KR20210137977A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric element 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, it is possible to lower driving voltage of the organic electric element, and it is possible to improve luminous efficiency and lifespan of the organic electric element.

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 generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material 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, for example, 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 moves 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 a 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 its size is increasing, and thus, a higher 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 simply by improving the organic material layer. This is because, when the energy level and T1 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.

In addition, recently, in order to solve the problem of light emission in the hole transport layer in the organic electroluminescent device, 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, most of the materials used for the hole transport layer have a low T ₁ value because they should have a low HOMO 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 a suitable 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-life 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 during device driving, and the material may be deformed due to heat generated during device driving, which is reported to have a significant impact on device lifespan.

In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance.

That is, in order to sufficiently exhibit the excellent characteristics of an organic electric device, the material constituting the organic layer in the device, for example, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc. is stable and efficient. It should be supported by materials, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently made. Therefore, the development of new materials is continuously required, and in particular, the development of materials used for the light-emitting auxiliary layer, the light-emitting layer, and the like is urgently 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 is an exemplary view of an organic electroluminescent device according to the present invention.
2 shows a chemical formula according to an embodiment 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, but are not limited thereto. In the present invention, the aryl group or the arylene group includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like. In addition, unless otherwise described herein, the aryl group may include a fluorenyl group, and the arylene group may include a fluorenylene group.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a It includes the case of forming a compound as a spy together.

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 heteroatoms 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, such as the following compound instead of carbon forming a ring, a compound including a heteroatom group may also be included.

The term "aliphatic ring group" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic ring, 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 is 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, and in this case, the indication of hydrogen bonded to carbon is shown. 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 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.

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

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

Also, 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” the other component, but also when there is another component in between. It should be understood that cases may be included. Conversely, it should be understood that when an element is said to be "on top of" another part, it means that there is no other part in the middle.

1 is an exemplary view 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 120 , a second electrode 180 , and a first electrode 120 formed on a substrate 110 , and An organic material layer including the compound according to the present invention is included between the second electrodes 180 . In this case, the first electrode 120 may be an anode (anode), the second electrode 180 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 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, an electron injection layer 170, etc. sequentially stacked on the first electrode 120. . At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It may also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface of both surfaces of the first electrode that does not contact the organic material layer or on a surface of both surfaces of the second electrode that does not contact the organic material layer.

The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), a host or dopant of the light emitting layer 150, or may be used as a material for a light efficiency improving layer, but preferably the compound according to Formula 1 of the present invention is used as a material of the light emitting auxiliary layer and/or as a host of the light emitting layer .

On the other hand, even with the same and similar core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of the sub-substituents coupled thereto 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, a 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 the material of the light-emitting auxiliary layer and/or the host of the light-emitting layer, the energy level and T ₁ value between each organic material layer, the intrinsic properties of the material (mobility, interfacial properties, etc.), etc. It is possible to simultaneously improve the lifespan and efficiency of the organic electric device by optimizing it.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 120, and the hole injection layer 130 thereon. , after forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon. have. In addition, an auxiliary light emitting layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150 , and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160 .

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 the 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.

R ¹ to R ³ are each independently hydrogen; heavy hydrogen; halogen; 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 aliphatic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ); may be selected from the group consisting of, and adjacent groups may be bonded to each other to form a ring.

When R ¹ to R ³ is an aryl group, it may be preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, and the like. When R ¹ to R ³ is an alkyl group, it may be preferably a C ₁ to C ₁₀ alkyl group, for example, methyl, t-butyl, or the like.

a is an integer from 0 to 4, b is an integer from 0 to 5, c is an integer from 0 to 3, and when each of these is an integer of 2 or more, a plurality of R ^{1 ,} each of a plurality of R ² , a plurality of R ³ each is the same as or different from each other.

Adjacent R ¹ , adjacent R ^{2 ,} or adjacent R ³ may be bonded to each other to form a ring. At this time, the ring formed is C ₆ ~ C ₆₀ aromatic hydrocarbons; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic group; and combinations thereof. For example, when adjacent groups are bonded to each other to form aromatic hydrocarbons, preferably C ₆ to C ₃₀ aromatic hydrocarbons, more preferably C ₆ to C ₁₄ aromatic hydrocarbons, such as benzene ring, naphthalene, phenanthrene, etc. and, when adjacent groups are bonded to each other to form a heterocycle, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₂ heterocyclic group, such as pyridine, pyrimidine, Rings such as quinazoline may be formed.

A 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 aliphatic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and N(Ar ¹ )(Ar ² ); may be selected from the group consisting of, n is an integer of 1 to 3, and when n is an integer of 2 or more, a plurality of A may be the same as or different from each other.

Preferably, A is a C ₆ ~ C ₆₀ aryl group; Or O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; may be.

Also, preferably, A may be N(Ar ¹ )(Ar ² ).

When A 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, fluoranthene, phenanthrene, benzophenanthrene and the like.

When A is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₆ heterocyclic group, such as phenylpyrrole, pyrimidine, triazine, quinazoline, benzoquinazoline , isoquinoline, dibenzoquinazoline, pyridopyrimidine, benzothienopyrimidine, benzofuropyrimidine, phenanthrofuropyrimidine, naphthofuropyrimidine, naphthothienopyrimidine, dihydro -Dimethyl-cyclopentanaphthopyrimidine, dibenzothiophene, dibenzofuran, carbazole, phenylcarbazole, benzocarbazole, naphthocarbazole, phenylnaphthocarbazole, naphthalen-yl-carbazole, pyri midoindole, phenylpyrimidoindole, cyanthrene, and the like.

When A is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, or the like.

The Ar ¹ and Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} 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 ).

When Ar ¹ and Ar ² 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, fluoranthene , phenanthrene, anthracene, phenalene, and the like.

When Ar ¹ and Ar ² are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₆ heterocyclic group, such as pyridine, pyrimidine, triazine, carbazole, phenylcarbazole, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, quinazoline, dibenzoquinazoline, benzothienopyrimidine, phenyl-pyridoindole, phenylindole, indole, and the like.

When Ar ¹ and Ar ² are fluorenyl groups, they may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirobifluorene, or the like.

Preferably, Ar ¹ and Ar ² may be -L′-N(R _a )(R _b ).

L and 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 aliphatic group; and combinations thereof.

When L and L' are an arylene group, it is preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₆ arylene group, such as phenylene, naphthalene, biphenyl, pyrene, anthracene, etc. have.

L and L' are preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₂₂ heterocyclic group such as pyridine, pyrimidine, triazine, isoquinoline, quinazoline, dibenzoquina Zoline, benzothienopyrimidine, benzofuropyrimidine, dihydro-dimethyl-cyclopentanaphthopyrimidine, phenanthrofuropyrimidine, naphthofuropyrimidine, naphthothienopyrimidine, phenyl pyrimidoindole, carbazole, phenylcarbazole, benzocarbazole, phenylbenzocarbazole, dibenzothiophene, dibenzofuran, or the like.

When L and L' are fluorenyl groups, they may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, or the like.

The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; is selected from the group consisting of.

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, pyrene, anthracene, etc.;

When R _a and R _b are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₆ heterocyclic group such as pyridine, pyrimidine, triazine, thiophene, Benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, carbazole, phenylcarbazole, benzothienopyrimidine, benzofuropyrimidine, pyridoindole, phenylpyridoindole, quinazoline, benzoquinazoline, benzoxazole, phenoxatin, benzothiazole, and the like.

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

Substituents indicated by each of the above symbols may be further substituted. For example, the R ¹ to R ³ , L, A, Ar ¹ , Ar ² , L′, R _a , R _b and the like are each 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; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy 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; _{a C 6} -C ₂₀ aryl group substituted with deuterium; 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; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof.

Formula 1 may be represented by one of Formulas 2 to 6 below.

<Formula 2> <Formula 3>

<Formula 4>

<Formula 5> <Formula 6>

In the above formula, R ¹ to R ³ , Ar ¹ , Ar ² , L, R _a , R _b , L′, a to c, n, etc. are the same as defined in Formula 1 above.

X is N(Ar ³ ), C(R _c )(R _d ), S or O, Z ¹ to Z ⁴ are independently of each other CH, N or CR′, and Z ¹ to Z ⁴ that binds to L In case CR' to R' is a single bond.

The Ar ³ is a C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic group; and combinations thereof.

Wherein R _c , R _d and R' are each independently deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; boron group; germanium group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy 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; _{a C 6} -C ₂₀ aryl group substituted with deuterium; 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; C ₈ -C ₂₀ arylalkenyl group; and combinations thereof.

Preferably, R _c and R _d may be bonded to each other to form a ring, and adjacent R′ may be bonded to each other to form a ring. When R _c and R _d combine with each other to form a ring, a spiro compound may be formed.

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 a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is represented by Formula 1 It includes one single compound or two or more compounds.

The organic layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound is the light emitting auxiliary layer and/or the light emitting layer. can be included in

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 the 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 (final products) is synthesized by reacting Sub 1 and Sub 2 or Sub 1 and Sub 3 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

1. Examples of Sub 1 and Synthesis example

The compound belonging to Sub 1 of Scheme 1 is as follows, but is not limited thereto.

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

[Table 1]

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

<Scheme 2>

Sub1 -One Synthesis example

(1) Sub1-I-1 synthesis

1-bromo-2-chlorobenzene (35.0 g, 184.2 mol), Cu powder (0.6 g, 9.2 mmol), K ₂ CO ₃ (38 g, 276.2 mol) in 1H-benzo[a]carbazole (20 g, 92.1 mmol) ), 18-Crown-6 (2.5 g, 9.3 mol), and nitrobenzene (184 ml) were added and refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, nitrobenzene was 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 by a silica gel column to obtain 23.1 g (76.5%) of a product.

(2) Sub1 -II-1 synthesis

Sub1-I-1 (25.0 g, 76.3 mol) in Pd(OAc) ₂ (0.5 g, 2.3 mmol), P(t-Bu) ₃ (0.9 g, 4.6 mmol), K ₂ CO ₃ (31.6 g, 228.8) m mol) and DMA (190 ml) were added and refluxed at 170° C. for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated by a silica gel column to obtain 18 g (81.0%) of a product.

(3) Sub1 -1 synthesis

Sub1-II-1 (18.0 g, 61.1 mmol) was dissolved in MC (130 mL), and then Br ₂ (10 g, 0.06 mol) was slowly added dropwise. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated by a silica gel column to obtain 20.0 g (87.0%) of a product.

Sub1 -4 Synthesis example

(1) Sub1-I-4 synthesis

2-bromo-3-chloronaphthalene (45.2 g, 184.2 mol), Cu powder (0.6 g, 9.2 mmol), K ₂ CO ₃ (38 g, 276.2 mol) in 1H-benzo[a]carbazole (20 g, 92.1 mmol) ), 18-Crown-6 (2.5 g, 9.3 mol), and nitrobenzene (184 ml) were added and refluxed for 12 hours, followed by separation in the same manner as in Sub1-I-1 above to obtain 30 g (86.4%) of the product.

(2) Sub1 -II-4 synthesis

Sub1-I-4 (26.0 g, 68.8 mmol) in Pd(OAc) ₂ (0.5 g, 2.1 mmol), P(t-Bu) ₃ (0.8 g, 4.1 mmol), K ₂ CO ₃ (28.5 g, 206.4) mmol), DMA (200 ml) was added and refluxed at 170° C. for 12 hours, followed by separation in the same manner as in Sub1-II-1, to obtain 16.0 g (68.1%) of the product.

(3) Sub1 -4 synthesis

Sub1-II-5 (28.0 g, 82.0 mol) was dissolved in MC (110 mL), Br ₂ (11.8 g, 73.8 mol) was slowly added dropwise, and the product was separated in the same manner as in Sub1-1, 30.0 g (87.0%) ) was obtained.

Sub1 -11 Synthesis example

(1) Sub1-I-2 synthesis

1-bromo-2-chlorobenzene (36.2 g, 189.1 mol), Cu powder (0.6 g, 9.5 mmol), K ₂ CO ₃ (39.2) in 9-bromo-11H-benzo[a]carbazole (28.0 g, 94.5 mmol) g, 283.5 mol), 18-Crown-6 (2.5 g, 9.5 mol), and nitrobenzene (200 ml) were added and refluxed for 12 hours, followed by separation in the same manner as in Sub1-I-1 above, and 31.0 g (80.6%) of the product ) was obtained.

(2) Sub1 -2 synthesis

Sub1-I-2 (28.0 g, 68.8 mmol) in Pd(OAc) ₂ (0.5 g, 2.1 mmol), P(t-Bu) ₃ (0.8 g, 4.1 mmol), K ₂ CO ₃ (28.5 g, 206.5) mmol), DMA (220 ml) was added, refluxed at 170° C. for 12 hours, and separated in the same manner as in Sub1-II-1 to obtain 21.0 g (82.4%).

(3) Sub1 -11 synthesis

Sub1-2 (25.0 g, 67.5 mmol), (4-bromophenyl)boronic acid (16.3 g, 81.0 mmol), Pd(PPh ₃ ) ₄ (2.3 g, 2.0 mmol), K ₂ CO ₃ (28.0 g, 202.6 mmol) ) was dissolved in THF (200ml), water (60ml) was added, and the mixture was stirred at 90°C. When the reaction is completed, the temperature of the reactant is cooled to room temperature, 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 to obtain 23.0 g (yield: 76.3%) of the product.

Sub1 -27 Synthesis example

(1) Sub1-I-27 synthesis

1-bromo-2-chlorobenzene (24.0 g, 125.2 mol) in 7-bromo-N,N-diphenyl-11H-benzo[a]carbazol-4-amine (29.0 g, 62.6 mmol), Cu powder (0.4 g, 6.3 mmol), K ₂ CO ₃ (25.9 g, 187.8 mol), 18-Crown-6 (1.7 g, 6.3 mol), and nitrobenzene (210 ml) were added and refluxed for 12 hours. separation method to obtain 30.0 g (83.5%) of the product.

(2) Sub1 -II-27 synthesis

Sub1-I-27 (29.0 g, 50.5 mmol) in Pd(OAc) ₂ (0.3 g, 1.5 mmol), P(t-Bu) ₃ (0.6 g, 3.0 mmol), K ₂ CO ₃ (20.9 g, 151.6) mmol), DMA (225 ml) was added and refluxed at 170° C. for 12 hours, followed by separation in the same manner as in Sub1-II-1, to obtain 23.0 g (84.7%).

(3) Sub1 -27 Synthesis

Sub1-II-27 (26.0 g, 48.4 mmol), (4-bromophenyl)boronic acid (11.7 g, 58.1 mmol), Pd(PPh ₃ ) ₄ (1.7 g, 1.5 mmol), K ₂ CO ₃ (20.1 g, 145.1 mmol) was dissolved in THF (150ml), water (50ml) was added, and the mixture was stirred at 90°C. Thereafter, the product was separated in the same manner as in Sub1-11 to obtain 16.0 g (74.1%) of the product.

Sub1 -33 Synthesis example

<Scheme 7>

Sub1-3 (27.0 g, 72.9 mmol), (8-bromodibenzo[b,d]furan-2-yl)boronic acid (25.5 g, 87.5 mmol), Pd(PPh ₃ ) ₄ (2.5 g, 2.2 mmol), K ₂ CO ₃ (40 g, 0.4 mol) was added to THF (210 ml) with water (70 ml) and stirred at 90°C. Thereafter, the product was separated in the same manner as in Sub1-11 to obtain 30.0 g (yield: 76.7%) of the product.

Sub1 -38 Synthesis example

<Scheme 8>

Sub1-1 (28.0 g, 75.6 mmol), (3-bromo-5-chlorophenyl)boronic acid (23.0 g, 90.7 mmol), Pd(PPh ₃ ) ₄ (2.6 g, 2.3 mmol), K ₂ CO ₃ (32.3 g, 226.9 mmol) was added to THF (270ml) with water (90ml) and stirred at 90°C. Thereafter, the product was separated in the same manner as in Sub1-11 to obtain 27.0 g (yield: 74.3%) of the product.

Sub1 -49 Synthesis example

<Scheme 9>

(1) Sub1-I-49 synthesis

1-bromo-2-chlorobenzene (45.6 g, 238.4 mmol), Cu powder (0.8 g, 11.9 mmol), K ₂ CO ₃ (49.4) in 10-chloro-11H-benzo[a]carbazole (30.0 g, 111.9 mmol) g, 357.6 mol), 18-Crown-6 (3.2 g, 11.9 mol), and nitrobenzene (210 ml) were added and refluxed for 12 hours, followed by separation in the same manner as in Sub1-I-1, and 33.0 g (76.4%) of the product ) was obtained.

(2) Sub1 -II-49 synthesis

Sub1-I-49 (30.0 g, 82.8 mmol) in Pd(OAc) ₂ (0.6 g, 2.5 mmol), P(t-Bu) ₃ (1.0 g, 5.0 mmol), K ₂ CO ₃ (34.3 g, 248.4) mmol), DMA (280 ml) was added, and refluxed at 170° C. for 12 hours, followed by separation in the same manner as in Sub1-II-1, to obtain 22.0 g (81.5%) of the product.

(3) Sub1 -49 Synthesis

Sub1-II-49 (29.0 g, 89.0 mol) was dissolved in MC (200 mL), and then Br ₂ (12.8 g, 80.1 mmol) was slowly added dropwise. Thereafter, the product was separated in the same manner as in Sub1-1 to obtain 30.0 g (83.2%) of the product.

2. Examples of Sub 2 and Synthesis example

Compounds belonging to Sub 2 of Scheme 1 are as follows, but are not limited thereto.

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

[Table 2]

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

<Scheme 3>

Sub 2-4 Synthesis example

3-bromo-1,1'-biphenyl (51 g, 218.8 mmol) in aniline (30.6 g, 328.2 mmol), Pd ₂ (dba) ₃ (6.0 g, 6.6 mmol), 50% P( t- Bu) ₃ (5.4ml, 13.1 mmol), NaO t -Bu (63.1 g, 656.3 mmol), was added to toluene (500ml) and stirred at 80 ℃. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated by a silica gel filter to obtain 43.0 g of a product (yield: 80.1%).

Sub 2-10 Synthesis example

2-bromonaphthalene (30.0 g, 144.9 mmol) in pyridin-3-amine (20.5 g, 217.3 mmol), Pd ₂ (dba) ₃ (4.0 g, 4.3 mmol), 50% P( t- Bu) ₃ (1.8ml , 8.7 mmol), NaO t -Bu (41.8 g, 434.6 mmol), and toluene (1000 ml) were added and the same method was followed for the synthesis of Sub2-4 to obtain 26 g (yield: 81.1%) of the product.

Sub 2-19 Synthesis example

4-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 (35.7 g, 150.1 mmol) in aniline (21.0 g, 225.1 mmol), Pd ₂ (dba) ₃ (4.1 g, 4.5 mmol), 50% P( t- Bu) ₃ (3.6ml, 9.0 mmol), NaO t- Bu (43.3 g, 450.4 mmol), and toluene (500ml) were added, followed by the above Sub2-4 synthesis method It proceeded in the same way to obtain 25 g (yield: 66.5%) of the product.

Sub 2-46 Synthesis example

9-bromo-7-phenyl-7H-benzo[c]carbazole (42.4 g, 114.0 mmol) in aniline (15.9 g, 171.0 mmol), Pd ₂ (dba) ₃ (3.1 g, 3.4 mmol), 50% P ( t -Bu) ₃ (2.8ml, 6.8 mmol), NaO t -Bu (32.9 g, 342.0 mmol), and toluene (400ml) were added and proceeded in the same manner as in the above Sub2-4 synthesis method, resulting in 22 g of product (yield: 70.1 %) was obtained.

Sub 2-51 Synthesis example

[1,1'-biphenyl]-4-amine (6.7 g, 212.5 mmol) in 3-bromodibenzo[b,d]furan (35.0 g, 141.6 mmol), Pd ₂ (dba) ₃ (3.9 g, 4.2 mmol) , 50% P( t -Bu) ₃ (3.9ml, 8.5 mmol), NaO t -Bu (40.9 g, 424.9 mmol), and toluene (515ml) were added and proceeded in the same manner as in the synthesis method of Sub2-4 above to proceed with the product 31 g (yield: 65.2%) was obtained.

Sub 2-55 Synthesis example

2-bromodibenzo[b,d]thiophene (30.0 g, 114.0 mmol) in aniline (15.9 g, 171.0 mmol), Pd ₂ (dba) ₃ (3.1 g, 3.4 mmol), 50% P( t- Bu) ₃ ( 2.8ml, 6.8 mmol), NaO t- Bu (32.9 g, 342.0 mmol), and toluene (400ml) were added, and the same method was followed for the synthesis of Sub2-4 to obtain 22 g (yield: 70.1%) of the product.

3. Examples of Sub 3 and Synthesis Examples

Compounds belonging to Sub 3 of Scheme 1 are as follows, but are not limited thereto.

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

[Table 3]

Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 4 below, but is not limited thereto.

<Scheme 4>

Sub 3-2 Synthesis example

2-chloro-4,6-diphenyl-1,3,5-triazine (23.0 g, 85.9 mmol) in bis(pinacolato)diboron (32.7 g, 128.9 mmol), Pd(dppf)Cl ₂ (1.9 g, 2.6 mmol) ), KOAc (25.3 g, 257.7 mmol) and toluene (500ml) were added and stirred at 120 °C. When the reaction was completed, the temperature of the reactant was cooled to room temperature, 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 filter to obtain 23.0 g (yield: 74.5%) of the product.

Sub 3-6 Synthesis example

Bis(pinacolato)diboron (18.8 g, 73.9 mmol) in 2-(3-bromophenyl)-4,6-di(naphthalen-1-yl)pyrimidine (24.0 g, 49.2 mmol), Pd(dppf)Cl ₂ (1.1 g, 1.5 mmol), KOAc (14.5 g, 147.7 mmol), and toluene (500ml) were added and stirred at 120 °C, followed by separation in the same manner as in Sub3-2, to obtain 19.0 g (yield: 72.2%) of the product. .

Sub 3-9 Synthesis example

Bis(pinacolato)diboron (32.1 g, 126.4 mmol) in 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (25.0 g, 84.2 mmol), Pd(dppf)Cl ₂ (1.8 g, 2.5 mmol), KOAc (24.8 g, 252.7 mmol), and toluene (450ml) were added and stirred at 120 °C, followed by separation in the same manner as in Sub3-2 to obtain 26.0 g (yield: 79.5%) of the product. .

Sub 3-37 Synthesis example

Bis(pinacolato)diboron (25.0 g, 98.7 mmol), Pd(dppf)Cl ₂ (2.0 g, 1.4 mmol), KOAc ( 19.4 g, 197.3 mmol) and toluene (600ml) were added and stirred at 120° C., followed by separation in the same manner as in Sub3-2, to obtain 25.0 g (yield: 85.9%) of the product.

Sub 3-38 Synthesis example

Bis(pinacolato)diboron (28.5 g, 112.1 mmol), Pd(dppf)Cl ₂ (1.6 g, 2.2 mmol), KOAc (22.0 g, 224.2) in 6-bromo-2,3-diphenylquinoxaline (27.0 g, 74.7 mmol) mmol), toluene (600ml) was added and stirred at 120° C., followed by separation in the same manner as in Sub3-2, to obtain 22.0 g (yield: 72.1%) of the product.

Sub 3-52 Synthesis example

Bis(pinacolato)diboron (26.8 g, 105.4 mmol), Pd(dppf)Cl ₂ (1.5 g, 2.1 mmol), KOAc ( 20.7 g, 210.9 mmol) and toluene (650ml) were added and stirred at 120° C., followed by separation in the same manner as in Sub3-2, to obtain 26.0 g (yield: 83.0%) of the product.

4. Synthesis of the final compound

P-12 Synthesis example

Sub1-1 (15 g, 40.5 mmol) to Sub2-4 (9.9 g, 40.5 mol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), t-BuONa (12.7 g, 121.5 mmol), P(t -bu) ₃ (0.4 g, 2.4 mmol) and toluene (200 ml) were added and stirred at 130° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated by a silica gel filter to obtain 19 g (88%) of the product.

P-19 Synthesis example

Sub1-1 (15 g, 40.5 mmol) to Sub2-57 (14.2 g, 40.5 mol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), NaO t -Bu (12.7 g, 121.5 mmol), P ( t-bu) ₃ (0.4 g, 2.4 mmol) and toluene (100 ml) were added and stirred at 130° C., followed by separation in the same manner as in P-12, to obtain 22 g (yield: 84.7%) of the product.

P-35 Synthesis example

Sub1-44 (17 g, 32.5 mmol) to Sub2-57 (8.0 g, 32.5 mol), Pd ₂ (dba) ₃ (0.9 g, 1.0 mmol), NaO t -Bu (9.4 g, 97.6 mmol), P ( t-bu) ₃ (0.4 g, 2.0 mmol) and toluene (100 ml) were added and stirred at 130° C., followed by separation in the same manner as in P-12 to obtain 19 g (yield: 85.0 %) of the product.

P-77 Synthesis example

Sub1-38 (18 g, 37.4 mmol) to Sub2-57 (20.6 g, 74.8 mol), Pd ₂ (dba) ₃ (1.0 g, 1.1 mmol), NaO t -Bu (10.8 g, 112.3 mmol), P ( t-bu) ₃ (0.5 g, 2.2 mmol) and toluene (200 ml) were added and stirred at 130° C., followed by separation in the same manner as in P-12, to obtain 30 g of a product (yield: 87.7%).

P-96 Synthesis example

Sub1-2 (19 g, 51.3 mmol), Sub3-2 (41.5 g, 77.0 mmol), Pd(PPh ₃ ) ₄ (1.8 g, 1.5 mmol), K ₂ CO ₃ (20.5 g, 154.0 mmol) in THF ( 120ml) was added and dissolved, then water (40ml) was added and stirred at 90°C. Thereafter, the product was separated in the same manner as in P-12 to obtain 21 g (yield: 78.3%) of the product.

P-120 Synthesis example

Sub1-3 (20 g, 54.0 mmol), Sub3-4 (31.0 g, 81.1 mol), Pd(PPh ₃ ) ₄ (1.9 g, 1.6 mmol), K ₂ CO ₃ (21.5 g, 162.1 mmol) in THF ( 200ml) was added and dissolved, then water (60ml) was added and stirred at 90°C. Thereafter, the product was separated in the same manner as in P-12 to obtain 22 g (yield: 74.6%) of the product.

P-151 Synthesis example

Sub1-6 (21 g, 56.7 mmol), Sub3-57 (37.9 g, 85.1 mol), Pd(PPh ₃ ) ₄ (2.1 g, 1.8 mmol), K ₂ CO ₃ (23.7 g, 178.4 mmol) in THF ( 300ml) was added and dissolved, then water (100ml) was added and stirred at 90°C. Thereafter, the product was separated in the same manner as in P-12 to obtain 27 g (yield: 74.6%) of the product.

P-158 Synthesis example

Sub1-3 (22 g, 59.5 mmol), Sub3-2 (39.7 g, 89.2 mmol), Pd(PPh ₃ ) ₄ (2.1 g, 1.8 mmol), K ₂ CO ₃ (23.7 g, 178.4 mmol) in THF ( 330ml) was added and dissolved, then water (110ml) was added and stirred at 90°C. Thereafter, the product was separated in the same manner as in P-12 to obtain 23 g (yield: 63.6%) of the product.

FD-MS values of compounds P-1 to P-158 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example One] Red organic electroluminescent device (host)

On the ITO layer (anode) formed on the glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene After vacuum deposition of -1,4-diamine (hereinafter abbreviated as "2-TNATA") to a thickness of 60 nm to form a hole injection layer, 4,4-bis[N-(1) -Naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPB") was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Then, on the hole transport layer, compound P-96 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 a dopant so 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.

Then, 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 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 5 was used instead of the compound P-96 as the host material of the light emitting layer.

[ comparative example One]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P-96 of the present invention as a host material for the light emitting layer.

<Comparative compound A>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 15 and Comparative Example 1 of the present invention, the electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, The T95 lifetime was measured using a lifetime measuring device of McScience at 2500cd/m ² standard luminance, and the measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results of Table 5, when a red organic light emitting device was manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, the organic electroluminescent device was more sensitive than Comparative Example 1 using Comparative Compound A. Not only can the driving voltage be lowered, but the luminous efficiency and lifespan can be significantly improved.

In the case of Comparative Compound A, there is a difference in that the same core or substituents are all hydrogen as in the present invention, and a difference in physical properties occurs due to the substitution or fusion of substituents in the same core, and this change is crucial for improving device performance during device deposition. seems to have played a role. Accordingly, by using the compound according to the present invention as a host material, a remarkable effect that is difficult for those skilled in the art to predict occurs.

[ Example 16] Red organic electroluminescent device ( light emitting layer )

After vacuum deposition of 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the glass substrate to form a hole injection layer, NPB was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. .

Then, the compound P-3 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 60 nm to form a light-emitting auxiliary layer, and 4,4'-N,N'-dicarbazole-biphenyl (hereinafter (referred to as 'CBP') as a host, (piq) ₂ Ir(acac) was used as a dopant, but the dopant was doped so that the weight ratio was 95:5, and a light emitting layer with a thickness of 30 nm was deposited.

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.

Then, 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 17] to [ Example 29]

An organic electroluminescent device was always prepared in the same manner as in Example 16, except that the compound of the present invention described in Table 6 was used instead of the compound P-3 as the material of the light emitting auxiliary layer.

[ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A was used instead of Compound P-3 as a material of the light emitting auxiliary layer.

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 16 to 29 and Comparative Example 2 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, 2500cd T95 lifetime was measured using a life measuring device of McScience at /m ² standard luminance, and the measurement results are shown in Table 6 below.

[Table 6]

From Table 6 above, when a red organic light emitting device was manufactured using the material for an organic light emitting device of the present invention as a light emitting auxiliary layer material, the driving voltage of the organic light emitting device could be lowered than that of Comparative Example 2 using Comparative Compound A. In addition, it can be seen that the luminous efficiency and lifespan can be significantly improved.

As described above, even if the core is the same, a substituent is substituted or a ring is fused to the core, resulting in a difference in physical properties of the compound. In particular, when a specific substituent called an amine group is substituted, physical properties completely different from those of the core itself appear, and this change seems to have played a decisive role in improving device performance during device deposition. Therefore, when the compound according to the present invention is used as a light emitting auxiliary layer material by substituting a substituent on the same core or by further fusing a ring, a remarkable effect that cannot be predicted by those skilled in the art occurs.

Above, the present invention has been described by way of example, and various modifications will be possible without departing from the essential characteristics of the present invention by those of ordinary skill in the art to which the present invention pertains. 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: organic electric device 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (9)

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

In Formula 1,
n is an integer of 1 to 3, and when n is an integer of 2 or more, a plurality of A are the same as or different from each other,
_{L is a C 2} ~ C ₆₀ heterocyclic group containing a 6-membered ring including N,
_{A is a C 10} ~ C ₆₀ heterocyclic group in which three or more rings containing at least one heteroatom of O or S are condensed,
R ¹ to R ³ are each independently hydrogen; heavy hydrogen; halogen; 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 ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; And -L'-N(R _a ) (R _b ); is selected from the group consisting of, adjacent groups may combine with each other to form an aromatic hydrocarbon ring,
a is an integer from 0 to 4, b is an integer from 0 to 5, c is an integer from 0 to 3, and when each of these is an integer of 2 or more, a plurality of R ^{1 ,} each of a plurality of R ² , a plurality of R ³ each is the same as or different from each other,
The L' are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; And O, N, S, Si and P including at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group. A compound represented by the following formula (4):
<Formula 4>

In Formula 4,
R ¹ to R ³ are each independently hydrogen; heavy hydrogen; halogen; 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 ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; And -L'-N(R _a ) (R _b ); is selected from the group consisting of, adjacent groups may combine with each other to form an aromatic hydrocarbon ring,
a is an integer from 0 to 4, b is an integer from 0 to 5, c is an integer from 0 to 3, and when each of these is an integer of 2 or more, a plurality of R ^{1 ,} each of a plurality of R ² , a plurality of R ³ each is the same as or different from each other,
L is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
X is NAr ³ , C(R _c )(R _d ), S or O;
Z ¹ ~ Z ⁴ are independently N, CH or CR to each other, and, Z ¹ ~ Z ⁴ at least one of is N, Z ¹ ~ Z ⁴ if one associates with L from, CR 'in R' are single is a bond,
The L' are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; And O, N, S, Si and P including at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group.
The Ar ³ is a C ₆ ~ C ₂₀ aryl group; fluorenyl group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group,
Wherein R _c , R _d and R' are each independently hydrogen; heavy hydrogen; halogen; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₆ -C ₂₀ Aryl group; _{a C 6} -C ₂₀ aryl group substituted with deuterium; fluorenyl group; _{and a C 2} -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, _{and R c} and R _d are bonded to each other to form a ring and adjacent R's may combine with 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:

. 3. The method of claim 2,
The compound represented by Formula 4 is a compound characterized in that it is one of the following compounds:

. 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 at least one of the compound represented by the formula (1) of claim 1 or the compound represented by the formula (4) of claim 2. 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 emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. 7. The method of claim 6,
The organic electric device, characterized in that the compound represented by Formula 1 or Formula 4 is included in the light emitting layer. 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. 9. The method of claim 8,
The organic electric device is an electronic device, characterized in that 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.

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