KR102072019B1 - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound that can improve the luminous efficiency, stability and life of the device, an organic electric device using the same, and an electronic device thereof.

Description

COMPONENT FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF

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

In general, organic light emitting phenomenon refers to a phenomenon of converting 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, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of 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 element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.

The biggest problem for organic electroluminescent devices is life and efficiency. As the display becomes larger, these efficiency and life problems must be solved.

Efficiency, lifespan, and driving voltage are related to each other.As the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases. It shows a tendency to increase the lifetime.

However, simply improving the organic material layer does not maximize the efficiency. This is because a long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value between each organic material layer and intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved.

In addition, in order to solve the light emission problem in the hole transport layer in the recent organic electroluminescent device, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.

In general, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.

However, in the case of the material used in the hole transport layer, since it has to have a low HOMO value, most have a low T1 value, which causes the exciton generated in the light emitting layer to pass to the hole transport layer, resulting in charge unbalance in the light emitting layer. This causes light emission at the hole transport layer interface.

When the light is emitted from the hole transport layer interface, the color purity and efficiency of the organic electric element is lowered and the lifespan is shortened. Therefore, the development of a light emitting auxiliary layer having a high T1 value and a HOMO level between the hole transport layer HOMO energy level and the light emitting layer HOMO energy level is urgently required.

On the other hand, while delaying the diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. There is a need for development of a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has the property of lowering the uniformity of the surface of the thin film when the device is driven, which has been reported to have a great influence on the device life. In addition, the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, materials forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting auxiliary layer material, a light emitting material, an electron transport material, and an electron injection material, are stable and efficient. Supported by the material should be preceded, but the development of a stable and efficient organic material layer for an organic electric device has not been made enough, and thus, the development of new materials is still required.

An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity and lifetime of an element, an organic electric element using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following formula.

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

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and life of the device can be greatly improved.

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

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

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

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

On the other hand, the terms "halo" or "halogen" as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.

As used herein, the term "alkyl" or "alkyl group" has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.

As used herein, the terms "alkenyl" or "alkynyl" have a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto.

The term "cycloalkyl" as used herein, unless otherwise indicated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.

As used herein, the terms "aryl group" and "arylene group" each have a carbon number of 6 to 60 unless otherwise stated, it is not limited thereto.

In the present invention, an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 3 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.

As used herein, the terms "heterocycloalkyl" and "heterocyclic group" include one or more heteroatoms, unless otherwise indicated, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination. In addition, "heterocyclic group" may mean an alicyclic and / or aromatic including a heteroatom.

As used herein, the term "heteroatom" refers to N, O, S, P and Si unless otherwise stated.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term "saturated or unsaturated ring" as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

In addition, unless otherwise stated, the term "substituted" in the term "substituted or unsubstituted" is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy groups, C ₁ to C ₂₀ alkylamine groups, C ₁ to C ₂₀ alkylthiophene groups, C ₆ to C ₂₀ arylthiophene groups, C ₂ to C ₂₀ alkenyl groups, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ aryl alkenyl group, silane group, boron Group, germanium group, and C ₅ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

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

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110. It is provided with an organic material layer containing a compound represented by the formula (1) between. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic 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 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, and the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound of the present invention may be used as the light emitting layer 150 and / or the light emitting auxiliary layer 151.

Meanwhile, even in the same core, band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions, so the selection of cores and the combination of sub-substituents bound thereto are also very significant. Importantly, long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

As described above, in order to solve the problem of light emission in the hole transport layer in the organic electroluminescent device, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each light emitting layer (R, G, B) It is time to develop different emission auxiliary layers. On the other hand, in the case of the light emitting auxiliary layer, it is very difficult to infer its characteristics when the organic material layer used is different even if a similar core is used because the correlation between the hole transport layer and the light emitting layer (host) must be understood.

Therefore, in the present invention, by forming a light emitting layer or an auxiliary light emitting layer using a compound represented by the formula (1) by optimizing the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interfacial characteristics, etc.) of the organic material, etc. It is possible to improve the life and efficiency of the electrical device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD method. For example, the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon. After forming the organic material layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.

In addition, the organic material layer using a variety of polymer materials is less by a solution or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition method It can be prepared in a number of layers. 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 forming method.

The organic electric element according to the present invention may be a top emission type, a bottom emission type or a double side emission type according to the material used.

In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a device for monochrome or white illumination.

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

Hereinafter, the compound which concerns on one aspect of this invention is demonstrated.

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

In Chemical Formula 1,

The A ring may be an aromatic ring or heterocycle fused to a pentagram ring containing neighboring N (nitrogen). That is, ring A shares one side with a pentagram ring containing N. In addition, the A ring may be monocyclic or polycyclic. In the case of a polycyclic ring, the ring may be fused to each other, a plurality of rings may not be fused to each other, or a ring in which the fused and non-fused forms are mixed. Herein, the aromatic ring and the hetero ring may have 6 to 60 carbon atoms, and preferably 6 to 14 carbon atoms. That is, the A ring may be benzene, naphthalene, phenanthrene, or the like.

In addition, when the A ring is a hetero ring, it may be a hetero ring having 2 to 60 carbon atoms, for example, thiophene, furan, pyridine, indole, quinoline and the like.

In Formula 1, X is CR'R ", NR ', or S and O, where R' and R" are independently an aryl group of C ₆ ~ C ₆₀ to each other; C ₂ ~ C ₆₀ Heterocyclic group; Or an alkyl group of C ₁ to C ₅₀ .

로 표시될 수 있다.In addition, in Formula 1, R ₁

It may be represented as.

L and o are integers of 0 or 1, and l + o may be 1 or more. If l is 0, L means no presence (also called direct bond or single bond).

In the above formula, L may be monovalent or divalent depending on the value of o. For example, when o is 0 and l is 1, L may be monovalent, and when o = l = 1, L may be bivalent. Thus, L is selected from the group of univalent substituents consisting of iv) a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ monovalent heterocyclic group and a fluorenyl group, or ii) C ₆ -C ₆₀ aryl It may be selected from the group of divalent substituents consisting of a ylene group, a C ₂ -C ₆₀ divalent heterocyclic group and a fluorenylene group.

In the above formula, Y is hydrogen, deuterium, tritium, halogen group, -N (Ar ₃ ) (Ar ₄ ), nitro group, nitrile group, amide group, silane group, C ₁ ~ C ₅₀ alkyl group, C ₆ ~ In the group consisting of C ₆₀ aryl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₆₀ heterocyclic group, and C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ aliphatic ring condensed ring group Can be selected.

And p of R <_1> is an integer of 1 or more. In this case, p may be determined according to the A ring. For example, when A ring is a benzene ring, p may be an integer of 1 to 4 since the benzene ring has 4 carbon atoms, and when A ring is naphthyl, 1 to 6 may be used.

In this case, when p is 2 or more, a plurality of R ₁ may be the same as or different from each other. When p is 2 or more, adjacent R ₁ may be bonded to each other to form one or more rings. That is, when p is 2 or more, adjacent R ₁ may be bonded to each other to form a fused form with A ring. Thus, although A ring itself may be a polycyclic ring, even if A ring is a monocyclic ring, substituents R ₁ may be bonded to each other to form a polycyclic ring fused to A ring.

로 표시될 수 있고, 여기서 L, Y, l, o 등은 R₁에서 정의된 것과 동일하게 정의될 수 있다.R ₂ to R ₅ may be defined to be the same as R ₁ . That is, they

It may be represented by, wherein L, Y, l, o and the like may be defined the same as defined in R ₁ .

Meanwhile, in Chemical Formula 1, m and n may be 0 or 1, respectively, but m + n is preferably 1 or more. That is, at least one of Ar ₁ and Ar ₂ should be present.

Meanwhile, Ar ₁ may have different substituent definitions depending on m and n. For example, when m = 0, Ar _{1 corresponds} to a direct bond (that is, Ar ₁ does not exist), and m = 1 and n = 0. Ar ₁ is a C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ aliphatic ring It is selected from the group consisting of monovalent substituents such as condensed ring group, C ₁ ~ C ₅₀ alkyl group and fluorenyl group, and when m = n = 1 Ar ₁ is an arylene group of C ₆ ~ C ₆₀ , C ₂ ~ C ₂₀ alkenylene group, C ₂ to C ₆₀ divalent heterocyclic group, C ₆ to C ₆₀ aromatic ring and C ₃ to C ₆₀ aliphatic ring, C ₂ to C ₂₀ alkylene group and flu It may be selected from the group consisting of a divalent substituent, such as an orylene monomer.

In Formula 1, Ar ₂ is not present when n = 0, and when n = 1 Ar ₂ is a halogen group; Cyano group; Nitro group; Nitrile group; Amide group; Silane group; C ₆ ~ C ₆₀ aryl group; C ₂ -C ₂₀ alkenyl group; C ₂ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; It may be selected from the group of monovalent substituents consisting of a condensed ring group of -N (Ar ₃ ) (Ar ₄ ) and C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ Aliphatic ring.

In this case, Ar ₃ and Ar ₄ are independently of each other C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ heterocyclic group, fluorenyl group, C ₁ ~ C ₅₀ Alkyl group and C ₂ ~ C ₂₀ Al It may be selected from the group consisting of a kenyl group, or Ar ₃ and Ar ₄ may combine with each other to form a heterocycle with N.

Meanwhile, the aromatic ring of the A ring, R ₁ to R ₅ , R ′, R ″ of X, and Ar ₁ to Ar ₄ may be further substituted with other substituents.

Specifically, when the aromatic ring of the A ring, L, Y, Ar ₁ to Ar ₄ , R ′ and R ″ are C ₆ ~ C ₆₀ aryl group, and when Y, Ar ₁ and Ar ₂ are condensed ring groups When C ₆ to C ₆₀ of L and Ar ₁ are an arylene group, these are deuterium; Halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₁ ~ C ₂₀ Alkylamine group; C ₁ ~ C ₂₀ alkyl group of the import; C ₆ -C ₂₀ arylthio group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; A C ₃ -C ₂₀ cycloalkyl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₈ -C ₂₀ arylalkenyl group; Silane group; Boron group; Germanium group; And it may be substituted with one or more substituents selected from the group consisting of C ₂ ~ C ₂₀ heterocyclic group.

In addition, the heterocyclic groups of C ₂ to C ₆₀ of A, L, Y, Ar ₁ to Ar ₄ , R ′, and R ″ may include a halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₆ ~ C ₆₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of an acetylene group.

In addition, the fluorenyl group of L, Ar ₁ , Ar ₃ and Ar _4, the fluorenylene group of L and Ar ₁ is a deuterium, a halogen group, a C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ Alkoxy group, C ₆ -C ₂₀ aryl group, C ₇ -C ₂₀ arylalkyl group, C ₈ -C ₂₀ arylalkenyl group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ heterocyclic group, nitrile It may be substituted with one or more substituents selected from the group consisting of a group and an acetylene group.

Further, the alkenyl group of the Y, Ar ₁ to Ar4, R 'and R "of the C ₁ ~ C ₅₀ alkyl group, and a group of C ₂ ~ C ₂₀ alkylene group of said Ar _1, C ₂ ~ C ₂₀ of; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; C ₂ -C ₂₀ heterocyclic group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of an acetylene group.

Also, the Y, Ar ₁ to alkenylene group, heavy hydrogen of Ar ₄ of C ₂ ~ C ₂₀ alkenyl group, said Ar ₁ of C ₂ ~ C ₂₀ of; Halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₆ ~ C ₆₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; C ₃ -C ₂₀ heterocyclic group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of an acetylene group.

On the other hand, Formula 1 may be represented by one of the following formula.

<Formula 2>

<Formula 3>

<Formula 4>

In Formula 1, when A ring is a benzene ring, it may be represented by Formula 2, in the case where A ring is a benzene ring in Formula 1 and at least one of R ₁ ~ R ₄ is -LN (Ar ₃ ) (Ar ₄ ) In Formula 1, when A ring is benzene ring and (Ar ₂ ) m is -N (Ar ₃ ) (Ar ₄ ) in Formula 1, it may be represented by Formula 4.

In Formulas 2 to 4, R ₁₁ to R ₁₄ are defined in the same manner as in Formula 1) i) R ₁ , or ii) adjacent R ₁₁ and R ₁₂ , adjacent R ₁₂ and R ₁₃ and / or neighbor One R ₁₃ and R _{14 may} combine with each other to form at least one ring. At this time, adjacent pairs of R ₁₁ to R ₁₄ may be bonded to each other, or only some pairs or only one pair may be bonded to each other to form at least one ring, wherein a group not forming a ring is defined in iii). Likewise it can be defined the same as R ₁ .

Meanwhile, in Formulas 2 to 4, Ar ₁ to Ar ₄ , R ₂ to R ₅ , X, L, m, and n may be defined in the same manner as defined in Formula 1.

For example, in Formula 3, L is a single bond; C ₆ ~ C ₆₀ arylene group; C ₂ ~ C ₆₀ Heterocyclic group; And it may be selected from the group consisting of divalent aliphatic hydrocarbon, Ar ₃ and Ar ₄ are independently of each other ⅰ) C ₆ ~ C ₆₀ An aryl group; C ₂ ~ C ₆₀ Heterocyclic group; Fluorenyl groups; Or an alkyl group of C ₁ to C ₅₀ ; and an alkenyl group of C ₂ to C ₂₀ , or ii) Ar ₃ and Ar ₄ may be bonded to each other to form a heterocycle with N.

At this time, the arylene group, heterocyclic group, aliphatic hydrocarbon group of L, Ar ₃ And an aryl group, heterocyclic group, pulluorenyl group, alkyl group and alkenyl group of Ar ₄ may be further substituted with a substituent. For example, they are deuterium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group or a C ₂ to C ₂₀ heterocyclic group substituted with an amine group, C ₁ ~ C ₂₀ coming of the alkyl amine group, C ₁ ~ alkyl group of C _20, C ₆ ~ of the C ₂₀ arylthio group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C of ₂₀ cycloalkyl group, C ₆ -C ₆₀ aryl group; One or more substituents selected from the group consisting of C ₆ to C ₂₀ aryl groups, C ₈ to C ₂₀ arylalkenyl groups, silane groups, boron groups, germanium groups, and C ₃ to C ₂₀ heterocyclic groups substituted with deuterium; It may be substituted by.

In addition, the chemical formula represented by Chemical Formula 1 may be represented by one of the following chemical formulas.

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

<Formula 8> <Formula 9> <Formula 10>

<Formula 11> <Formula 12> <Formula 13>

<Formula 14> <Formula 15>

In Formulas 5 to 15, Ar ₁ to Ar ₄ , R ₁ to R ₅ , m, n, L, X, and p are the same as defined in Formula 1.

In addition, Formula 1 may be represented by one of the following formula.

<Formula 16> <Formula 17> <Formula 18>

<Formula 19> <Formula 20> <Formula 21>

<Formula 22> <Formula 23> <Formula 24>

<Formula 25> <Formula 26> <Formula 27>

In Formulas 16 to 51, Ar ₁ to Ar ₄ , R ′, R ″, m, n, R ₂ to R ₅ And L is the same as defined in formula (1).

Specifically, Formula 1 may be one of the following compounds.

Hereinafter, the synthesis examples of the compounds of the present invention represented by the above formula and the preparation examples of the organic electric element will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

Manufacturing Evaluation of Organic Electrical Device

Synthesis Example

For example, the compound according to the present invention may be prepared by reacting one of Sub 1 or Sub 3 with Sub 2, or by reacting Sub 1 with Sub 4, as shown in Scheme 1 below.

<Scheme 1>

Sub  1 Synthesis Example:

<Scheme 2-a>

(One) Sub  Example of 1-1-1

Examples of Sub 1-1-1 are as follows and their FD-MS values are shown in Table 1, but are not limited thereto.

Table 1

(2) Sub  Synthesis method of 1-1-2

Sub 1-1-1 (1 equivalent) was dissolved in anhydrous Ether, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5M in hexane) (1.1 equivalent) was slowly added dropwise, and then the reaction was carried out for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 ℃ and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1-1-2.

(3) Sub  Synthesis method of 1-1-4

Sub 1-1-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-1-3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After the addition, the mixture was stirred under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-1-4.

(4) Sub  1-1 Synthesis

The obtained Sub 1-1-4 (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-1.

Examples of Sub 1-1 are as follows, FD-MS values are shown in Table 2, but is not limited thereto.

Table 2

<Scheme 2-b>

(One) Sub  Synthesis of 1-2-2

Sub 1-2-1 (1 equiv) was dissolved in anhydrous Ether, the reaction temperature was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and then the reaction was carried out for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 ℃ and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1-2-2.

(2) Sub  1-2-3 Synthesis

After Sub 1-2-2 (1 equivalent) obtained in the above synthesis was dissolved in THF, Sub 1-1-3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was stirred under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain the product Sub 1-2-3.

(3) One- 2 synthesis method

Sub 1-2-3 and (1 equivalent) and triphenylphosphine (2.5 equivalents) obtained in the synthesis were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-2.

Examples of Sub 1-2 are as follows, and FD-MS values are shown in Table 3, but are not limited thereto.

Table 3

<Scheme 2-c>

(One) Sub  Synthesis of 1-3-2

Sub 1-3-1 (1 equiv) was dissolved in anhydrous Ether, the reaction temperature was lowered to -78 ?, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and the reaction was allowed to proceed for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78? And Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, and the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1-3-2.

(2) Sub  1-3-3 Synthesis

After Sub 1-3-2 (1 equivalent) obtained in the above synthesis was dissolved in THF, Sub 1-1-3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was stirred under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-3-3.

(3) Sub  1-3 Synthesis

The obtained Sub 1-3-3 and (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-3.

Examples of Sub 1-3 are as follows, and FD-MS values are shown in Table 4, but are not limited thereto.

Table 4

<Scheme 2-d>

(One) Sub  Synthesis method of 1-4-2

Sub 1-4-1 (1 equiv) was dissolved in anhydrous Ether, the temperature of the reactant was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and then the reaction was carried out for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 ℃ and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub 1-4-2.

(2) Sub  Synthesis of 1-4-3

Sub 1-4-2 (1 equivalent) obtained in the synthesis was dissolved in THF, then Sub 1-1-3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was stirred under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-4-3.

(3) Sub  Synthesis method of 1-4

Sub 1-4-3 and (1 equivalent) and triphenylphosphine (2.5 equivalents) obtained in the above synthesis were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-4.

Examples of Sub 1-4 are as follows, FD-MS values are shown in Table 5, but is not limited thereto.

TABLE 5

Sub  2 Synthesis Example:

Examples of Sub 2 are as follows, FD-MS values are shown in Table 6, but is not limited thereto.

TABLE 6

Sub  3 Synthesis Example:

Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below.

<Scheme 3>

After Sub 3-1 (1 equiv) was dissolved in THF, Sub 3-2 (1.1 equiv), Pd (PPh ₃ ) ₄ (0.03 equiv), NaOH (3 equiv), and water were added thereto, followed by stirring under reflux. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 3.

Examples of Sub 3 are as follows, FD-MS values are shown in Table 7, but is not limited thereto.

TABLE 7

Sub  4 Synthesis Example:

Examples of Sub 4 are as follows, and FD-MS values are shown in Table 8, but are not limited thereto.

TABLE 8

Product  Synthesis example:

Sub 1 or Sub 3 (1 equiv) and Sub 2 or Sub 4 (1.1 equiv) are added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv) and NaO t -Bu (3 equiv) were added respectively, followed by stirring under reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain a final product.

Synthesis Example of 1-9

7,7-dimethyl-7,12-dihydrobenzo [6,7] indeno [1,2-b] indole (5.7 g, 20 mmol) and 5-bromo-2,4-diphenylpyrimidine (7.5 g, 24 mmol) in toluene Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was stirred under reflux at 100 ° C for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 7.2g (70% yield) of the final product.

Synthesis Example of 2-24

12-phenyl-7,12-dihydrobenzo [e] indolo [3,2-b] indole (6.4 g, 20 mmol) and 4-bromo-1,1'-biphenyl (5.6 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was refluxed at 100 ° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 7.2g (74% yield) of the final product.

Synthesis Example of 3-56

14H-phenanthro [9 ', 10': 4,5] thieno [3,2-b] indole (6.5 g, 20 mmol) and 2-bromo-4-phenylquinazoline (6.8 g, 24 mmol) were added to toluene and Pd ₂ ( dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was stirred under reflux at 100 ° C for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 7.5g (71% yield) of the final product.

Synthesis Example of 4-94

10 H-benzofuro [3,2-b] indole (4.1 g, 20 mmol) and 2- (4-bromophenyl) triphenylene (9.2 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was stirred under reflux at 100 ° C for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 6.6 g (65% yield) of the final product.

Synthesis Example of 1-61

N-([1,1'-biphenyl] -4-yl) -N- (4- (7,7-dimethyl-7,12-dihydrobenzo [g] indeno [1,2-b] indol-9-yl ) phenyl)-[1,1'-biphenyl] -4-amine (13.6 g, 20 mmol) and bromobenzene (3.8 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ ( 0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added thereto, followed by stirring under reflux for 24 hours at 100 ° C. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain the final product 11.5g (76% yield).

Synthesis Example of 2-67

12-phenyl-7,12-dihydrobenzo [g] indolo [3,2-b] indole (6.6 g, 20 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4 ' -bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (14.2 g, 24 mmol) was added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added thereto, and the mixture was stirred under reflux at 100 ° C. for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain the final product 10.1g (60% yield).

Synthesis Example of 3-85

14H-phenanthro [9 ', 10': 4,5] thieno [3,2-b] indole (6.5 g, 20 mmol) and N-([1,1'-biphenyl] -4-yl) -7-bromo -N- (9,9-diphenyl-9H-fluoren-2-yl) -9,9-dimethyl-9H-fluoren-2-amine (18.2 g, 24 mmol) was added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added thereto, followed by stirring under reflux at 100 ° C. for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to give the final product 12.8g (64% yield).

Synthesis Example of 4-90

10H-benzofuro [3,2-b] indole (4.1 g, 20 mmol) and N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl ] -4-amine (13.3 g, 24 mmol) is added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was stirred under reflux at 100 ° C for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain the final product 9.0g (66% yield).

The FD-MS values of the compounds according to the present invention prepared in the same or similar manner as in the above preparation method are shown in Table 9 below.

TABLE 9

Manufacturing Evaluation of Organic Electrical Device

[ Experimental Example  One] ( Light emitting layer )

An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention obtained through synthesis as a light emitting host material of a light emitting layer. First, on the ITO layer (anode) formed on the glass substrate, N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N ^1- A phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was formed by vacuum deposition to a thickness of 60 nm to form a hole injection layer, followed by 4,4-bis [ N- (1-nap) on the hole injection layer. Til) -N -phenylamino] biphenyl (abbreviated as -NPD) was vacuum deposited to a thickness of 20 nm to form a hole transport layer. In addition, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant material. . Subsequently, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm on the light emitting layer. A blocking layer was formed and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Subsequently, LiF, which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

[ Comparative example  One]

An organic light emitting display device was manufactured in the same manner as in Experiment 1, except that Comparative Compound 1 (CBP) was used instead of the compound of the present invention as a host material in forming the emission layer.

<Comparative Compound 1>

[ Comparative example  2]

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 2 was used instead of the compound of the present invention as a host material in forming the emission layer.

<Comparative Compound 2>

The electroluminescent (EL) characteristics of the organic electroluminescent devices prepared by Experimental Example 1, Comparative Example 1 and Comparative Example 2 of the present invention were applied by a forward bias DC voltage to the photoresearch company PR-650. Is shown in Table 10 below. At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.

On the other hand, the organic light emitting display device manufactured according to Experimental Example 1 of the present invention is shown in Examples 1 to 269 in Table 10 below.

TABLE 10

As can be seen from the above results, the organic electroluminescent device using the compound according to the present invention as the light emitting layer material not only significantly improved the luminous efficiency and lifespan, but also the color purity also significantly compared to the comparative example. In particular, the organic light emitting display device according to Examples 134 to 201, in which X is S, exhibits low driving voltage, high efficiency, and high lifetime, and has the best results as a phosphorescent host.

In addition, when comparing the results of the devices of Examples (69) to (133) which are the compounds of the present invention, the compound of the present invention having a structure in which a ring is bonded to the core has a higher efficiency than that of Comparative Example 2. It was confirmed that high lifetime was shown.

This can be confirmed that even in the case of applying the same or similar substituents in the case of the polycyclic heterocyclic core as in the present invention and Comparative Example 2 as shown in Table 10 shows a large difference in efficiency and lifespan by the structure of the core core. This is a result showing that the efficiency and life is determined by the band gap of the core, rather than LUMO, HOMO control by the substituent effect. Therefore, the similarity of the substituent effect and the core alone may not easily predict the result shown in Table 10.

[ Experimental Example  2]( Luminous auxiliary layer )

First, a 2-TNATA film is vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer by forming a hole injection layer, and then a NPD is vacuum deposited on the hole injection layer by 20 nm thickness to form a hole transport layer. Formed. The compound of the present invention was vacuum deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer. Subsequently, CBP [4,4'-N, N'-dicarbazole-biphenyl], Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant material was used as a host on the emission auxiliary layer. A 30 nm thick light emitting layer was deposited by doping by weight. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was deposited to a thickness of 40 nm to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

[ Comparative example  3]

An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that the light emitting auxiliary layer was not formed in Experimental Example 2.

[ Comparative example  4]

An organic light emitting display device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound 3 was used instead of the compound of the present invention when forming the emission auxiliary layer.

Comparative Compound 3

[ Comparative example  5]

An organic light emitting display device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound 4 was used instead of the compound of the present invention when forming the emission auxiliary layer.

<Comparative Compound 4>

As a result of measuring the electroluminescence (EL) characteristics with the PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Example 5 and Comparative Example 4 or 5 thus prepared It is shown in Table 11 below. At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.

On the other hand, the organic light emitting device manufactured according to Experimental Example 2 of the present invention is shown in Table 11 to Examples 270 to 385.

TABLE 11

As can be seen from the above results, in the case of the organic electroluminescent device using the compound according to the present invention as a material of the light emitting auxiliary layer, it can be confirmed that the luminous efficiency and life is improved while the driving voltage is lower than in Comparative Examples 3 to 5. That is, it can be seen that the device characteristics are improved in the case of the organic electric device to which the compound according to the present invention is applied.

In particular, in the case of Examples 328 to 356 where X is S, the driving voltage was remarkably low, and the daytime efficiency and the lifespan were remarkably improved.

In addition, comparing the results of the devices of Examples (299) to (327) of Inventive Compounds similar to Comparative Example 4, it was confirmed that the compound of the present invention having a structure in which the core is bonded to the ring exhibits higher efficiency and higher lifetime. It was.

This can be explained as having a high T1 energy level when the compound of the present invention is used as a light emitting auxiliary layer alone, and improving the low voltage, high luminous efficiency, and device life of the organic electroluminescent device due to the deep HOMO energy level. .

The same effect may be obtained even when the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer.

The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential features of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

100: organic electric 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 (13)

Compound represented by the following formula (4):
<Formula 4>

In Chemical Formula 4,
X is CR′R ″, NR ′, S or O (where R ′ and R ″ are independently of each other an aryl group of C ₆ to C ₃₀ , a heterocyclic group of C ₂ to C ₂₀ or C ₁ to C ₁₀ Is an alkyl group),
R ₂ to R ₅ is

Displayed,
R ₁₁ to R ₁₄ are i) hydrogen; heavy hydrogen; or

Or ii) R ₁₁ and R ₁₂ , R ₁₂ and R _13, and / or R ₁₃ and R ₁₄ combine with each other to form at least one ring, provided that they do not form a ring of R ₁₁ to R ₁₄ . Groups are defined in the same manner as defined in iii), iii) R ₁₁ and R ₁₂ comrades, R ₁₂ and R ₁₃ comrades, or R ₁₃ and R ₁₄ combinate with each other to form at least one ring, _At least one of ₁₁ to R ₁₄ is not hydrogen,
l and o are integers of 0 or 1, l + o is 1 or more,
L is iii) an aryl group of C ₆ -C ₃₀ ; C ₂ ~ C ₂₀ monovalent heterocyclic group; And it is selected from the group consisting of fluorenyl group, or ii) C ₆ ~ C ₃₀ arylene group; C ₂ -C ₂₀ divalent heterocyclic group; And it is selected from the group consisting of fluorenylene group,
Y is hydrogen; heavy hydrogen; Tritium; -N (Ar ₃ ) (Ar ₄ ); C ₁ ~ C ₅₀ Alkyl group; C ₆ ~ C ₃₀ An aryl group; And it is selected from the group consisting of a condensed ring group of C ₆ ~ C ₃₀ aromatic ring and C ₃ ~ C ₃₀ Aliphatic ring,
m is 0 or 1,
Ar ₁ is ⅰ) C ₆ ~ C ₃₀ An aryl group; C ₂ ~ C ₂₀ monovalent heterocyclic group; Monovalent condensed ring group of C ₆ -C ₃₀ aromatic ring and C ₃ -C ₃₀ aliphatic ring; And it is selected from the group consisting of fluorenyl group, or ii) C ₆ ~ C ₃₀ arylene group; C ₂ -C ₂₀ divalent heterocyclic group; Divalent condensed ring group of C ₆ -C ₃₀ aromatic ring and C ₃ -C ₃₀ aliphatic ring; And it is selected from the group consisting of fluorenylene group,
Ar ₃ and Ar ₄ are each independently of the C ₆ ~ C ₃₀ An aryl group; C ₂ ~ C ₃₀ heterocyclic group; And fluorenyl groups.
Wherein each of Y, Ar ₃ , Ar ₄ , R ′ and R ″, R ₂ to R _5, and R ₁₁ to R _{14 is} each an alkyl group of C ₁ to C ₂₀ ; an aryl group of C ₆ to C ₂₀ ; deuterium At least one substituent selected from the group consisting of C ₆ ~ C ₂₀ aryl group and C ₂ ~ C ₂₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; Can be substituted)
delete The method of claim 1,
Compound represented by one of the following formula.
<Formula 11><Formula12><Formula13>

<Formula 15>

(In the above formula, Ar ₁ ~ Ar ₄ , R ₁ ~ R ₅ , m, n, X, L and p are the same as defined in formula 1) The method of claim 1,
Compounds, characterized in that one of the formula.
<Formula 16><Formula17><Formula18>

<Formula 19><Formula20><Formula21>

<Formula 22><Formula23><Formula24>

<Formula 25><Formula26><Formula27>

(In the above formulae, Ar ₃ to Ar ₄ , R ′, R ″, R ₂ to R ₅ , m, n, X, L and p are the same as defined in Formula 1). The method of claim 1,
Compound represented by one of the following formula.

(Wherein R ′, R ″, Ar ₁ to Ar ₄ , L, m and n are the same as defined in Formula 1) The method of claim 1,
Compound represented by one of the following formula.

(In the above formula, R ₂ ~ R ₅ , R ', R ", Ar ₁ , Ar3, Ar4 and m are the same as defined in the formula (1)) The method of claim 1,
Compound which is one of the following compounds.

In an organic electric device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer of claim 1, 3, 6 and 7, characterized in that it contains a compound of any one of claims. The method of claim 8,
And forming the compound into the organic material layer by a soluble process. The method of claim 8,
The organic material layer comprises at least one of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer and a light emitting auxiliary layer. The method of claim 10,
And the light emitting layer or the light emitting auxiliary layer is formed of the compound. A display device comprising the organic electroluminescent element of claim 8; And
A controller for driving the display device; Electronic device comprising a. The method of claim 12,
The organic electroluminescent device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination element.

Images