hole injection material, a hole transport material, and light emission Materials, electron transport materials, electron injection materials, light emitting auxiliary layer materials, etc. should be supported by stable and efficient materials in advance. In particular, development of materials used for light emission auxiliary layers and light emitting layers 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, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan of the device can be greatly improved.

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
4 shows a chemical formula according to an aspect of 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 terms "fluorenyl group", "fluorenylene group", and "fluorentriyl group" refer to monovalent, 2 It refers to a valent or trivalent functional group, and "a substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorentriyl group" means that at least one of the substituents R, R', R" is other than hydrogen. It means that it is a substituent, and includes cases in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In the present specification, the fluorenyl group, fluorenylene group, and fluorentriyl group may all be referred to as fluorene groups regardless of the valence.

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 at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.

As used herein, the term "heterocyclic group" refers to a ring containing a heteroatom such as N, O, S, P or Si instead of carbon forming the ring, and "heteroaryl group" or "heteroarylene group" It includes not only an aromatic ring, but also a non-aromatic ring, such as SO ₂ , P=O, etc. instead of carbon forming a ring, such as the following compound, a compound including a heteroatom group may also be included.

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 neighbors It means a case where one group is 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 elements from other elements, and the essence, order, or order of the elements are not limited by the terms. 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 also 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 a multilayer stack structure method as shown in FIG. 3, an organic electroluminescent device that emits white light by the mixing effect of 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 the light efficiency improvement layer 180 may be used as a material, preferably, the light emitting auxiliary layer 220, the light emitting layer (140, 340, 440) ) and/or may be used as a material of the light efficiency improving layer 180 .

A study on the selection of a core and a combination of sub-substituents bonded thereto because the band gap, electrical properties, and interfacial properties, etc. may vary depending on which position and which substituent is bonded even for the same and similar core In particular, 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, long lifespan and high efficiency can be achieved at the same time.

Therefore, in the present invention, by using the compound represented by Formula 1 as a material for the light emitting auxiliary layer 220 , the light emitting layers 140 , 340 , 440 and/or the light efficiency improving layer 180 , the energy level between each organic material layer and T ₁ It is possible to simultaneously improve the lifespan and efficiency of organic electric devices by optimizing values and intrinsic properties of materials (mobility, interfacial properties, etc.).

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>

In Formula 1, each symbol may be defined as follows.

X is O or S.

R ¹ to R ⁴ 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; C ₆ ~ C ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; -L ¹ -Ar ¹ ; and -L ² -N(Ar ² )(Ar ³ ) selected from the group consisting of, and adjacent groups may be bonded to each other to selectively form a ring. Preferably, R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro 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; C ₆ ~ C ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; -L ¹ -Ar ¹ ; and -L ² -N(Ar ² )(Ar ³ ) selected from the group consisting of, and adjacent groups may be bonded to each other to selectively form a ring.

When adjacent groups are bonded to each other to form an aromatic ring, preferably a C ₆ ~ C ₂₀ aromatic ring, more preferably a C ₆ ~ C ₁₄ aromatic ring, such as benzene, naphthalene, phenanthrene, etc. may be formed. can

a is an integer of 0-3, when a is an integer of 2 or more, ^{each R 1} is the same as or different from each other, b is an integer of 0-4, and when b is an integer of 2 or more, ^{each R 2} is the same as or different from each other, c is an integer of 0-4, when c is an integer of 2 or more, ^{each of R 3} is the same as or different from each other, d is an integer of 0-2, and when d is an integer of 2 or more, ^{each of R 4} is the same as or different from each other.

When R ¹ to R ⁴ are an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, etc. can

When R ^{1 To} R ⁴ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, such as pyridine, pyrimidine, triazine, pyridazine, Quinoline, isoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, benzothienopyrimidine, benzofuropyrimidine, pyridopyrazine, benzothienopyrazine, dibenzothi offene, dibenzofuran, carbazole, phenylcarbazole, and the like.

The L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C ₆₀ It may be selected from the group consisting of a heterocyclic group.

The L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C ₆₀ It may be selected from the group consisting of a heterocyclic group.

When L ¹ and L ² are an arylene group, preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₈ arylene group, for example, phenylene, biphenylene, naphthalene, terphenyl, etc. can

When L ¹ and L ² are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, for example, pyridine, pyrimidine, triazine, quinazoline. , benzoquinazoline, benzothienopyrimidine, benzofuropyrimidine, benzoquinoxaline, pyridopyrazine, benzothienopyrazine, quinoline, carbazole, phenylcarbazole, and the like.

Ar ^{1 To} Ar ^{3 Are} each independently 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; and -L′-N(R _a )(R _b ).

When Ar ^{1 To} Ar ³ is an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, It may be triphenylene or the like.

When Ar ^{1 To} Ar ³ is a fluorenyl group, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, spiro[benzo [b] fluorene -11,9'- fluorene], benzo [b] fluorene, diphenyl-11,11- -11 H - benzo [b] fluorene, 9- (naphthalen-2-yl) 9 phenyl -9 H - may be a fluorene.

When Ar ^{1 To} Ar ³ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, such as pyridine, pyrazine, triazine, dibenzothiophene , quinoxaline, benzothienopyrimidine, dibenzofuran, benzonaphthothiophene, benzonaphthofuran, carbazole, phenylcarbazole, and the like.

The L' 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; C ₃ ~ C ₆₀ An aliphatic group; And it may be selected from the group consisting of combinations thereof.

When L' is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₈ arylene group, for example, phenylene, biphenylene, naphthalene, terphenyl, and the like.

The R _a and R _b are each independently 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; And selected from the group consisting of combinations thereof,

When R _a and R _b are aryl groups, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, phenanthrene , and triphenylene.

When R _a and R _b are fluorenyl groups, they may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirofluorene, or the like.

The R ¹ to R ⁴ , Ar ¹ to Ar ³ , L ¹ , L ² , and a ring formed by bonding adjacent groups to each other are deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; 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; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; And it may be further substituted with one or more substituents selected from the group consisting of a _{C 8} -C _{20 arylalkenyl group.}

Preferably, the R ¹ to R ⁴ at least one of the -L ¹ -Ar ¹ may il, R ¹ to R ⁴ is one or -L ¹ -Ar to the case where ¹ is the general formula (1) in the formula 1-1 to 1-4.

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

In Formulas 1-1 to 1-4, R ¹ to R ⁴ , a to d, X, L ¹ and Ar ¹ are the same as defined in Formula 1 above.

Also, preferably, at least one of ^{R 1} to R ^{4 may be -L 2} -N(Ar ² )(Ar ³ ), and one of ^{R 1} to R ^{4 is -L 2} -N(Ar ² ) In the ^{case of (Ar 3} ), Chemical Formula 1 may be represented by the following Chemical Formulas 1-5 to 1-8.

<Formula 1-5> <Formula 1-6> <Formula 1-7> <Formula 1-8>

In Formulas 1-5 to Formula 1-8, R ¹ to R ⁴ , a to d, X, L ² , Ar ² and Ar ³ are the same as defined in Formula 1 above.

Preferably, Ar ¹ may include a compound represented by Formula 2 or Formula 3 below, and more preferably, Ar ¹ may be represented by Formula 2 or Formula 3 below.

<Formula 2> <Formula 3>

In Chemical Formulas 2 and 3, each symbol may be defined as follows.

Z ¹ to Z ⁸ are each independently N or C(R ₁ ), ^{at least one of Z 1} to Z ⁵ is N, and at least one of Z ⁶ to Z ⁸ is N.

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

C ring is C ₆ ~ C ₆₀ aromatic ring group; Or O, N, S, Si and P containing at least one heteroatom C ₂ ~ C _{60 It} is a heterocyclic group. Ring C may be further substituted with one or more of the same or different R _{1 .}

wherein R ₁ is 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;} siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy 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; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group selected from the group consisting of two groups, and adjacent groups may be bonded to each other to form a ring.

Preferably, Formula 3 includes a compound represented by one of Formulas 3-1 to 3-6, and more preferably, Formula 3 may be represented by one of Formulas 3-1 to 3-6 have.

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

<Formula 3-4> <Formula 3-5> <Formula 3-6>

In Formulas 3-1 to 3-6, Z ⁶ to Z ⁸ , R ₁ , and L ₁ are the same as defined in Formula 3, o is an integer of 0-4, p is an integer of 0-6, q is an integer from 0 to 8, and when each of these is an integer of 2 or more, _{each of R 1} is the same as or different from each other, X ¹ and X ² are each independently O or S, e and f are each an integer of 0 or 1, At least one of e and f is 1.

Preferably ^{, at least one of Ar 2} and Ar ³ may include a compound represented by Formula 4 below, and more preferably ^{, at least one of Ar 2} and Ar ³ may be represented by Formula 4 below.

<Formula 4>

In Formula 4, each symbol may be defined as follows.

Y is O, S, N(R ₄ ) or C(R′)(R″).

R ₂ , R ₃ , R′ and R″ are each independently hydrogen; deuterium; halogen; a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group unsubstituted or substituted silane group; siloxane group; boron group ; germanium group; a cyano group; a nitro group; a C ₁ -C ₂₀ come alkylthio; C ₁ -C ₂₀ alkoxy group; Im coming aryl of C ₆ -C _20;; C ₆ -C ₂₀ aryloxy 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; O, N, S, Si and P _{C 2} -C ₂₀ heterocyclic group comprising at least one heteroatom selected from; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group It is selected from the group consisting of two, and adjacent groups may combine with each other to form a ring, and R' and R" may combine with each other to form a ring.

wherein R ₄ 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 may be selected from the group consisting of an aliphatic cyclic group.

i is an integer of 0-4, and when i is an integer of 2 or more, _{each R 2} is the same as or different from each other, j is an integer of 0-3, and when j is an integer of 2 or more, _{each of R 3} is the same as or different from each other.

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 comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer is a single compound or two or more types represented by Formula 1 including compounds.

In another aspect of the present invention, the present invention provides an organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improving layer. In this case, the light efficiency improving layer is formed on one side not in contact with the organic material layer among both surfaces of the anode or the cathode, and the organic material layer or the light efficiency improving 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 may be included in the light emission auxiliary 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, a synthesis example of the compound represented by Formula 1 according to the present invention and a manufacturing example of an organic electric device 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 (final products) is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

I. Synthesis example of Sub 1

Sub1 of Scheme 1 may be synthesized by the reaction route of Schemes 2-1 to 2-4, but is not limited thereto.

<Reaction Scheme 2-1>

<Reaction Scheme 2-2>

<Reaction Scheme 2-3>

<Reaction Scheme 2-4>

One. Sub1 -One Synthesis example

(1) Sub1-1b synthesis

Sub1-1a (40 g, 0.15 mol), 2-chloroaniline (19.4 g, 0.15 mol), Pd ₂ (dba) ₃ (4.2 g, 0.005 mol), 50% P( t- Bu) ₃ (3.7 g, 0.009) mol), NaO t -Bu (44 g, 0.46 mol) was added to toluene (310 ml) and stirred at 90°C. When the reaction is complete, the temperature of the reactant is cooled to room temperature, toluene is removed, extracted with MC, and washed with water. Thereafter, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated using a silica gel column to obtain 40 g (85%) of a product.

(2) Sub1-1c synthesis

Sub1-1b (40 g, 0.13 mol) to Pd(OAc) ₂ (0.9 g, 0.004 mol), P(t-Bu) ₃ (3.1 g, 0.008 mol), K ₂ CO ₃ (53.5 g, 0.40 mol) , DMA (260 ml) was added and refluxed at 170° C. for 12 hours. When the reaction is complete, the temperature of the reactant is cooled to room temperature, toluene is removed, extracted with MC, and washed with water. Thereafter, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated using a silica gel column to obtain 30 g (85.1%) of a product.

(3) Sub1-1d synthesis

Sub1-1c (30 g, 0.11 mol), 1-bromo-4-chloro-2-iodobenzene (35 g, 0.11 mol), Pd ₂ (dba) ₃ (3 g, 0.003 mol), 50% P( t - Bu) ₃ (2.7 g, 0.006 mol), NaO t -Bu (31.7 g, 0.33 mol), and toluene (220 ml) were carried out in the same manner as in the synthesis of Sub1-1b to obtain 41 g (80.6%) of the product. got it

(4) Sub1-1 synthesis

Sub1-1d (40 g, 0.09 mol), Pd(OAc) ₂ (0.6 g, 0.003 mol), P(t-Bu) ₃ (2.1 g, 0.005 mol), K ₂ CO ₃ (35.8 g, 0.26 mol) , and DMA (180 ml) was used to obtain 27 g (81.8%) of the product in the same manner as in the synthesis of Sub1-1c.

2. Sub1 -6 Synthesis example

(1) Sub1-6b synthesis

Sub1-6a (40 g, 0.15 mol), 2,4-dichloroaniline (24.6 g, 0.15 mol), Pd ₂ (dba) ₃ (4.2 g, 0.005 mol), 50% P( t- Bu) ₃ (3.7 g , 0.009 mol), NaO t -Bu (44 g, 0.46 mol), and toluene (310ml) were carried out in the same manner as in the synthesis method of Sub1-1b to obtain 44 g (84%) of the product.

(2) Sub1-6c synthesis

Sub1-6b (44 g, 0.13 mol), Pd(OAc) ₂ (0.9 g, 0.004 mol), P(t-Bu) ₃ (3.1 g, 0.008 mol), K ₂ CO ₃ (53.5 g, 0.40 mol) , and DMA (260 ml) was used to obtain 34 g (86.4%) of the product in the same manner as in the synthesis of Sub1-1c.

(3) Sub1-6d synthesis

Sub1-6c (34 g, 0.11 mol), 1-bromo-2-iodobenzene (31 g, 0.11 mol), Pd ₂ (dba) ₃ (3 g, 0.003 mol), 50% P( t -Bu) ₃ ( 2.7 g, 0.006 mol), NaO t -Bu (31.7 g, 0.33 mol), and toluene (220 ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 45 g (88.1%) of the product.

(4) Sub1-6 synthesis

Sub1-6d (45 g, 0.10 mol), Pd(OAc) ₂ (0.7 g, 0.003 mol), P(t-Bu) ₃ (2.4 g, 0.006 mol), K ₂ CO ₃ (35.8 g, 0.26 mol) , and DMA (180 ml) was used in the same manner as in the synthesis of Sub1-1c to obtain 32 g (86.2%) of the product.

3. Sub1 -16 Synthesis example

(1) Sub1-16b synthesis

Sub1-16a (48 g, 0.15 mol), 2,4-dichloroaniline (24.6 g, 0.15 mol), Pd ₂ (dba) ₃ (4.2 g, 0.005 mol), 50% P( t- Bu) ₃ (3.7 g , 0.009 mol), NaO t -Bu (44 g, 0.46 mol), and toluene (310 ml) were carried out in the same manner as in the synthesis of Sub1-1b to obtain 45 g (85%) of the product.

(2) Sub1-16c synthesis

Sub1-16b (45 g, 0.13 mol), Pd(OAc) ₂ (0.9 g, 0.004 mol), P(t-Bu) ₃ (3.1 g, 0.008 mol), K ₂ CO ₃ (53.5 g, 0.40 mol) , and DMA (260 ml) was used to obtain 39 g (83.4%) of the product in the same manner as in the synthesis of Sub1-1c.

(3) Sub1-16d synthesis

Sub1-16c (39 g, 0.11 mol), 1-bromo-2-iodobenzene (31 g, 0.11 mol), Pd ₂ (dba) ₃ (3 g, 0.003 mol), 50% P( t -Bu) ₃ ( 2.7 g, 0.006 mol), NaO t -Bu (31.7 g, 0.33 mol), and toluene (220 ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 48 g (85.9%) of the product.

(4) Sub1-16 synthesis

Sub1-16d (48 g, 0.09 mol), Pd(OAc) ₂ (0.6 g, 0.003 mol), P(t-Bu) ₃ (2.3 g, 0.006 mol), K ₂ CO ₃ (38.8 g, 0.28 mol) , and DMA (187 ml) was used to obtain 37 g (91.5%) of the product in the same manner as in the synthesis of Sub1-1c.

4. Sub1 -23 Synthesis example

(1) Sub1-23b synthesis

Sub1-23a (45 g, 0.10 mol), 2,5-dichloroaniline (16.9 g, 0.10 mol), Pd ₂ (dba) ₃ (2.9 g, 0.003 mol), 50% P( t- Bu) ₃ (2.5 g) , 0.006 mol), NaO t -Bu (30 g, 0.31 mol), and toluene (209ml) were carried out in the same manner as in the synthesis of Sub1-1b to obtain 43 g (80.4%) of the product.

(2) Sub1-23c synthesis

Sub1-23b (43 g, 0.08 mol), Pd(OAc) ₂ (0.6 g, 0.003 mol), P(t-Bu) ₃ (2 g, 0.006 mol), K ₂ CO ₃ (34.9 g, 0.25 mol) , DMA (170 ml) was used in the same manner as in the synthesis of Sub1-1c to obtain 33 g (82.6%) of the product.

(3) Sub1-23d synthesis

Sub1-23c (33 g, 0.07 mol), 1-bromo-2-iodobenzene (19.6 g, 0.07 mol), Pd ₂ (dba) ₃ (1.9 g, 0.002 mol), 50% P( t -Bu) ₃ ( 1.7 g, 0.004 mol), NaO t -Bu (20 g, 0.21 mol), and toluene (140 ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 40 g (91.4%) of the product.

(4) Sub1-23 synthesis

Sub1-23d (40 g, 0.06 mol), Pd(OAc) ₂ (0.4 g, 0.002 mol), P(t-Bu) ₃ (1.5 g, 0.004 mol), K ₂ CO ₃ (26.3 g, 0.19 mol) , and DMA (127 ml) was used to obtain 30 g (86.1%) of the product in the same manner as in the synthesis of Sub1-1c.

5. Sub1 -30 Synthesis example

(1) Sub1-30b synthesis

Sub1-30a (42 g, 0.15 mol), 2-chloroaniline (18.9 g, 0.15 mol), Pd ₂ (dba) ₃ (4.1 g, 0.005 mol), 50% P( t- Bu) ₃ (3.6 g, 0.009) mol), NaO t -Bu (43 g, 0.45 mol), and toluene (300 ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 40 g (81.7%) of the product.

(2) Sub1-30c synthesis

Sub1-30b (40 g, 0.12 mol), Pd(OAc) ₂ (0.82 g, 0.004 mol), P(t-Bu) ₃ (3 g, 0.007 mol), K ₂ CO ₃ (50 g, 0.37 mol) , and DMA (245 ml) was used to obtain 30 g (84.6%) of the product in the same manner as in the synthesis of Sub1-1c.

(3) Sub1-30d synthesis

Sub1-30c (30 g, 0.10 mol), 1-bromo-2-iodobenzene (29.1 g, 0.10 mol), Pd ₂ (dba) ₃ (2.8 g, 0.003 mol), 50% P( t -Bu) ₃ ( 2.5 g, 0.006 mol), NaO t -Bu (29.7 g, 0.31 mol), and toluene (200ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 37 g (80.5%) of the product.

(4) Sub1-30 synthesis

Sub1-30d (37 g, 0.08 mol), Pd(OAc) ₂ (0.6 g, 0.002 mol), P(t-Bu) ₃ (2 g, 0.005 mol), K ₂ CO ₃ (34.4 g, 0.25 mol) , and DMA (166 ml) was used to obtain 24 g (79.1%) of the product in the same manner as in the synthesis of Sub1-1c.

6. Sub1 -36 Synthesis example

(1) Sub1-36b synthesis

Sub1-36a (48 g, 0.15 mol), 2-chloroaniline (18.9 g, 0.15 mol), Pd ₂ (dba) ₃ (4.1 g, 0.005 mol), 50% P( t- Bu) ₃ (3.6 g, 0.009) mol), NaO t -Bu (43 g, 0.45 mol), and toluene (300 ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 47 g (85.6%) of the product.

(2) Sub1-36c synthesis

Sub1-36b (47 g, 0.13 mol), Pd(OAc) ₂ (0.85 g, 0.004 mol), P(t-Bu) ₃ (3.1 g, 0.008 mol), K ₂ CO ₃ (52 g, 0.38 mol), Using DMA (255 ml), the same method as for the synthesis of Sub1-1c was carried out to obtain 35 g (82.6%) of the product.

(3) Sub1-36d synthesis

Sub1-36c (35 g, 0.10 mol), 2-bromo-4-chloro-1-iodobenzene (33.2 g, 0.10 mol), Pd ₂ (dba) ₃ (2.8 g, 0.003 mol), 50% P( t - Bu) ₃ (2.5 g, 0.006 mol), NaO t -Bu (29.7 g, 0.31 mol), and toluene (210 ml) were used in the same manner as in the synthesis of Sub1-1b to obtain 44 g (80.2%) of the product. got it

(4) Sub1-36 synthesis

Sub1-36d (44 g, 0.08 mol), Pd(OAc) ₂ (0.6 g, 0.002 mol), P(t-Bu) ₃ (2 g, 0.005 mol), K ₂ CO ₃ (34.4 g, 0.25 mol) , and DMA (168 ml) was used to obtain 27 g (72.6%) of the product in the same manner as in the synthesis of Sub1-1c.

The compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.

[Table 1]

II. Exemplary compounds of Sub 2

The compound belonging to Sub 2 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS values of the following compounds.

[Table 2]

Ⅲ. of the final compound Synthesis example

1. P-3 Synthesis

Sub1-5 (10 g, 0.03 mol) to Sub2-12 (9.4 g, 0.03 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.001 mol), NaOH (3.1 g, 0.08 mol), THF (52 mL), It was added to water (15mL) and reacted for 6 hours. After completion of the reaction, the temperature of the reactant was cooled to room temperature, THF and H ₂ O were removed, and the mixture was extracted with MC and washed with water. Thereafter, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated by a silica gel column and recrystallized to obtain 12 g (79.2%) of the product.

2. Synthesis of P-20

Sub1-7 (10 g, 0.03 mol), Sub2-24 (10.7 g, 0.03 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.001 mol), NaOH (3.1 g, 0.08 mol), THF (52mL), 14 g (85.2%) of the product was obtained by proceeding in the same manner as in the synthesis of P-3 using water (15 mL).

3. Synthesis of P-22

Sub1-26 (20 g, 0.05 mol), Sub2-17 (20.6 g, 0.05 mol), Pd(PPh ₃ ) ₄ (1.8 g, 0.002 mol), NaOH (6 g, 0.16 mol), THF (110 mL), 28 g (88.2%) of the product was obtained by proceeding in the same manner as in the synthesis of P-3 using water (35 mL).

4. P-33 Synthesis Example

Sub1-3 (10 g, 0.03 mol), Sub2-26 (8.7 g, 0.03 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol), NaOH (3.1 g, 0.08 mol), THF (60 mL), 9 g (62.2%) of the product was obtained by proceeding in the same manner as in the synthesis of P-3 using water (20 mL).

5. P-44 Synthesis Example

Sub1-6 (15 g, 0.04 mol), Sub2-43 (14.5 g, 0.04 mol), Pd(PPh ₃ ) ₄ (1.4 g, 0.002 mol), NaOH (4.7 g, 0.12 mol), THF (80 mL), 19 g (82.1%) of the product was obtained by proceeding in the same manner as in the synthesis of P-3 using water (23 mL).

6. P-56 Synthesis Example

Sub1-7 (30 g, 0.08 mol) to Sub2-54 (25.3 g, 0.08 mol), Pd ₂ (dba) ₃ (2.1 g, 0.002 mol), 50% P( t- Bu) ₃ (1.9 g, 0.004) mol), NaO t -Bu (23.4 g, 0.24 mol), and toluene (160ml) were added and stirred at 90°C. After the reaction was completed, the temperature of the reactant was cooled to room temperature, toluene was removed, extracted with MC, and the organic layer was concentrated. Then, the resulting organic material was separated by a silica gel column and recrystallized to obtain 45 g (85.7%) of the product.

7. P-81 Synthesis example

Sub1-6 (30 g, 0.08 mol) to Sub2-80 (22 g, 0.08 mol), Pd(PPh ₃ ) ₄ (2.7 g, 0.002 mol), NaOH (9.4 g, 0.24 mol), THF (160 mL), Water (40 mL) was used to proceed in the same manner as in the synthesis of P-3 to obtain 30 g (76.4%) of the product.

FD-MS values of compounds P-1 to P-90 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

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

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

Then, on the hole transport layer, compound P-3 of the present invention as a host material and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter _{abbreviated as “(piq) 2} Ir(acac)”) as a dopant A light emitting layer having a thickness of 30 nm was deposited by doping with a dopant such that the weight ratio was 95:5.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter _{abbreviated as Alq 3} ) was deposited on the hole blocking layer to a thickness of 40 nm 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 32]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 was used instead of the compound P-3 of the present invention as a host material.

[ comparative example 1] and [ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A or comparative compound B was used as a host material.

<Comparative compound A> <Comparative compound B>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 32, Comparative Examples 1 and 2 of the present invention, electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch. and 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 of Table 4, when the compound of the present invention is used as the light emitting layer material, the driving voltage is lowered and the efficiency and lifespan are lower than when the comparative compound A or the comparative compound B is used (Comparative Examples 1-2). It can be seen that there is a significant improvement.

That is, when Comparative Compound B having a similar basic skeleton to Chemical Formula 1 of the present invention is used as a host material (Comparative Example 2), the driving voltage, efficiency, lifespan, etc. are higher than when Comparative Compound A is used as a host material (Comparative Example 1). All were improved, and compared to Comparative Example 2, when the compound of the present invention was used as a host material, the driving voltage, efficiency, and lifespan were all significantly improved.

More specifically, the compound of the present invention has a higher refractive index and a higher Tg value than the comparative compound by including a heteroatom such as S or O in the ring of formula 1, and has a LUMO level with maximized energy transfer effect. do. As a result, the luminous efficiency is greatly improved and the lifetime is also significantly improved due to the high thermal stability.

In addition, the compound of the present invention containing the element S or O has increased planarity compared to the comparative compound B containing the element N, and as a result, the packing density is improved and the device performance is improved. .

These results show that even with a similar compound, the energy level or thin film characteristics of the compound are significantly different depending on the type of hetero element or specific substituent, and such a difference is a major factor in device performance improvement during device deposition (eg energy balance, stability, etc.) , suggesting that the device results may vary.

[ Example 33] Red organic electroluminescent device ( light emitting layer )

After vacuum deposition of the 2-TNATA film on the ITO layer (anode) formed on the glass substrate to form a hole injection layer to a thickness of 60 nm, the NPB was vacuum evaporated to form a hole transport layer having a thickness of 60 nm. Then, the compound P-44 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.

Then, on the light emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") as a host material and (piq) ₂ Ir(acac) as a dopant material were used, but these A light emitting layer having a thickness of 30 nm was formed by doping with a dopant so that the weight ratio was 95:5.

Next, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was formed on the hole blocking layer to a thickness of 40 nm 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 34] to [ Example 57 ]

An organic electroluminescent device was manufactured in the same manner as in Example 33, except that the compound of the present invention shown in Table 5 was used instead of the compound P-44 of the present invention as a light emitting auxiliary layer material.

[Comparative Example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 33, except that the light-emitting auxiliary layer was not formed.

[Comparative Example 4] and [Comparative Example 5]

An organic electroluminescent device was manufactured in the same manner as in Example 33, except that the following comparative compound C or comparative compound D was used instead of the compound P-44 of the present invention as a light emitting auxiliary layer material.

<Comparative compound C> <Comparative compound D>

By applying a forward bias DC voltage to the organic electric devices manufactured by Examples 33 to 57 and Comparative Examples 3 to 5 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 of a photoresearch company. and T95 lifespan was measured using the life measuring equipment of McScience at 2500cd/m ^{2 standard luminance.} The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results of Table 5, when the compound of the present invention is used as a material for the light-emitting auxiliary layer, the light-emitting auxiliary layer is not formed, or compared to Comparative Examples 3 to 5 using Comparative Compound C or Comparative Compound D, the device is driven It can be seen that the voltage is lowered and the efficiency and lifespan are significantly improved.

Comparing Comparative Examples 3 to 5, the device results were excellent when Comparative Compound C or Comparative Compound D was used (Comparative Examples 4 to 5) rather than when the light emission auxiliary layer was not used (Comparative Example 3). And, compared to Comparative Examples 4 to 5, the device results are better when the compound of the present invention having a structure similar to that of the comparative compound but containing hetero atoms such as S and O in the polycyclic core is used as a light emitting auxiliary layer material. did

Comparing the results of Comparative Example 4, Comparative Example 5, and Examples 33 to 57, the inclusion of S and O in the polycyclic core has a higher refractive index and a higher Tg value than that of a cyclic compound including N, so the luminous efficiency And thermal stability seems to be improved to increase the lifespan. In addition, by using the compound of the present invention as a light emitting auxiliary layer, the HOMO or LUMO energy level of the compound of the present invention has an appropriate value between the hole transport layer and the light emitting layer. ) and light emission occurs inside the light emitting layer rather than the hole transport layer interface, so efficiency and lifespan seem to be maximized.

On the other hand, in the embodiment of the present invention, when a compound containing a substituent of dibenzothiophene or dibenzofuran is used as a light emitting auxiliary layer material, compared to the case where a compound having a simple aryl substituent is used as a light emitting auxiliary layer material, the driving voltage , efficiency, etc. were improved. This is due to a difference in hole mobility in the light emitting auxiliary layer, which is considered to affect overall device characteristics.

In the case of the light-emitting auxiliary layer, it is necessary to understand the relationship between the hole transport layer and the light-emitting layer (host). It will be very difficult.

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 spirit and scope of the present invention are 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 (16)

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

In Formula 1,
X is O or S;
R ¹ to R ⁴ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro 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; C ₆ ~ C ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; -L ¹ -Ar ¹ ; And -L ² -N(Ar ² )(Ar ³ ) is selected from the group consisting of, adjacent groups may be bonded to each other to selectively form a ring, provided that at least one of ^{R 1} to R ^{4 is -L 1} -Ar ¹ or -L ² -N(Ar ² )(Ar ³ ),
a is an integer of 0-3, when a is an integer of 2 or more, ^{each R 1} is the same as or different from each other, b is an integer of 0-4, and when b is an integer of 2 or more, ^{each R 2} is the same as or different from each other, c is an integer of 0-4, when c is an integer of 2 or more, ^{each of R 3} is the same as or different from each other, d is an integer of 0-2, and when d is an integer of 2 or more, ^{each of R 4} is the same as or different from each other, However, except when a, b, c and d are all 0,
The L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
The L ² is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
Ar ^{1 To} Ar ^{3 Are} each independently 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; And -L'-N(R _a ) (R _b ) is selected from the group consisting of,
The L' 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; C ₃ ~ C ₆₀ An aliphatic group; And selected from the group consisting of combinations thereof,
The R _a and R _b are each independently 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; And selected from the group consisting of combinations thereof,
The R ¹ to R ⁴ , Ar ¹ to Ar ³ , L ¹ , L ² , and a ring formed by bonding adjacent groups to each other are deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; 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; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; And it may be further substituted with one or more substituents selected from the group consisting of a _{C 8} -C _{20 arylalkenyl group.} According to claim 1,
At least one of R ¹ to R ⁴ _{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; and -L′-N(R _a )(R _b ). According to claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 1-1 to 1-4:
<Formula 1-1><Formula1-2><Formula1-3><Formula1-4>

In Formulas 1-1 to 1-4, R ¹ to R ⁴ , a to d, X, L ¹ and Ar ¹ are the same as defined in claim 1. According to claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 1-5 to 1-8:
<Formula 1-5><Formula1-6><Formula1-7><Formula1-8>

In Formulas 1-5 to Formula 1-8, R ¹ to R ⁴ , a to d, X, L ² , Ar ² and Ar ³ are the same as defined in claim 1 . According to claim 1,
Wherein Ar ¹ is an organic electric device comprising a compound represented by the following Chemical Formula 2 or Chemical Formula 3:
<Formula 2><Formula3>

In Formula 2 and Formula 3,
Z ¹ to Z ⁸ are each independently N or C(R ₁ ), ^{at least one of Z 1} to Z ⁵ is N, and at least one of Z ⁶ to Z ⁸ is N,
L ₁ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
C ring is C ₆ ~ C ₆₀ aromatic ring group; Or O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group, wherein the C ring may be further substituted with one or more of the same or different R _{1 ,}
wherein R ₁ is 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;} siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy 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; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group selected from the group consisting of two groups, and adjacent groups may be bonded to each other to form a ring. 6. The method of claim 5,
Formula 3 is a compound, characterized in that selected from the group consisting of Formulas 3-1 to 3-6:
<Formula 3-1><Formula3-2><Formula3-3>

<Formula 3-4><Formula3-5><Formula3-6>

In Formulas 3-1 to 3-6, Z ⁶ to Z ⁸ , R ₁ , L _{1 Are} the same as defined in claim 5, o is an integer from 0 to 4, p is an integer from 0 to 6, q is an integer from 0 to 8, and when each of these is an integer of 2 or more, _{each of R 1} is the same as or different from each other, X ¹ and X ² are each independently O or S, e and f are each an integer of 0 or 1, At least one of e and f is 1. The method of claim 1,
At least one of Ar ² and Ar ³ is a compound comprising a compound represented by the following formula (4):
<Formula 4>

In Formula 4,
Y is O, S, N(R ₄ ) or C(R')(R"),
R ₂ , R ₃ , R′ and R″ are each independently hydrogen; deuterium; halogen; a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group unsubstituted or substituted silane group; siloxane group; boron group ; germanium group; a cyano group; a nitro group; a C ₁ -C ₂₀ come alkylthio; C ₁ -C ₂₀ alkoxy group; Im coming aryl of C ₆ -C _20;; C ₆ -C ₂₀ aryloxy 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; O, N, S, Si and P _{C 2} -C ₂₀ heterocyclic group comprising at least one heteroatom selected from; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group It is selected from the group consisting of two, and adjacent groups may combine with each other to form a ring, and R' and R" may combine with each other to form a ring,
wherein R ₄ 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,
i is an integer of 0-4, and when i is an integer of 2 or more, _{each of R 2} is the same as or different from each other,
j is an integer of 0 to 3, and when j is an integer of 2 or more, _{each of R 3} is the same as or different from each other. The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:

. In the organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode,
The organic material layer is an organic electric device comprising a single compound or two or more compounds represented by the formula (1) of claim 1. In the organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improving layer,
The light efficiency improving layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer,
The organic material layer or the light efficiency improving layer is an organic electric device comprising a compound represented by the formula (1) of claim 1. 11. The method of claim 9 or 10,
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. 12. The method of claim 11,
The compound is an organic electric device, characterized in that included in at least one of the light emitting layer and the light emitting auxiliary layer. 11. The method of claim 9 or 10,
The organic material layer is an organic electric device comprising two or more stacks including a hole transport layer, a light emitting layer and an electron transport layer sequentially formed on the anode. 14. The method of claim 13,
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 9 or 10; and
An electronic device comprising a; a control unit for driving the display device. 16. The method of claim 15,
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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