KR102366722B1 - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are an organic electric device comprising a compound represented by Chemical Formula 1, a first electrode, a second electrode, and an organic material layer between the first and second electrodes, and an electronic device including the same, wherein the organic material layer is a compound represented by Chemical Formula 1 By including, it is possible to lower the driving voltage of the organic electric device, it is possible to improve the luminous efficiency and lifespan.

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 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, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

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 (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 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, most of the materials used for the hole transport layer have a low T ₁ value because they must 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 an appropriate driving voltage range (within the blue device driving voltage range of the full device) hole mobility (hole The development of a light emitting auxiliary layer having mobility) is urgently required.

However, this cannot be achieved simply by 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 transporting layer, and the light-emitting auxiliary layer and the light-emitting layer. 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.

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.

In other words, in order to sufficiently exhibit the excellent characteristics of the organic electric device, the material constituting the organic material 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. Supported by materials should be preceded, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently developed. 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, color purity 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, color purity, and lifespan of the device can be greatly improved.

1 is an exemplary view of an organic electroluminescent device according to the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

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.

As used in this specification and the appended claims, unless otherwise indicated, the following terms have the following meanings.

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has a single bond of 1 to 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo means a radical of saturated aliphatic functional groups including alkyl groups and cycloalkyl-substituted alkyl groups.

As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group substituted with halogen unless otherwise specified.

The term "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise specified, has a double or triple bond of 2 to 60 carbon atoms, respectively, and includes a straight or branched chain group, and is limited thereto it is not

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms unless otherwise specified, and is limited thereto. it is not

As used herein, the term “aryloxyl group” or “aryloxy group” refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

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 It includes the case of forming a compound as a spy together.

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 includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.

The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to 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.

In addition, the "heterocyclic group" may include a ring containing SO ₂ instead of carbon forming the ring. For example, "heterocyclic group" includes the following compounds.

As used herein, the term "ring" includes monocyclic and polycyclic rings, and includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems and spiro compounds, and includes aromatic as well as non-aromatic, hydrocarbon Rings include, of course, heterocycles containing at least one heteroatom.

As used herein, the term "ring assemblies" refers to two or more ring systems (single or fused ring systems) directly connected to each other through a single bond or a double bond, and a direct connection between such rings It means that the number of linkages is one less than the total number of ring systems in the compound. In a ring aggregate, the same or different ring systems may be directly linked to each other through single or double bonds.

As used herein, the term "fused multiple ring system" refers to a fused ring form shared by at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. and a form in which at least one heterocyclic system is fused. The fused multiple ring system may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.

The term "spiro compound" used in the present invention has a 'spiro union', and the spiro linkage means a connection formed by sharing only one atom in 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.

Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group, where The arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, unless otherwise explicitly stated, in the term "substituted or unsubstituted" used herein, "substitution" means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, C ₁ -C ₂₀ Alkylamine group, C ₁ -C ₂₀ Alkylthiophene group, C ₆ -C ₂₀ Arylthiophene group, C ₂ -C ₂₀ Alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₂₀ heterocyclic group means substituted with one or more substituents selected from the group consisting of and is not limited to these substituents.

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. there is.

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.

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 the second electrode 120 . An organic material layer including the compound according to the present invention is provided between the two 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 sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 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 further includes a protective layer or a light efficiency improving layer (Capping layer) formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer. can do.

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) and the like, a host or dopant material of the light emitting layer 150, or a material of the light efficiency improving layer. For example, the compound of the present invention may be used as a material for the light emitting layer 150 , the hole transport layer 140 and/or the light emitting auxiliary layer 151 , and is preferably used as a material for the light emitting auxiliary layer or as a host material for the light emitting layer 150 . can

On the other hand, even with the same 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 bonded thereto Research is required, and 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 forming the light emitting layer 150 or the light emission auxiliary layer 151 using the compound represented by Formula 1, the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, 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 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 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. there is. 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 a material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent in processability, and can be manufactured using the existing color filter technology of LCD. Various structures for a white organic light emitting diode mainly used as a backlight device have been proposed and patented. Typically, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting units are mutually planar, and a stacking method in which R, G, and B light emitting layers are stacked up and down There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light emitting layer and photo-luminescence of an inorganic phosphor using the light therefrom. could also be applied to such WOLEDs.

In addition, the organic electric device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a device for single-color or white lighting.

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.

Ring A is each independently C ₆ ~ C ₆₀ Aromatic hydrocarbon; fluorene; O, N, S, Si and P containing at least one hetero atom of C ₂ ~ C ₆₀ Heterocycle; And C ₆ ~ C ₆₀ A fused ring of an aromatic ring and a C ₃ ~ C ₆₀ aliphatic ring; is selected from the group consisting of.

Ring A is deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ An alkoxyl 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 cycloalkyl group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; -L ² -N(R _a )(R _b ); And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof.

When Ring A is an aromatic hydrocarbon, it may be preferably a C ₆ ~ C ₃₀ aromatic hydrocarbon, more preferably a C ₆ ~ C ₁₄ aromatic hydrocarbon, specifically benzene, naphthalene, phenanthrene, or the like.

X ₁ and X ₂ are each independently a single bond, N(L ¹ )(Ar ¹ ), O, S, C(R')(R") or Si(R')(R").

The L ¹ is C ₆ ~ C ₆₀ A single bond; arylene group; fluorenylene group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group; And C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and a C ₃ ~ C ₆₀ aliphatic ring; may be selected from the group consisting of.

When L ¹ is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₂ arylene group, specifically phenyl, naphthalene, biphenyl, or the like. When L ¹ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₃ heterocyclic group, specifically pyridine, pyrimidine, triazine, quinazoline, benzoquina zoline, quinoxaline, phthalazine, carbazole, pyridopyrimidine, benzoquinoline, phenanthridinebenzothienopyrimidine, benzofuropyrimidine, and the like.

The Ar ¹ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; and -L ² -N(R _a )(R _b ).

When Ar ¹ is an aryl group, it may be preferably a C ₆ ~ C ₃₀ aryl group, more preferably a C ₆ ~ C ₁₂ aryl group, specifically phenyl, biphenyl, naphthyl, or the like. When Ar ¹ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, specifically pyridine, pyrimidine, triazine, quinazoline, benzothi enopyrimidine, benzofuropyrimidine, benzoquinazoline, quinoxaline, phthalazine, carbazole, pyridopyrimidine, benzoquinoline, phenanthridine, indolocarbazole, dibenzofuran, and the like.

Wherein R' and R" are each independently C ₁ ~ C ₅₀ Alkyl group; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group of; is selected from the group consisting of, and R' and R" may combine with each other to form a ring.

R ¹ to R ⁹ 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 hetero atom C ₂ ~ C ₆₀ A heterocyclic group; C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and a C ₃ ~ C ₆₀ aliphatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ² -N(R _a )(R _b ), and adjacent groups may be bonded to each other to form a ring.

The L ² is a single bond; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group; And C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and a C ₃ ~ C ₆₀ aliphatic ring; is selected from the group consisting of.

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 a C ₆ ~ C ₆₀ aromatic ring; And O, N, S, Si, and P containing at least one heteroatom of C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of, R _a and R _b may be bonded to each other to form a ring there is.

The aryl group, arylene group, aromatic hydrocarbon, fluorenyl group, fluorenylene group, fluorene, heterocyclic group, heterocyclic group, fused ring group, fused ring, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group , a ring formed by bonding adjacent groups from among R ¹ to R ⁹ , a ring formed by bonding R′ and R″ to each other, and a ring formed by bonding R _a and R _b to each other are deuterium; halogen; C ₁ - A silane group unsubstituted or substituted with a C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ Alkoxy 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; Deuterium substituted C ₆ -C ₂₀ Aryl group; Fluorenyl group; C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ Cycloalkyl group; C ₇ It may be further substituted with one or more substituents selected from the group consisting of -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; and combinations thereof.

Specifically, Chemical Formula 1 may be represented by one of Chemical Formulas 2 to 41 below.

<Formula 2> <Formula 3> <Formula 4>

<Formula 5> <Formula 6> <Formula 7>

<Formula 8> <Formula 9>

<Formula 10> <Formula 11> <Formula 12>

<Formula 13> <Formula 14> <Formula 15>

<Formula 16> <Formula 17>

<Formula 18> <Formula 19> <Formula 20>

<Formula 21> <Formula 22> <Formula 23>

<Formula 24> <Formula 25>

<Formula 26> <Formula 27> <Formula 28>

<Formula 29> <Formula 30> <Formula 31>

<Formula 32> <Formula 33>

<Formula 34> <Formula 35> <Formula 36>

<Formula 37> <Formula 38> <Formula 39>

<Formula 40> <Formula 41>

In Formulas 2 to 41, R ¹ to R ⁹ are as defined in Formula 1, In Formulas 2 to 9, X ₁ and X ₂ are as defined in Formula 1, and in Formulas 10 to 17 , Ar ¹ are as defined in Formula 1, and in Formulas 18 to 25, R' and R" are as defined in Formula 1.

In Formulas 2 to 41, R ¹⁰ to R ¹⁷ 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 hetero atom C ₂ ~ C ₆₀ A heterocyclic group; C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and a C ₃ ~ C ₆₀ aliphatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L ² -N(R _a )(R _b ), wherein L ² , R _a and R _b are as defined in Formula 1 .

More specifically, Chemical Formula 1 may be one of the following compounds.

In another aspect of the present invention, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode.

The organic material layer is at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and a light emitting layer, and the organic material layer may include at least one of the compounds. The organic layer may include one compound or two or more compounds represented by Chemical Formula 1, and the compound represented by Chemical Formula 1 may be used as a material of the emission control layer or a host material of the emission layer, in particular, a red phosphorescent host material. .

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

Synthesis example

The compound represented by Formula 1 according to the present invention (final product 1) may be prepared by a reaction route as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1> When X ₁ or X ₂ is N(Ar ¹ )

In the Core, one of Z ₁ and Z ₂ is —NH and the other is a single bond.

I. Synthesis of Core

1. of Core-1 Synthesis example

Synthesis of Core-1-a

1-(2-chloro-1H-indol-3-yl)ethan-1-one (10.00 g, 51.64 mmol), (4-bromobut-1-en-1-yl)benzene (11.99 g, 56.81 mmol), K ₂ CO ₃ (10.71 g, 77.47 mmol), and acetone (200 ml) were added and refluxed at 60° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with EA, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 16.05 g (96%) of the product.

Synthesis of Core-1-b

Add pyridine (5 ml) and acetone (120 ml) to Core-1-a (5.10 g, 15.75 mmol) and irradiate with light having a wavelength of 300 nm or more at room temperature. When the reaction was completed, the solvent of the reactant was removed, and the resulting organic material was separated using a silicagel column to obtain 3.33 g (87%) of the product.

Synthesis of Core-1-c

2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (5.97 g, 26.30 mmol) and MC (50 ml) were added to Core-1-b (3.20 g, 13.15 mmol) and stirred at room temperature for 12 hours. When the reaction was completed, NaHCO ₃ aqueous solution (50 ml) was added, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 2.86 g (90%) of the product.

Synthesis of Core-1-d

N -bromosuccimide (3.33 g, 18.71 mmol) and DMF (50 mL) were added to Core-1-c (4.3 g, 17.82 mmol) and stirred at room temperature for 6 hours. When the reaction was completed, the mixture was extracted with MC and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 4.39 g (77%) of the product.

Synthesis of Core-1-e

Core-1-d (5.50 g, 17.18 mmol) in 2-chloroaniline (2.19 g, 17.18 mmol), Pd ₂ (dba) ₃ (0.47 g, 0.52 mmol), t-BuONa (1.82 g, 18.90 mmol), P (t-bu) ₃ (0.35 g, 1.72 mmol) and toluene (50 ml) were added and refluxed 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 using a silicagel filter to obtain 5.48 g (87%) of the product.

Synthesis of Core-1

Pd(OAc) ₂ (0.12 g, 0.52 mmol), P(t-Bu) ₃ (0.30 g, 1.04 mmol), K ₂ CO ₃ (4.29 g, 31.08) in Core-1-e (3.80 g, 10.36 mmol) mmol), DMA (50 ml) was 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 using a silicagel column to obtain 2.74 g (80%) of the product.

2. Core-2 Synthesis example

Synthesis of Core-2-a

Core-1-d (3.9 g, 12.18 mmol), 1-chloronaphthalen-2-amine (2.16 g, 12.18 mmol), Pd ₂ (dba) ₃ (0.33 g, 0.37 mmol), t-BuONa ( 1.29 g, 13.40 mmol), P(t-bu) ₃ (0.25 g, 1.22 mmol), and toluene (50 ml) were added and 4.27 g (84%) of the product was obtained by using the synthesis method of Core-1-e.

Synthesis of Core-2

Core-2-a (3.10 g, 7.44 mmol), Pd(OAc) ₂ (0.08 g, 0.37 mmol), P(t-Bu) ₃ (0.22 g, 0.74 mmol), K ₂ CO ₃ (3.08 g, 22.31) mmol), DMA (50 ml) was used for the synthesis of Core-1 to obtain 2.32 g (82%) of the product.

3. Core-3 Synthesis example

Synthesis of Core-3-a

Core-1-d (5.60 g, 17.49 mmol) in 3-chloronaphthalen-2-amine (3.11 g, 17.49 mmol), Pd ₂ (dba) ₃ (0.48 g, 0.52 mmol), t-BuONa (1.85 g, 19.24) mmol), P(t-bu) ₃ (0.35 g, 1.75 mmol), and toluene (70 ml) were added, and 5.91 g (81%) of the product was obtained using the synthesis method of Core-1-e.

Synthesis of Core-3

Core-3-a (3.70 g, 8.87 mmol), Pd(OAc) ₂ (0.10 g, 0.44 mmol), P(t-Bu) ₃ (0.26 g, 0.89 mmol), K ₂ CO ₃ (3.68 g, 26.62) mmol) and DMA (50 ml) were used for the synthesis of Core-1 to obtain 4.4 g (64%) of the product.

4. Core-4 Synthesis example

Synthesis of Core-4-a

Core-1-d (2.50 g, 7.81 mmol) in 2-chloronaphthalen-1-amine (1.39 g, 7.81 mmol), Pd ₂ (dba) ₃ (0.21 g, 0.23 mmol), t-BuONa (0.83 g, 8.59) mmol), P(t-bu) ₃ (0.32 g, 0.78 mmol), and toluene (50 ml) were added, and 2.54 g (78%) of the product was obtained using the synthesis method of Core-1-e.

Synthesis of Core-4

Core-4-a (6.60 g, 15.83 mmol), Pd(OAc) ₂ (0.18 g, 0.79 mmol), P(t-Bu) ₃ (0.46 g, 1.58 mmol), K ₂ CO ₃ (6.56 g, 47.49) mmol) and DMA (80 ml) were used for the synthesis of Core-1 above to obtain 4.52 g (75%) of the product.

5. Core-5 Synthesis example

Synthesis of Core-5-a

Core-1-d (12.30 g, 38.41 mmol) in (2-nitrophenyl)boronic acid (6.41 g, 38.41 mmol), Pd(PPh ₃ ) ₄ (1.33 g, 1.15 mmol), K ₂ CO ₃ (7.96 g, 57.62 mmol), THF (150 ml), and H ₂ O (80 ml) were added and refluxed at 90° 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 using a silicagel column to obtain 12.25 g (88%) of the product.

Synthesis of Core-5

Core-5-a (15.50 g, 42.77 mmol) was added with triphenylphosphine (28.05 g, 106.93 mmol) and o-dichlorobenzene (o-DCB) (150 ml) and refluxed at 180° C. for 6 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, and o-DCB is removed. The resulting organic material was separated using a silicagel column to obtain 13.00 g (92%) of the product.

6. Core-6's Synthesis example

Synthesis of Core-6-a

Core-1-d (7.80 g, 24.36 mmol) in (2-nitronaphthalen-1-yl)boronic acid (5.29 g, 24.36 mmol), Pd(PPh ₃ ) ₄ (0.84 g, 0.73 mmol), K ₂ CO ₃ (5.05 g, 36.54 mmol), THF (100 ml), and H ₂ O (50 ml) were added and 8.44 g (84%) of the product was obtained by using the synthesis method of Core-5-a.

Synthesis of Core-6

Core-6-a (8.10 g, 19.64 mmol), triphenylphosphine (12.88 g, 49.10 mmol), o-dichlorobenzene (o-DCB) (100 ml) was synthesized using the above Core-5 synthesis method to 6.50 g (87%) of the product ) was obtained.

7. Core-7 Synthesis example

Synthesis of Core-7-a

Core-1-d (5.30 g, 16.55 mmol) in (3-nitronaphthalen-2-yl)boronic acid (3.59 g, 16.55 mmol), Pd(PPh ₃ ) ₄ (0.57 g, 0.50 mmol), K ₂ CO ₃ (3.43 g, 24.83 mmol), THF (100 ml), and H ₂ O (50 ml) were added and 6.08 g (89%) of the product was obtained using the synthesis method of Core-5-a.

Synthesis of Core-7

Core-7-a (5.90 g, 14.30 mmol), triphenylphosphine (9.38 g, 35.76 mmol), o-dichlorobenzene (o-DCB) (70 ml) was synthesized using the above Core-5 synthesis method to 4.84 g (89%) of the product ) was obtained.

8. Core-8 Synthesis example

Synthesis of Core-8-a

Core-1-d (6.20 g, 19.36 mmol) in (1-nitronaphthalen-2-yl)boronic acid (4.20 g, 19.36 mmol), Pd(PPh ₃ ) ₄ (0.67 g, 0.58 mmol), K ₂ CO ₃ (4.01 g, 29.05 mmol), THF (100 ml), and H ₂ O (50 ml) were added and 7.03 g (88%) of the product was obtained using the synthesis method of Core-5-a.

Synthesis of Core-8

Core-8-a (2.90 g, 7.03 mmol), triphenylphosphine (4.61 g, 17.58 mmol), and o-dichlorobenzene (o-DCB) (50 ml) were synthesized using the above Core-5 synthesis method to 2.19 g (82%) of the product ) was obtained.

<Scheme 2> When X ₁ and X ₂ are S, O or CR'R”

One of X ₁ and X ₂ is S, O or CR'R", and the other is a single bond.

9. Core-9's Synthesis example

Synthesis of Core-9-a

N -iodosuccimide (9.11 g, 40.47 mmol) and DMF (150 mL) were added to Core-1-c (9.30 g, 38.54 mmol) and stirred at room temperature for 6 hours. When the reaction was completed, the mixture was extracted with MC and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 9.26 g (75%) of the product.

Synthesis of Core-9-b

2,5-dibromobenzenethiol (2.99 g, 11.17 mmol) in Core-9-a (4.10 g, 11.17 mmol), Pd ₂ (dba) ₃ (0.31 g, 0.33 mmol), (Oxydi-2,1-phenylene)bis (diphenylphosphine) (DPEPhos) (0.60 g, 1.12 mmol), t-BuONa (1.18 g, 12.28 mmol), and toluene (100 ml) were added and refluxed at 60° C. for 2 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 using a silicagel filter to obtain 1.62 g (40%) of the product.

Synthesis of Core-9-c

Core-9-b (3.90 g, 7.69 mmol), Pd(OAc) ₂ (0.09 g, 0.38 mmol), P(t-Bu) ₃ (0.22 g, 0.77 mmol), K ₂ CO ₃ (3.19 g, 23.07) mmol), DMA (50 ml) was used for the synthesis of Core-1 above to obtain 2.23 g (68%) of the product.

Synthesis of Core-9

Core-9-c (6.20 g, 14.54 mmol) in bis(pinacolato)diboron (5.30 g, 18.91 mmol), PdCl ₂ (dppf) ₂ (0.59 g, 0.73 mmol), KOAc (4.28 g, 43.63 mmol), DMF (100 ml) was added and refluxed at 120° C. for 6 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 using a silicagel column to obtain 6.06 g (88%) of the product.

10. Core-10's Synthesis example

Synthesis of Core-10-a

Core-1-d (9.40 g, 29.36 mmol), bis(pinacolato)diboron (10.69 g, 38.16 mmol), PdCl ₂ (dppf) ₂ (1.20 g, 1.47 mmol), KOAc (8.64 g, 88.07 mmol), DMF (100 ml) was used for the synthesis of Core-9 to obtain 9.06 g (84%) of the product

Synthesis of Core-10-b

Core-10-a (7.90 g, 21.51 mmol) in 2,4-dibromophenol (5.42 g, 21.51 mmol), Pd(PPh ₃ ) ₄ (0.75 g, 0.65 mmol), K ₂ CO ₃ (4.46 g, 32.27 mmol) ), THF (100 ml), EtOH (50 ml), H ₂ O (50 ml) were added and refluxed at 90° 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 using a silicagel column to obtain 4.88 g (55%) of the product.

Synthesis of Core-10-c

Core-10-b (4.10 g, 9.94 mmol), Pd(OAc) ₂ (0.11 g, 0.50 mmol), 3-nitropyridine (0.06 g, 0.50 mmol), BzOOtBu (tert-butyl peroxybenzoate) (3.86 g, 19.89 mmol) ), C ₆ F ₆ (hexafluorobenzene) (100 ml), DMI (N,N'-dimethylimidazolidinone) (65 ml), and reflux at 90°C for 3 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with EA, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 1.88 g (46%) of the product.

Synthesis of Core-10

Core-10-c (2.80 g, 6.82 mmol), bis(pinacolato)diboron (2.49 g, 8.87 mmol), PdCl ₂ (dppf) ₂ (0.28 g, 0.34 mmol), KOAc (2.01 g, 20.47 mmol), DMF (50 ml) was used for the synthesis of Core-9 to obtain 2.75 g (88%) of the product.

11. Core-11 Synthesis example

Synthesis of Core-11-a

In Core-10-a (6.80 g, 18.52 mmol), methyl 5-bromo-2-iodobenzoate (6.31 g, 18.52 mmol), Pd(PPh ₃ ) ₄ (0.64 g, 0.56 mmol), K ₂ CO ₃ (3.84 g) , 27.77 mmol), THF (100 ml), and H ₂ O (50 ml) were used for the synthesis of Core-10-b above to obtain 3.53 g (42%) of the product.

Synthesis of Core-11-b

Core-11-a (3.40 g, 7.48 mmol) and THF (50 ml) were added, and 1.6M methylmagnesium bromide (11.7 ml) was added at 0°C and stirred at room temperature for 24 h. When the reaction is complete, 1 N HCl is added, stirred for 10 minutes, extracted with EA, and washed with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 2.35 g (69%) of the product.

Synthesis of Core-11-c

After dissolving Core-11-b (4.20 g, 9.24 mmol) in THF (100 ml), slowly add 4 ml of methanesulfonic acid at 0° C. and stir at room temperature for 1 hour. When the reaction is complete, add sodium carbonate aqueous solution (100 ml), stir for 10 minutes, extract with MC, and wash with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 2.58 g (64%) of the product.

Synthesis of Core-11

Core-11-c (5.20 g, 11.92 mmol), bis(pinacolato)diboron (4.34 g, 15.49 mmol), PdCl ₂ (dppf) ₂ (0.49 g, 0.60 mmol), KOAc (3.51 g, 35.75 mmol), DMF (70 ml) was obtained by using the synthesis method of Core-9 above to obtain 5.13 g (89%) of the product.

II. Sub 1 example

On the other hand, the compound belonging to Sub 1 may be the following compounds, but is not limited thereto, and Table 1 shows the FD-MS values of the compounds belonging to Sub 1.

[Table 1]

III. Product synthesis

1. P-3 Synthesis example

Put Core-1 (3.30 g, 9.99 mmol) in a round-bottom flask, Sub-1-45 (2.67 g, 9.99 mmol), Pd ₂ (dba) ₃ (0.27 g, 0.30 mmol), t-BuONa (1.06 g, 10.99 mmol), P(t-bu) ₃ (0.54 g, 1.08 mmol), and toluene (50 ml) were added and refluxed 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 using a silicagel filter to obtain 4.60 g (82%) of the product.

2. P-30 Synthesis example

Core-2 (3.90 g, 10.25 mmol), Sub-1-51 (2.47 g, 10.25 mmol), Pd ₂ (dba) ₃ (0.28 g, 0.31 mmol), t-BuONa (1.08 g, 11.28 mmol), P (t-bu) ₃ (0.55 g, 1.03 mmol) and toluene (50 ml) were used for the above synthesis of P-3 to obtain 4.84 g (84%) of the product.

3. P-37 Synthesis example

Core-3 (2.80 g, 7.36 mmol), Sub-1-44 (2.33 g, 7.36 mmol), Pd ₂ (dba) ₃ (0.20 g, 0.22 mmol), t-BuONa (0.78 g, 8.10 mmol), P (t-bu) ₃ (0.40 g, 0.74 mmol) and toluene (40 ml) were used for the above synthesis of P-3 to obtain 2.69 g (65%) of the product.

4. P-53 Synthesis example

Core-4 (2.20 g, 5.78 mmol), Sub-1-39 (1.68 g, 5.78 mmol), Pd ₂ (dba) ₃ (0.16 g, 0.17 mmol), t-BuONa (0.61 g, 6.36 mmol), P (t-bu) ₃ (0.31 g, 0.62 mmol) and toluene (30 ml) were used for the above synthesis of P-1-7 to obtain 3.19 g (87%) of the product.

5. P-73 Synthesis example

Core-5 (4.10 g, 12.41 mmol), Sub-1-46 (3.68 g, 12.41 mmol), Pd ₂ (dba) ₃ (0.34 g, 0.37 mmol), t-BuONa (1.31 g, 13.65 mmol), P (t-bu) ₃ (0.67 g, 1.24 mmol) and toluene (50 ml) were used for the above synthesis of P-3 to obtain 6.74 g (92%) of the product.

6. P-88 Synthesis example

Core-6 (4.70 g, 12.35 mmol), Sub-1-2 (3.30 g, 12.35 mmol), Pd ₂ (dba) ₃ (0.34 g, 0.37 mmol), t-BuONa (1.31 g, 13.59 mmol), P (t-bu) ₃ (0.67 g, 1.24 mmol) and toluene (50 ml) were used for the above synthesis of P-3 to obtain 5.96 g (79%) of the product.

7. P-110 Synthesis example

Core-7 (2.20 g, 5.78 mmol), Sub-1-72 (1.62 g, 5.78 mmol), Pd ₂ (dba) ₃ (0.16 g, 0.17 mmol), t-BuONa (0.61 g, 6.36 mmol), P (t-bu) ₃ (0.31 g, 0.62 mmol) and toluene (30 ml) were used for the above synthesis of P-3 to obtain 3.29 g (91%) of the product.

8. P-120 Synthesis example

Core-8 (4.00 g, 10.51 mmol), Sub-1-32 (3.33 g, 10.51 mmol), Pd ₂ (dba) ₃ (0.29 g, 0.32 mmol), t-BuONa (1.11 g, 11.57 mmol), P (t-bu) ₃ (0.57 g, 1.05 mmol) and toluene (50 ml) were used for the above synthesis of P-3 to obtain 5.97 g (86%) of the product.

9. P-16 Synthesis example

Core-9 (3.30 g, 6.97 mmol), Sub-1-62 (1.95 g, 6.97 mmol), Pd(PPh ₃ ) ₄ (0.24 g, 0.21 mmol), K ₂ CO ₃ (1.45 g, 10.46 mmol), THF (80 ml), H ₂ O (40 ml) was used for the synthesis of Core-5-a above to obtain 3.62 g (88%) of the product.

10. P-19 Synthesis example

Core-10 (6.50 g, 14.21 mmol), Sub 1-67 (8.55 g, 14.21 mmol), Pd(PPh ₃ ) ₄ (0.49 g, 0.43 mmol), K ₂ CO ₃ (2.95 g, 21.32 mmol), THF (80 ml), H ₂ O (40 ml) was used for the synthesis of Core-5-a above to obtain 6.47 g (85%) of the product.

11. P-20 Synthesis example

Core-11 (3.60 g, 7.45 mmol), Sub-1-14 (2.37 g, 7.45 mmol), Pd(PPh ₃ ) ₄ (0.26 g, 0.22 mmol), K ₂ CO ₃ (1.54 g, 11.17 mmol), THF (100 ml), H ₂ O (50 ml) was used for the synthesis of Core-5-a above to obtain 3.90 g (82%) of the product.

FD-MS values for the final compound synthesized by the above synthesis method are shown in Table 2 below.

[Table 2]

Manufacturing evaluation of organic electric devices

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

On the ITO layer (anode) formed on the glass substrate, a 4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as "2-TNATA") film was vacuum-deposited to form a 60 nm-thick hole After forming the injection layer, a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPD") film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Then, on the hole transport layer, compound P-1 of the present invention as a host material and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate as a dopant material (hereinafter abbreviated as "(piq) ₂ Ir(acac)") A light emitting layer with a thickness of 30 nm was formed by doping at a weight ratio of 95:5 using (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum ( Hereinafter, abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm to form a hole blocking layer, and tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as "Alq ₃ ") was 40 nm on the hole blocking layer. Then, on the electron transport layer, LiF, an alkali metal halide, was deposited 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. An organic electroluminescent device was manufactured by depositing to a thickness to form a cathode.

[ Example 2] to [ Example 53]

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 3 was used instead of the compound P-1 of the present invention as the host material of the light emitting layer.

[ comparative example 1] to [ comparative example 3]

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

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

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 53 and Comparative Examples 1 to 3 of the present invention, the electroluminescence (EL) characteristics of the PR-650 of photoresearch company was measured, and the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 2500 cd/m ² standard luminance, and the measurement results are shown in Table 3 below.

[Table 3]

As can be seen from the results of Table 3, the organic electroluminescent device using the compound of the present invention as a phosphorescent host material lowered the driving voltage and significantly improved luminous efficiency and lifespan compared to the case where the comparative compound was used.

Compared to Comparative Compound A, which is CBP, which is mainly used as a host material, when Comparative Compound B and Comparative Compound C, which have indoloyrrolocarbazole as the main skeleton, were used as host materials, device characteristics were improved, and Comparative Compound B and Comparative Compound When the compound of the present invention was used as a host material rather than C, the device characteristics were further improved.

In the compound of the present invention, at least one benzene is fused to the main backbone compared to Comparative Compound B and Comparative Compound C. As with the compound of the present invention, as one or more benzene is fused to the main backbone, physical properties such as HOMO value, T1 value, and thermal stability are changed, and the difference in these properties is a major factor in device performance improvement during device deposition (e.g. For example, it seems that different device results were derived by acting as an energy balance).

[ Example 54] 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-18 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light emitting auxiliary layer, and then 4,4'-N,N'-dicarbazole- as a host on the light emission auxiliary layer A light emitting layer having a thickness of 30 nm was formed by doping biphenyl (hereinafter abbreviated as "CBP") at a weight of 95:5 using (piq) ₂ Ir(acac) as a dopant. 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 to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, 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 prepare a cathode.

[ Example 55] to [ Example 62]

An organic electroluminescent device was manufactured in the same manner as in Example 54, except that the compound of the present invention described in Table 4 was used instead of the compound P-18 of the present invention as a material of the light emitting auxiliary layer.

[ comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 54, except that the light-emitting auxiliary layer was not formed.

[ comparative example 5] and [ comparative example 6]

An organic electroluminescent device was manufactured in the same manner as in Example 54, except that the following comparative compound D or comparative compound F was used instead of the compound P-18 of the present invention as a material for the light emitting auxiliary layer.

<Comparative compound D> <Comparative compound F>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 54 to 62 and Comparative Examples 4 to 6 of the present invention, electroluminescence (EL) characteristics with PR-650 of photoresearch company was measured, and the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 2500 cd/m ² standard luminance, and the measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, the red organic light emitting device using the compound of the present invention as a light emitting auxiliary layer material did not form a light emitting auxiliary layer or had a lower driving voltage than Comparative Examples using Comparative Compound D and Comparative Compound F. , and the efficiency and lifespan were significantly improved.

Device characteristics of Comparative Examples 5 and 6 using Comparative Compound D or Comparative Compound F were superior to Comparative Example 4 without using a light emitting auxiliary layer, and when the compound of the present invention was used rather than Comparative Compound D or Comparative Compound F The device characteristics were the best.

This suggests that, as described in Table 3, when one or more benzenes are further fused to the core of Comparative Compound C or Comparative Compound F, the chemical and physical properties of the compound may change, which may lead to different device results. there is.

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 (13)

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

In Formula 1,
Ring A is benzene or naphthalene,
One of X ₁ and X ₂ is a single bond, and the other is N(L ¹ )(Ar ¹ ), O, S or C(R')(R");
R ¹ to R ⁹ are hydrogen,
The Ar ¹ is a C ₆ ~ C ₃₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₃₀ A heterocyclic group; and -L ² -N(R _a )(R _b ),
The L ¹ and L ² are each independently a single bond; C ₆ ~ C ₃₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one hetero atom of C ₂ ~ C ₃₀ It is selected from the group consisting of a heterocyclic group,
The R' and R" are each independently a C ₁ ~ C ₁₀ alkyl group,
The R _a and R _b are each independently a C ₆ ~ C ₃₀ aryl group; fluorenyl group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C ₃₀ It is selected from the group consisting of a heterocyclic group,
The A ring, the aryl group, the arylene group, the fluorenyl group, the fluorenylene group, the heterocyclic group and the alkyl group are each deuterium; halogen; C ₁ -C ₂₀ Alkyl 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; and -L ² -N(R _a )(R _b ) may be substituted with one or more substituents selected from the group consisting of. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 2 to 9:
<Formula 2><Formula3><Formula4>

<Formula 5><Formula6><Formula7>

<Formula 8><Formula9>

In Formulas 2 to 9,
R ¹⁰ to R ¹⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L ² -N(R _a )(R _b ),
R ¹ to R ⁹ , X ₁ , X ₂ , L ² , R _a and R _b are as defined in claim 1 . The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 10 to 17:
<Formula 10><Formula11><Formula12>

<Formula 13><Formula14><Formula15>

<Formula 16><Formula17>

In Formulas 10 to 17,
R ¹⁰ to R ¹⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L ² -N(R _a )(R _b ),
R ¹ to R ⁹ , Ar ¹ , L ² , R _a and R _b are as defined in claim 1 . The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 18 to 25:
<Formula 18><Formula19><Formula20>

<Formula 21><Formula22><Formula23>

<Formula 24><Formula25>

In Formulas 18 to 25,
R ¹⁰ to R ¹⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L ² -N(R _a )(R _b ),
R ¹ to R ⁹ , R′, R″, L ² , R _a and R _b are as defined in claim 1 . The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 26 to 33:
<Formula 26><Formula27><Formula28>

<Formula 29><Formula30><Formula31>

<Formula 32><Formula33>

In Formulas 26 to 33,
R ¹⁰ to R ¹⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L ² -N(R _a )(R _b ),
R ¹ to R ⁹ , L ² , R _a and R _b are as defined in claim 1 . The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 34 to 41:
<Formula 34><Formula35><Formula36>

<Formula 37><Formula38><Formula39>

<Formula 40><Formula41>

In Formulas 34 to 41,
R ¹⁰ to R ¹⁷ are each independently hydrogen; heavy hydrogen; halogen; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and -L ² -N(R _a )(R _b ),
R ¹ to R ⁹ , L ² , R _a and R _b are as defined in claim 1 . The method of claim 1,
Formula 1 is a compound, characterized in that 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 and containing the compound of any one of claims 1 to 7. 9. The method of claim 8,
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,
The compound is included in at least one layer 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 the compound represented by Formula 1 alone or two or more types Organic electric device, characterized in that it is included. 10. The method of claim 9,
The compound is included in the light emitting auxiliary layer or organic electric device, characterized in that used as a host material of the light emitting layer. 9. The method of claim 8,
The organic material layer is an organic electric device, characterized in that formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electric device of claim 8; and
An electronic device comprising a; a control unit for driving the display device. 13. The method of claim 12,
The organic electroluminescent device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and an electronic device, characterized in that one of a single color or white lighting device.

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