KR20200069449A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides an electronic device including an organic electric element. The organic electric element comprises: 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. The organic material layer includes compounds represented by chemical formula 1 and chemical formula 2. Therefore, the driving voltage of the organic electric element can be lowered and the luminous efficiency and lifespan thereof can be increased.

Description

Compounds for organic electrical devices, organic electrical devices using the same, and electronic devices thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device thereof.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy 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 composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. In addition, the light-emitting material may be classified into a polymer type and a low-molecular type according to the molecular weight, and a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the 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 light emission color.

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

Currently, the portable display market is increasing in size as a large-area display, and accordingly, power consumption greater than that required in the existing portable display is required. Accordingly, power consumption has become a very important factor for portable displays that have a limited power supply, such as batteries, and the efficiency and lifespan problems must also be solved.

Efficiency, life, and driving voltage are related to each other, and when the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase the life. However, simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .

Therefore, there is a need to develop a light emitting material having high thermal stability and efficiently achieving charge balance in the light emitting layer. That is, in order to sufficiently exhibit the excellent characteristics of the organic electric device, materials constituting an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material, are supported by stable and efficient materials. It should be preceded, but the development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently developed, and among them, development of a host material of a light emitting layer 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 lifetime of the device, an organic electrical device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by Formula 1, an organic electric device using the same, and an electronic device thereof.

<Formula 1>

In another aspect, the present invention provides an organic electric device and an electronic device including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 in a light emitting layer.

<Formula 2>

By using the compound according to the embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency and lifetime 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 aspect of the present invention.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified. In the present invention, an aryl group or an arylene group may include a monocyclic, ring aggregate, several conjugated ring systems, spiro compounds, and the like. In addition, unless otherwise specified herein, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

The term "fluorenyl group" or "fluorenylene group" as used in the present invention means a monovalent or divalent functional group in which R, R'and R" are both hydrogen in the following structures, unless otherwise specified. Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and R and R'are bonded to each other to form a carbon to which they are attached. It includes the case where a compound was formed as a spy together.

The term "spyro compound" used in the present invention has a'spyro linkage', and a spiro linkage refers to a linkage formed by two rings sharing only one atom. At this time, the atoms shared between the two rings are called'spyro atoms', and these are'monospyro-','dispiro-', and'trispyro' depending on the number of spy atoms in a compound. It is called a compound.

The term "heterocyclic group" used in the present invention includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and each carbon number containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P or Si unless otherwise indicated, and the heterocyclic group is a monocyclic, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like.

The term "heterocyclic group" used in the present invention means a ring containing a hetero atom such as N, O, S, P or Si instead of carbon forming a ring, and "heteroaryl group" or "heteroarylene group" It includes not only aromatic rings such as non-aromatic rings, but also compounds containing heteroatom groups such as SO ₂ , P=O, and the like, instead of carbon forming a ring.

The term "aliphatic ring group" used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like, unless otherwise indicated. It means a 3 to 60 ring, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it corresponds to the aliphatic ring.

In the present specification, the'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of a group reflecting a singer', but is described as a'parent compound name' 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 can be classified as singer such as'phenanthrylene', but the name of the group can be described. Regardless, the parent compound name may be described as'phenanthrene'. Similarly, in the case of pyrimidine, it can be described as'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidinylene, etc., as the'group name' of the corresponding singer. have.

In addition, in this specification, in describing a compound name or a substituent name, a number, an alphabet, etc. indicating a position may be omitted. For example, pyrido[4,3-d]pyrimidine is pyridopyrimidine, benzofuro[2,3-d]pyrimidine is benzofuropyrimidine, and 9,9-dimethylfluorene is di Methyl fluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless explicitly stated, the formula used in the present invention is applied in the same manner as the definition of a substituent based on the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring. The formula or compound may be omitted. In addition, when a is an integer of 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, 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 or different.

In addition, unless otherwise specified in the present specification, the rings formed by bonding with adjacent groups are C ₆ ~ C ₆₀ aromatic ring groups; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; And combinations thereof.

Hereinafter, a stacked structure of an organic electric device including the compound of the present invention will be described with reference to FIG. 1.

In describing the present invention, when it is determined that a detailed description of related known configurations or functions may obscure the subject matter of the present invention, the detailed description will be omitted.

Also, if a component such as a layer, film, region, plate, etc. is said to be "above" or "on" another component, this is not only when the other component is "directly above", but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

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. Between the second electrode 180 includes an organic material layer containing the compound according to the present invention. At this time, 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, and an electron injection layer 170 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 emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It can 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 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 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), the host or dopant of the light-emitting layer 150, or may be used as a material of the light efficiency improving layer, preferably a compound represented by Formula 1 of the present invention, or a compound represented by Formula 1 of the present invention and Formula 2 A mixture of compounds represented by is used as a host for the light emitting layer.

On the other hand, even in the case of the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is attached to which position, and thus, the selection of the core and the combination of sub-substituents coupled thereto. In particular, it is necessary to study the energy level, especially when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using a compound represented by Formula 1, or a mixture of a compound represented by Formula 1 and a compound represented by Formula 2 as a host of the light emitting layer, energy levels and T ₁ values between each organic material layer, By optimizing the intrinsic characteristics (mobility, interfacial characteristics, etc.), it is possible to simultaneously improve the life and efficiency of the organic electric device.

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 conductive metal oxide or an alloy thereof on a substrate to form an anode 120, and a hole injection layer 130 thereon , After forming the 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, can be prepared by depositing a material that can be used as the cathode 180 thereon have. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

In addition, the organic material layer is a solution process or a solvent process (e.g., spin coating process), nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blade using various polymer materials It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, 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 front emission type, a back emission type, or a double-sided emission type depending on the material used.

In addition, the organic electroluminescent 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 monochromatic lighting device and a quantum dot display device.

Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention, and a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.

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

The compound according to an aspect of the present invention is represented by Formula 1 below.

<Formula 1>

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

X ₁ is O or S.

Ar ¹ and Ar ² are independently of each other C ₆ ~ C ₁₈ aryl group; Fluorenyl group; C ₂ ~ C ₁₆ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C ₃₀ It may be selected from the group consisting of an aryloxy group.

When Ar ¹ and Ar ² are aryl groups, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, pyrene, triphenylene, anthracene, and the like. When Ar ¹ and Ar ² are heterocyclic groups, dibenzothiophene, dibenzofuran, carbazole, phenylcarbazole, benzonaphthofuran, and benzonaphthothiophene may be used. When Ar ¹ and Ar ² are fluorenyl groups, it may be 9,9-diphenylfluorene, 9,9-dimethylfluorene, and the like. When Ar ¹ and Ar ² are an aliphatic ring group, preferably an aliphatic ring of C ₃ to C ₃₀ , more preferably an aliphatic ring of C ₃ to C ₁₂ , such as cyclohexane, cyclohexylcyclohexane, and the like. When Ar ¹ and Ar ² are alkyl groups, they may preferably be C ₂ to C ₁₀ alkynyl groups such as methyl, t-butyl, and the like. When Ar ¹ and Ar ² are alkenyl groups, preferably C ₂ to C ₁₀ may be alkenyl groups, for example, ethene, propene, or the like.

L ¹ to L ³ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And it may be selected from the group consisting of a fused ring of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

When L ¹ to L ³ are arylene groups, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthyl, terphenyl, etc. . When L ¹ to L ³ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₆ heterocyclic groups, such as carbazole, phenylcarbazole, dibenzofuran, Dibenzothiophene, and the like.

R ¹ is hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring.

a is an integer of 0-9, and when a is an integer of 2 or more, a plurality of R ^{1 s} are the same as or different from each other.

Rings formed by bonding adjacent R ^{1 to} each other include an aromatic ring group of C ₆ to C ₆₀ ; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60. When adjacent R ^{1 is} bonded to each other to form an aromatic ring, preferably an aromatic ring of C ₆ ~ C ₃₀ , more preferably an aromatic ring of C ₆ ~ C ₁₄ , such as benzene, naphthalene, phenanthrene, etc. The same aromatic ring can be formed.

When R ¹ is an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , such as phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, etc. .

L'is independently of each other a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C ₆₀ aliphatic ring and a fused ring group of an aromatic ring of C ₆ ~ C ₆₀ ; may be selected from the group consisting of.

R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C ₆₀ aliphatic ring and a fused ring group of an aromatic ring of C ₆ ~ C ₆₀ ; may be selected from the group consisting of.

Formula 1 may be represented by one of the following formulas.

<Formula 1-A> <Formula 1-B>

<Formula 1-C> <Formula 1-D>

<Formula 1-E> <Formula 1-F>

<Formula 1-G>

In Chemical Formulas 1-A to 1-G, each symbol may be defined as follows.

Ar ¹ , Ar ² , L ¹ ~L ³ , X ₁ , R ¹ , a are as defined in Chemical Formula 1. Preferably, in Formulas 1-F and 1-G, Ar ¹ and Ar ² are different from each other, and preferably Ar ¹ and Ar ² may be independently of each other an aryl group, more preferably naphthyl.

X ₂ and X ₃ are each independently O or S.

R ⁴ and R ⁵ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N(R ^a )(R ^b ); and adjacent groups may combine with each other to form a ring.

The'rings formed by bonding adjacent groups together' are C ₆ ~ C ₆₀ aromatic ring groups; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60. When adjacent R ⁴ or adjacent R ⁵ are bonded to each other to form an aromatic ring, preferably an aromatic ring of C ₆ ~C ₃₀ , more preferably an aromatic ring of C ₆ ~C ₁₄ , such as benzene, naphthalene , Can form an aromatic ring such as phenanthrene.

d is an integer from 0 to 7, e is an integer from 0 to 6, and when each of these is an integer of 2 or more, each of the plurality of R ^{4 and} each of the plurality of R ⁵ are the same or different from each other.

L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,

R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

Formula 1-F may be represented by one of the following formulas.

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

In Formula 1-F-1 and 1-F-2, X ₁ , X ₃ , Ar ¹ , Ar ² , L ¹ , L ² , R ¹ , R ⁵ , a and e are defined in Formula 1-F It's like that.

Formula 1-G may be represented by one of the following formulas.

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

<Formula 1-G-3> <Formula 1-G-4> <Formula 1-G-5>

In Formula 1-G-1 to Formula 1-G-5, X ₁ , Ar ¹ , Ar ² , L ¹ , L ² , R ¹ and a are as defined in Formula 1-G.

Preferably, each symbol in the above formula may be further substituted. For example, in Formula 1, Formula 1-A to Formula 1-G, Formula 1-F-1, Formula 1-F-2, Formula 1-G-1 to Formula 1-G-5, etc., Ar ¹ , Ar ² , L ¹ ~ L ³ , L', L ^a , R ¹ , R ⁴ , R ⁵ , R _a , R _b , R ^a , R ^b , and rings formed by bonding between adjacent groups are deuterium; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Aryloxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ Aryl alkenyl group; It may be further substituted with one or more substituents selected from the group consisting of.

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 formed between the first electrode and the second electrode, wherein the organic material layer is represented by Formula 1 It includes a compound, preferably includes a compound represented by one of the formula 1-A to formula 1-G, more preferably, the compound represented by the formula 1-F and / or formula 1-G is an organic layer It is included in the light emitting layer.

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 formed between the first electrode and the second electrode, wherein the organic material layer comprises a phosphorescent light emitting layer. Included, the host of the phosphorescent light emitting layer includes a first compound represented by the formula (1) and a second compound represented by the formula (2).

<Formula 2>

In Chemical Formula 2, each symbol may be defined as follows.

Ar ³ to Ar ⁵ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group, Ar ⁴ and Ar ⁵ may be bonded to each other to form a ring. At this time, the formed ring is a heterocycle containing one or more N.

n is an integer of 1 to 3, and when n is an integer of 2 or more, each of the plurality of Ar ^{4 and} each of the plurality of Ar ⁵ may be the same or different from each other.

When Ar ³ to Ar ⁵ are aryl groups, preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene Etc. When Ar ³ to Ar ⁵ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₈ heterocyclic groups, such as pyridine, pyrimidine, triazine, carbazole , Phenylcarbazole, dibenzothiophene, dibenzofuran, and the like. When Ar ³ to Ar ⁵ are fluorenyl groups, it may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirofluorene, or the like.

L ⁴ is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And it may be selected from the group consisting of a fused ring of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

When L ⁴ is an arylene group, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthyl, terphenyl, and the like. When L ⁴ is a heterocyclic group, preferably a heterocyclic group of C ₂ to C ₃₀ , more preferably a heterocyclic group of C ₂ to C ₁₈ , such as pyridine, triazine, dibenzothiophene, dibenzofuran Etc. When L ⁴ is a fluorenyl group, it may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirofluorene, or the like.

R ² and R ³ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, adjacent rings are formed by bonding with each other ring C ₆ ~ C ₆₀ aromatic ring group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

When adjacent R ² or adjacent R ³ are bonded to each other to form an aromatic ring, preferably C ₆ ~ C ₃₀ aromatic ring, more preferably C ₆ ~ C ₁₄ aromatic ring, such as benzene, naphthalene , Can form an aromatic ring such as phenanthrene.

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

L'is independently of each other a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C ₆₀ aliphatic ring and a fused ring group of an aromatic ring of C ₆ ~ C ₆₀ ; may be selected from the group consisting of.

R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C ₆₀ aliphatic ring and a fused ring group of an aromatic ring of C ₆ ~ C ₆₀ ; may be selected from the group consisting of.

The Chemical Formula 2 may be represented by the following Chemical Formula 2-A or Chemical Formula 2-B.

<Formula 2-A> <Formula 2-B>

In Formulas 2-A and 2-B, L ⁴ , Ar ³ to Ar ⁵ , R ² , R ³ , b and c are as defined in Formula 2.

In addition, Chemical Formula 2 may be represented by one of the following Chemical Formulas 2-C to 2-F.

<Formula 2-C> <Formula 2-D>

<Formula 2-E> <Formula 2-F>

In the above formulas 2-C to 2-F, each symbol may be defined as follows.

Ar ³ to Ar ⁵ , R ² , R ³ , b and c are as defined in Formula 2.

R ¹⁰ to R ¹³ are independently of each other hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L ^a -N(R ^a )(R ^b ); And it is selected from the group consisting of a combination of these, adjacent groups can be combined with each other to form a ring.

Rings formed by bonding adjacent groups to each other include an aromatic ring group of C ₆ ~C ₆₀ ; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

When neighboring R ¹⁰ , neighboring R ¹¹ , neighboring R ¹² , or neighboring R ¹³ are combined with each other to form an aromatic ring, preferably an aromatic ring of C ₆ ~C ₃₀ , more preferably An aromatic ring such as C ₆ to C ₁₄ may be formed, such as benzene, naphthalene, and phenanthrene.

k and l are each integers of 0 to 4, n and m are integers of 0 to 3, respectively, when each of these is an integer of 2 or more, each of a plurality of R ¹⁰ each, a plurality of R ¹¹ each, a plurality of R ¹² each, a plurality Each of R ¹³ may be the same or different from each other.

V is N-(L ^a -Ar ^a ), O, S or C(R')(R").

R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₂₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); R'and R" may be bonded to each other to form a ring.

Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

The Chemical Formula 2 may be represented by one of the following Chemical Formulas 2-G to 2-T.

<Formula 2-G> <Formula 2-H> <Formula 2-I>

<Formula 2-J> <Formula 2-K> <Formula 2-L>

<Formula 2-M> <Formula 2-N> <Formula 2-O>

<Formula 2-P> <Formula 2-Q> <Formula 2-R>

<Formula 2-S> <Formula 2-T>

In Formulas 2-G to 2-T, Ar ³ to Ar ⁵ , L ⁴ , R ² , R ³ , b and c are as defined in Formula 2.

Formula 2 may be represented by the following formula 2-U.

<Formula 2-U>

In the above formula 2-U, each symbol can be defined as follows.

Ar ³ , Ar ⁵ , L ⁴ , R ² , R ³ , b, c and n are as defined in Formula 2.

U is N-(L ^a -Ar ^a ), O, S or C(R')(R").

R ¹⁴ and R ¹⁵ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; And -L ^a -N(R ^a )(R ^b ); and adjacent groups may combine with each other to form a ring.

When adjacent R ¹⁴ or adjacent R ¹⁵ are bonded to each other to form an aromatic ring, preferably C ₆ ~ C ₃₀ aromatic ring, more preferably C ₆ ~ C ₁₄ aromatic ring, such as benzene, Aromatic rings such as naphthalene and phenanthrene can be formed.

o is an integer from 0 to 3, p is an integer from 0 to 4, and when each of these is an integer of 2 or more, each of the plurality of R ^{14 and} each of the plurality of R ¹⁵ may be the same or different from each other.

R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); R'and R" may be bonded to each other to form a ring.

Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

In Chemical Formula 2, Chemical Formula 2-A to Chemical Formula 2-U, each symbol may be further substituted. For example, Ar ³ to Ar ⁵ , R ² , R ³ , R ¹⁰ to R ¹⁵ , L ⁴ , L', L ^a , Ar ^a , R _a , R _b , R', R", R ^a , R ^b , And a ring formed by bonding adjacent groups to each other is deuterium; halogen; a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group substituted or unsubstituted silane group; siloxane group; boron group; germanium group; cyanide No group; Nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group ; alkynyl of C ₂ -C _20; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; an aryl group of C ₆ -C ₂₀ fluorenyl group; O, N, S, selected from the group consisting of Si and P Consisting of a heterocyclic group of C ₂ -C ₂₀ containing at least one heteroatom; an aliphatic ring group of C ₃ -C ₂₀ ; an arylalkyl group of C ₇ -C ₂₀ ; and an arylalkenyl group of C ₈ -C ₂₀ ; It may be further substituted with one or more substituents selected from the group.

Preferably, in Formulas 1 and 2, L ¹ to L ⁴ may be each independently one of the following Formulas b-1 to b-13.

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

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

<Formula b-9> <Formula b-10>

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

In the above formulas b-1 to b-13, each symbol can be defined as follows.

R ⁵ to R ⁷ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N(R ^a )(R ^b ); and adjacent groups may combine with each other to form a ring.

When adjacent R ^{5 is formed} , adjacent R ⁶ is formed, or adjacent R ^{7 is} bonded to each other to form an aromatic ring, preferably C ₆ ~ C ₃₀ aromatic ring, more preferably C ₆ ~ C ₁₄ Aromatic rings such as benzene, naphthalene, and phenanthrene can be formed.

Y is N-(L ^a -Ar ^a ), O, S or C(R')(R").

Z ¹ to Z ³ are each independently C, C(R') or N, and at least one of Z ¹ to Z ³ is N.

f is an integer from 0 to 6, e, g, h, and i are integers from 0 to 4, j and k are integers from 0 to 3, l is an integer from 0 to 2, and m is from 0 to It is an integer of 3, and when each of these is an integer of 2 or more, each of the plurality of R ^5, each of the plurality of R ^{6, and} each of the plurality of R ⁷ may be the same or different from each other.

R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); may be selected from the group consisting of.

In C(R')(R"), R'and R" may combine with each other to form a ring, and in C(R'), adjacent R's may combine with each other to form a ring.

Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof.

The R ⁵ to R ⁷ , L ^a , Ar ^a , R', R", R ^a , R ^b , and rings formed by bonding adjacent groups are each deuterium; halogen; alkyl group of C ₁ -C ₂₀ or C Silane group unsubstituted or substituted with _6- C ₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C _6- C ₂₀ aryloxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; C ₆ substituted with deuterium -C ₂₀ aryl group; fluorenyl group; C ₂ -C ₂₀ heterocyclic group including at least one hetero atom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic Ring group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of.

Specifically, the compound represented by Formula 1 is one of the following compounds, but is not limited thereto.

.

.

Specifically, the compound represented by Formula 2 may be one of the following compounds, but is not limited thereto.

.

.

Hereinafter, examples of the synthesis of the compounds represented by Chemical Formulas 1 and 2 according to the present invention and manufacturing examples of organic electric devices will be specifically described with reference to Examples, but the present invention is not limited to the following Examples.

[ Synthetic example 1] Formula 1

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

<Scheme 1>

The compounds belonging to Sub 1 of Scheme 1 may be the following compounds, but are not limited thereto.

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

[Table 1]

The compound belonging to Sub 2 of Scheme 1 may be the following compound, but is not limited thereto.

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

[Table 2]

1.Sub 1's Synthetic example

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

<Reaction Scheme 2>

Sub 1-3 Synthetic example

2-bromonaphtho[2,3-b]benzofuran (35.4g, 119.13mmol) bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (33.28g, 131.04mmol), PdCl ₂ (dppf) (2.92g, 3.57mmol), KOAc (35.07g, 357.40mmol), and DMF (596ml) were added, followed by stirring under reflux. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated, and then the resulting organic material was separated by a silica gel column and recrystallized to obtain 34.86 g of product (yield: 85%).

Sub 1-21 Synthetic example

8-bromobenzo[b]naphtho[2,3-d]thiophene (35.40g, 113.02mmol) bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (31.57g, 124.33mmol), PdCl ₂ ( dppf) (2.77g, 3.39mmol), KOAc (33.28g, 339.07mmol), and DMF (565ml) were added, and the reaction was carried out in the same manner as in the synthesis method of 1-3 to obtain the product 33.39g (yield: 82%). .

Sub 1-37 Synthetic example

(1) Sub 1-37a synthesis

4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-2-yl)-1,3,2-dioxaborolane (60g, 174.31mmol), 1-bromo-4-iodonaphthalene ( 69.65g, 209.17mmol), Pd(PPh3)4 (8.06g, 6.97mmol), K2CO3 (72.27g, 522.92mmol), THF (639ml), and water (320ml) were added, followed by reflux with stirring. When the reaction was completed, the organic layer was concentrated after extraction with ether and water, dried over MgSO ₄ and concentrated, and the resulting organic material was separated by a silica gel column and recrystallized to obtain 45.01 g of product (yield: 61%).

(2) Sub 1-37 synthesis

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (29.70g, 116.96mmol), PdCl ₂ (dppf) (2.60g, 3.19mmol), KOAc to Sub 1-37a (45.01g, 106.33mmol) (31.31g, 318.99mmol), DMF (532ml) was added, and the reaction proceeded in the same manner as in the synthesis method of 1-3 to obtain 39.01g of product (yield: 78%).

Sub 1-68 Synthetic example

(1) Sub 1-68a synthesis

1-bromo-8-iododibenzo[4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-2-yl)-1,3,2-dioxaborolane (60g, 174.31mmol)] b,d]thiophene (81.38g, 209.17mmol), Pd(PPh ₃ ) ₄ (8.06g, 6.97mmol), K ₂ CO ₃ (72.27g, 522.92mmol), THF (639ml), water (320ml) added Then, the reaction was performed in the same manner as in the synthesis method of Sub 1-37a to obtain 56.82 g of a product (yield: 68%).

(2) Sub 1-68 synthesis

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (33.11g, 130.38mmol), PdCl ₂ (dppf) on Sub 1-68a (56.82g, 118.53mmol) (2.90g, 3.56mmol), KOAc (34.90g, 355.58mmol), DMF (593ml) was added, and the reaction was carried out in the same manner as in the synthesis method of 1-3 to obtain product 46.80g (yield: 75%). .

Sub 1-98 Synthetic example

(1) Sub 1-98a synthesis

1-bromo- in 2-(benzo[b]naphtho[2,3-d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (60g, 166.54mmol) 5-iodonaphthalene (66.54g, 199.84mmol), Pd(PPh ₃ ) ₄ (7.70g, 6.66mmol), K ₂ CO ₃ (69.05g, 499.61mmol), THF (611ml), water (305ml) was added, The reaction was performed in the same manner as in the synthesis method of Sub 1-37a to obtain 46.83 g of product (yield: 64%).

(2) Sub 1-98 synthesis

1-98a (46.83g, 106.58mmol) bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (29.77g, 117.24mmol), PdCl ₂ (dppf) (2.61g, 3.20mmol), KOAc (31.38g, 319.75mmol), DMF (533ml) was added, and the reaction was carried out in the same manner as in the synthesis method of 1-3 to obtain the product 37.33g (yield: 72%). .

6. Sub 1-111 Synthetic example

(1) Sub 1-111a synthesis

1-bromo- in 2-(benzo[b]naphtho[2,3-d]thiophen-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (60g, 166.54mmol) 8-iododibenzo[b,d]thiophene (77.75g, 199.84mmol), Pd(PPh ₃ ) ₄ (7.70g, 6.66mmol), K ₂ CO ₃ (69.05g, 499.61mmol), THF (611ml), water ( 305 ml) was added, and the reaction proceeded in the same manner as in the synthesis method of Sub 1-37a to obtain 54.46 g (yield: 66%) of the product.

(2) Sub 1-111 synthesis

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (30.70g, 120.91mmol), PdCl in Sub 1-111a (54.46g, 109.92mmol)₂(dppf) (2.69g, 3.30mmol), KOAc (32.36g, 329.76mmol), and DMF (550ml) were added, and the reaction was carried out in the same manner as in the synthesis method of 1-3 to obtain the product 41.15g (yield: 69%). .

2. Synthesis Example of Sub 2

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

<Scheme 3>

Sub 2-2 Synthetic example

2,4-dichloro-6-phenyl-1,3,5-triazine (35.4g, 156.60mmol) to [1,1'-biphenyl]-3-ylboronic acid (31.01g, 156.60mmol), Pd(PPh ₃ ) ₄ (7.24g, 6.26mmol), K ₂ CO ₃ (64.93g, 469.79mmol), THF (522ml), and water (261ml) were added, followed by reflux with stirring. When the reaction is completed, the organic layer is concentrated after extraction with ether and water, then dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 43.07 g (yield: 80%) of the product.

Sub 2-6 Synthetic example

2,4-dichloro-6-phenyl-1,3,5-triazine (35.4g, 156.60mmol) naphthalen-1-ylboronic acid (26.93g, 156.60mmol), Pd(PPh ₃ ) ₄ (7.24g, 6.26mmol), K ₂ CO ₃ (64.93g, 469.79mmol), THF (522ml), and water (261ml) were added and the reaction was carried out in the same manner as the synthesis method for Sub 2-2 above to give the product 36.82 g (Yield: 74%).

Sub 2-22 Synthetic example

Dibenzo[b,d]thiophen-4-ylboronic acid in 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (35.4g, 117.16mmol) (26.72g, 117.16mmol), Pd(PPh ₃ ) ₄ (5.42g, 4.69mmol), K ₂ CO ₃ (48.58g, 351.47mmol), THF (391ml), water (195ml) was added and the Sub 2- The reaction was conducted in the same manner as in the synthesis method of 2 to obtain 40.06 g of product (yield: 76%).

Sub 2-24 Synthetic example

Dibenzo[b,d]furan-1-ylboronic acid (33.20 g, 156.60 mmol), Pd(PPh ₃ ) in 2,4-dichloro-6-phenyl-1,3,5-triazine (35.4g, 156.60mmol) ₄ (7.24 g, 6.26 mmol), K ₂ CO ₃ (64.93 g, 469.79 mmol), THF (522 ml), and water (261 ml) were added and the reaction was carried out in the same manner as in the synthesis method for Sub 2-2, to give the product 38.66 g (Yield: 69%).

Sub 2-47 Synthetic example

2,4-dichloro-6-phenyl-1,3,5-triazine (35.4g, 156.60mmol) benzo[b]naphtho[2,1-d]thiophen-5-ylboronic acid (43.55 g, 156.60 mmol) , Pd(PPh ₃ ) ₄ (7.24 g, 6.26 mmol), K ₂ CO ₃ (64.93 g, 469.79 mmol), THF (522 ml), water (261 ml) was added and in the same manner as in the synthesis method of Sub 2-2. The reaction proceeded to obtain 19.58 g of product (yield: 45%).

3. Final compound Synthetic example

1-6 Synthetic example

Sub 1-6 (56.7g, 164.72mmol) was put in a round bottom flask, dissolved in THF (604mL), Sub 2-3 (67.96 g, 197.66 mmol), Pd(PPh ₃ ) ₄ (7.61 g, 6.59 mmol) , K ₂ CO ₃ (68.30 g, 494.16 mmol), water (302 mL) was added, followed by stirring under reflux. After the reaction was completed, the mixture was extracted with ether and water, and the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was separated by a silica gel column and recrystallized to obtain 64.93 g of product. (Yield 75%)

1-46 Synthetic example

THF (604 mL), Sub 2-22 (88.94 g, 197.66 mmol), Pd(PPh ₃ ) ₄ (7.61 g, 6.59 mmol), K ₂ CO ₃ (68.30) to Sub 1-9 (56.7 g, 164.72 mmol) g, 494.16 mmol), and after adding water (302 mL), the reaction was performed in the same manner as in the above 1-6 synthesis method to obtain 81.17 g of the product. (Yield 73%)

1-81 Synthetic example

THF (495 mL), Sub 2-65 (70.24 g, 161.88 mmol), Pd(PPh ₃ ) ₄ (6.24 g, 5.40 mmol), K ₂ CO ₃ (55.93) to Sub 1-29 (56.7 g, 134.90 mmol) g, 404.69 mmol), and after adding water (247 mL), the reaction was performed in the same manner as in the above 1-6 synthesis method to obtain 59.73 g of the product. (Yield: 64%)

1-92 Synthetic example

THF (442 mL), Sub 2-6 (45.97 g, 144.65 mmol), Pd(PPh ₃ ) ₄ (5.57 g, 4.82 mmol), K ₂ CO ₃ (49.98) to Sub 1-38 (56.7 g, 120.54 mmol) g, 361.62 mmol), and after adding water (221 mL), the reaction was performed in the same manner as in the above 1-6 synthesis method to obtain 65.62 g of the product. (Yield: 87%)

1-122 Synthetic example

THF (407 mL), Sub 2-6 (42.36 g, 133.31 mmol), Pd(PPh ₃ ) ₄ (5.13 g, 4.44 mmol), K ₂ CO ₃ (46.06) in Sub 1-67 (56.7 g, 111.09 mmol) g, 333.27 mmol) and water (204 mL) were added, and then the reaction was performed in the same manner as in the above 1-6 synthesis method to obtain 59.17 g of the product. (Yield: 80%)

1-148 Synthetic example

THF (427 mL), Sub 2-6 (44.45 g, 139.87 mmol), Pd(PPh ₃ ) ₄ (5.39 g, 4.66 mmol), K ₂ CO ₃ (48.33) to Sub 1-97 (56.7 g, 116.56 mmol). g, 349.68 mmol), and after adding water (214 mL), the reaction was performed in the same manner as in the above 1-6 synthesis method to obtain 62.84 g of the product. (Yield 84%)

1-157 Synthetic example

THF (395 mL), Sub 2-6 (41.07 g, 129.24 mmol), Pd(PPh ₃ ) ₄ (4.98 g, 4.31 mmol), K ₂ CO ₃ (44.66) to Sub 1-106 (56.7 g, 107.70 mmol). g, 323.10 mmol), and after adding water (197 mL), the reaction was performed in the same manner as in the above 1-6 synthesis method to obtain 59.48 g of product. (Yield 81%)

FD-MS values of the compounds 1-1 to 1-176 of the present invention synthesized in the same manner as in the synthesis example are shown in Table 3 below.

[Table 3]

[ Synthetic example 2] Formula 2

The compound represented by Formula 2 of the present invention (Final product 2) may be prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 4 below, but is not limited thereto.

<Reaction Scheme 4>

The compounds belonging to Sub 3 of Scheme 4 are as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 3 are shown in Table 4 below.

[Table 4]

The compounds belonging to Sub 4 of Scheme 4 are as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 4 are shown in Table 5 below.

[Table 5]

1.Sub 3's Synthetic example

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

<Reaction Scheme 4-1>

Synthesis Example of Sub 3-c(1)

After dissolving 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in DMF 980 mL, bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), KOAc ( 41.3 g, 420 mmol) was added in order and stirred for 24 hours, and the obtained intermediate product was separated by a silica gel column and recrystallized to obtain 35.2 g (68%) of the final compound.

Synthesis Example of Sub 3-c(2)

After dissolving 2-bromo-9-phenyl-9H-carbazole (76.78 g, 238.3 mmol) in 980 mL of DMF, bis(pinacolato)diboron (66.57 g, 262.1 mmol), Pd(dppf)Cl ₂ (5.84 g, 7.1 mmol), KOAc (70.16 g, 714.9 mmol) was added and stirred for 24 hours, and the obtained intermediate product was separated by a silica gel column and recrystallized to obtain 73.92 g (yield: 84%) of the final compound.

Sub 3-3 Synthetic example

After dissolving Sub 3-c(2) (29.5 g, 80 mmol) in 360 mL of THF, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol) , NaOH (9.6 g, 240mmol), 180 mL of water was added and stirred to reflux. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 22.9 g (72%) of the product.

Synthesis Example of Sub 3-5

Sub 3-c(2) (73.92 g, 200.2 mmol) was dissolved in round bottom flask with THF 880 mL, and then 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd(PPh ₃ ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol), 440 mL of water was added and stirred to reflux. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 55.8 g of product (yield: 70%).

Synthesis Example of Sub 3-10

After dissolving Sub 3-c(1) (29.5 g, 80 mmol) in 360 mL of THF, 3-bromo-3'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol), and 180 mL of water were added and stirred to reflux. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 26.56 g (70%) of the product.

Synthesis Example of Sub 3-15

After dissolving Sub 3-c(2) (73.92 g, 200.2 mmol) in THF 880 mL in a round bottom flask, 2-bromo-7-iododibenzo[b,d]furan (112.0g, 300.3 mmol), Pd(PPh ₃ ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol), 440 mL of water was added and stirred to reflux. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 72.4 g of product (yield: 74%).

Synthesis Example of Sub 3-22

Sub 3-c(2) (73.92 g, 200.2 mmol) was dissolved in 880 mL of THF in a round bottom flask, 1,3-dibromo-5-iodobenzene (108.65 g, 300.3 mmol), Pd(PPh ₃ ) ₄ (11.6 g, 10 mmol), K ₂ CO ₃ (83 g, 600.6 mmol), 440 mL of water was added and stirred to reflux. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 69.7 g of product (yield: 73%).

2. Sub 4 synthesis example

Sub 4 of Scheme 4 may be synthesized by the following Reaction Scheme 4-2, but is not limited thereto.

<Reaction Scheme 4-2>

Synthesis Example of Sub 4-1

In a round bottom flask, add bromobenzene (37.1 g, 236.2 mmol) and dissolve with toluene (2200 mL), then aniline (20 g, 214.8 mmol), Pd ₂ (dba) ₃ (9.83 g, 10.7 mmol), P( t -Bu ) ₃ (4.34 g, 21.5 mmol), NaO t -Bu (62 g, 644.3 mmol) was added in order and stirred at 100°C. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 28 g of product (yield: 77%).

Synthesis Example of Sub 4-13

3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol) was added to a round bottom flask, dissolved in toluene (1550 mL), and then [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol) , Pd ₂ (dba) ₃ (6.76 g, 7.4 mmol), P( t -Bu) ₃ (3 g, 14.8 mmol), NaO t -Bu (42.6 g, 443.2 mmol) was added and stirred at 100°C. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 37.9 g (yield: 73%) of the product.

3. Synthesis Example of Final Compound

2-10 Synthetic example

Sub 3-5 (20.7 g, 52.0 mmol) was put in a round bottom flask and dissolved in toluene (500 mL), Sub 4-35 (24.5 g, 59.8 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol) ), P( t -Bu) ₃ (1.05 g, 5.2 mmol), NaO t -Bu (13.6 g, 141.8 mmol) was added and stirred at 100°C. When the reaction is completed, the mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 26.48 g (yield: 70%) of the product.

2-37 Synthetic example

Sub 3-6 (20.7 g, 52.0 mmol), toluene (500 mL), Sub 4-1 (8.0 g, 47.3 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), P( t -Bu) ₃ (1.05 g, 5.2 mmol), NaO t -Bu (13.6 g, 141.8 mmol) was carried out in the same manner as in the synthesis method of 2-10 above to obtain 16.1 g (yield: 70%) of the product.

2-54 Synthetic example

(1) Synthesis of Inter_A-1

Sub 3-22 (24.8g, 52.0 mmol), Sub 4-2 (11.6g, 47.3 mmol), toluene (500 mL), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), P( t -Bu) ₃ (1.05 g, 5.2 mmol), NaO t -Bu (13.6 g, 141.8 mmol) was carried out in the same manner as in the synthesis method of 2-10 above to obtain 25.01 g of product Inter_A-1 (yield: 62%).

(2) Synthesis of 2-54

Inter_A-1 (20.5 g, 32 mmol), Sub 4-13 (10.1 g, 36.7 mmol), toluene (305 mL), Pd ₂ (dba) ₃ (1.5 g, 1.6 mmol), P( t -Bu) ₃ (0.65 g, 3.2 mmol), NaO t -Bu (8.4 g, 87.2 mmol) was carried out in the same manner as in the synthesis method of 2-10 to obtain 19.7 g (yield: 74%) of product 2-54.

2-73 Synthetic example

Sub 3-33 (8.73 g, 22 mmol), Sub 4-46 (9.1 g, 25.2 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), P(t-Bu) ₃ (0.4 g, 2.2 mmol), NaO t -Bu (5.74 g, 60 mmol), and toluene (210 mL) were carried out in the same manner as in the synthesis method of 2-10 above to obtain 12.7 g of product 2-73 (yield: 85%).

2-86 Synthetic example

Sub 3-34 (12.2 g, 22 mmol), Sub 4-12 (12.3 g, 25.4 mmol), Pd ₂ (dba) ₃ (1.0 g, 1.1 mmol), P(t-Bu) ₃ (0.4 g, 2.2 mmol), NaO t -Bu (5.8 g, 60 mmol), toluene (210 mL) was carried out in the same manner as in the synthesis method of 2-10, to obtain 17.1 g (yield: 81%) of product 2-86.

2-128 Synthetic example

Sub 3-35 (13.9 g, 24.1 mmol), Sub 4-16 (12.1 g, 55.4 mmol), Pd ₂ (dba) ₃ (2.2 g, 2.4 mmol), P(t-Bu) ₃ (1 g, 4.8 mmol), NaO t -Bu (8.3 g, 86.7 mmol), toluene (260 mL) was carried out in the same manner as in the synthesis method of 2-10 above to obtain 16.5 g of product 2-128 (yield: 80%).

The FD-MS values of the compounds 2-1 to 2-136 of the present invention synthesized by the above synthesis method are shown in Table 6 below.

[Table 6]

Manufacturing evaluation of organic electric devices

[Example 1] Red organic light emitting device

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

Next, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer, wherein Compound 1-19 of the present invention was used as a host, and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter (piq) ₂ Ir(acac)) was used. Abbreviation) was used, but the host and the dopant were used in a weight ratio of 95:5.

Next, on the light emitting layer, (1,1'-bisphenyl)-4-oleito)bis(2-methyl-8-quinolineoleito)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10 nm. A hole blocking layer was formed, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter abbreviated as BeBq ₂ ) was formed thereon to form a 40 nm thick electron transport layer. Subsequently, an organic electroluminescent device was manufactured by depositing LiF on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 13]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 7 was used instead of Compound 1-19 as the host material of the light emitting layer.

[ Comparative example 1] to [ Comparative example 5]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following Comparative Compounds 1 to 5 was used instead of Compound 1-19 of the present invention as the host material of the light emitting layer.

<Comparative compound 1> <Comparative compound 2> <Comparative compound 3>

<Comparative compound 4> <Comparative compound 5>

Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a net bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 13 and Comparative Examples 1 to 5 of the present invention. , T95 life was measured using a life measurement equipment of Max Science at 2500 cd/m ² standard luminance. The measurement results are shown in Table 7 below.

[Table 7]

From Table 7, the device (Examples 1 to 13) using the compound represented by Formula 1-F or 1-G of the present invention as the phosphorescent host material of the light-emitting layer is used for the phosphorescence of Comparative Compound 1 to Comparative Compound 5 in the light-emitting layer. It can be seen that the electrical properties are significantly improved than the devices used as hosts (Comparative Examples 1 to 5).

Comparative Compounds 1 to 5 and the compounds of the present invention are similar in that the basic skeleton includes a triazine and an aromatic ring fused heterocyclic ring, but Comparative Compound 1 is triazine and benzo[b]naphtho[2,3-d ]Furan (benzo[b]naphtho[2,3-d]thiophene) directly binds, and Comparative Compound 2 is triazine and benzo[b]naphtho[2,3-d]furan (benzo[b]naphtho[2) ,3-d]thiophene) is connected to the phenyl linkage group is different from the compound of the present invention. In addition, Comparative Compound 3 is similar to Comparative Compound 2 as a whole, but the difference is that benzo[b]naphtho[2,1-d]furan is linked to triazine. have. And the comparative compound 4 is similar to the compound (Formula 1-F) of the present invention having a tricyclic linking group between the triazine and the 4 ring, but the difference is that the hetero element of the 4 ring heterocycle connected by the triazine and the linker is N. , Comparative compound 5 is a phenyl-naphthyl linkage group introduced between benzo[b]naphtho[2,3-d]furan (benzo[b]naphtho[2,3-d]thiophene) and triazine, and triazine The difference is that the naphthyl is coupled to the ortho position.

When comparing Comparative Examples 1 to 3, triazine and benzo are compared to Comparative Compound 1 (hereinafter also referred to as'Trz-fused DBF') in which triazine and benzo[b]naphtho[2,3-d]furan are directly bonded. When using comparative compounds 2 and 3 (hereinafter, also referred to as'Trz-L-fused DBF') as a host in which a coupling group was introduced between naphthofurans, the electrical properties of the device were better.

Comparing Comparative Example 2 and Comparative Example 3, the point that the aromatic ring additionally has a fused form of dibenzofuran is the same, but the comparison includes benzo[b]naphtho[2,3-d]furan When the compound 2 was used, the electrical properties were better than those of the comparative compound 3 containing benzo[b]naphtho[2,1-d]furan.

Therefore, it can be seen that the condensed heterocyclic ring attached to the triazine has a linear condensed structure, and the introduction of a linking group between the triazine and the tetracyclic heterocycle affects the performance of the device. From this, it can be seen that the difference in structure and structure of the compound affects the electrical properties of the device.

Comparative Compound 2 and Comparative Compound 5 are identical in that the linking group is introduced between triazine and benzo[b]naphtho[2,3-d]furan, but the linking groups are phenyl and phenyl-naphthyl, respectively. Example 2 was slightly improved in terms of efficiency of the device than Comparative Example 5, but showed a deteriorated result in terms of life. This is because the efficiency of the device was lowered due to the change in energy level due to the structural properties of the phenyl-naphthyl, which is the comparative compound 5 linker, but it seems to be because the molecular weight of the compound was increased to improve the life.

On the other hand, in the case of Comparative Compound 4 having a specific heterocyclic group as a linking group between the triazine and the condensed heterocycle, the thermal stability of the compound increases by having a heterocyclic group linking group, thereby increasing the Electrical properties were improved.

Therefore, when comparing the compounds of the present invention with Comparative Examples 1 to 5, the condensed heterocyclic ring having a triazine and linear structure is mediated by a linker of a less bent structure (a structure bonded at a meta- or para- position rather than an ortho-). Thus, it can be confirmed that they exhibit the best performance when they are interconnected and a specific substituent such as dibenzothiophene or dibenzofuran is introduced as a linker.

Compounds of the present invention represented by Formula 1-F or Formula 1-G of the present invention include triazine and benzo[b]naphtho[2,3-d]thiophene or benzo[b]naphtho[2,3-d] A linker must exist between furans (hereinafter also referred to as'fused DBT/DBF'), and specific linking groups such as naphthyl, dibenzofuran, and dibenzothiophene are introduced into the linker, thereby making the device more than Comparative Examples 1 to 5 The properties were significantly improved.

That is, the compound represented by Chemical Formula 1-G of the present invention (compounds 1-91, 1-92, 1-103, 1-148, 1-149) has a naphthalene as a linking group between triazine and fused DBT/DBF. In the case, the properties of the device were significantly improved compared to the comparative compound 1 in which triazine and fused DBT/DBF are connected by a single bond, comparative compound 2 connected by a phenyl linkage group, and comparative compound 5 connected by a phenyl-naphthyl linkage.

This can be explained by the LUMO value of each compound. Table 8 below shows the LUMO values of Comparative Compounds 1, 2, 5 and Compound 1-103 of the present invention.

[Table 8]

Referring to Table 8 above, among the comparative compounds, the LUMO level of the comparative compound 2 is the lowest, and the compound of the present invention has a lower LUMO level (deep) than the comparative compound 2.

Therefore, it can be seen that when the phenyl linker is present, the LUMO level is lower than when the linker is not present, and the LUMO level is lower when the naphthalene linker is used like the compound of the present invention as compared to the phenyl linker. In addition, it can be seen that the LUMO level of Example Compound 1-103 of the present invention containing meta-naphthyl as a linker is lower than that of Comparative Compound 5 comprising ortho-naphthyl as a linker.

This suggests that the physical properties of the compound vary significantly depending on the type of the linking group and the degree of bending of the molecule, and in the case of the compound represented by the formula 1-G of the present invention, the electrons in the light emitting layer compared to the comparative compounds 1, 2, 5 It is considered that the device characteristics are improved because it has an appropriate LUMO level that is easy to move over.

In addition, the compounds represented by Formula 1-F of the present invention (Compounds 1-121, 1-122, 1-158, 1-160, 1-172, 1-173, 1-174) are triazine and fused DBT/DBF In between, specific connectors such as DBF and DBT are introduced. When using a compound in which such a specific linking group was introduced as a host (Examples 4, 5, 9 to 13), the life of the device was improved as compared to Comparative Compound 4, whereby condensation in the compound represented by Formula 1-F of the present invention It can be seen that the life of the device is improved when the hetero element of the hetero ring is O or S rather than N.

In addition, when the compound represented by Formula 1-G of the present invention was used as a host (Examples 1 to 3 and Examples 6 to 8), a compound represented by Formula 1-F of the present invention was used (Example 4, 5, 9~13) The lifetime of the device was improved, which seems to be due to the increased thermal stability of the compound due to the lower deposition temperature due to the larger molecular weight of Formula 1-F.

On the other hand, in the case of Examples 12 and 13 of the present invention, the life of the device was remarkably improved, whereby hydrogen (H) was added to the benzene ring of the 4-ring (benzonaphthothiophene, benzonaphthofuran) bound to the triazine. It can be confirmed that the properties of the organic electric device are improved when the substituents of are combined. This has a lower deposition temperature because it forms a three-dimensional structure compared to the case where hydrogen is substituted by a substituent other than hydrogen (H) attached to the 4-ring benzene ring bound to the triazine, and the glass transition temperature ( It seems that Tg) is improved to suppress decomposition during deposition and to increase thermal stability.

Therefore, from the results of Table 7, the energy level (HOMO, LUMO, T1, etc.) of the compound may be significantly changed according to the type of the substituent constituting the compound, the position of substitution, and the type of hetero atom, and the difference in the compound properties It suggests that different device results can be derived by acting as a major factor in improving device performance during device deposition. Moreover, among the compounds having a basic skeleton of a DBT/DBF type fused with triazine, such as the compounds represented by Formula 1-F and Formula 1-G of the present invention, there are naphthyl and a specific heterosubstituted group as a linking group, and fused DBT/DBF It can be seen that 2,3-fused DBF/DBT having a linear condensation direction is a structure suitable for improving device performance.

[ Example 14] Emitting layer Mixed phosphorescent host

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

Next, a 30 nm-thick light-emitting layer was formed on the hole transport layer, wherein a mixture of compounds 1-61 (first host) and compounds 2-9 (second host) of the present invention in a weight ratio of 3:7 was hosted. Furnace, (piq) ₂ Ir(acac) was used as a dopant, but a host and a dopant were used in a weight ratio of 95:5.

Next, a hole blocking layer was formed by vacuum-depositing BAlq to a thickness of 10 nm on the light-emitting layer, and BeBq ₂ was formed to a thickness of 50 nm to form an electron transport layer. Subsequently, an organic electroluminescent device was manufactured by depositing LiF on the electron transport layer to a thickness of 0.2 nm, and then depositing Al on a thickness of 150 nm to form a cathode.

[ Example 15] to [ Example 73]

An organic electroluminescent device was manufactured in the same manner as in Example 14, except that a mixture of the first host compound and the second host compound shown in Table 9 below was used as a host material for the light emitting layer.

[ Comparative example 6] to [ Comparative example 9]

Organic electroluminescence in the same manner as in Example 14, except that only Compound 1-61, Compound 1-92, Compound 1-145, or Compound 1-160 was used as the host material of the light emitting layer, as shown in Table 9 below. The device was fabricated.

[ Comparative example 10] and [ Comparative example 11]

An organic electroluminescent device was manufactured in the same manner as in Example 14, except that a mixture of Comparative Compounds 6 and 7 or a mixture of Comparative Compounds 6 and 8 was used as the host material of the light emitting layer, as shown in Table 9 below.

The electro-luminescence (EL) characteristics of the organic electroluminescent devices manufactured by Examples 14 to 73 and Comparative Examples 6 to 11 of the present invention were applied to PR-650 by Photoresearch by applying a direct bias DC voltage. The T95 lifespan was measured through the life measurement equipment of Mac Science at a reference luminance of 2500 cd/m ² , and the measurement results are shown in Table 9 below.

<Comparative compound 5> <Comparative compound 6> <Comparative Compound 7>

[Table 9]

When using the compound for an organic electroluminescent device of the present invention represented by Formula 1 and Formula 2 from Table 9 as a phosphorescent host (Examples 14 to 73), a single material is used (Comparative Examples 6 to 9), and It can be seen that the driving voltage, efficiency and lifespan are significantly improved compared to the devices (Comparative Examples 10 and 11) used by mixing Comparative Compounds 6-8.

That is, in Comparative Example 10 and Comparative Example 11 in which two compounds were mixed and used as a host compared to Comparative Examples 6 to 9 using the compound of the present invention represented by Formula 1 as a single host, the driving voltage was lowered. It can be seen that the efficiency is improved, and in the case of Examples 14 to 73 in which the compounds of the present invention are mixed, it can be seen that device characteristics are significantly improved.

From these results, the inventors of the present invention determined that the mixture of the substance of Formula 1 and the substance of Formula 2 has novel characteristics other than those of each substance, and uses each of these substances and mixtures to PL The lifetime was measured. As a result, in the case of a mixture of Formula 1 and Formula 2 of the present invention, it was confirmed that a new PL wavelength was formed unlike that of a single compound.

When the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each material, but also electrons and holes are moved by a new exciplex having a new energy level formed due to mixing. Or, it is judged that the efficiency and lifetime have increased due to energy transfer. This can be said to be an important example of using the mixture of the present invention to show the exciplex energy transfer and emission process of the mixed thin film.

In addition, when the compound of the present invention is used in combination, the reason why the device characteristics are excellent is that the hole characteristics are strong in the polycyclic compound represented by Chemical Formula 1, which has characteristics such as electron stability as well as high hole T1. When the compound represented by the formula (2) is mixed, the electron blocking ability is improved due to the high T1 and high LUMO energy values, and more holes move quickly and easily in the light emitting layer, and accordingly, charges in the light emitting layer of holes and electrons (charge) This is because light emission is well achieved inside the light emitting layer rather than the hole transport layer interface due to an increase in balance). As a result, it is determined that deterioration is also reduced at the hole transport layer interface to maximize the driving voltage, efficiency, and lifetime of the entire device. That is, the combination of compounds represented by Formulas 1 and 2 electrochemically synergizes the entire device. It is thought that the performance was improved.

[ Example 74] and [ Example 76]

An organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound 1-92 and Compound 2-54 of the present invention were used in a weight ratio of 7:3 as described in Table 10 below.

[ Example 75] and [ Example 77]

An organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound 1-121 and Compound 2-117 of the present invention were used in a weight ratio of 5:5 as described in Table 10 below.

Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a direct bias DC voltage to the organic electroluminescent devices manufactured in Examples 74 to 77 of the present invention, and based on 2500 cd/m ² The T95 life was measured by the life measurement equipment of Max Science at luminance. The results are shown in Table 10 below. Example 46 and Example 63 are the result of measuring the device characteristics when the first host and the second host are mixed in a ratio of 3:7 as in Table 9.

Table 10

From Table 10, when the mixing ratio is 3:7 when compound 1-92 and compound 2-54 are mixed or compound 1-121 and compound 2-117 are used, the driving voltage, efficiency, and life are the best. It can be seen that the device characteristics decrease as the mixing amount of the first host increases. This is considered to be because charge balance in the light emitting layer is maximized when the amount of the compound represented by Formula 2 (second host) is relatively stronger than the compound represented by Formula 1 (first host).

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed herein are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the claims below, and all technologies within the equivalent range should be interpreted as being included in the scope of the present invention.

100: organic electrical element 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 (23)

In the organic electrical device including a first electrode, a second electrode and an organic material layer formed between the first electrode and the second electrode,
The organic material layer includes a phosphorescent light-emitting layer, the host of the phosphorescent light-emitting layer is an organic electric device comprising a first compound represented by the following formula (1) and a second compound represented by the following formula (2):
<Formula 1><Formula2>

In the above formula,
X ₁ is O or S,
Ar ¹ and Ar ² are independently of each other C ₆ ~ C ₁₈ aryl group; Fluorenyl group; C ₂ ~ C ₁₆ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group,
Ar ³ to Ar ⁵ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group, Ar ⁴ and Ar ⁵ may be bonded to each other to form a ring,
L ¹ to L ⁴ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C ₆ ~ C ₆₀ ,
R ¹ to R ³ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
a is an integer from 0 to 9, b is an integer from 0 to 4, c is an integer from 0 to 3, and each of them is an integer of 2 or more, each of a plurality of R ^1, each of a plurality of R ^2, each of a plurality of R ³ Are the same or different from each other,
n is an integer of 1 to 3, and when n is an integer of 2 or more, each of a plurality of Ar ^{4 and} each of a plurality of Ar ⁵ are the same or different from each other,
L'is independently of each other a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C ₆ ~ C ₆₀ ,
R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C ₆ ~ C ₆₀ . According to claim 1,
The L ¹ to L ⁴ are each independently an organic electric device characterized in that one of the following formulas b-1 to b-13:
<Formula b-1><Formulab-2><Formulab-3><Formulab-4>

<Formula b-5><Formulab-6><Formulab-7><Formulab-8>

<Formula b-9><Formulab-10>

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

In the above formula,
R ⁵ to R ⁷ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
Y is N-(L ^a -Ar ^a ), O, S or C(R')(R"),
Z ¹ to Z ³ are each independently C, C(R') or N, and at least one of Z ¹ to Z ³ is N,
f is an integer from 0 to 6, e, g, h, and i are integers from 0 to 4, j, k are integers from 0 to 3, l is an integer from 0 to 2, and m is 0, respectively. An integer of 3 to 3, each of which is an integer of 2 or more, each of a plurality of R ^5, each of a plurality of R ^6, each of a plurality of R ⁷ is the same or different from each other,
R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of,
In C(R')(R"), R'and R" may combine with each other to form a ring, and in C(R'), adjacent R's may combine with each other to form a ring,
Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. According to claim 1,
Formula 1 is an organic electric device characterized in that represented by one of the following formula 1-A to formula 1-D:
<Formula 1-A><Formula1-B>

<Formula 1-C><Formula1-D>

In the above formula, Ar ¹ , Ar ² , L ¹ ~L ³ , X ₁ , R ¹ , a are as defined in claim 1. According to claim 1,
Formula 1 is an organic electric device characterized in that represented by one of the following formula 1-E to formula 1-G:
<Formula 1-E><Formula1-F>

<Formula 1-G>

In the above formula, Ar ¹ , Ar ² , L ¹ ~L ³ , X ₁ , R ¹ , a are the same as defined in claim 1,
X ₂ and X ₃ are each independently O or S,
R ⁴ and R ⁵ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
d is an integer from 0 to 7, e is an integer from 0 to 6, and when each of them is an integer of 2 or more, each of the plurality of R ^{4 and} each of the plurality of R ⁵ are the same or different from each other,
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by the following formula 2-A or formula 2-B:
<Formula 2-A><Formula2-B>

In the above formula, L ⁴ , Ar ³ to Ar ⁵ , R ² , R ³ , b and c are as defined in claim 1. According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by one of the following formula 2-C to formula 2-F:
<Formula 2-C><Formula2-D>

<Formula 2-E><Formula2-F>

In the above formula, Ar ³ to Ar ⁵ , R ² , R ³ , b and c are the same as defined in claim 1,
R ¹⁰ to R ¹³ are independently of each other hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L ^a -N(R ^a )(R ^b ); And it is selected from the group consisting of a combination of, adjacent groups can be combined with each other to form a ring,
k and l are each integers of 0 to 4, n and m are integers of 0 to 3, respectively, when each of these is an integer of 2 or more, each of a plurality of R ¹⁰ each, a plurality of R ¹¹ each, a plurality of R ¹² each, a plurality Each of R ¹³ is the same or different from each other,
V is N-(L ^a -Ar ^a ), O, S or C(R')(R"),
R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₂₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, R'and R" may be bonded to each other to form a ring,
Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by one of the following formula 2-G to formula 2-R:
<Formula 2-G><Formula2-H><Formula2-I>

<Formula 2-J><Formula2-K><Formula2-L>

<Formula 2-M><Formula2-N><Formula2-O>

<Formula 2-P><Formula2-Q><Formula2-R>

In the above formula, Ar ³ to Ar ⁵ , L ⁴ , R ² , R ³ , b and c are as defined in claim 1. According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by the following formula 3-S or formula 3-T:
<Formula 2-S><Formula2-T>

In the above formula, Ar ³ to Ar ⁵ , L ⁴ , R ² , R ³ , b and c are as defined in claim 1. According to claim 1,
An organic electric device, characterized in that n = 1 in the formula (2). According to claim 1,
An organic electric device, characterized in that n = 2 in the formula (2). According to claim 1,
The formula 2 is an organic electric device, characterized in that represented by the following formula 3-U:
<Formula 2-U>

In the above formula, Ar ³ , Ar ⁵ , L ⁴ , R ² , R ³ , b, c and n are the same as defined in claim 1,
U is N-(L ^a -Ar ^a ), O, S or C(R')(R"),
R ¹⁴ and R ¹⁵ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; And -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
o is an integer from 0 to 3, p is an integer from 0 to 4, and when each of them is an integer of 2 or more, each of a plurality of R ^{14 and} each of a plurality of R ¹⁵ may be the same or different from each other,
R'and R" are independently of each other hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P at least one heteroatom C ₂ ~ C ₂₀ heterocyclic group containing; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ Alkyl group of; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₃₀ aryloxy group; and -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, R'and R" may be bonded to each other to form a ring,
Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. According to claim 1,
The compound represented by Formula 1 is an organic electric device, characterized in that one of the following compounds:

. According to claim 1,
The compound represented by Formula 2 is one of the following compounds:

. A compound represented by the following Formula 1-F or Formula 1-G:
<Formula 1-F>

<Formula 1-G>

In the above formula,
X ₁ and X ₃ are each independently O or S,
Ar ¹ and Ar ² are independently of each other C ₆ ~ C ₁₈ aryl group; Fluorenyl group; C ₂ ~ C ₁₆ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; And C ₆ ~ C _{30 It} is selected from the group consisting of an aryloxy group,
L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C ₆ ~ C ₆₀ ,
R ¹ is hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
R ⁵ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ^a -N (R ^a ) (R ^b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring,
a is an integer from 0 to 9, e is an integer from 0 to 6, and when each of them is an integer of 2 or more, each of the plurality of R ^{4 and} each of the plurality of R ⁵ are the same or different from each other,
L'is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C ₆ ~ C ₆₀ ,
R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of.
L ^a is ^a single bond independently of each other; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof,
R ^a and R ^b are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And combinations thereof. The method of claim 14,
Formula 1-F is a compound characterized in that represented by one of the following formula:
<Formula 1-F-1><Formula1-F-2>

In the above formula, X ₁ , X ₃ , Ar ¹ , Ar ² , L ¹ , L ² , R ¹ , R ⁵ , a and e are as defined in claim 14. The method of claim 14,
Formula 1-G is a compound characterized in that represented by one of the following formula:
<Formula 1-G-1><Formula1-G-2>

<Formula 1-G-3><Formula1-G-4><Formula1-G-5>

In the above formula, X ₁ , Ar ¹ , Ar ² , L ¹ , L ² , R ¹ and a are as defined in claim 14. The method of claim 14,
The Ar ¹ and Ar ² are compounds, characterized in that different from each other. The method of claim 14,
The Ar ¹ and Ar ² is an aryl group, characterized in that the compound. The method of claim 14,
A compound characterized in that Ar ¹ or Ar ² is a naphthyl group. In the organic electrical device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising a compound represented by the formula 1-F or formula 1-G of claim 14. The method of claim 20,
The organic material layer includes a light emitting layer, and the compound is an organic electric device, characterized in that included in the light emitting layer. A display device comprising the organic electroluminescent device of claim 1 or 20; And
An electronic device comprising; a control unit for driving the display device. The method of claim 22,
The organic electric device is an electronic device characterized in that it is selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

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