KR101108519B1 - Composition for organic elelctronic element and an organic elelctronic element using the same - Google Patents

Abstract

PURPOSE: A composition for an organic electric device containing a carbazole derivative mixture, and the organic electric device using thereof are provided to offer low voltage operation function and high luminous efficiency. CONSTITUTION: An organic electric device includes a first electrode, more than one layer of organic material layer, and a second electrode. The organic material layers are formed by a solution process, and are used as a light emitting layer, a hole injection layer, or a hole transport layer. The organic electric device contains a composition formed with a mixture of a compound marked with chemical formula 1, and a compound marked with chemical formula 2.

Description

COMPOSITION FOR ORGANIC ELELCTRONIC ELEMENT AND AN ORGANIC ELELCTRONIC ELEMENT USING THE SAME

The present invention relates to a material for an organic electric device and an organic electric device using the same, and more particularly, a material for a raised electric device containing a novel carbazole derivative mixture for improving low voltage driving, high luminous efficiency and device life. An organic electric element to be used.

The present invention relates to a hole injection layer and a hole transport layer material having a low driving voltage characteristics and an organic electric element comprising the same.

The flat panel display plays a very important role in supporting a highly visual information society, centered on the internet which is rapidly growing in recent years. In particular, organic electroluminescent devices (organic EL devices) capable of low voltage driving with self-luminous type have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), which are mainstream flat panel displays, and require no backlight. Light weight and thinness are possible, and it has an advantage in terms of power consumption. In addition, the fast response speed and wide color reproduction range have attracted attention as a next generation display device. In general, an organic EL device is formed on a glass substrate in order of an anode made of a transparent electrode, an organic thin film including a light emitting region, and a metal electrode. In this case, the organic thin film may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer in addition to the emitting layer (EML). , EIL), and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to light emission characteristics of the light emitting layer. When an electric field is applied to the organic EL device having such a structure, holes are injected from the anode and electrons are injected from the cathode, and the injected holes and electrons are recombined in the emission layer through the hole transport layer and the electron transport layer, respectively, to emit light excitons. To form. The light emitting excitation emits light as it transitions to ground states, in which a light emitting layer (guest) is doped into the light emitting layer (host) to increase the efficiency and stability of the light emitting state. In order to utilize the organic electronic device in various display media, the life of the device is important, and various studies are being conducted to increase the life of the organic electronic device. In particular, various studies have been conducted on organic materials inserted into the hole transport layer or the buffer layer for excellent life characteristics of the organic electric device, and for this purpose, a thin film after deposition is provided while providing high hole transport characteristics from the anode to the organic layer. There is a need for a hole injection layer material having high uniformity and low crystallinity in forming.

Delays penetration of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of the shortening of the life of the organic electric device, and stable properties for Joule heating generated when driving the device, that is, high glass transition temperature. There is a need for development of a hole injection layer material having In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

In particular, the current major challenge of the organic light emitting device is the urgent need to overcome the problems of power consumption and lifespan as the size of the panel of a mobile phone or a tablet PC is increased.

However, it is difficult to simultaneously overcome the driving voltage and the lifetime as the hole transport layer material. The reason for this is that most of the materials having excellent hole transporting ability, that is, high hole mobility, have a planar structure rich in electrons in order to lower the driving voltage. Examples are naphthyl, fluorene and phenanthrene. However, when the compound of the above structure is introduced into the hole transport material as a substituent, the hole mobility increases to a certain number and has a good effect on the lifetime, but the number of introduction into the molecule is required to reach the low voltage driving target required by the current industry. Increasingly, the driving voltage is lowered, but the low voltage driving is possible, but the life characteristics are rapidly worsened. This is because in the case of molecules in which electron-rich planar structures are excessively introduced, when a constant current is continuously supplied during device life evaluation, holes are trapped and stabilized between the plate structures, which lowers hole mobility, thus As the driving voltage increases in order to apply a constant current, the device life is drastically deteriorated. This is represented by the following formula.

J = Space Charge limited current

ε = Permittibility

μ = Mobility Coefficient

θ = Charge Trap Coefficient (Free Carrier / total Carrier)

V = Voltage

d = Thickness

When the number of free carriers is reduced due to the trap phenomenon, the value of θ decreases. Therefore, the driving voltage increases in the current-driven organic electroluminescent device which requires a constant current, which is very fatal for life. You can get results. Therefore, as described above, the introduction of a certain number of electron-rich plate structures capable of increasing hole mobility adversely affects the lifespan, so the possibility of using the same to lower the driving voltage is not great.

The present invention provides a low voltage drive and a high life time device by mixing a deuterium substituted and deuterium substituted compound in an amine compound including carbazole having excellent lifespan in order to implement a low voltage driving and a high lifespan device, which are required characteristics of an organic electric device. It aims to complete.

Therefore, in the present invention, in order to solve the above-mentioned problems of the prior art and to achieve the object of the present invention, by using a material having a good life, it is possible to lower the driving voltage without introducing a plate-like molecular structure which adversely affects the life. In this way, a method of lowering the driving voltage by using a mixture of deuterium at an appropriate ratio and a compound having a similar structure substituted with heavy water is used.

Compounds substituted with deuterium showed much thermodynamic behavior compared to unsubstituted compounds. Among these thermal properties, when the iridium compound is substituted with deuterium, the intermolecular molecules generated by the shorter bond length of the compound consisting of carbon and deuterium having a shorter bond length according to the difference in carbon, hydrogen, carbon, and deuterium bond lengths It was confirmed that due to the weakening of van der Waals force can have a higher luminous efficiency.

In addition, when deuterium is substituted, zero point energy (ie, bottom energy) is reduced, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and thus the electrical polarization is also reduced. It was confirmed that the electrolytic polarizability can be reduced, and the thin film volume can be increased by weakening the intermolecular interaction. This property can reduce the crystallinity of the thin film, i.e., create an amorphous state, and in general, it was determined that it would be very effective to realize the necessary amorphous state in order to increase OLED lifetime and driving characteristics.

However, there have not been many studies on the method of lowering the driving voltage by increasing the deuterium, that is, increasing the mobility of the hole transport material, and in this study, various kinds of compounds are used to confirm such characteristics. Thus, many experiments were conducted. In addition, when a thin film is formed by mixing a compound having a similar structure substituted with deuterium, it can be very advantageous because it creates an amorphous glass state that can greatly affect the hole mobility of the thin film, and this amorphous glass state By reducing the grain boundary through the isotropic and homogeneous properties, it is confirmed that the flow of charges, or hole mobility, can be increased.

In more detail, the present invention used an amine compound including carbazole as an excellent material for life. In particular, the carbazole-based amine compound has excellent life characteristics according to the present study, but has a disadvantage in that driving voltage is increased. However, the prior art has not proved the effect of the improvement on this part, and in particular, the prior art which improves the driving characteristics through deuterium substitution at a specific position has not been reported yet.

As a result of the research and development of these inventors, the present invention provides a compound in which an amine group substituted with deuterium is bonded to maintain the excellent properties of the organic material layers of the organic electronic device described above and to meet the requirements of the organic material.

In order to achieve the above object, the present invention provides a composition for an organic electric device comprising a mixture of a compound represented by the formula (1) and a compound represented by the formula (2).

In Chemical Formula 1

1) Ar ₁ to Ar ₃ are the same as or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C _3- C ₂₀ cycloalkyl group, C ₆ ~ C 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, C ₅ ~ an aryl group of C ₂₀ with one or more substituents selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₆ ~ C ₆₀ of; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, and the heteroaryl group in the C ₅ ~ C ₆₀ having at least one of S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Halogen group, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C of the arylamine group with one or more substituents selected from the ₆₀ heteroaryl group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ of _30; Or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ aryl group substituted with deuterium, C of ₈ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ Alkyl group . Here, at least one of Ar ₁ to Ar ₃ includes at least one deuterium, and when Ar ₂ is a substituted or unsubstituted fluorene group, Ar ₃ must include at least one deuterium.

2) R ₁ And Each R ₂ is independently the same or different and is a hydrogen atom ; heavy hydrogen; halogen; Nitro group ; Nitrile group ; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C ₂ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group, a substituted or unsubstituted C ₆ ~ C _60; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₂ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, or substituted heteroaryl, unsubstituted C ₅ ~ C ₆₀ group having from S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ aryl group substituted with deuterium, C of ₈ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ Alkyl group . Where R ₁ And R ₂ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or heterocycle.

3) L is nitro, nitrile, halogen, alkyl group, alkoxy group and substituted with one or more substituents selected from the group consisting of an amino group or unsubstituted arylene group, a C ₆ ~ C _60; Or a C ₅ to C ₆₀ hetero arylene group unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, alkyl, alkoxy and amino groups .

4) a is an integer of 1-4, b is an integer of 1-3, c is an integer of 0-2.

In Chemical Formula 2

1) Ar ₁ To Ar ₃ is the same or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of , 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, C ₅ ~ C ₂₀ heterocyclic ring C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of groups ; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, a heteroaryl group of C ₅ ~ C ₆₀ with at least one of S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Halogen group, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C ₃₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ arylamine group of C with one or more substituents selected from the ₆₀ heteroaryl group the group consisting of substituted or unsubstituted C ₆ ~ C _60; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ of the alkoxy group, C ₆ ~ substituted by an aryl group, a heavy hydrogen of the C _20, C ₆ ~ C ₂₀ aryl group, a C ₈ ~ C C ₁ ~ C ₅₀ Alkyl group unsubstituted or substituted with a substituent selected from the group consisting of ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ hetero ring group, nitrile group and acetylene group . Wherein at least one of Ar ₁ to Ar ₃ includes one or more deuterium.

2) the R ₁ To Each R ₄ is independently the same or different and is a hydrogen atom ; heavy hydrogen; halogen; Nitro group ; Nitrile group ; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C ₂ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group, a substituted or unsubstituted C ₆ ~ C _60; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₂ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, or substituted heteroaryl, unsubstituted C ₅ ~ C ₆₀ group having from S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₈ C ₁ ~ C ₅₀ alkyl group unsubstituted or substituted with a substituent selected from the group consisting of-C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group to be. Where R ₁ To R ₄ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or a heterocycle.

3) R ' And R ″ are the same as or different from each other independently, and are hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl an amine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of Alkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ hetero C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ hetero Selected from the group consisting of cyclic, nitrile and acetylene groups C ₁ to C ₅₀ alkyl group unsubstituted or substituted with the selected substituent, wherein R ' And R ″ may be bonded to each other to form a saturated or unsaturated aliphatic ring, heterocycle, or spiro compound.

4) a is an integer of 1 to 3, and b, c, and d are integers of 1 to 4, respectively.

In the composition for an organic electric device comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 2, any one compound may be mixed in the range of 90% by weight or less of the total weight of the composition.

In another aspect, the present invention provides an organic electric device using the composition for an organic electric device comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 2.

The term "halo" or "halogen" as used herein includes fluorine, chlorine, bromine, and iodine.

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

As used herein, the term "alkenyl" or "alkynyl" has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.

The term "cycloalkyl" as used herein, unless otherwise stated, 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" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.

As used herein, the term “heteroalkyl” means an alkyl having 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 having one or more heteroatoms unless otherwise specified, and is not limited thereto. It is not.

As used herein, the terms "heterocycloalkyl" and "heterocyclic group" include one or more heteroatoms and, unless stated otherwise, have from 2 to 60 carbon atoms.

The term "heteroatom" as used herein refers to N, O, S, P and Si.

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.

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

Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention 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, 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.

More specifically, at least one of Ar ₁ to Ar ₃ of Formula 1 and Formula 2 may be independently any one selected from the group consisting of Formula 3, which may be the same or different from each other. As described above, Ar ₁ , Ar ₂ , and Ar ₃ At least one of them must contain deuterium. That is, at least one of a to v in Formula 3 is not 0.

In Chemical Formula 3,

a is an integer from 0 to 5, b is an integer from 0 to 7, c is an integer from 0 to 4, d is an integer from 0 to 5, e is an integer from 0 to 6, f is 0 to 5 It is an integer of, g is an integer of 0-4, h is an integer of 0-4, i is an integer of o-4, j is an integer of 0-4, k is an integer of 0-5. L is an integer from 0 to 2, m is an integer from 0 to 5, n is an integer from 0 to 4, o, p, and r are integers from 0 to 3, s and t are integers from 0 to 5, u and v is an integer of 0-4.

는 a가 0 내지 5인 경우 각각에 대하여 다음 구조식에 대응한다:In the structural formula shown in Formula 3, for example,

Corresponds to the following structural formula for each when a is from 0 to 5:

The same applies to the remaining structural formulas.

More specifically, the general formula (1) and Ar _1, which contains the heavy hydrogen in Ar ₁ to Ar ₃ of the general formula (2) Ar ₃ is represented as follows, but the kind thereof is not limited thereto.

More specifically, the compound represented by Formula 1 may be any one of the following Compounds (P-1) to (P-132), but is not limited thereto.

The compounds represented by Formula 1 may be one of the compounds shown in Formula 5, but is not limited thereto. In this case, since the substituents of the compounds represented by the general formula (1) are practically difficult to exemplify all the compounds in a broad relationship, the exemplary compounds have been described by way of example, but the compounds represented by the general formula (1) not shown in the general formula (5) also Some can be configured.

More specifically, the compound represented by Formula 2 may be any one of the following Compounds (P2-1) to (P2-120), but is not limited thereto.

Compounds represented by Formula 2 may be one of the compounds shown in Formula 6, but is not limited thereto. In this case, since the substituents of the compounds represented by the formula (2) are practically difficult to exemplify all the compounds in a broad relationship, the exemplary compounds have been described by way of example, but the compounds represented by the formula (2) not shown in the formula (6) also Some can be configured.

The present invention provides a composition for an organic electric device comprising a mixture of the novel compounds presented in the present invention, and an organic electric device using the composition as a hole injection layer material or a hole transport layer material, which has excellent driving characteristics and lifespan. By using excellent materials in combination, low-voltage driving, high luminous efficiency and long life of the organic electric element can be improved.

1 to 6 show examples of the organic electroluminescent device to which the compound of the present invention can be applied.

Hereinafter, some embodiments of the present invention will be described in detail through exemplary 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 the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

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 should be understood that the elements may be "connected", "coupled" or "connected".

Compositions containing a compound having the above structural formula or a mixture thereof can be used in a soluble process. In other words, the composition containing the compound or a mixture thereof may form an organic material layer of the organic electric element to be described later by a solution process (soluble process). In other words, when the compound or composition is used as an organic material layer, the organic material layer may be formed using a variety of polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by methods such as law.

The composition of the present invention is a metal oxide organic layer from the positive electrode electrode which is one of the causes of the hole injection layer material having high uniformity and low crystallization when forming a thin film, and shortening the life while maximizing the characteristics of the organic material layer of the organic electric device as described below Stabilization of Joule heating generated during device operation while delaying penetration diffusion into the device, namely the demand for a hole injection layer material having a high glass transition temperature, and withstanding the deposition method in the formation of an organic electroluminescent device It can meet the requirements of materials that can be used, that is, materials with strong heat resistance characteristics.

As described above, the inventors have found many thermodynamic behaviors of a composition comprising a mixture of compounds substituted with deuterium or a compound not substituted with deuterium or the compound itself substituted with deuterium, and confirmed carbon, hydrogen and carbon, deuterium bonds. According to the difference in length, it was confirmed that a compound composed of carbon and deuterium having a smaller bond length has a higher luminous efficiency due to the weakening of the intermolecular van der Waals forces generated by a short bond length. As the zero point energy, or ground energy, is lowered, and the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, thereby reducing the electrical polarizability. Thin film volume by weakening intermolecular interactions It was confirmed that increase.

The properties of the compound of the present invention substituted with deuterium may create an effect of lowering the crystallinity of the thin film, that is, an amorphous state, and in general, in order to increase the lifespan and driving characteristics of the organic electroluminescent device, We decided it would be very effective to implement.

As a result, among the characteristics of the mixture of the deuterium-substituted compound, it has a low visible light absorption characteristics than the low carbon, hydrogen bonding material, it was determined that this can be an advantage to increase the efficiency in light emitting devices such as organic electroluminescent devices. In addition, it was determined that the mixture of the compound of the present invention substituted with deuterium has a great increase in heat resistance.

Manufacturing example

Hereinafter, the preparation or synthesis examples of the compounds belonging to Formula 1 or Formula 2 will be described. However, some of the compounds belonging to the general formula (1) or the formula (2) because of the large number of compounds belonging to the general formula (1) or (2) will be described by way of example. Those skilled in the art to which the present invention pertains, that is, those skilled in the art can prepare the compounds belonging to the present invention which are not illustrated through the preparation examples described below.

General Synthetic Method

General synthetic methods of the compounds of the present invention are as follows.

i) General Synthesis of Compounds of Formula 1

ii General Synthesis of Compounds of Formula 2

Synthesis of Compound of Formula 1

One) Sub  1 Synthesis Example: ( Ar _One , L = Phenyl )

Sub  1-1 Synthesis: 9- phenyl -9H- carbazole

Carbazole (50.2 g, 300 mmol) and bromobenzene (56.5 g, 360 mmol) were mixed in 2800 mL of toluene, followed by Pd ₂ (dba) ₃ (8.24 g, 9 mmol), PPh ₃ (7.87 g, 30 mmol), NaO t -Bu (86.5 g, 900 mmol) was added, and the mixture was stirred at reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated and the resulting organic was purified and recrystallized by a silica gel column to give 52.5 g (75%) of the product.

Sub  1-2 Synthesis: 3- bromo -9- phenyl -9H- carbazole

After dissolving in 600 mL of methylene chloride in Sub 1-1 (48.66 g, 200 mmol) obtained in the above synthesis, NBS (N-bromosuccimide) (59.4 g, 210 mmol) was slowly added, followed by stirring at room temperature for 24 hours. .

After the reaction was completed, 300 mL of 5% HCl was added, 300 mL of water was added to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic substance was purified by silica gel column. Purification and recrystallization were carried out to give 47.7 (74%) of the product.

Sub  1-3 Synthesis: 9- phenyl -3- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -9H- carbazole

Sub 1-2 (45.1 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), KOAc ( 41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound, and the obtained compound was separated through a silica gel column and recrystallized to obtain 35.2 g (68%) of the borate compound.

Sub  1 synthesis: 3- (4- bromophenyl ) -9- phenyl -9H- carbazole

Sub 1-3 (29.5 g, 80 mmol) obtained in the above synthesis was dissolved in 360 mL of THF, followed by 1-bromo-4-iodo benzene (23.8 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, 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 , concentrated, and the resulting organic was purified and recrystallized by a silica gel column to obtain 22.9 g (72%) of the product.

2) R _One  Example substitution synthesis: ( Ar _One , R _One , L = Phenyl )

Sub  1-1-1 Synthesis: 3,9- 피덴 -9H- carbazole

Sub 1-2 (25.8 g, 80 mmol) obtained in Example 1 was dissolved in 360 mL of THF, followed by Phenyl boronic acid (10.7 g, 88 mmol), Pd (PPh ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water were used to obtain 18.9 g (74%) of the product using the synthesis method of Example sub 1, and the same yield was obtained when the scale-up reaction proceeded to the same experimental method.

Sub  1-2 Synthesis: 3- bromo -6,9- 피덴 -9H- carbazole

Sub 1-1-1 (63.88 g, 200 mmol) obtained in the above synthesis was added with 600 mL of methylene chloride and NBS (N-bromosuccimide) (59.4 g, 210 mmol) using the sub 1-2 synthesis method of Example 1 To give 55.8 g (70%) of the product.

Sub  1-3 Synthesis: 3,9- 피덴 -6- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -9H- carbazole

Sub-1-2 obtained in the above synthesis (55.8 g, 140 mmol), 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 obtained using the synthesis method of sub 1-3 of Example 1 to obtain 40.5 g (65%) of the product.

Sub  1 synthesis: 3- (4- bromophenyl ) -6,9- 피덴 -9H- carbazole

Sub-1-3 (35.6 g, 80 mmol) obtained in the above synthesis was dissolved in 360 mL of THF, followed by 1-bromo-4-iodo benzene (23.8 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, 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 was purified and recrystallized by a silica gel column to obtain a product 27.7 g (73%).

3) Dibenzothiophene  Example of starting material synthesis method

Synthesis of Intermediate A

Dissolve 2-Bromothioanisole in a glacial acetic acid solvent, lower the temperature of the reaction to 0 ° C, and then slowly add Hydrogen peroxide. When the addition was completed, the reaction was heated to room temperature and stirred for 12 hours to proceed with the reaction. After the reaction was completed, the solvent was removed using a pressure reduction apparatus, extracted with CH ₂ Cl ₂ , and washed with NaHCO ₃ aqueous solution. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired intermediate A in a yield of 43 g (98%).

Synthesis of Intermediate B

Intermediate A, 2-Bromocarbazole, Pd (PPh ₃ ) ₄ , and Na ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water and refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain 30.6 g (51%) of the desired intermediate B.

Synthesis of Intermediate C

To Intermediate B (30.5 g, 100 mmol) obtained in the above synthesis, 300 mL of methylene chloride and NBS (N-bromosuccimide) (29.7 g, 105 mmol) were prepared using 28.058 g ( 73%) of the product.

Synthesis of Intermediate D

Intermediate C was dissolved in trifluoromethanesulfonic acid solvent and stirred at room temperature for 48 hours.

After the reaction was completed, the reaction was poured into a mixture of water and pyridine solvent and refluxed for 20 minutes. The reaction mixture was cooled to room temperature, extracted with CH2Cl2, and washed with water. A small amount of water was removed with MgSO4, and the residue was filtered under reduced pressure, and the organic solvent was concentrated. (82%) got.

Starting material synthesis

Intermediate D (21.1 g, 60 mmol), Iodobenzene (18.4 g, 90 mmol), DMF 300 mL, K ₂ CO ₃ (12.4 g, 90 mmol), Cu powder (4.2 g, 66 mmol), 18-crown-6 ( 1.6 g, 6 mmol) was added to a round bottom flask and refluxed at 170 ° C. for 24 hours. After the reaction is completed, the mixture is extracted with water and CH 2 Cl 2 and washed with 5% aqueous HCl solution. Finally clean it with brine. The obtained organic layer was dried with MgSO 4, filtered, and concentrated under reduced pressure. The resulting product was separated using column chromatography to obtain 19 g (74%) of the desired starting material.

4) 3- Cyano -9- phenylcarbazole  Synthesis Example

Synthesis of Intermediate A

After adding DMF (43.4 mL) to the round bottom flask, create a nitrogen zone and adjust the reaction temperature to 0 ℃. Then, slowly add dropwise phosphoryl chloride (32 g, 200 mmol), raise the temperature to room temperature, and stir for 1 hour.

The reaction temperature was adjusted to 0 ° C. and a solution of 9-phenyl carbazole (2.92 g, 120 mmol) in 1,2-dichloroethane (52 mL) was added dropwise for 1 hour.

After the reaction temperature was stirred at 90 ° C. for 8 hours and the reaction was completed, the mixture was extracted with ice water and CH ₂ Cl ₂ , and the obtained organic layer was separated using MgSO 4, water removal and column chromatography. 75%) of 3-aldehyde-9-phenyl carbazole (Intermediate A) compound was obtained.

Synthesis of Intermediate B

3-aldehyde-9-phenyl carbazole (31.4 g, 116 mmol) obtained above, hydroxylamine hydrochloride (10 g, 140.4 mmol), acetic acid (25.1 g, 418 mmol), pyridine (16.72 g, 209 mmol), DMF ( 83 mL) was added to the reaction flask in order and stirred at 140 ° C. for 5 hours.

After completion of the reaction, the mixture was extracted with water and CH ₂ Cl ₂ , and the obtained organic layer was separated with MgSO ₄ by water removal and column chromatography, and recrystallized with ethanol and hexane to give 23 g (74%) of 3-cyano-9. -phenylcarbazole (intermediate B) compound was obtained.

Synthesis of Intermediate C

In intermediate B (23 g, 85.72 mmol) obtained in the above synthesis, 80 mL of methylene chromide (N-bromosuccimide) (25.46 g, 90 mmol) was added to 20.54 g ( 69%) of the product.

5) Sub  2 Synthesis Example

Sub  2- 1 of  synthesis

Aniline-d5 (23.56 g, 240 mmol) and bromobenzene-d5 (32.41 g, 200 mmol ) were mixed into the flask, followed by Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol) , NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were added and then stirred under reflux for 24 hours. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was purified and recrystallized by a silica gel column to obtain 26.17 g (73%) of the product.

Sub  2- 2 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 1-bromo-4-fluorobenzene (35 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 26.14 g (68%) of the product.

Sub  2- 3 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), bromobenzene (31.4 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 26.14 g (75%) of the product.

Sub  2- 4 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (54.6 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the experimental method of Sub-2-1 to obtain 41.24 g (71%) of a product.

Sub  2- 5 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-9,9-diphenyl-9H-fluorene (79.5 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the experimental method of Sub-2-1 to give 57.2 g (69%) of the product.

Sub  2- 6 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-9,9-diphenyl-9H-fluorene (79.5 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the experimental method of Sub-2-1 to give 57.2 g (69%) of the product.

Sub  2- 7 of  synthesis

1-naphtylamine (34.37 g, 240 mmol), 4'-bromo-2,3,4,5,6-d5-biphenyl (47.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol) , PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-2-1 to obtain 44.5 g (74%) of the product. .

Sub  2- 8 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromonaphthalene (41.41 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-2-1, to obtain 32.3 g (72%) of a product.

Sub  2- 9 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 4-bromobiphenyl (46.62 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 36.55 g (73%) of the product.

Sub  2- 10 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 1- (4-bromophenyl) naphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol) , NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-2-1 to obtain 41.46 g (69%) of the product.

Sub  2- Of 11  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2- (4-bromophenyl) naphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol) , NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-2-1 to obtain 40.86 g (68%) of the product.

Sub  2- 12 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 1-bromo-4-phenylnaphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 39.05 g (65%) of the product.

Sub  2- Of 13  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-6-phenylnaphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 39.05 g (65%) of the product.

Sub  2- 14 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 3,5-diphenyl bromobenzene (61.84 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t- Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 44.4 g (68%) of the product.

Sub  2- 15 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 4-bromo-N, N-diphenylaniline (64.84 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol ), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-2-1 to obtain 45.76 g (67%) of the product.

Sub  2- 16 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-dibenzothiophene (52.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 39.82 g (71%) of the product.

Sub  2- Of 17  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-dibenzofuran (49.42 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-2-1 to obtain 37 g (70%) of the product.

Sub  2- Of 18  synthesis

Aniline-d5 (23.56 g, 240 mmol), 1-bromonaphthalene-d7 (42.82 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiment of Sub-2-1 to obtain 34.24 g (74%) of the product.

Sub  2- Of 19  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromonaphthalene-d7 (42.82 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 33.32 g (72%) of the product.

Sub  2- 20 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 4'-bromo-2,3,4,5,6-d5-biphenyl (47.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol) , PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 36.77 g (72%) of the product. .

Sub  2- Of 21  synthesis

Aniline-d5 (23.56 g, 240 mmol), 1- (4-bromophenyl) -2,3,4,5,6,7,8-d7-naphthalene (58.04 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-2-1. 43.04 g (70%) was obtained.

Sub  2- 22 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2- (4-bromo-2,3,5,6-d4-phenyl) naphthalene (57.44 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in Sub-2-1, and the product was 43.23 g (71%). )

Sub  2- 23 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 1-bromo-4- (2,3,4,5,6-d5-phenyl) naphthalene (57.64 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g , 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in Sub-2-1, and the product was 42.15 g ( 69%).

Sub  2- 24 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 2-bromo-6- (2,3,4,5,6-d5-phenyl) naphthalene (57.64 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g , 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in Sub-2-1, and the product was 42.15 g ( 69%).

Sub  2- 25 of  synthesis

Aniline-d5 (23.56 g, 240 mmol), 3,6-Diphenyl-d10-bromobenzene (63.85 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol ), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-2-1 to obtain 43.07 g (64%) of the product.

Sub  2- Of 26  synthesis

4-Phenyl-d5-Aniline (41.82 g, 240 mmol), 4'-bromo-2,3,4,5,6-d5-biphenyl (47.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g , 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in Sub-2-1, and the product was 45.08 g ( 68%).

compound FD-MS compound FD-MS Sub 2-1 m / z = 179.15 (C ₁₂ HD ₁₀ N = 179.28) Sub 2-2 m / z = 192.11 (C ₁₂ H ₅ D ₅ FN = 192.24) Sub 2-3 m / z = 174.12 (C ₁₂ H ₆ D ₅ N = 174.25) Sub 2-4 m / z = 290.18 (C ₂₁ H ₁₄ D ₅ N = 290.41) Sub 2-5 m / z = 414.21 (C ₃₁ H ₁₈ D ₅ N = 414.55) Sub 2-6 m / z = 412.20 (C ₃₁ H ₁₆ D ₅ N = 412.54) Sub 2-7 m / z = 300.17 (C ₂₂ H ₁₂ D ₅ N = 300.41) Sub 2-8 m / z = 224.14 (C ₁₆ H ₈ D ₅ N = 224.31) Sub 2-9 m / z = 250.15 (C ₁₈ H ₁₀ D ₅ N = 250.35) Sub 2-10 m / z = 300.17 (C ₂₂ H ₁₂ D ₅ N = 300.41) Sub 2-11 m / z = 300.17 (C ₂₂ H ₁₂ D ₅ N = 300.41) Sub 2-12 m / z = 300.17 (C ₂₂ H ₁₂ D ₅ N = 300.41) Sub 2-13 m / z = 300.17 (C ₂₂ H ₁₂ D ₅ N = 300.41) Sub 2-14 m / z = 326.18 (C ₂₄ H ₁₄ D ₅ N = 326.45) Sub 2-15 m / z = 341.19 (C ₂₄ H ₁₅ D ₅ N ₂ = 341.46) Sub 2-16 m / z = 280.11 (C ₁₈ H ₈ D ₅ NS = 280.40) Sub 2-17 m / z = 264.13 (C ₁₈ H ₅ D ₅ NO = 264.33) Sub 2-18 m / z = 231.18 (C ₁₆ HD ₁₂ N = 231.36) Sub 2-19 m / z = 231.18 (C ₁₆ HD ₁₂ N = 231.36) Sub 2-20 m / z = 255.18 (C ₁₈ H ₅ D ₁₀ N = 255.38) Sub 2-21 m / z = 307.21 (C ₂₂ H ₅ D ₁₂ N = 307.45) Sub 2-22 m / z = 304.19 (C ₂₂ H ₈ D ₉ N = 304.43) Sub 2-23 m / z = 305.20 (C ₂₂ H ₇ D ₁₀ N = 305.44) Sub 2-24 m / z = 305.20 (C ₂₂ H ₇ D ₁₀ N = 305.44) Sub 2-25 m / z = 336.25 (C ₂₄ H ₄ D ₁₅ N = 336.51) Sub 2-26 m / z = 331.21 (C ₂₄ H ₉ D ₁₀ N = 331.48)

6) Sub  3 Synthesis Example

Sub  3- 1 of  synthesis

Sub 2-7 (30.04 g, 100 mmol), 2,5-dibromothiophene (26.61 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t- Bu (28.9 g, 300 mmol) and toluene (970 mL) were prepared in the same manner as in the Experiments of Sub-2-1 to obtain 30.92 g (67%) of the product.

Sub  3- 2 of  synthesis

N- (2,3,5,6-d4-biphenyl-4-yl) naphthalen-1-amine (29.94 g, 100 mmol), 2-bromo-5- (4-iodophenyl) thiophene (40.15 g, 110 mmol ), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t -Bu (28.9 g, 300 mmol), toluene (970 mL) were obtained from Sub-2-1. In the same manner as the experimental method, 33.80 g (63%) of a product were obtained.

Sub  3- 3 of  synthesis

bis (2 ', 3', 4 ', 5', 6'-d5-biphenyl-4-yl) amine (33.15 g, 100 mmol), 2,6-dibromopyridine (26.06 g, 110 mmol), Pd ₂ ( dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t -Bu (28.9 g, 300 mmol), toluene (970 mL) were prepared in the same manner as in the Experiment of Sub-2-1. To give 31.68 g (65%) of the product.

Sub  3- 4 of  synthesis

N-phenyl-d5-naphthalen-1-amine (22.43 g, 100 mmol), 2,7-dibromo-9,9-dimethyl fluorene (38.73 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t -Bu (28.9 g, 300 mmol) and toluene (970 mL) were prepared in the same manner as in the Sub-2-1 experiment to obtain 34.19 g (69%). )

Sub  3- 5 of  synthesis

N-phenyl-d5-naphthalen-2-amine (22.43 g, 100 mmol), 2,7-dibromo-9,9-diphenyl fluorene (52.38 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t -Bu (28.9 g, 300 mmol) and toluene (970 mL) were prepared in the same manner as in the above Experiment of Sub-2-1 to obtain 41.51 g (67%). )

Sub  3- 6 of  synthesis

Sub 2-3 (17.43 g, 100 mmol), 2,7-dibromo-9,9'-spirobi [fluorene] (52.16 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t -Bu (28.9 g, 300 mmol) and toluene (970 mL) were obtained in the same manner as in the Experiment of Sub-2-1 to obtain 38.02 g (67%) of the product.

Sub  3- 7 of  synthesis

Sub 2-2 (19.22 g, 100 mmol), 2,7-dibromophenanthrene (36.96 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t- Bu (28.9 g, 300 mmol) and toluene (970 mL) were prepared in the same manner as in the Experiment of Sub-2-1 to obtain 29.53 g (66%) of the product.

Sub  3- 8 of  synthesis

Sub 2-3 (17.43 g, 100 mmol), 4,4'-dibromobiphenyl (34.32 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t -Bu (28.9 g, 300 mmol) and toluene (970 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 27.97 g (69%) of the product.

Sub  3- 9 of  synthesis

Sub 2-3 (17.43 g, 100 mmol), 2,6-dibromonaphthalene (31.46 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t- Bu (28.9 g, 300 mmol) and toluene (970 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 26.17 g (69%) of the product.

Sub  3- 10 of  synthesis

Sub 2-3 (17.43 g, 100 mmol), 1,4-dibromonaphthalene (31.46 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t- Bu (28.9 g, 300 mmol) and toluene (970 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 25.79 g (68%) of the product.

Sub  3- Of 11  synthesis

Sub 2-3 (17.43 g, 100 mmol), 1,5-dibromonaphthalene (31.46 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaO t- Bu (28.9 g, 300 mmol) and toluene (970 mL) were obtained in the same manner as in the Experiments of Sub-2-1 to obtain 25.41 g (67%) of the product.

compound FD-MS compound FD-MS Sub 3-1 m / z = 486.15 (C ₂₆ H ₁₃ D ₅ BrNS = 487.46) Sub 3-2 m / z = 535.09 C ₃₂ H ₁₈ D ₄ BrNS = 536.52) Sub 3-3 m / z = 486.15 (C ₂₉ H ₁₁ D ₁₀ BrN ₂ = 487.46) Sub 3-4 m / z = 494.14 (C ₃₁ H ₁₉ D ₅ BrN = 495.46) Sub 3-5 m / z = 618.17 (C ₄₁ H ₂₃ D ₅ BrN = 619.60) Sub 3-6 m / z = 566.14 (C ₃₇ H ₁₉ D ₅ BrN = 567.53) Sub 3-7 m / z = 446.08 (C ₂₆ H ₁₂ D ₅ BrFN = 447.35) Sub 3-8 m / z = 404.09 (C ₂₄ H ₁₃ D ₅ BrN = 405.34) Sub 3-9 m / z = 378.08 (C ₂₂ H ₁₁ D ₅ BrN = 379.30) Sub 3-10 m / z = 378.08 (C ₂₂ H ₁₁ D ₅ BrN = 379.30) Sub 3-11 m / z = 378.08 (C ₂₂ H ₁₁ D ₅ BrN = 379.30)

Final product ( Final Product ) Synthesis

Method  1 Synthesis

Sub 1 (1 equiv), Sub 2 (1 equiv), Pd ₂ (dba) ₃ (0.05 mol%), PPh ₃ (0.1 equiv), NaO t -Bu (3 equiv), toluene (10.5 mL) / 1 mmol) and then proceed with the reaction at 100 ° C. 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 was purified and recrystallized by a silica gel column to obtain a product.

Method  2 synthesis method

In a round bottom flask, Sub 1-3 (1 equiv), Sub 3 (1.1 equiv), Pd (PPh ₃ ) ₄ (0.05 equiv), NaOH (3 equiv), THF (3 mL / 1 mmol), water (1.5 mL / 1 mmol).

Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. After the reaction is completed, distilled water is diluted at room temperature. Thereafter, the mixture was extracted with methylene chloride and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was purified and recrystallized by a silica gel column to obtain a product.

Finally, the mass spectrometry HRMS was measured for structural analysis of the synthesized compound, and purity was measured using THF as an eluent solvent using HPLC (Model, SPB-20A) manufactured by Shimadzu Corporation to confirm the purity. It was.

compound FD-MS compound FD-MS P-1 m / z = 572.30 (C ₄₂ H ₂₀ D ₁₀ N ₂ = 572.76) P-2 m / z = 622.32 (C ₄₆ H ₂₂ D ₁₀ N ₂ = 622.82) P-1 m / z = 622.32 (C ₄₆ H ₂₂ D ₁₀ N ₂ = 622.82) P-4 m / z = 602.26 (C ₄₂ H ₁₈ D ₁₀ N ₂ S = 602.81) P-5 m / z = 521.27 (C ₃₇ H ₁₅ D ₁₀ N ₃ = 521.68) P-6 m / z = 623.24 (C ₄₄ H ₂₅ D ₅ N ₂ S = 623.82) P-7 m / z = 698.27 (C ₅₀ H ₃₀ D ₄ N ₂ S = 698.91) P-8 m / z = 649.33 (C ₄₇ H ₂₃ D ₁₀ N ₃ = 649.85) P-9 m / z = 657.32 (C ₄₉ H ₃₁ D ₅ N ₂ = 657.85) P-10 m / z = 781.35 (C ₅₉ H ₃₅ D ₅ N ₂ = 781.99) P-11 m / z = 729.32 (C ₅₅ H ₃₁ D ₅ N ₂ = 729.92) P-12 m / z = 609.26 (C ₄₄ H ₂₄ D ₅ FN ₂ = 609.74) P-13 m / z = 567.27 (C ₄₂ H ₂₅ D ₅ N ₂ = 567.73) P-14 m / z = 541.26 (C ₄₀ H ₂₃ D ₅ N ₂ = 541.69) P-15 m / z = 541.26 (C ₄₀ H ₂₃ D ₅ N ₂ = 541.69) P-16 m / z = 541.26 (C ₄₀ H ₂₃ D ₅ N ₂ = 541.69) P-17 m / z = 541.26 (C ₄₀ H ₂₃ D ₅ N ₂ = 541.69) P-18 m / z = 591.27 (C ₄₄ H ₂₅ D ₅ N ₂ = 591.75) P-19 m / z = 617.29 (C ₄₆ H ₂₇ D ₅ N ₂ = 617.79) P-20 m / z = 649.26 (C ₄₆ H ₂₇ D ₅ N ₂ S = 649.86) P-21 m / z = 643.30 (C ₄₈ H ₂₉ D ₅ N ₂ = 643.83) P-22 m / z = 607.30 (C ₄₅ H ₂₉ D ₅ N ₂ = 607.80) P-23 m / z = 731.33 (C ₅₅ H ₃₃ D ₅ N ₂ = 731.93) P-24 m / z = 729.32 (C ₅₅ H ₃₁ D ₅ N ₂ = 729.92) P-25 m / z = 597.23 (C ₄₂ H ₂₃ D ₅ N ₂ S = 597.78) P-26 m / z = 581.25 (C ₄₂ H ₂₃ D ₅ N ₂ O = 581.72) P-27 m / z = 658.31 (C ₄₈ H ₃₀ D ₅ N ₃ = 658.84) P-28 m / z = 546.29 (C ₄₀ H ₁₈ D ₁₀ N ₂ = 546.73) P-29 m / z = 598.32 (C ₄₄ H ₁₈ D ₁₂ N ₂ = 598.80) P-30 m / z = 624.33 (C ₄₆ H ₂₀ D ₁₂ N ₂ = 624.83) P-31 m / z = 654.29 (C ₄₆ H ₂₂ D ₁₀ N ₂ S = 654.89) P-32 m / z = 624.33 (C ₄₆ H ₂₀ D ₁₂ N ₂ = 624.83) P-33 m / z = 621.31 (C ₄₆ H ₂₃ D ₉ N ₂ = 621.82) P-34 m / z = 622.32 (C ₄₆ H ₂₂ D ₁₀ N ₂ = 622.82) P-35 m / z = 622.32 (C ₄₆ H ₂₂ D ₁₀ N ₂ = 622.82) P-36 m / z = 653.37 (C ₄₈ H ₁₉ D ₁₅ N ₂ = 653.89) P-37 m / z = 543.27 (C ₄₀ H ₂₁ D ₇ N ₂ = 543.71) P-38 m / z = 593.28 (C ₄₄ H ₂₃ D ₇ N ₂ = 593.77) P-39 m / z = 593.28 (C ₄₄ H ₂₃ D ₇ N ₂ = 593.77) P-40 m / z = 619.30 (C ₄₆ H ₂₅ D ₇ N ₂ = 619.80) P-41 m / z = 669.32 (C ₅₀ H ₂₇ D ₇ N ₂ = 669.86) P-42 m / z = 669.32 (C ₅₀ H ₂₇ D ₇ N ₂ = 669.86) P-43 m / z = 669.32 (C ₅₀ H ₂₇ D ₇ N ₂ = 669.86) P-44 m / z = 669.32 (C ₅₀ H ₂₇ D ₇ N ₂ = 669.86) P-45 m / z = 695.33 (C ₅₂ H ₂₉ D ₇ N ₂ = 695.90) P-46 m / z = 659.33 (C ₄₉ H ₂₉ D ₇ N ₂ = 659.87) P-47 m / z = 783.36 (C ₅₉ H ₃₃ D ₇ N ₂ = 784.01) P-48 m / z = 781.35 (C ₅₉ H ₃₁ D ₇ N ₂ = 781.99) P-49 m / z = 649.26 (C ₄₆ H ₂₃ D ₇ N ₂ S = 649.85) P-50 m / z = 633.28 (C ₄₆ H ₂₃ D ₇ N ₂ O = 633.79) P-51 m / z = 710.34 (C ₅₂ H ₃₀ D ₇ N ₃ = 710.91) P-52 m / z = 548.30 (C ₄₀ H ₁₆ D ₁₂ N ₂ = 548.74) P-53 m / z = 600.33 (C ₄₄ H ₁₆ D ₁₄ N ₃ = 600.81) P-54 m / z = 600.33 (C ₄₄ H ₁₆ D ₁₄ N ₂ = 600.81) P-55 m / z = 624.33 (C ₄₆ H ₂₀ D ₁₂ N ₂ = 624.83) P-56 m / z = 676.36 (C ₅₀ H ₂₀ D ₁₄ N ₂ = 676.90) P-57 m / z = 673.34 (C ₅₀ H ₂₃ D ₁₁ N ₂ = 673.89) P-58 m / z = 673.34 (C ₅₀ H ₂₃ D ₁₁ N ₂ = 673.89) P-59 m / z = 674.35 (C ₅₀ H ₂₂ D ₁₂ N ₂ = 674.89) P-60 m / z = 705.39 (C ₅₂ H ₁₉ D ₁₇ N ₂ = 705.96) P-61 m / z = 567.27 (C ₄₂ H ₂₅ D ₅ N ₂ = 567.73) P-62 m / z = 617.29 (C ₄₆ H ₂₇ D ₅ N ₂ = 617.79) P-63 m / z = 617.29 (C ₄₆ H ₂₇ D ₅ N ₂ = 617.79) P-64 m / z = 643.30 (C ₄₈ H ₂₉ D ₅ N ₂ = 643.83) P-65 m / z = 692.31 (C ₅₂ H ₃₂ D ₄ N ₂ = 692.88) P-66 m / z = 692.31 (C ₅₂ H ₃₂ D ₄ N ₂ = 692.88) P-67 m / z = 697.34 (C ₅₂ H ₂₇ D ₉ N ₂ = 697.91) P-68 m / z = 697.34 (C ₅₂ H ₂₇ D ₉ N ₂ = 697.91) P-69 m / z = 718.33 (C ₅₄ H ₃₄ D ₄ N ₂ = 718.92) P-70 m / z = 683.33 (C ₅₁ H ₃₃ D ₅ N ₂ = 683.89) P-71 m / z = 807.37 (C ₆₁ H ₃₇ D ₅ N ₂ = 808.03) P-72 m / z = 805.35 (C ₆₁ H ₃₅ D ₅ N ₂ = 806.01) P-73 m / z = 677.29 (C ₄₈ H ₂₃ D ₉ N ₂ S = 677.90) P-74 m / z = 661.31 (C ₄₈ H ₂₃ D ₉ N ₂ O = 661.84) P-75 m / z = 738.37 (C ₅₄ H ₃₀ D ₉ N ₃ = 738.96) P-76 m / z = 572.30 (C ₄₂ H ₂₀ D ₁₀ N ₂ = 572.76) P-77 m / z = 624.33 (C ₄₆ H ₂₀ D ₁₂ N ₂ = 624.83) P-78 m / z = 624.33 (C ₄₆ H ₂₀ D ₁₂ N ₂ = 624.83) P-79 m / z = 648.33 (C ₄₈ H ₂₄ D ₁₀ N ₂ = 648.86) P-80 m / z = 699.36 (C ₅₂ H ₂₅ D ₁₁ N ₂ = 699.92) P-81 m / z = 696.34 (C ₅₂ H ₂₈ D ₈ N ₂ = 696.90) P-82 m / z = 702.38 (C ₅₂ H ₂₂ D ₁₄ N ₂ = 702.94) P-83 m / z = 702.38 (C ₅₂ H ₂₂ D ₁₄ N ₂ = 702.94) P-84 m / z = 728.39 (C ₅₄ H ₂₄ D ₁₄ N ₂ = 728.98) P-85 m / z = 619.30 (C ₄₆ H ₂₅ D ₇ N ₂ = 619.80) P-86 m / z = 669.32 (C ₅₀ H ₂₇ D ₇ N ₂ = 669.86) P-87 m / z = 667.30 (C ₅₀ H ₂₉ D ₅ N ₂ = 667.85) P-88 m / z = 694.33 (C ₅₂ H ₃₀ D ₆ N ₂ = 694.89) P-89 m / z = 742.33 (C ₅₆ H ₃₄ D ₄ N ₂ = 742.94) P-90 m / z = 742.33 (C ₅₆ H ₃₄ D ₄ N ₂ = 742.94) P-91 m / z = 743.33 (C ₅₆ H ₃₃ D ₅ N ₂ = 743.95) P-92 m / z = 743.33 (C ₅₆ H ₃₃ D ₅ N ₂ = 743.95) P-93 m / z = 768.34 (C ₅₈ H ₃₆ D ₄ N ₂ = 768.98) P-94 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) P-95 m / z = 856.38 (C ₆₅ H ₄₀ D ₄ N ₂ = 857.08) P-96 m / z = 855.37 (C ₆₅ H ₃₇ D ₅ N ₂ = 856.07) P-97 m / z = 729.31 (C ₅₂ H ₂₃ D ₁₁ N ₂ S = 729.97) P-98 m / z = 713.34 (C ₅₂ H ₂₃ D ₁₁ N ₂ O = 713.91) P-99 m / z = 790.40 (C ₅₈ H ₃₀ D ₁₁ N ₃ = 791.03) P-100 m / z = 624.33 (C ₄₆ H ₂₀ D ₁₂ N ₂ = 624.83) P-101 m / z = 676.36 (C ₅₀ H ₂₀ D ₁₄ N ₂ = 676.90) P-102 m / z = 674.35 (C ₅₀ H ₂₂ D ₁₂ N ₂ = 674.89) P-103 m / z = 699.36 (C ₅₂ H ₂₅ D ₁₁ N ₂ = 699.92) P-104 m / z = 749.37 (C ₅₆ H ₂₇ D ₁₁ N ₂ = 749.98) P-105 m / z = 746.35 (C ₅₆ H ₃₀ D ₈ N ₂ = 746.96) P-106 m / z = 748.37 (C ₅₆ H ₂₈ D ₁₀ N ₂ = 748.98) P-107 m / z = 748.37 (C ₅₆ H ₂₈ D ₁₀ N ₂ = 748.98) P-108 m / z = 778.41 (C ₅₈ H ₂₆ D ₁₄ N ₂ = 779.04) P-109 m / z = 643.30 (C ₄₈ H ₂₉ D ₅ N ₂ = 643.83) P-110 m / z = 693.32 (C ₅₂ H ₃₁ D ₅ N ₂ = 693.89) P-111 m / z = 697.34 (C ₅₂ H ₂₇ D ₉ N ₂ = 697.91) P-112 m / z = 723.36 (C ₅₄ H ₂₉ D ₉ N ₂ = 723.95) P-113 m / z = 699.28 (C ₅₀ H ₂₉ D ₅ N ₂ S = 699.91) P-114 m / z = 775.31 (C ₅₆ H ₃₃ D ₅ N ₂ S = 776.01) P-115 m / z = 775.31 (C ₅₆ H ₃₃ D ₅ N ₂ S = 776.01) P-116 m / z = 779.33 (C ₅₆ H ₂₉ D ₉ N ₂ S = 780.03) P-117 m / z = 835.40 (C ₆₃ H ₄₁ D ₅ N ₂ = 836.08) P-118 m / z = 923.43 (C ₇₀ H ₄₅ D ₅ N ₂ = 924.19) P-119 m / z = 1045.44 (C ₈₀ H ₄₇ D ₅ N ₂ = 1046.31) P-120 m / z = 1045.44 (C ₈₀ H ₄₇ D ₅ N ₂ = 1046.31) P-121 m / z = 913.35 (C ₆₇ H ₃₉ D ₅ N ₂ S = 914.18) P-122 m / z = 897.38 (C ₆₇ H ₃₉ D ₅ N ₂ O = 898.11) P-123 m / z = 972.42 (C ₇₃ H ₄₄ D ₅ N ₃ = 973.22) P-124 m / z = 648.33 (C ₄₈ H ₂₄ D ₁₀ N ₂ = 648.86) P-125 m / z = 700.36 (C ₅₂ H ₂₄ D ₁₂ N ₂ = 700.93) P-126 m / z = 704.39 (C ₅₂ H ₂₀ D ₁₆ N ₂ = 704.95) P-127 m / z = 728.39 (C ₅₄ H ₂₄ D ₁₄ N ₂ = 728.98) P-128 m / z = 706.32 (C ₅₀ H ₂₂ D ₁₂ N ₂ S = 706.96) P-129 m / z = 779.33 (C ₅₆ H ₂₉ D ₉ N ₂ S = 780.03) P-130 m / z = 780.34 (C ₅₆ H ₂₈ D ₁₀ N ₂ S = 781.04) P-131 m / z = 784.36 (C ₅₆ H ₂₄ D ₁₄ N ₂ S = 785.07) P-132 m / z = 845.46 (C ₆₃ H ₃₁ D ₁₅ N ₂ = 846.15)

Synthesis of Compound of Formula 2

One) Sub  1b Synthesis Example:

Sub  1b- 1 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), bromobenzene (37.68 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were added and then refluxed for 24 hours. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was purified and recrystallized by a silica gel column to obtain 26.14 g (75%) of the product.

Sub  1b- 2 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 1-bromonaphthalene (49.70 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-1b-1, to obtain 32.3 g (72%) of a product.

Sub  1b- 3 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 2-bromonaphthalene (49.70 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-1b-1, to obtain 32.3 g (72%) of a product.

Sub  1b- 4 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 4-bromobiphenyl (55.94 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1, to obtain 36.55 g (73%) of the product.

Sub  1b- 5 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 2-bromo-5-phenylthiophene (57.39 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Sub-1b-1 experiment to obtain 35.89 g (70%) of the product.

Sub  1b- 6 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 1-bromo-4-methoxybenzene (44.89 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-1b-1 to obtain 29.42 g (72%) of the product.

Sub  1b- 7 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 2-bromodibenzo [b, d] furan (59.30 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol ), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-1b-1 to obtain 35.95 g (68%) of the product.

Sub  1b- 8 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 1-bromo-4-fluorobenzene (42 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Sub-1b-1 experiment to obtain 23.84 g (62%) of the product.

Sub  1b- 9 of  synthesis

Aniline-d5 (19.63 g, 200 mmol), 4-bromobenzonitrile (43.68 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1, to obtain 26.30 g (66%) of the product.

compound FD-MS compound FD-MS Sub 1b-1 m / z = 174.12 (C ₁₂ H ₆ D ₅ N = 174.25) Sub 1b-2 m / z = 224.14 (C ₁₆ H ₈ D ₅ N = 224.31) Sub 1b-3 m / z = 224.14 (C ₁₆ H ₈ D ₅ N = 224.31) Sub 1b-4 m / z = 250.15 (C ₁₈ H ₁₀ D ₅ N = 250.35) Sub 1b-5 m / z = 256.11 (C ₁₆ H ₈ D ₅ NS = 256.38) Sub 1b-6 m / z = 204.13 (C ₁₃ H ₈ D ₅ NO = 204.28) Sub 1b-7 m / z = 199.12 (C ₁₈ H ₈ D ₅ NO = 264.33) Sub 1b-8 m / z = 192.11 (C ₁₂ H ₅ D ₅ FN = 192.24) Sub 1b-9 m / z = 264.13 (C ₁₃ H ₅ D ₅ N ₂ =: 199.26)

2) Sub  Example 2b synthesis:

Sub  2b- 1 of  synthesis

phenylaniline-d5 (34.85 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol) , NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub-1b-1 to obtain 55.13 g (68%) of the product.

Sub  2b- 2 of  synthesis

N-phenyl-d5-naphthalen-1-amine (44.86g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1, to give 62.85 g (69%) of the product.

Sub  2b- 3 of  synthesis

N-phenyl-d5-naphthalen-2-amine (44.86g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1 to obtain 61.93 g (68%) of the product.

Sub  2b- 4 of  synthesis

N-phenyl-d5-biphenyl-4-amine (50.07 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1, to obtain 65.48 g (68%) of the product.

Sub  2b- 5 of  synthesis

N-phenyl-d5-phenylthiophen-2-amine (51.28g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Sub-1b-1 Experiment to obtain 63.37 g (65%) of the product.

Sub  2b- 6 of  synthesis

N- (4-methoxyphenyl) -aniline-2,3,4,5,6-d5 (40.86g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in Sub-1b-1. 59.21 g (68%) was obtained.

Sub  2b- 7 of  synthesis

N-phenyl-d5-dibenzo [b, d] furan-2-amine (52.87 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g , 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in the Experiment of Sub-1b-1, and the product was 64.40 g ( 65%).

Sub  2b- 8 of  synthesis

N-phenyl-d5-4-fluorophenyl-1-amine (38.45 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol) , PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as the Sub-1b-1 experiment to give 56.73 g (67%) of the product. .

Sub  2b- 9 of  synthesis

4- (phenyl-d5-amino) benzonitrile (39.85 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1 to obtain 59.39 g (69%) of the product.

compound FD-MS compound FD-MS Sub 2b-1 m / z = 404.09 (C ₂₄ H ₁₃ D ₅ BrN = 405.34) Sub 2b-2 m / z = 454.11 (C ₂₈ H ₁₅ D ₅ BrN = 455.40) Sub 2b-3 m / z = 454.11 (C ₂₈ H ₁₅ D ₅ BrN = 455.40) Sub 2b-4 m / z = 480.12 (C ₃₀ H ₁₇ D ₅ BrN = 481.44) Sub 2b-5 m / z = 486.08 (C ₂₈ H ₁₅ D ₅ BrNS = 487.46) Sub 2b-6 m / z = 434.10 (C ₂₅ H ₁₅ D ₅ BrNO = 435.37) Sub 2b-7 m / z = 494.10 (C ₃₀ H ₁₅ D ₅ BrNO = 495.42) Sub 2b-8 m / z = 422.08 (C ₂₄ H ₁₂ D ₅ BrFN = 423.33) Sub 2b-9 m / z = 429.09 (C ₂₅ H ₁₂ D ₅ BrN ₂ = 430.35)

3) Sub  Example 3b synthesis:

Sub  Synthesis of 3b-1

aniline (18.63 g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Sub-1b-1 experiment to obtain 38.81 g (68%) of the product.

Sub  Synthesis of 3b-2

naphthalene-2-anime (28.64g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as the Sub-1b-1 experiment to obtain 45.62 g (68%) of the product.

Sub  Synthesis of 3b-3

naphthalene-1-anime (28.64g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Sub-1b-1 experiment to obtain 44.95 g (67%) of the product.

Sub  Synthesis of 3b-4

biphenyl-4-amine (33.84g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1 to obtain 49.88 g (69%) of the product.

Sub  Synthesis of 3b-5

9,9-dimethyl-9H-fluoren-2-amine (41.86 g, 200 mmol), 2-bromo-5-phenylthiophene (57.39 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as the Experimental Method of Sub-1b-1 to obtain 47.78 g (65%) of the product.

Sub  Synthesis of 3b-6

4-methoxyaniline (24.63g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1 to obtain 43.53 g (69%) of the product.

Sub  Synthesis of 3b-7

9,9-dimethyl-9H-fluoren-2-amine (41.86 g, 200 mmol), 2-bromodibenzo [b, d] furan (59.3 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol ), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 47.31 g (63%). Got it.

Sub  Synthesis of 3b-8

d5-aniline (32.65 g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1 to obtain 38.91 g (67%) of the product.

Sub  Synthesis of 3b-9

4-phenyl-d5-phenyl-1-amine (34.85 g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 50.58 g (69 %) Got.

Sub  Synthesis of 3b-10

2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), 2-Aminonaphthalene-d7 (30.05g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub-1b-1, to obtain 45.89 g (67%) of the product.

Sub  Synthesis of 3b-11

2-bromo-9,9-dimethyl-9H-fluorene (65.56 g, 240 mmol), biphenyl-d9-4-amine (35.66 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were obtained in the same manner as the Sub-1b-1 experiment to obtain 48.91 g (66%) of the product.

Sub  Synthesis of 3b-12

1-amino-4-phenyl-naphthalene-d6 (45.06g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as the Sub-1b-1. %) Got.

Sub  Synthesis of 3b-13

2-amino-6-phenyl-naphthalene-d6 (45.06g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 54.28 g (65 %) Got.

Sub  Synthesis of 3b-14

4- (naphthalen-1-yl-d7) aniline (45.26 g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g , 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in the Sub-1b-1, and the product was 51.90 g ( 62%).

Sub  Synthesis of 3b-15

2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), 4- (naphthalen-2-yl) aniline-d11 (46.07 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g , 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in the Sub-1b-1, and the product was 53.25 g ( 63%).

Sub  Synthesis of 3b-16

4- (biphenyl-4-yl-d9) -aniline (50.87 g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 56.28 g. Got (63%).

Sub  Synthesis of 3b-17

9,9-dimethyl-9H-fluoren-2-amine (41.86 g, 200 mmol), 4'-bromo-3-phenyl-d5-biphenyl-d4 (76.38 g, 240 mmol), Pd ₂ (dba) ₃ ( 5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 54.49. g (61%) was obtained.

Sub  Synthesis of 3b-18

, 9-dimethyl-9H-fluoren-2-amine (41.86 g, 200 mmol), 2-bromo-5-phenyl-d5-thiophene (57.39 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol) and toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 47.69 g (64%). )

Sub  Synthesis of 3b-19

9,9-dimethyl-7-phenyl-d5-9H-fluoren-2-amine (58.08g, 200 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) are the same as the experimental method of Sub-1b-1. To give 64.68 g (67%) of the product.

Sub  Synthesis of 3b-20

2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), 7- (phenyl-d5) -9,9-diphenyl-9H-fluoren-2-amine (82.91g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) were tested for Sub-1b-1. In the same manner to give 78.88 g (65%) of the product.

Sub  Synthesis of 3b-21

2-bromo-9,9-dimethyl-9H-fluorene (65.56g, 240 mmol), 7- (phenyl-d5) -9,9 'spirobi [fluoren] -2-amine (82.51g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaO t -Bu (57.7 g, 600 mmol), toluene (1930 mL) and the experimental method of Sub-1b-1 In the same manner, 72.57 g (60%) of product was obtained.

compound FD - MS compound FD - MS Sub 3b-1 m / z = 285.15 (C ₂₁ H ₁₉ N = 285.38) Sub 3b-2 m / z = 335.17 (C ₂₅ H ₂₁ N = 335.44) Sub 3b-3 m / z = 335.17 (C ₂₅ H ₂₁ N = 335.44) Sub 3b-4 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 3b-5 m / z = 367.14 (C ₂₅ H ₂₁ NS = 367.51) Sub 3b-6 m / z = 315.16 (C ₂₂ H ₂₁ NO = 315.41) Sub 3b-7 m / z = 375.16 (C ₂₇ H ₂₁ NO = 375.46) Sub 3b-8 m / z = 290.18 (C ₂₁ H ₁₄ D ₅ N = 290.41) Sub 3b-9 m / z = 366.21 (C ₂₇ H ₁₈ D ₅ N = 366.51) Sub 3b-10 m / z = 342.21 (C ₂₅ H ₁₄ D ₇ N = 342.48) Sub 3b-11 m / z = 370.24 (C ₂₇ H ₁₄ D ₉ N = 370.53) Sub 3b-12 m / z = 417.24 (C ₃₁ H ₁₉ D ₆ N = 417.57) Sub 3b-13 m / z = 417.24 (C ₃₁ H ₁₉ D ₆ N = 417.57) Sub 3b-14 m / z = 418.24 (C ₃₁ H ₁₈ D ₇ N = 418.58) Sub 3b-15 m / z = 422.27 (C ₃₁ H ₁₄ D ₁₁ N = 422.60) Sub 3b-16 m / z = 446.27 (C ₃₃ H ₁₈ D ₉ N = 446.63) Sub 3b-17 m / z = 446.27 (C ₃₃ H ₁₈ D ₉ N = 446.63) Sub 3b-18 m / z = 372.17 (C ₂₅ H ₁₆ D ₅ NS = 372.54) Sub 3b-19 m / z = 482.28 (C ₃₆ H ₂₆ D ₅ N = 482.67) Sub 3b-20 m / z = 606.31 (C ₄₆ H ₃₀ D ₅ N = 606.81) Sub 3b-21 m / z = 604.29 (C ₄₆ H ₂₈ D ₅ N = 604.79)

Final product ( Final Product ) Synthesis Example

Compound of Sub2b (1.2 equiv), Compound of Sub3b (1 equiv), Pd ₂ (dba) ₃ (0.06 ~ 0.1 mmol), PPh ₃ (0.2 equiv), NaO t -Bu (6 equiv), toluene (10.5 mL / 1 mmol) was added and the reaction proceeds at 100 ° C. 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 was purified and recrystallized by a silica gel column to obtain a product.

compound FD-MS compound FD-MS P2-1 m / z = 609.32 (C ₄₅ H ₃₁ D ₅ N ₂ = 609.81) P2-2 m / z = 659.33 (C ₄₉ H ₃₃ D ₅ N ₂ = 659.33) P2-3 m / z = 659.33 (C ₄₉ H ₃₃ D ₅ N ₂ = 659.87) P2-4 m / z = 685.35 (C ₅₁ H ₃₅ D ₅ N ₂ = 685.91) P2-5 m / z = 691.31 (C ₄₉ H ₃₃ D ₅ N ₂ S = 691.94) P2-6 m / z = 639.33 (C ₄₆ H ₃₃ D ₅ N ₂ O = 639.84) P2-7 m / z = 699.33 (C ₅₁ H ₃₃ D ₅ N ₂ O = 699.89 P2-8 m / z = 659.33 (C ₄₉ H ₃₃ D ₅ N ₂ = 659.87) P2-9 m / z = 659.33 (C ₄₉ H ₃₃ D ₅ N ₂ = 659.87) P2-10 m / z = 685.35 (C ₅₁ H ₃₅ D ₅ N ₂ = 685.91) P2-11 m / z = 691.31 (C ₄₉ H ₃₃ D ₅ N ₂ S = 691.94) P2-12 m / z = 639.33 (C ₄₆ H ₃₃ D ₅ N ₂ O = 639.84) P2-13 m / z = 699.33 (C ₅₁ H ₃₃ D ₅ N ₂ O = 699.89) P2-14 m / z = 661.35 (C ₄₉ H ₃₁ D ₇ N ₂ = 661.88) P2-15 m / z = 661.35 (C ₄₉ H ₃₁ D ₇ N ₂ = 661.88) P2-16 m / z = 689.38 (C ₅₁ H ₃₁ D ₉ N ₂ = 689.93) P2-17 m / z = 736.37 (C ₅₅ H ₃₆ D ₆ N ₂ = 736.97) P2-18 m / z = 736.37 (C ₅₅ H ₃₆ D ₆ N ₂ = 736.97) P2-19 m / z = 737.38 (C ₅₅ H ₃₅ D ₇ N ₂ = 737.98) P2-20 m / z = 741.40 (C ₅₅ H ₃₁ D ₁₁ N ₂ = 742.00) P2-21 m / z = 765.41 (C ₅₇ H ₃₅ D ₉ N ₂ = 766.03) P2-22 m / z = 765.41 (C ₅₇ H ₃₅ D ₉ N ₂ = 766.03) P2-23 m / z = 691.31 (C ₄₉ H ₃₃ D ₅ N ₂ S = 691.94) P2-24 m / z = 773.38 (C ₅₈ H ₃₉ D ₅ N ₂ = 774.01) P2-25 m / z = 925.44 (C ₇₀ H ₄₇ D ₅ N ₂ = 926.21) P2-26 m / z = 923.43 (C ₇₀ H ₄₅ D ₅ N ₂ = 924.19) P2-27 m / z = 609.32 (C ₄₅ H ₃₁ D ₅ N ₂ = 609.81) P2-28 m / z = 685.35 (C ₅₁ H ₃₅ D ₅ N ₂ = 685.91) P2-29 m / z = 661.35 (C ₄₅ H ₃₁ D ₇ N ₂ = 661.88) P2-30 m / z = 689.38 (C ₅₁ H ₃₁ D ₉ N ₂ = 689.93) P2-31 m / z = 736.37 (C ₅₅ H ₃₆ D ₆ N ₂ = 736.97) P2-32 m / z = 736.37 (C ₅₅ H ₃₆ D ₆ N ₂ = 736.97) P2-33 m / z = 737.38 (C ₅₅ H ₃₅ D ₇ N ₂ = 737.98) P2-34 m / z = 741.40 (C ₅₅ H ₃₁ D ₁₁ N ₂ = 742.00) P2-35 m / z = 765.41 (C ₅₇ H ₃₅ D ₉ N ₂ = 766.03) P2-36 m / z = 765.41 (C ₅₇ H ₃₅ D ₉ N ₂ = 766.03) P2-37 m / z = 695.34 (C ₄₉ H ₃₇ D ₅ N ₂ S = 695.97) P2-38 m / z = 801.41 (C ₆₀ H ₄₃ D ₅ N ₂ = 802.07) P2-39 m / z = 925.44 (C ₇₀ H ₄₇ D ₅ N ₂ = 926.21) P2-40 m / z = 923.43 (C ₇₀ H ₄₅ D ₅ N ₂ = 924.19) P2-41 m / z = 733.35 (C ₅₅ H ₃₅ D ₅ N ₂ = 733.95) P2-42 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) P2-43 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) P2-44 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) P2-45 m / z = 815.34 (C ₅₉ H ₃₇ D ₅ N ₂ S = 816.07) P2-46 m / z = 763.36 (C ₅₆ H ₃₇ D ₅ N ₂ O = 763.98) P2-47 m / z = 823.36 (C ₆₁ H ₃₇ D ₅ N ₂ O = 824.03) P2-48 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) P2-49 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) P2-50 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) P2-51 m / z = 815.34 (C ₅₉ H ₃₇ D ₅ N ₂ S = 816.07) P2-52 m / z = 763.36 (C ₅₆ H ₃₇ D ₅ N ₂ O = 763.98) P2-53 m / z = 823.36 (C ₆₁ H ₃₇ D ₅ N ₂ O = 824.03) P2-54 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) P2-55 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) P2-56 m / z = 813.41 (C ₆₁ H ₃₅ D ₉ N ₂ = 814.07) P2-57 m / z = 860.40 (C ₆₅ H ₄₀ D ₆ N ₂ = 861.11) P2-58 m / z = 860.40 (C ₆₅ H ₄₀ D ₆ N ₂ = 861.11) P2-59 m / z = 861.41 (C ₆₅ H ₃₉ D ₇ N ₂ = 862.12) P2-60 m / z = 865.44 (C ₆₅ H ₃₅ D ₁₁ N ₂ = 866.14) P2-61 m / z = 889.44 (C ₆₇ H ₃₉ D ₉ N ₂ = 890.17) P2-62 m / z = 889.44 (C ₆₇ H ₃₉ D ₉ N ₂ = 890.17) P2-63 m / z = 815.34 (C ₅₉ H ₃₇ D ₅ N ₂ S = 816.07) P2-64 m / z = 897.41 (C ₆₈ H ₄₃ D ₅ N ₂ = 898.15) P2-65 m / z = 1049.48 (C ₈₀ H ₅₁ D ₅ N ₂ = 1050.34) P2-66 m / z = 1047.46 (C ₈₀ H ₄₉ D ₅ N ₂ = 1048.33) P2-67 m / z = 733.35 (C ₅₅ H ₃₅ D ₅ N ₂ = 733.95) P2-68 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) P2-69 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) P2-70 m / z = 813.41 (C ₆₁ H ₃₅ D ₉ N ₂ = 814.07) P2-71 m / z = 860.40 (C ₆₅ H ₄₀ D ₆ N ₂ = 861.11) P2-72 m / z = 860.40 (C ₆₅ H ₄₀ D ₆ N ₂ = 861.11) P2-73 m / z = 861.41 (C ₆₅ H ₃₉ D ₇ N ₂ = 862.12) P2-74 m / z = 865.44 (C ₆₅ H ₃₅ D ₁₁ N ₂ = 866.14) P2-75 m / z = 889.44 (C ₆₇ H ₃₉ D ₉ N ₂ = 890.17) P2-76 m / z = 889.44 (C ₆₇ H ₃₉ D ₉ N ₂ = 890.17) P2-77 m / z = 819.37 (C ₅₉ H ₄₁ D ₅ N ₂ S = 820.11) P2-78 m / z = 925.44 (C ₇₀ H ₄₇ D ₅ N ₂ = 926.21) P2-79 m / z = 1049.48 (C ₈₀ H ₅₁ D ₅ N ₂ = 1050.34) P2-80 m / z = 1047.46 (C ₈₀ H ₄₉ D ₅ N ₂ = 1048.33) P2-81 m / z = 731.33 (C ₅₅ H ₃₃ D ₅ N ₂ = 731.93) P2-82 m / z = 781.35 (C ₅₉ H ₃₅ D ₅ N ₂ = 781.99) P2-83 m / z = 781.35 (C ₅₉ H ₃₅ D ₅ N ₂ = 781.99) P2-84 m / z = 807.37 (C ₆₁ H ₃₇ D ₅ N ₂ = 808.03) P2-85 m / z = 813.32 (C ₅₉ H ₃₅ D ₅ N ₂ S = 814.06) P2-86 m / z = 761.35 (C ₅₆ H ₃₅ D ₅ N ₂ O = 761.96) P2-87 m / z = 821.35 (C ₆₁ H ₃₅ D ₅ N ₂ O = 822.01) P2-88 m / z = 781.35 (C ₅₉ H ₃₅ D ₅ N ₂ = 781.99) P2-89 m / z = 781.35 (C ₅₉ H ₃₅ D ₅ N ₂ = 781.99) P2-90 m / z = 807.37 (C ₆₁ H ₃₇ D ₅ N ₂ = 808.03) P2-91 m / z = 813.32 (C ₅₉ H ₃₅ D ₅ N ₂ S = 814.06) P2-92 m / z = 761.35 (C ₅₆ H ₃₅ D ₅ N ₂ O = 761.96) P2-93 m / z = 821.35 (C ₆₁ H ₃₅ D ₅ N ₂ O = 822.01) P2-94 m / z = 783.36 (C ₅₉ H ₃₃ D ₇ N ₂ = 784.01) P2-95 m / z = 783.36 (C ₅₉ H ₃₃ D ₇ N ₂ = 784.01) P2-96 m / z = 811.39 (C ₆₁ H ₃₃ D ₉ N ₂ = 812.06) P2-97 m / z = 858.39 (C ₆₅ H ₃₈ D ₆ N ₂ = 859.10) P2-98 m / z = 858.39 (C ₆₅ H ₃₈ D ₆ N ₂ = 589.10) P2-99 m / z = 859.39 (C ₆₅ H ₃₇ D ₇ N ₂ = 860.10) P2-100 m / z = 863.42 (C ₆₅ H ₃₃ D ₁₁ N ₂ = 864.13) P2-101 m / z = 887.42 (C ₆₇ H ₃₇ D ₉ N ₂ = 888.15) P2-102 m / z = 887.42 (C ₆₇ H ₃₇ D ₉ N ₂ = 888.15) P2-103 m / z = 813.32 (C ₅₉ H ₃₅ D ₅ N ₂ S = 814.06) P2-104 m / z = 895.40 (C ₆₈ H ₄₁ D ₅ N ₂ = 896.14) P2-105 m / z = 1047.46 (C ₈₀ H ₄₉ D ₅ N ₂ = 1048.33) P2-106 m / z = 1045.44 (C ₈₀ H ₄₇ D ₅ N ₂ = 1046.31) P2-107 m / z = 731.33 (C ₅₅ H ₃₃ D ₅ N ₂ = 731.93) P2-108 m / z = 807.37 (C ₆₁ H ₃₇ D ₅ N ₂ = 808.03) P2-109 m / z = 783.36 (C ₅₉ H ₃₃ D ₇ N ₂ = 784.01) P2-110 m / z = 811.39 (C ₆₁ H ₃₃ D ₉ N ₂ = 812.06) P2-111 m / z = 858.39 (C ₆₅ H ₃₃ D ₆ N ₂ = 859.10) P2-112 m / z = 858.39 (C ₆₅ H ₃₈ D ₆ N ₂ = 859.10) P2-113 m / z = 859.39 (C ₆₅ H ₃₇ D ₇ N ₂ = 860.10) P2-114 m / z = 863.42 (C ₆₅ H ₃₃ D ₁₁ N ₂ = 864.13) P2-115 m / z = 887.42 (C ₆₇ H ₃₇ D ₉ N ₂ = 888.15) P2-116 m / z = 887.42 (C ₆₇ H ₃₇ D ₉ N ₂ = 888.15) P2-117 m / z = 817.35 (C ₅₉ H ₃₉ D ₅ N ₂ S = 818.09) P2-118 m / z = 923.43 (C ₇₀ H ₄₅ D ₅ N ₂ = 924.19) P2-119 m / z = 1047.46 (C ₈₀ H ₄₉ D ₅ N ₂ = 1048.33) P2-120 m / z = 1045.44 (C ₈₀ H ₄₇ D ₅ N ₂ = 1046.31)

On the other hand, each of the substituents of the compounds represented by the formula (1) or (2) is a broad relationship, the compounds represented by the formula (1) or formula (2) that is illustratively described a synthesis example of representative compounds, but not illustratively described as a synthesis example Also part of the present specification.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.

The compound according to the present invention can be used for various purposes in the organic electroluminescent device according to the type and nature of the substituent.

The compounds of the present invention can act as various layers other than the host of the phosphorescent or fluorescent light emitting layer because they are freely controlled by the core and the substituents.

The organic electric device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electric device except for forming one or more organic material layers using the above-described compounds.

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, it is obvious that the same effect can be obtained.

Meanwhile, the compound of the present invention can be used in a soluble process. In other words, the compound may form an organic material layer of the organic electronic device, which will be described later, by a solution process. In other words, when the compound is used as an organic material layer, the organic material layer may be formed by using various polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by the method.

Organic electroluminescent devices in which the compounds of the present invention may be used include, for example, organic electroluminescent devices (OLEDs), organic solar cells, organic photoconductor (OPC) drums, organic transistors (organic TFTs), and the like.

As an example of the organic electroluminescent device to which the compounds of the present invention can be applied, an organic electroluminescent device (OLED) will be described. However, the present invention is not limited thereto, and the above-described compounds may be applied to various organic electroluminescent devices.

Another embodiment of the present invention is an organic electroluminescent device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer comprises an organic electroluminescent device comprising the compounds of the present invention to provide.

1 to 6 show examples of the organic electroluminescent device to which the compound of the present invention can be applied.

The organic electroluminescent device according to another embodiment of the present invention, except that at least one layer of the organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer to include the compound of the present invention. Can be prepared with a structure known in the art using conventional manufacturing methods and materials in the art.

The structure of the organic electroluminescent device according to another embodiment of the present invention is illustrated in Figures 1 to 6, but is not limited to these structures. In this case, reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode.

Although not shown, the organic electroluminescent device further includes a hole blocking layer (HBL) that prevents the movement of holes, an electron blocking layer (EBL) that prevents the movement of electrons, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.

In this case, the compound of the present invention may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.

Specifically, the compound of the present invention is used in place of or in combination with one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer and a protective layer It may be used to form. Of course, the organic layer may be used not only in one layer but also in two or more layers.

In particular, it can be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a luminescent material and a passivation (kepping) material according to the compound of the present invention, in particular a host or in a luminescent material and host / dopant alone Can be used as a dopant, can be used as a hole injection, a hole transport layer.

For example, the organic electroluminescent device according to another embodiment of the present invention is a metal having metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. Can be prepared.

In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.

In addition, the organic layer may be formed using a variety of polymer materials, but not by a deposition process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made with a small number of layers.

The organic electroluminescent device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process.

The substrate is a support of the organic electroluminescent device, and a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, or the like can be used.

An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon. The positive electrode material may be a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

The hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.

The hole injection material is a material that can be injected well from the anode at a low voltage, the highest occupied molecular orbital (HOMO) of the hole injection material may be between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is positioned on the hole injection layer. The hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons. In addition to these general requirements, applications for vehicle body display require heat resistance to the device, and may be a material having a glass transition temperature (Tg) of 70 ° C. or higher.

Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compound, a silicon-based arylamine compound, and the like.

The organic light emitting layer is positioned on the hole transport layer. The organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and may be a material having good quantum efficiency for fluorescence or phosphorescence.

Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenollithium salt ), Bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 '[ (1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine) can be used by doping in small amounts. In the case of red, DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H Small amounts of doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile) can be used.

When forming a light emitting layer using a process such as inkjet printing, roll coating, or spin coating, a polymer of polyphenylene vinylene (PPV) -based polymer or poly fluorene may be used for the organic light emitting layer. .

The electron transport layer is positioned on the organic light emitting layer. The electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons.

Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.

The electron injection layer is stacked on the electron transport layer. The electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ~ 300Å.

The cathode is positioned on the electron injection layer. This cathode serves to inject electrons. The material used as the cathode may use the material used for the anode, and may be a metal having a low work function for efficient electron injection. In particular, a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used. In addition, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 μm or less may also be used.

As described above, according to the compound of the present invention, it can be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, and white, It can be used as a host or dopant material of various colors.

The organic electroluminescent device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.

Meanwhile, the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.

Comparative example

Manufacturing Evaluation of Organic Electrical Device

Various compounds obtained through synthesis were used as light emitting host materials or hole transport layers of the light emitting layer, respectively, to fabricate an organic electroluminescent device according to a conventional method. First, a 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the organic substrate as a hole injecting layer to form a thickness of 10 nm. Subsequently, the inventive compound (Formula 1, Formula 2) and the comparative example were vacuum deposited to a thickness of 20 nm with the hole transport layer. Vacuum deposition was carried out for comparative experiments. Thereafter, BD-052X (Idemitsu Co., Ltd.) was used as a light emitting dopant, and the host material was 9, 10-di- (naphthalene-2-anthracene) = AND], and the doping concentration was fixed at 4%. It was. Subsequently, tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm with an electron injection layer. Thereafter, LiF, which is an alkyl halide metal, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device using the Al / LiF as a cathode.

The electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices prepared as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage. The T90 life was measured using a life measurement instrument manufactured by McScience. The following table shows the results of device fabrication and evaluation.

(Compound of Formula 1) compound Voltage Current density Brightness
(cd / m2) Efficiency Lifetime
T (90) CIE
(x, y) Comparative Example (1) Comparative Example (1) 6.6 7.5 300.0 4.0 57.4 (0.15, 0.15) Comparative Example (2) Comparative Example (2) 5.8 5.7 300.0 5.3 93.7 (0.15, 0.15) Comparative Example (3) Comparative Example (3) 5.6 6.0 300.0 5.0 85.9 (0.15, 0.14) Example (1) Compound (P-1) 5.4 7.5 300.0 4.0 88.9 (0.15, 0.14) Example (2) Compound (P-2) 5.1 7.5 300.0 4.0 85.1 (0.15, 0.14) Example (3) Compound (P-3) 5.6 5.7 300.0 5.3 90.6 (0.14, 0.14) Example (4) Compound (P-4) 5.3 6.6 300.0 4.5 95.0 (0.15, 0.14) Example (5) Compound (P-5) 5.6 6.0 300.0 5.0 87.7 (0.14, 0.14) Example (6) Compound (P-6) 5.3 6.1 300.0 4.9 86.6 (0.15, 0.15) Example (7) Compound (P-7) 5.5 5.8 300.0 5.2 99.6 (0.15, 0.13) Example (8) Compound (P-8) 5.5 7.6 300.0 3.9 89.8 (0.15, 0.14) Example (9) Compound (P-9) 5.4 6.8 300.0 4.4 90.4 (0.15, 0.16) Example (10) Compound (P-10) 5.6 6.5 300.0 4.6 96.9 (0.15, 0.14) Example (11) Compound (P-11) 5.6 7.5 300.0 4.0 99.5 (0.14, 0.14) Example (12) Compound (P-12) 5.2 6.6 300.0 4.5 93.5 (0.14, 0.14) Example (13) Compound (P-13) 5.8 6.5 300.0 4.6 88.9 (0.15, 0.13) Example (14) Compound (P-14) 5.6 6.6 300.0 4.6 95.1 (0.15, 0.15) Example (15) Compound (P-15) 5.2 6.5 300.0 4.6 96.0 (0.15, 0.16) Example (16) Compound (P-16) 5.9 6.8 300.0 4.4 86.7 (0.15, 0.14) Example (17) Compound (P-17) 5.2 6.4 300.0 4.7 98.5 (0.15, 0.14) Example (18) Compound (P-18) 5.6 6.0 300.0 5.0 85.9 (0.15, 0.15) Example (19) Compound (P-19) 5.3 6.1 300.0 4.9 98.4 (0.15, 0.14) Example (20) Compound (P-20) 5.5 7.1 300.0 4.2 98.9 (0.15, 0.14) Example (21) Compound (P-21) 5.7 6.8 300.0 4.4 96.1 (0.14, 0.14) Example (22) Compound (P-22) 5.0 6.2 300.0 4.8 87.1 (0.15, 0.14) Example (23) Compound (P-23) 5.2 5.8 300.0 5.2 93.3 (0.15, 0.13) Example (24) Compound (P-24) 5.1 7.0 300.0 4.3 93.1 (0.15, 0.14) Example (25) Compound (P-25) 5.8 5.7 300.0 5.3 93.7 (0.15, 0.14) Example (26) Compound (P-26) 5.1 6.3 300.0 4.8 86.1 (0.15, 0.14) Example (27) Compound (P-27) 5.6 6.4 300.0 4.7 89.4 (0.15, 0.13) Example (28) Compound (P-28) 5.0 7.6 300.0 4.0 95.6 (0.15, 0.13) Example (29) Compound (P-29) 5.9 6.1 300.0 4.9 85.7 (0.15, 0.14) Example (30) Compound (P-30) 5.3 7.0 300.0 4.3 85.0 (0.15, 0.15) Example (31) Compound (P-31) 5.6 7.4 300.0 4.1 85.5 (0.15, 0.15) Example (32) Compound (P-32) 5.7 5.8 300.0 5.2 92.3 (0.15, 0.14) Example (33) Compound (P-33) 5.8 6.8 300.0 4.4 96.9 (0.15, 0.14) Example (34) Compound (P-34) 5.3 5.8 300.0 5.2 87.9 (0.15, 0.16) Example (35) Compound (P-35) 5.4 7.1 300.0 4.3 85.1 (0.14, 0.14) Example (36) Compound (P-36) 5.7 6.1 300.0 5.0 85.5 (0.15, 0.13) Example (37) Compound (P-37) 5.2 7.1 300.0 4.2 97.5 (0.15, 0.14) Example (38) Compound (P-38) 5.7 6.3 300.0 4.7 89.4 (0.15, 0.14) Example (39) Compound (P-39) 5.3 6.7 300.0 4.5 93.3 (0.15, 0.13) Example (40) Compound (P-40) 5.1 7.3 300.0 4.1 96.3 (0.15, 0.14) Example (41) Compound (P-41) 5.9 6.4 300.0 4.7 89.5 (0.15, 0.15) Example (42) Compound (P-42) 5.8 6.7 300.0 4.5 91.6 (0.15, 0.13) Example (43) Compound (P-43) 5.5 7.3 300.0 4.1 92.6 (0.15, 0.14) Example (44) Compound (P-44) 5.1 5.7 300.0 5.2 90.6 (0.15, 0.13) Example (45) Compound (P-45) 5.0 5.7 300.0 5.3 98.6 (0.15, 0.14) Example (46) Compound (P-46) 5.3 5.5 300.0 5.5 85.1 (0.15, 0.14) Example (47) Compound (P-47) 4.9 5.9 300.0 5.1 86.1 (0.15, 0.14) Example (48) Compound (P-48) 5.2 5.7 300.0 5.3 89.3 (0.15, 0.14) Example (49) Compound (P-49) 5.8 6.1 300.0 4.9 96.3 (0.14, 0.14) Example (50) Compound (P-50) 5.3 7.7 300.0 3.9 92.8 (0.14, 0.14) Example (51) Compound (P-51) 5.4 6.1 300.0 5.0 88.3 (0.15, 0.14) Example (52) Compound (P-52) 5.2 7.5 300.0 4.0 97.7 (0.15, 0.13) Example (53) Compound (P-53) 5.3 6.0 300.0 5.0 99.6 (0.15, 0.15) Example (54) Compound (P-54) 5.4 6.3 300.0 4.8 93.6 (0.15, 0.13) Example (55) Compound (P-55) 5.1 7.0 300.0 4.3 89.0 (0.15, 0.14) Example (56) Compound (P-56) 5.3 7.4 300.0 4.0 96.6 (0.15, 0.14) Example (57) Compound (P-57) 5.0 7.1 300.0 4.2 97.0 (0.14, 0.14) Example (58) Compound (P-58) 5.2 6.1 300.0 4.9 89.0 (0.15, 0.13) Example (59) Compound (P-59) 5.5 7.2 300.0 4.1 92.4 (0.15, 0.14) Example (60) Compound (P-60) 5.3 6.8 300.0 4.4 85.2 (0.15, 0.14) Example (61) Compound (P-61) 5.1 5.8 300.0 5.2 89.7 (0.14, 0.14) Example (62) Compound (P-62) 5.2 6.4 300.0 4.7 97.9 (0.15, 0.16) Example (63) Compound (P-63) 5.2 6.0 300.0 5.0 94.6 (0.15, 0.13) Example (64) Compound (P-64) 5.1 5.9 300.0 5.1 90.1 (0.15, 0.14) Example (65) Compound (P-65) 5.4 7.0 300.0 4.3 95.2 (0.15, 0.14) Example (66) Compound (P-66) 5.7 6.2 300.0 4.9 86.5 (0.15, 0.14) Example (67) Compound (P-67) 5.5 6.4 300.0 4.7 96.0 (0.15, 0.16) Example (68) Compound (P-68) 5.7 6.1 300.0 4.9 93.8 (0.14, 0.14) Example (69) Compound (P-69) 5.3 6.6 300.0 4.6 94.2 (0.15, 0.14) Example (70) Compound (P-70) 4.6 5.3 300.0 5.6 102.2 (0.14, 0.14) Example (71) Compound (P-71) 5.0 5.7 300.0 5.3 108.8 (0.15, 0.15) Example (72) Compound (P-72) 4.9 5.2 300.0 5.7 105.9 (0.15, 0.13) Example (73) Compound (P-73) 5.2 6.3 300.0 4.8 92.1 (0.15, 0.14) Example (74) Compound (P-74) 5.8 7.5 300.0 4.0 88.9 (0.15, 0.13) Example (75) Compound (P-75) 5.0 7.2 300.0 4.1 85.6 (0.15, 0.14) Example (76) Compound (P-76) 5.2 7.4 300.0 4.0 86.4 (0.14, 0.14) Example (77) Compound (P-77) 5.5 7.2 300.0 4.2 93.9 (0.14, 0.14) Example (78) Compound (P-78) 5.2 6.7 300.0 4.5 94.2 (0.15, 0.15) Example (79) Compound (P-79) 4.9 6.3 300.0 4.8 94.2 (0.15, 0.14) Example (80) Compound (P-80) 5.2 7.2 300.0 4.2 98.0 (0.15, 0.14) Example (81) Compound (P-81) 5.2 7.3 300.0 4.1 90.9 (0.14, 0.14) Example (82) Compound (P-82) 5.3 6.3 300.0 4.7 96.1 (0.15, 0.13) Example (83) Compound (P-83) 5.2 6.8 300.0 4.4 93.4 (0.15, 0.14) Example (84) Compound (P-84) 5.8 5.8 300.0 5.2 95.8 (0.15, 0.14) Example (85) Compound (P-85) 5.5 7.5 300.0 4.0 90.5 (0.15, 0.13) Example (86) Compound (P-86) 5.5 6.4 300.0 4.7 85.3 (0.14, 0.14) Example (87) Compound (P-87) 5.1 6.7 300.0 4.5 91.8 (0.15, 0.14) Example (88) Compound (P-88) 5.5 6.9 300.0 4.4 96.5 (0.15, 0.14) Example (89) Compound (P-89) 5.1 6.7 300.0 4.4 88.5 (0.14, 0.14) Example (90) Compound (P-90) 5.5 6.7 300.0 4.5 90.8 (0.15, 0.13) Example (91) Compound (P-91) 5.0 5.9 300.0 5.1 92.0 (0.15, 0.16) Example (92) Compound (P-92) 5.8 7.4 300.0 4.1 95.5 (0.15, 0.14) Example (93) Compound (P-93) 5.5 6.4 300.0 4.7 85.1 (0.15, 0.13) Example (94) Compound (P-94) 5.1 6.2 300.0 4.8 91.2 (0.14, 0.14) Example (95) Compound (P-95) 5.0 5.6 300.0 5.3 93.0 (0.15, 0.14) Example (96) Compound (P-96) 5.0 6.7 300.0 4.5 89.3 (0.15, 0.13) Example (97) Compound (P-97) 5.5 5.7 300.0 5.3 93.5 (0.14, 0.14) Example (98) Compound (P-98) 5.6 7.6 300.0 3.9 93.6 (0.14, 0.14) Example (99) Compound (P-99) 5.6 5.9 300.0 5.1 91.0 (0.15, 0.13) Example (100) Compound (P-100) 5.7 7.1 300.0 4.2 99.2 (0.15, 0.14) Example (101) Compound (P-101) 5.1 6.1 300.0 4.9 98.6 (0.14, 0.14) Example (102) Compound (P-102) 5.4 6.8 300.0 4.4 87.7 (0.15, 0.13) Example (103) Compound (P-103) 5.4 5.9 300.0 5.1 88.3 (0.14, 0.14) Example (104) Compound (P-104) 5.3 6.1 300.0 4.9 86.6 (0.15, 0.14) Example 105 Compound (P-105) 5.0 7.1 300.0 4.2 92.3 (0.14, 0.14) Example 106 Compound (P-106) 5.5 7.5 300.0 4.0 88.9 (0.15, 0.14) Example 107 Compound (P-107) 5.7 7.6 300.0 3.9 95.8 (0.15, 0.16) Example 108 Compound (P-108) 5.3 7.4 300.0 4.1 90.8 (0.14, 0.14) Example 109 Compound (P-109) 5.1 6.8 300.0 4.4 92.2 (0.14, 0.14) Example (110) Compound (P-110) 5.3 7.2 300.0 4.2 89.8 (0.15, 0.14) Example (111) Compound (P-111) 5.5 7.3 300.0 4.1 96.7 (0.15, 0.14) Example (112) Compound (P-112) 5.3 7.5 300.0 4.0 96.4 (0.14, 0.14) Example (113) Compound (P-113) 5.6 6.3 300.0 4.8 93.6 (0.15, 0.14) Example 114 Compound (P-114) 5.2 5.9 300.0 5.1 95.1 (0.14, 0.14) Example 115 Compound (P-115) 5.4 7.5 300.0 4.0 95.1 (0.15, 0.13) Example 116 Compound (P-116) 5.1 5.9 300.0 5.1 87.6 (0.14, 0.14) Example 117 Compound (P-117) 5.0 5.9 300.0 5.1 90.6 (0.15, 0.14) Example 118 Compound (P-118) 5.1 5.5 300.0 5.5 85.8 (0.14, 0.14) Example (119) Compound (P-119) 5.0 6.5 300.0 4.6 91.4 (0.15, 0.13) Example 120 Compound (P-120) 5.2 5.7 300.0 5.3 92.6 (0.15, 0.14) Example (121) Compound (P-121) 5.2 6.1 300.0 4.9 97.7 (0.15, 0.16) Example (122) Compound (P-122) 5.1 6.9 300.0 4.4 89.9 (0.15, 0.13) Example (123) Compound (P-123) 5.1 6.1 300.0 4.9 94.5 (0.15, 0.16) Example 124 Compound (P-124) 5.6 6.5 300.0 4.6 88.9 (0.15, 0.14) Example (125) Compound (P-125) 5.8 7.7 300.0 3.9 95.0 (0.15, 0.13) Example 126 Compound (P-126) 5.2 6.9 300.0 4.4 95.2 (0.14, 0.14) Example (127) Compound (P-127) 5.8 6.2 300.0 4.8 97.2 (0.15, 0.14) Example 128 Compound (P-128) 5.7 7.4 300.0 4.1 91.6 (0.15, 0.16) Example (129) Compound (P-129) 5.2 6.1 300.0 4.9 99.3 (0.15, 0.13) Example 130 Compound (P-130) 5.6 7.7 300.0 3.9 91.8 (0.15, 0.14) Example 131 Compound (P-131) 5.8 7.5 300.0 4.0 88.0 (0.15, 0.16) Example 132 Compound (P-132) 5.0 6.8 300.0 4.4 93.6 (0.15, 0.14)

(Compound of formula 2) Example (133) Compound (P2-1) 5.9 9.3 300.0 3.2 72.4 (0.15, 0.14) Example 134 Compound (P2-2) 6.2 8.6 300.0 3.5 99.8 (0.15, 0.14) Example (135) Compound (P2-3) 5.5 9.7 300.0 3.1 95.9 (0.14, 0.14) Example 136 Compound (P2-4) 5.9 9.0 300.0 3.4 90.4 (0.15, 0.14) Example (137) Compound (P2-5) 5.9 7.7 300.0 3.9 94.9 (0.14, 0.14) Example (138) Compound (P2-6) 5.6 9.9 300.0 3.0 98.7 (0.15, 0.15) Example (139) Compound (P2-7) 5.9 6.8 300.0 4.4 82.7 (0.15, 0.13) Example 140 Compound (P2-8) 5.8 7.1 300.0 4.2 93.4 (0.15, 0.14) Example 141 Compound (P2-9) 5.1 8.5 300.0 3.5 87.0 (0.15, 0.16) Example 142 Compound (P2-10) 5.6 7.9 300.0 3.8 79.6 (0.15, 0.14) Example 143 Compound (P2-11) 5.9 6.7 300.0 4.5 80.3 (0.14, 0.14) Example 144 Compound (P2-12) 5.9 9.3 300.0 3.2 96.1 (0.14, 0.14) Example 145 Compound (P2-13) 5.1 7.0 300.0 4.3 74.6 (0.15, 0.13) Example (146) Compound (P2-14) 5.2 9.2 300.0 3.3 91.7 (0.15, 0.15) Example (147) Compound (P2-15) 6.4 7.2 300.0 4.2 97.3 (0.15, 0.16) Example (148) Compound (P2-16) 5.2 7.0 300.0 4.3 79.6 (0.15, 0.14) Example 149 Compound (P2-17) 5.4 8.3 300.0 3.6 90.7 (0.15, 0.14) Example (150) Compound (P2-18) 6.1 6.5 300.0 4.6 75.0 (0.15, 0.15) Example 151 Compound (P2-19) 6.1 6.9 300.0 4.4 94.2 (0.15, 0.14) Example 152 Compound (P2-20) 5.1 6.6 300.0 4.5 74.5 (0.15, 0.14) Example 153 Compound (P2-21) 5.5 8.1 300.0 3.7 74.5 (0.14, 0.14) Example 154 Compound (P2-22) 5.6 8.8 300.0 3.4 71.0 (0.15, 0.14) Example (155) Compound (P2-23) 6.2 7.7 300.0 3.9 98.1 (0.15, 0.13) Example 156 Compound (P2-24) 5.8 8.0 300.0 3.8 89.3 (0.15, 0.14) Example (157) Compound (P2-25) 5.1 7.1 300.0 4.2 80.1 (0.15, 0.14) Example 158 Compound (P2-26) 5.5 6.9 300.0 4.4 78.1 (0.15, 0.14) Example 159 Compound (P2-27) 6.2 9.8 300.0 3.1 83.2 (0.15, 0.13) Example 160 Compound (P2-28) 5.1 5.8 300.0 5.1 95.5 (0.15, 0.13) Example 161 Compound (P2-29) 5.9 8.9 300.0 3.4 70.7 (0.15, 0.14) Example 162 Compound (P2-30) 6.3 7.8 300.0 3.8 89.7 (0.15, 0.15) Example 163 Compound (P2-31) 6.3 7.8 300.0 3.9 93.6 (0.15, 0.15) Example 164 Compound (P2-32) 6.0 6.7 300.0 4.5 77.9 (0.15, 0.14) Example (165) Compound (P2-33) 5.8 6.9 300.0 4.3 83.1 (0.15, 0.14) Example 166 Compound (P2-34) 5.7 8.1 300.0 3.7 97.5 (0.15, 0.16) Example 167 Compound (P2-35) 5.7 9.7 300.0 3.1 74.0 (0.14, 0.14) Example 168 Compound (P2-36) 6.4 8.5 300.0 3.5 73.8 (0.15, 0.13) Example (169) Compound (P2-37) 6.5 6.7 300.0 4.5 78.7 (0.15, 0.14) Example 170 Compound (P2-38) 6.3 6.5 300.0 4.6 76.2 (0.15, 0.14) Example 171 Compound (P2-39) 5.7 9.1 300.0 3.3 86.6 (0.15, 0.13) Example 172 Compound (P2-40) 5.1 9.0 300.0 3.3 97.2 (0.15, 0.14) Example (173) Compound (P2-41) 5.3 8.0 300.0 3.7 87.1 (0.15, 0.15) Example 174 Compound (P2-42) 6.2 8.2 300.0 3.7 84.5 (0.15, 0.13) Example (175) Compound (P2-43) 6.3 7.3 300.0 4.1 98.8 (0.15, 0.14) Example (176) Compound (P2-44) 5.3 7.9 300.0 3.8 71.4 (0.15, 0.13) Example (177) Compound (P2-45) 6.1 6.9 300.0 4.3 94.2 (0.15, 0.14) Example (178) Compound (P2-46) 6.2 7.5 300.0 4.0 73.5 (0.15, 0.14) Example (179) Compound (P2-47) 6.3 6.4 300.0 4.7 78.9 (0.15, 0.14) Example 180 Compound (P2-48) 5.8 7.0 300.0 4.3 83.9 (0.15, 0.14) Example (181) Compound (P2-49) 5.2 6.4 300.0 4.7 85.9 (0.14, 0.14) Example 182 Compound (P2-50) 6.5 8.0 300.0 3.8 71.0 (0.14, 0.14) Example (183) Compound (P2-51) 6.1 6.7 300.0 4.5 85.4 (0.15, 0.14) Example 184 Compound (P2-52) 5.2 6.7 300.0 4.4 77.2 (0.15, 0.13) Example (185) Compound (P2-53) 6.4 9.2 300.0 3.3 74.1 (0.15, 0.15) Example (186) Compound (P2-54) 5.6 8.3 300.0 3.6 85.3 (0.15, 0.13) Example (187) Compound (P2-55) 5.7 6.5 300.0 4.6 94.9 (0.15, 0.14) Example (188) Compound (P2-56) 5.6 7.1 300.0 4.2 98.0 (0.15, 0.14) Example (189) Compound (P2-57) 5.7 7.7 300.0 3.9 97.0 (0.14, 0.14) Example 190 Compound (P2-58) 5.5 9.3 300.0 3.2 96.4 (0.15, 0.13) Example (191) Compound (P2-59) 6.3 8.4 300.0 3.6 91.1 (0.15, 0.14) Example (192) Compound (P2-60) 6.2 6.6 300.0 4.6 71.7 (0.15, 0.14) Example (193) Compound (P2-61) 5.3 8.6 300.0 3.5 74.3 (0.14, 0.14) Example 194 Compound (P2-62) 5.5 9.2 300.0 3.3 94.1 (0.15, 0.16) Example (195) Compound (P2-63) 5.7 9.4 300.0 3.2 97.6 (0.15, 0.13) Example (196) Compound (P2-64) 5.5 7.1 300.0 4.2 71.9 (0.15, 0.14) Example (197) Compound (P2-65) 5.8 6.5 300.0 4.6 95.2 (0.15, 0.14) Example (198) Compound (P2-66) 5.3 7.4 300.0 4.1 94.6 (0.15, 0.14) Example (199) Compound (P2-67) 5.2 6.5 300.0 4.6 80.9 (0.15, 0.16) Example (200) Compound (P2-68) 4.8 5.4 300.0 5.5 99.3 (0.14, 0.14) Example 201 Compound (P2-69) 6.0 8.7 300.0 3.5 82.0 (0.15, 0.14) Example 202 Compound (P2-70) 5.8 8.2 300.0 3.7 84.7 (0.14, 0.14) Example (203) Compound (P2-71) 5.4 7.4 300.0 4.1 75.0 (0.15, 0.15) Example 204 Compound (P2-72) 6.5 7.4 300.0 4.1 71.1 (0.15, 0.13) Example (205) Compound (P2-73) 5.4 8.2 300.0 3.6 82.8 (0.15, 0.14) Example 206 Compound (P2-74) 5.3 9.0 300.0 3.3 78.4 (0.15, 0.13) Example (207) Compound (P2-75) 5.5 8.5 300.0 3.5 83.5 (0.15, 0.14) Example 208 Compound (P2-76) 5.3 6.9 300.0 4.3 76.6 (0.14, 0.14) Example (209) Compound (P2-77) 5.2 6.7 300.0 4.5 91.9 (0.14, 0.14) Example 210 Compound (P2-78) 5.7 7.4 300.0 4.1 95.4 (0.15, 0.15) Example 211 Compound (P2-79) 5.7 6.5 300.0 4.6 70.5 (0.15, 0.14) Example 212 Compound (P2-80) 5.9 7.8 300.0 3.9 72.0 (0.15, 0.14) Example (213) Compound (P2-81) 6.2 8.0 300.0 3.8 91.9 (0.14, 0.14) Example 214 Compound (P2-82) 6.5 7.0 300.0 4.3 82.7 (0.15, 0.13) Example 215 Compound (P2-83) 5.5 7.7 300.0 3.9 99.6 (0.15, 0.14) Example 216 Compound (P2-84) 5.3 6.6 300.0 4.6 84.1 (0.15, 0.14) Example 217 Compound (P2-85) 6.4 7.8 300.0 3.9 97.6 (0.15, 0.13) Example 218 Compound (P2-86) 5.6 6.6 300.0 4.5 76.0 (0.14, 0.14) Example 219 Compound (P2-87) 5.9 9.7 300.0 3.1 82.1 (0.15, 0.14) Example 220 Compound (P2-88 6.2 8.4 300.0 3.6 70.8 (0.15, 0.14) Example 221 Compound (P2-89) 5.9 8.9 300.0 3.4 74.8 (0.14, 0.14) Example 222 Compound (P2-90) 6.4 9.3 300.0 3.2 94.4 (0.15, 0.13) Example 223 Compound (P2-91) 6.4 9.6 300.0 3.1 71.1 (0.15, 0.16) Example 224 Compound (P2-92) 5.4 9.0 300.0 3.3 87.3 (0.15, 0.14) Example (225) Compound (P2-93) 6.4 6.5 300.0 4.6 85.7 (0.15, 0.13) Example (226) Compound (P2-94) 5.2 7.7 300.0 3.9 83.7 (0.14, 0.14) Example (227) Compound (P2-95) 6.4 8.0 300.0 3.7 86.5 (0.15, 0.14) Example (228) Compound (P2-96) 6.5 8.0 300.0 3.7 71.0 (0.15, 0.13) Example (229) Compound (P2-97) 5.3 7.1 300.0 4.2 99.7 (0.14, 0.14) Example 230 Compound (P2-98) 6.2 7.8 300.0 3.8 71.3 (0.14, 0.14) Example 231 Compound (P2-99) 5.6 8.2 300.0 3.7 91.1 (0.15, 0.13) Example 232 Compound (P2-100) 6.2 8.3 300.0 3.6 86.4 (0.15, 0.14) Example (233) Compound (P2-101) 6.3 9.5 300.0 3.1 91.3 (0.14, 0.14) Example 234 Compound (P2-102) 5.4 6.6 300.0 4.6 80.3 (0.15, 0.13) Example (235) Compound (P2-103) 6.1 8.8 300.0 3.4 72.2 (0.14, 0.14) Example 236 Compound (P2-104) 5.8 7.4 300.0 4.1 94.3 (0.15, 0.14) Example (237) Compound (P2-105) 6.3 6.9 300.0 4.3 89.9 (0.14, 0.14) Example (238) Compound (P2-106) 6.3 8.1 300.0 3.7 75.0 (0.15, 0.14) Example (239) Compound (P2-107) 5.3 8.2 300.0 3.6 79.4 (0.15, 0.16) Example (240) Compound (P2-108) 5.0 5.5 300.0 5.4 94.0 (0.14, 0.14) Example 241 Compound (P2-109) 6.4 6.6 300.0 4.6 72.6 (0.14, 0.14) Example 242 Compound (P2-110) 5.5 8.0 300.0 3.8 77.2 (0.15, 0.14) Example (243) Compound (P2-111) 5.7 7.9 300.0 3.8 91.2 (0.15, 0.14) Example (244) Compound (P2-112) 6.1 8.6 300.0 3.5 97.8 (0.14, 0.14) Example (245) Compound (P2-113) 6.3 9.2 300.0 3.3 87.0 (0.15, 0.14) Example 246 Compound (P2-114) 5.1 9.5 300.0 3.1 97.1 (0.14, 0.14) Example (247) Compound (P2-115) 5.5 8.5 300.0 3.5 85.0 (0.15, 0.13) Example 248 Compound (P2-116) 5.8 7.9 300.0 3.8 85.9 (0.14, 0.14) Example (249) Compound (P2-117) 6.3 8.6 300.0 3.5 93.9 (0.15, 0.14) Example 250 Compound (P2-118) 6.3 6.8 300.0 4.4 82.5 (0.14, 0.14) Example 251 Compound (P2-119) 5.2 9.5 300.0 3.1 90.8 (0.15, 0.13) Example 252 Compound (P2-120) 5.2 9.5 300.0 3.2 81.5 (0.15, 0.14)

Comparing the results of Comparative Examples and Examples of Table 8 and Table 9, the driving voltages of the example compounds substituted with deuterium were lower than those of Comparative Examples 1, 2, and 3, and the driving voltage was lowered as well as light emission. The results are high in terms of efficiency and lifetime.

Therefore, on the basis of these results, the materials of Table 9 and 50:50 were used using Examples 70, 71, and 72, which showed relatively high thermal stability, low driving voltage, and high lifetime. An element was fabricated in the same manner as above using the mixed hole transport layer, and the following device evaluation results were obtained.

compound Driving voltage Current (mA / cm2) Luminance (cd / m2) Efficiency (cd / A) T (90) Comparative Example (1) Comparative Example (1) 6.6 7.5 300 4 57.4 Comparative Example (2) Compound (P-70) 4.6 5.3 300 5.6 102.2 Comparative Example (3) Compound (P-71) 5 5.7 300 5.3 108.8 Comparative Example (4) Compound (P-72) 4.9 5.2 300 5.7 105.9 Example (253) Compound (P-70 + P2-1) 4.4 4.8 300.0 6.2 104.7 Example (254) Compound (P-70 + P2-2) 4.5 5.1 300.0 5.9 131.3 Example (255) Compound (P-70 + P2-3) 4.6 5.4 300.0 5.6 109.0 Example (256) Compound (P-70 + P2-4) 4.5 5.1 300.0 5.8 124.3 Example (257) Compound (P-70 + P2-5) 4.7 4.9 300.0 6.1 118.5 Example (258) Compound (P-70 + P2-6) 4.5 5.4 300.0 5.5 122.0 Example (259) Compound (P-70 + P2-7) 4.5 4.9 300.0 6.1 143.7 Example 260 Compound (P-70 + P2-8) 4.6 5.3 300.0 5.7 101.4 Example (261) Compound (P-70 + P2-9) 4.4 5.0 300.0 6.0 133.7 Example 262 Compound (P-70 + P2-10) 4.5 5.3 300.0 5.7 112.0 Example (263) Compound (P-70 + P2-11) 4.6 4.9 300.0 6.1 136.6 Example 264 Compound (P-70 + P2-12) 4.5 5.3 300.0 5.7 115.6 Example 265 Compound (P-70 + P2-13) 4.4 5.1 300.0 5.9 126.7 Example (266) Compound (P-70 + P2-14) 4.6 5.0 300.0 6.0 128.3 Example (267) Compound (P-70 + P2-15) 4.5 5.4 300.0 5.5 112.8 Example 268 Compound (P-70 + P2-16) 4.6 5.2 300.0 5.7 111.1 Example (269) Compound (P-70 + P2-17) 4.7 5.1 300.0 5.9 100.2 Example 270 Compound (P-70 + P2-18) 4.6 5.0 300.0 6.0 131.2 Example (271) Compound (P-70 + P2-19) 4.6 5.1 300.0 5.9 118.3 Example 272 Compound (P-70 + P2-20) 4.5 4.8 300.0 6.2 155.5 Example (273) Compound (P-70 + P2-21) 4.7 4.8 300.0 6.3 149.7 Example (274) Compound (P-70 + P2-22) 4.5 4.8 300.0 6.2 138.2 Example (275) Compound (P-70 + P2-23) 4.6 5.3 300.0 5.6 121.7 Example (276) Compound (P-70 + P2-24) 4.6 4.9 300.0 6.1 141.2 Example (277) Compound (P-70 + P2-25) 4.5 5.4 300.0 5.6 143.6 Example (278) Compound (P-70 + P2-26) 4.6 5.0 300.0 6.0 156.8 Example (279) Compound (P-70 + P2-27) 4.7 4.9 300.0 6.1 142.2 Example 280 Compound (P-70 + P2-28) 4.6 4.9 300.0 6.1 145.0 Example (281) Compound (P-70 + P2-29) 4.6 5.0 300.0 6.0 132.6 Example (282) Compound (P-70 + P2-30) 4.7 5.1 300.0 5.8 121.7 Example (283) Compound (P-70 + P2-31) 4.5 5.3 300.0 5.6 102.5 Example (284) Compound (P-70 + P2-32) 4.4 5.0 300.0 6.0 143.2 Example (285) Compound (P-70 + P2-33) 4.6 5.3 300.0 5.7 122.9 Example (286) Compound (P-70 + P2-34) 4.5 5.0 300.0 6.1 139.7 Example (287) Compound (P-70 + P2-35) 4.6 4.8 300.0 6.2 109.0 Example (288) Compound (P-70 + P2-36) 4.5 5.2 300.0 5.8 133.9 Example (289) Compound (P-70 + P2-37) 4.6 5.1 300.0 5.9 158.7 Example 290 Compound (P-70 + P2-38) 4.6 5.1 300.0 5.9 101.3 Example 291 Compound (P-70 + P2-39) 4.6 4.8 300.0 6.3 123.0 Example 292 Compound (P-70 + P2-40) 4.6 4.8 300.0 6.2 145.7 Example 293 Compound (P-70 + P2-41) 4.5 5.2 300.0 5.8 151.9 Example (294) Compound (P-70 + P2-42) 4.7 5.2 300.0 5.8 124.5 Example (295) Compound (P-70 + P2-43) 4.7 4.8 300.0 6.2 134.3 Example (296) Compound (P-70 + P2-44) 4.6 5.4 300.0 5.5 102.9 Example (297) Compound (P-70 + P2-45) 4.4 5.3 300.0 5.7 102.7 Example (298) Compound (P-70 + P2-46) 4.5 5.0 300.0 6.0 152.0 Example (299) Compound (P-70 + P2-47) 4.4 4.9 300.0 6.2 143.3 Example 300 Compound (P-70 + P2-48) 4.7 4.9 300.0 6.1 147.8 Example 301 Compound (P-70 + P2-49) 4.6 5.2 300.0 5.8 113.6 Example 302 Compound (P-70 + P2-50) 4.5 5.0 300.0 5.9 109.0 Example 303 Compound (P-70 + P2-51) 4.5 5.4 300.0 5.5 149.1 Example 304 Compound (P-70 + P2-52) 4.5 5.4 300.0 5.5 114.6 Example 305 Compound (P-70 + P2-53) 4.4 5.3 300.0 5.7 157.9 Example 306 Compound (P-70 + P2-54) 4.5 5.4 300.0 5.6 159.8 Example 307 Compound (P-70 + P2-55) 4.4 5.2 300.0 5.8 143.2 Example 308 Compound (P-70 + P2-56) 4.6 5.2 300.0 5.8 146.3 Example 309 Compound (P-70 + P2-57) 4.7 5.2 300.0 5.7 112.6 Example 310 Compound (P-70 + P2-58) 4.4 5.0 300.0 6.1 135.6 Example 311 Compound (P-70 + P2-59) 4.5 5.2 300.0 5.8 117.5 Example 312 Compound (P-70 + P2-60) 4.6 4.9 300.0 6.1 135.9 Example 313 Compound (P-70 + P2-61) 4.6 4.9 300.0 6.1 156.2 Example 314 Compound (P-70 + P2-62) 4.6 5.0 300.0 6.0 153.2 Example 315 Compound (P-70 + P2-63) 4.5 4.8 300.0 6.2 153.3 Example 316 Compound (P-70 + P2-64) 4.4 4.9 300.0 6.1 116.0 Example (317) Compound (P-70 + P2-65) 4.5 5.1 300.0 5.9 109.0 Example 318 Compound (P-70 + P2-66) 4.4 5.1 300.0 5.9 125.5 Example (319) Compound (P-70 + P2-67) 4.6 5.3 300.0 5.6 117.6 Example 320 Compound (P-70 + P2-68) 4.5 4.8 300.0 6.2 155.0 Example 321 Compound (P-70 + P2-69) 4.6 5.1 300.0 5.9 145.8 Example 322 Compound (P-70 + P2-70) 4.6 5.1 300.0 5.9 107.4 Example 323 Compound (P-70 + P2-71) 4.4 5.3 300.0 5.6 159.8 Example 324 Compound (P-70 + P2-72) 4.5 5.1 300.0 5.9 115.4 Example 325 Compound (P-70 + P2-73) 4.6 4.8 300.0 6.3 118.0 Example 326 Compound (P-70 + P2-74) 4.6 4.8 300.0 6.3 104.3 Example 327 Compound (P-70 + P2-75) 4.6 5.4 300.0 5.5 144.3 Example 328 Compound (P-70 + P2-76) 4.4 5.4 300.0 5.5 108.5 Example (329) Compound (P-70 + P2-77) 4.7 5.0 300.0 6.0 157.3 Example 330 Compound (P-70 + P2-78) 4.6 5.3 300.0 5.6 143.9 Example 331 Compound (P-70 + P2-79) 4.6 4.8 300.0 6.3 112.9 Example 332 Compound (P-70 + P2-80) 4.7 5.4 300.0 5.6 127.8 Example (333) Compound (P-70 + P2-81) 4.5 4.8 300.0 6.3 129.9 Example 334 Compound (P-70 + P2-82) 4.5 5.1 300.0 5.9 107.2 Example (335) Compound (P-70 + P2-83) 4.4 5.4 300.0 5.6 113.8 Example 336 Compound (P-70 + P2-84) 4.5 4.8 300.0 6.2 137.8 Example (337) Compound (P-70 + P2-85) 4.5 5.3 300.0 5.7 124.6 Example 338 Compound (P-70 + P2-86) 4.5 4.9 300.0 6.1 119.4 Example (339) Compound (P-70 + P2-87) 4.5 4.8 300.0 6.3 132.5 Example 340 Compound (P-70 + P2-88) 4.6 5.2 300.0 5.7 128.5 Example 341 Compound (P-70 + P2-89) 4.4 5.0 300.0 6.0 112.6 Example 342 Compound (P-70 + P2-90) 4.4 5.3 300.0 5.7 124.8 Example (343) Compound (P-70 + P2-91) 4.4 5.1 300.0 5.8 129.9 Example 344 Compound (P-70 + P2-92) 4.5 5.3 300.0 5.6 114.9 Example 345 Compound (P-70 + P2-93) 4.4 5.4 300.0 5.6 155.7 Example 346 Compound (P-70 + P2-94) 4.5 5.3 300.0 5.6 110.3 Example 347 Compound (P-70 + P2-95) 4.5 5.3 300.0 5.6 128.5 Example 348 Compound (P-70 + P2-96) 4.4 5.2 300.0 5.8 152.6 Example (349) Compound (P-70 + P2-97) 4.6 5.1 300.0 5.9 140.5 Example 350 Compound (P-70 + P2-98) 4.5 5.4 300.0 5.5 136.6 Example (351) Compound (P-70 + P2-99) 4.6 5.0 300.0 6.1 131.8 Example 352 Compound (P-70 + P2-100) 4.6 5.4 300.0 5.6 146.8 Example (353) Compound (P-70 + P2-101) 4.5 5.0 300.0 5.9 106.7 Example 354 Compound (P-70 + P2-102) 4.7 5.1 300.0 5.9 158.7 Example (355) Compound (P-70 + P2-103) 4.6 5.0 300.0 6.0 123.4 Example 356 Compound (P-70 + P2-104) 4.5 5.0 300.0 6.0 117.1 Example (357) Compound (P-70 + P2-105) 4.4 5.4 300.0 5.5 135.0 Example (358) Compound (P-70 + P2-106) 4.4 5.1 300.0 5.9 110.6 Example (359) Compound (P-70 + P2-107) 4.4 4.8 300.0 6.2 137.3 Example 360 Compound (P-70 + P2-108) 4.5 5.0 300.0 6.1 140.2 Example 361 Compound (P-70 + P2-109) 4.5 5.1 300.0 5.8 137.8 Example 362 Compound (P-70 + P2-110) 4.6 5.0 300.0 6.0 113.6 Example 363 Compound (P-70 + P2-111) 4.4 5.4 300.0 5.6 146.4 Example (364) Compound (P-70 + P2-112) 4.6 5.1 300.0 5.9 122.9 Example 365 Compound (P-70 + P2-113) 4.5 4.9 300.0 6.1 118.2 Example (366) Compound (P-70 + P2-114) 4.6 5.3 300.0 5.7 144.3 Example (367) Compound (P-70 + P2-115) 4.5 5.1 300.0 5.9 159.9 Example (368) Compound (P-70 + P2-116) 4.4 5.4 300.0 5.6 126.6 Example (369) Compound (P-70 + P2-117) 4.5 5.0 300.0 6.0 121.2 Example 370 Compound (P-70 + P2-118) 4.6 5.1 300.0 5.9 123.9 Example (371) Compound (P-70 + P2-119) 4.5 5.1 300.0 5.8 147.6 Example 372 Compound (P-70 + P2-120) 4.5 4.9 300.0 6.1 142.8 Example (373) Compound (P-71 + P2-1) 4.5 4.9 300.0 6.1 134.4 Example 374 Compound (P-71 + P2-2) 4.4 5.3 300.0 5.7 144.6 Example (375) Compound (P-71 + P2-3) 4.4 4.9 300.0 6.1 132.8 Example (376) Compound (P-71 + P2-4) 4.4 4.9 300.0 6.1 158.2 Example (377) Compound (P-71 + P2-5) 4.3 5.3 300.0 5.6 111.0 Example (378) Compound (P-71 + P2-6) 4.2 5.2 300.0 5.8 143.6 Example (379) Compound (P-71 + P2-7) 4.3 5.3 300.0 5.7 149.7 Example 380 Compound (P-71 + P2-8) 4.4 4.9 300.0 6.1 161.9 Example 381 Compound (P-71 + P2-9) 4.2 5.3 300.0 5.6 128.4 Example 382 Compound (P-71 + P2-10) 4.5 4.8 300.0 6.3 168.7 Example (383) Compound (P-71 + P2-11) 4.5 4.9 300.0 6.1 114.3 Example (384) Compound (P-71 + P2-12) 4.3 5.0 300.0 6.0 153.1 Example (385) Compound (P-71 + P2-13) 4.3 5.4 300.0 5.5 118.6 Example (386) Compound (P-71 + P2-14) 4.5 5.3 300.0 5.7 159.3 Example (387) Compound (P-71 + P2-15) 4.3 4.8 300.0 6.3 168.1 Example (388) Compound (P-71 + P2-16) 4.3 4.9 300.0 6.1 149.9 Example (389) Compound (P-71 + P2-17) 4.4 4.8 300.0 6.3 160.5 Example 390 Compound (P-71 + P2-18) 4.2 5.1 300.0 5.8 121.5 Example 391 Compound (P-71 + P2-19) 4.3 5.1 300.0 5.9 130.8 Example 392 Compound (P-71 + P2-20) 4.4 5.2 300.0 5.8 151.6 Example 393 Compound (P-71 + P2-21) 4.3 5.2 300.0 5.8 155.5 Example (394) Compound (P-71 + P2-22) 4.4 4.8 300.0 6.2 168.5 Example (395) Compound (P-71 + P2-23) 4.3 5.3 300.0 5.6 141.6 Example (396) Compound (P-71 + P2-24) 4.4 5.4 300.0 5.5 165.4 Example (397) Compound (P-71 + P2-25) 4.2 5.4 300.0 5.6 141.4 Example (398) Compound (P-71 + P2-26) 4.3 4.8 300.0 6.3 113.4 Example (399) Compound (P-71 + P2-27) 4.4 5.3 300.0 5.7 177.6 Example 400 Compound (P-71 + P2-28) 4.3 5.4 300.0 5.6 167.0 Example 401 Compound (P-71 + P2-29) 4.2 5.0 300.0 6.0 150.5 Example 402 Compound (P-71 + P2-30) 4.5 5.1 300.0 5.9 148.7 Example (403) Compound (P-71 + P2-31) 4.3 5.4 300.0 5.6 118.0 Example 404 Compound (P-71 + P2-32) 4.2 5.1 300.0 5.9 167.6 Example 405 Compound (P-71 + P2-33) 4.2 5.0 300.0 6.0 120.2 Example 406 Compound (P-71 + P2-34) 4.4 5.1 300.0 5.9 140.6 Example (407) Compound (P-71 + P2-35) 4.5 5.1 300.0 5.8 176.9 Example 408 Compound (P-71 + P2-36) 4.5 4.8 300.0 6.2 111.3 Example (409) Compound (P-71 + P2-37) 4.4 5.2 300.0 5.8 113.6 Example 410 Compound (P-71 + P2-38) 4.3 5.2 300.0 5.8 171.0 Example 411 Compound (P-71 + P2-39) 4.2 5.3 300.0 5.6 177.0 Example 412 Compound (P-71 + P2-40) 4.3 5.1 300.0 5.9 120.1 Example (413) Compound (P-71 + P2-41) 4.4 5.2 300.0 5.8 173.3 Example 414 Compound (P-71 + P2-42) 4.5 5.1 300.0 5.8 145.5 Example (415) Compound (P-71 + P2-43) 4.3 4.8 300.0 6.3 148.4 Example (416) Compound (P-71 + P2-44) 4.4 5.2 300.0 5.8 159.7 Example 417 Compound (P-71 + P2-45) 4.4 4.9 300.0 6.1 177.5 Example 418 Compound (P-71 + P2-46) 4.4 5.2 300.0 5.8 149.1 Example (419) Compound (P-71 + P2-47) 4.4 5.2 300.0 5.7 179.3 Example 420 Compound (P-71 + P2-48) 4.3 5.3 300.0 5.6 133.5 Example 421 Compound (P-71 + P2-49) 4.2 4.9 300.0 6.1 164.8 Example 422 Compound (P-71 + P2-50) 4.3 5.2 300.0 5.8 126.3 Example (423) Compound (P-71 + P2-51) 4.3 5.4 300.0 5.6 169.7 Example 424 Compound (P-71 + P2-52) 4.4 4.9 300.0 6.2 146.6 Example 425 Compound (P-71 + P2-53) 4.5 5.1 300.0 5.8 165.6 Example (426) Compound (P-71 + P2-54) 4.4 4.8 300.0 6.2 110.9 Example (427) Compound (P-71 + P2-55) 4.5 5.1 300.0 5.9 162.3 Example (428) Compound (P-71 + P2-56) 4.4 5.3 300.0 5.7 162.8 Example (429) Compound (P-71 + P2-57) 4.3 5.0 300.0 6.0 130.8 Example 430 Compound (P-71 + P2-58) 4.3 4.8 300.0 6.2 130.9 Example 431 Compound (P-71 + P2-59) 4.3 4.9 300.0 6.1 127.4 Example 432 Compound (P-71 + P2-60) 4.2 5.1 300.0 5.9 125.5 Example 433 Compound (P-71 + P2-61) 4.3 5.2 300.0 5.7 173.9 Example 434 Compound (P-71 + P2-62) 4.5 4.8 300.0 6.2 155.0 Example (435) Compound (P-71 + P2-63) 4.5 5.3 300.0 5.7 144.4 Example (436) Compound (P-71 + P2-64) 4.3 4.9 300.0 6.1 149.8 Example (437) Compound (P-71 + P2-65) 4.4 5.2 300.0 5.8 126.3 Example (438) Compound (P-71 + P2-66) 4.3 5.1 300.0 5.8 158.6 Example (439) Compound (P-71 + P2-67) 4.4 5.2 300.0 5.8 155.6 Example 440 Compound (P-71 + P2-68) 4.2 5.3 300.0 5.7 172.8 Example 441 Compound (P-71 + P2-69) 4.4 4.9 300.0 6.2 153.8 Example 442 Compound (P-71 + P2-70) 4.5 5.2 300.0 5.8 126.5 Example 443 Compound (P-71 + P2-71) 4.2 5.3 300.0 5.7 126.6 Example (444) Compound (P-71 + P2-72) 4.4 5.4 300.0 5.6 134.2 Example (445) Compound (P-71 + P2-73) 4.2 4.9 300.0 6.1 110.5 Example 446 Compound (P-71 + P2-74) 4.5 5.3 300.0 5.6 119.5 Example (447) Compound (P-71 + P2-75) 4.4 5.0 300.0 5.9 131.9 Example (448) Compound (P-71 + P2-76) 4.4 5.4 300.0 5.5 162.9 Example (449) Compound (P-71 + P2-77) 4.5 4.8 300.0 6.3 130.1 Example (450) Compound (P-71 + P2-78) 4.4 5.1 300.0 5.8 115.8 Example (451) Compound (P-71 + P2-79) 4.3 5.0 300.0 6.0 166.6 Example (452) Compound (P-71 + P2-80) 4.2 4.8 300.0 6.3 117.4 Example (453) Compound (P-71 + P2-81) 4.3 5.3 300.0 5.6 146.7 Example 454 Compound (P-71 + P2-82) 4.2 5.2 300.0 5.8 149.0 Example (455) Compound (P-71 + P2-83) 4.4 5.2 300.0 5.8 151.6 Example (456) Compound (P-71 + P2-84) 4.3 5.1 300.0 5.8 155.1 Example (457) Compound (P-71 + P2-85) 4.2 5.0 300.0 6.0 130.2 Example 458 Compound (P-71 + P2-86) 4.5 5.4 300.0 5.5 132.0 Example (459) Compound (P-71 + P2-87) 4.5 5.3 300.0 5.6 152.0 Example 460 Compound (P-71 + P2-88) 4.3 5.2 300.0 5.8 142.4 Example (461) Compound (P-71 + P2-89) 4.3 4.8 300.0 6.3 127.1 Example (462) Compound (P-71 + P2-90) 4.4 5.1 300.0 5.9 164.4 Example (463) Compound (P-71 + P2-91) 4.4 5.0 300.0 6.1 177.7 Example 464 Compound (P-71 + P2-92) 4.3 5.3 300.0 5.6 130.4 Example (465) Compound (P-71 + P2-93) 4.3 5.2 300.0 5.7 151.5 Example (466) Compound (P-71 + P2-94) 4.3 4.9 300.0 6.1 139.6 Example (467) Compound (P-71 + P2-95) 4.3 5.0 300.0 6.1 167.7 Example 468 Compound (P-71 + P2-96) 4.4 5.2 300.0 5.8 124.1 Example (469) Compound (P-71 + P2-97) 4.5 5.2 300.0 5.8 112.8 Example 470 Compound (P-71 + P2-98) 4.4 4.9 300.0 6.2 164.0 Example (471) Compound (P-71 + P2-99) 4.4 4.8 300.0 6.2 125.0 Example 472 Compound (P-71 + P2-100) 4.2 5.2 300.0 5.7 158.4 Example (473) Compound (P-71 + P2-101) 4.3 5.1 300.0 5.9 148.9 Example 474 Compound (P-71 + P2-102) 4.4 4.8 300.0 6.2 147.4 Example (475) Compound (P-71 + P2-103) 4.3 5.1 300.0 5.9 116.8 Example 476 Compound (P-71 + P2-104) 4.3 5.1 300.0 5.9 140.2 Example (477) Compound (P-71 + P2-105) 4.3 5.1 300.0 5.9 113.4 Example (478) Compound (P-71 + P2-106) 4.4 4.8 300.0 6.2 175.2 Example (479) Compound (P-71 + P2-107) 4.4 5.2 300.0 5.8 178.7 Example 480 Compound (P-71 + P2-108) 4.2 5.2 300.0 5.7 149.3 Example (481) Compound (P-71 + P2-109) 4.4 4.9 300.0 6.1 127.4 Example 482 Compound (P-71 + P2-110) 4.5 5.2 300.0 5.8 148.8 Example (483) Compound (P-71 + P2-111) 4.4 5.5 300.0 5.5 126.7 Example (484) Compound (P-71 + P2-112) 4.2 4.9 300.0 6.1 124.9 Example (485) Compound (P-71 + P2-113) 4.4 5.0 300.0 6.0 165.3 Example (486) Compound (P-71 + P2-114) 4.3 5.3 300.0 5.6 129.7 Example (487) Compound (P-71 + P2-115) 4.3 5.3 300.0 5.7 123.6 Example (488) Compound (P-71 + P2-116) 4.4 5.4 300.0 5.6 118.4 Example (489) Compound (P-71 + P2-117) 4.2 4.8 300.0 6.2 113.9 Example (490) Compound (P-71 + P2-118) 4.5 4.9 300.0 6.1 118.8 Example (491) Compound (P-71 + P2-119) 4.3 5.1 300.0 5.9 162.7 Example (492) Compound (P-71 + P2-120) 4.4 4.8 300.0 6.2 116.0 Example (493) Compound (P-72 + P2-1) 4.5 5.5 300.0 5.5 122.9 Example 494 Compound (P-72 + P2-2) 4.5 5.0 300.0 6.0 134.3 Example (495) Compound (P-72 + P2-3) 4.6 4.9 300.0 6.1 114.4 Example (496) Compound (P-72 + P2-4) 4.7 5.0 300.0 5.9 121.9 Example (497) Compound (P-72 + P2-5) 4.5 5.2 300.0 5.7 139.0 Example (498) Compound (P-72 + P2-6) 4.7 5.4 300.0 5.6 115.9 Example (499) Compound (P-72 + P2-7) 4.8 5.4 300.0 5.5 147.5 Example (500) Compound (P-72 + P2-8) 4.8 5.4 300.0 5.6 97.4 Example (501) Compound (P-72 + P2-9) 4.7 4.8 300.0 6.3 139.0 Example 502 Compound (P-72 + P2-10) 4.5 5.4 300.0 5.6 144.3 Example 503 Compound (P-72 + P2-11) 4.7 5.3 300.0 5.7 132.5 Example 504 Compound (P-72 + P2-12) 4.5 4.8 300.0 6.3 107.9 Example 505 Compound (P-72 + P2-13) 4.7 5.1 300.0 5.9 137.6 Example 506 Compound (P-72 + P2-14) 4.4 5.4 300.0 5.5 142.5 Example (507) Compound (P-72 + P2-15) 4.5 5.4 300.0 5.6 140.7 Example 508 Compound (P-72 + P2-16) 4.6 5.4 300.0 5.5 126.2 Example 509 Compound (P-72 + P2-17) 4.7 5.3 300.0 5.6 136.8 Example 510 Compound (P-72 + P2-18) 4.6 5.3 300.0 5.6 145.1 Example (511) Compound (P-72 + P2-19) 4.5 4.8 300.0 6.2 98.5 Example 512 Compound (P-72 + P2-20) 4.6 5.1 300.0 5.9 116.4 Example 513 Compound (P-72 + P2-21) 4.4 5.0 300.0 5.9 98.8 Example 514 Compound (P-72 + P2-22) 4.6 5.1 300.0 5.9 142.3 Example 515 Compound (P-72 + P2-23) 4.5 5.2 300.0 5.8 106.1 Example 516 Compound (P-72 + P2-24) 4.6 5.1 300.0 5.9 118.3 Example (517) Compound (P-72 + P2-25) 4.7 5.0 300.0 6.0 128.8 Example 518 Compound (P-72 + P2-26) 4.5 5.2 300.0 5.7 113.0 Example (519) Compound (P-72 + P2-27) 4.6 5.3 300.0 5.6 110.9 Example 520 Compound (P-72 + P2-28) 4.7 5.4 300.0 5.6 140.0 Example 521 Compound (P-72 + P2-29) 4.5 5.3 300.0 5.7 129.1 Example 522 Compound (P-72 + P2-30) 4.4 5.1 300.0 5.9 148.3 Example 523 Compound (P-72 + P2-31) 4.5 5.4 300.0 5.5 120.7 Example 524 Compound (P-72 + P2-32) 4.6 5.2 300.0 5.7 144.4 Example 525 Compound (P-72 + P2-33) 4.7 5.3 300.0 5.6 105.0 Example 526 Compound (P-72 + P2-34) 4.7 5.3 300.0 5.7 119.0 Example (527) Compound (P-72 + P2-35) 4.5 4.8 300.0 6.3 100.9 Example 528 Compound (P-72 + P2-36) 4.6 5.1 300.0 5.9 126.6 Example (529) Compound (P-72 + P2-37) 4.8 5.0 300.0 6.0 131.2 Example 530 Compound (P-72 + P2-38) 4.6 5.0 300.0 6.1 145.6 Example (531) Compound (P-72 + P2-39) 4.4 5.3 300.0 5.7 128.2 Example 532 Compound (P-72 + P2-40) 4.7 5.4 300.0 5.5 130.5 Example (533) Compound (P-72 + P2-41) 4.7 4.8 300.0 6.2 116.8 Example (534) Compound (P-72 + P2-42) 4.6 4.9 300.0 6.1 114.5 Example (535) Compound (P-72 + P2-43) 4.5 4.8 300.0 6.3 129.3 Example (536) Compound (P-72 + P2-44) 4.6 5.1 300.0 5.9 135.6 Example (537) Compound (P-72 + P2-45) 4.8 5.1 300.0 5.9 138.2 Example 538 Compound (P-72 + P2-46) 4.7 5.4 300.0 5.5 108.0 Example (539) Compound (P-72 + P2-47) 4.6 5.4 300.0 5.5 149.3 Example 540 Compound (P-72 + P2-48) 4.5 4.9 300.0 6.1 103.3 Example (541) Compound (P-72 + P2-49) 4.8 4.8 300.0 6.3 137.0 Example 542 Compound (P-72 + P2-50) 4.6 5.0 300.0 6.0 139.4 Example (543) Compound (P-72 + P2-51) 4.7 4.9 300.0 6.1 142.1 Example (544) Compound (P-72 + P2-52) 4.5 5.1 300.0 5.9 125.6 Example (545) Compound (P-72 + P2-53) 4.8 5.2 300.0 5.7 120.5 Example 546 Compound (P-72 + P2-54) 4.8 5.4 300.0 5.6 136.3 Example (547) Compound (P-72 + P2-55) 4.6 4.8 300.0 6.2 145.1 Example 548 Compound (P-72 + P2-56) 4.6 5.1 300.0 5.9 108.3 Example (549) Compound (P-72 + P2-57) 4.5 4.9 300.0 6.1 101.3 Example 550 Compound (P-72 + P2-58) 4.5 5.2 300.0 5.7 126.4 Example 551 Compound (P-72 + P2-59) 4.5 5.1 300.0 5.9 115.5 Example 552 Compound (P-72 + P2-60) 4.4 4.8 300.0 6.2 103.9 Example (553) Compound (P-72 + P2-61) 4.6 4.8 300.0 6.3 109.7 Example 554 Compound (P-72 + P2-62) 4.7 5.3 300.0 5.6 126.7 Example (555) Compound (P-72 + P2-63) 4.7 5.4 300.0 5.5 137.2 Example 556 Compound (P-72 + P2-64) 4.6 4.9 300.0 6.1 141.3 Example (557) Compound (P-72 + P2-65) 4.6 5.2 300.0 5.8 111.5 Example 558 Compound (P-72 + P2-66) 4.7 5.3 300.0 5.7 123.5 Example (559) Compound (P-72 + P2-67) 4.7 4.8 300.0 6.2 115.3 Example 560 Compound (P-72 + P2-68) 4.6 4.8 300.0 6.2 146.0 Example (561) Compound (P-72 + P2-69) 4.6 5.0 300.0 6.0 118.6 Example 562 Compound (P-72 + P2-70) 4.5 4.8 300.0 6.2 113.9 Example (563) Compound (P-72 + P2-71) 4.4 5.0 300.0 5.9 131.6 Example 564 Compound (P-72 + P2-72) 4.7 5.2 300.0 5.8 104.5 Example 565 Compound (P-72 + P2-73) 4.7 5.0 300.0 6.0 146.4 Example (566) Compound (P-72 + P2-74) 4.6 5.1 300.0 5.9 134.8 Example (567) Compound (P-72 + P2-75) 4.4 5.0 300.0 6.0 136.4 Example 568 Compound (P-72 + P2-76) 4.6 5.3 300.0 5.6 123.0 Example (569) Compound (P-72 + P2-77) 4.6 4.8 300.0 6.2 144.5 Example 570 Compound (P-72 + P2-78) 4.6 5.1 300.0 5.8 109.8 Example 571 Compound (P-72 + P2-79) 4.4 5.2 300.0 5.8 103.0 Example 572 Compound (P-72 + P2-80) 4.7 4.8 300.0 6.3 117.3 Example (573) Compound (P-72 + P2-81) 4.5 5.4 300.0 5.5 139.7 Example 574 Compound (P-72 + P2-82) 4.8 4.8 300.0 6.2 109.6 Example 575 Compound (P-72 + P2-83) 4.7 4.8 300.0 6.2 138.1 Example 576 Compound (P-72 + P2-84) 4.5 4.8 300.0 6.2 146.1 Example (577) Compound (P-72 + P2-85) 4.4 5.0 300.0 6.0 140.3 Example (578) Compound (P-72 + P2-86) 4.6 4.8 300.0 6.2 99.0 Example (579) Compound (P-72 + P2-87) 4.7 5.1 300.0 5.8 132.8 Example 580 Compound (P-72 + P2-88) 4.5 4.8 300.0 6.3 118.3 Example 581 Compound (P-72 + P2-89) 4.4 5.0 300.0 6.0 144.3 Example 582 Compound (P-72 + P2-90) 4.6 5.1 300.0 5.9 106.8 Example 583 Compound (P-72 + P2-91) 4.8 4.8 300.0 6.3 121.6 Example (584) Compound (P-72 + P2-92) 4.7 5.3 300.0 5.7 103.5 Example (585) Compound (P-72 + P2-93) 4.6 5.2 300.0 5.8 145.8 Example 586 Compound (P-72 + P2-94) 4.5 5.2 300.0 5.8 131.9 Example (587) Compound (P-72 + P2-95) 4.7 5.4 300.0 5.6 100.9 Example (588) Compound (P-72 + P2-96) 4.5 4.8 300.0 6.3 105.8 Example (589) Compound (P-72 + P2-97) 4.5 5.2 300.0 5.8 148.2 Example 590 Compound (P-72 + P2-98) 4.8 5.3 300.0 5.6 105.7 Example (591) Compound (P-72 + P2-99) 4.4 5.1 300.0 5.9 140.6 Example 592 Compound (P-72 + P2-100) 4.7 4.9 300.0 6.1 136.6 Example (593) Compound (P-72 + P2-101) 4.6 5.0 300.0 6.0 116.6 Example (594) Compound (P-72 + P2-102) 4.8 5.4 300.0 5.6 130.2 Example (595) Compound (P-72 + P2-103) 4.4 5.2 300.0 5.8 141.4 Example (596) Compound (P-72 + P2-104) 4.5 5.2 300.0 5.8 129.4 Example (597) Compound (P-72 + P2-105) 4.7 5.3 300.0 5.6 144.9 Example 598 Compound (P-72 + P2-106) 4.5 5.0 300.0 5.9 140.2 Example (599) Compound (P-72 + P2-107) 4.7 5.1 300.0 5.9 111.6 Example 600 Compound (P-72 + P2-108) 4.4 5.1 300.0 5.9 139.0 Example 601 Compound (P-72 + P2-109) 4.8 5.3 300.0 5.7 134.7 Example 602 Compound (P-72 + P2-110) 4.4 5.1 300.0 5.9 117.7 Example (603) Compound (P-72 + P2-111) 4.4 4.8 300.0 6.2 126.5 Example 604 Compound (P-72 + P2-112) 4.4 4.9 300.0 6.2 134.2 Example 605 Compound (P-72 + P2-113) 4.7 5.4 300.0 5.5 107.4 Example 606 Compound (P-72 + P2-114) 4.8 4.9 300.0 6.2 132.9 Example (607) Compound (P-72 + P2-115) 4.4 4.9 300.0 6.1 146.9 Example 608 Compound (P-72 + P2-116) 4.5 4.8 300.0 6.3 101.5 Example 609 Compound (P-72 + P2-117) 4.5 5.4 300.0 5.6 133.9 Example 610 Compound (P-72 + P2-118) 4.7 4.8 300.0 6.2 114.5 Example 611 Compound (P-72 + P2-119) 4.7 5.1 300.0 5.9 99.7 Example 612 Compound (P-72 + P2-120) 4.4 5.2 300.0 5.7 110.7

Example 70, Example 71, and Example 72, which showed the best results with NPB of Comparative Example Compound (1) in [Table 8], were determined as Comparative Examples in [Table 10], and P-70, P-71, Comparative device evaluation was carried out using a mixture of P-72 and other compounds in Table 9 as 50:50 as the hole transport layer. We can see that this is getting better.

This results in better morphology when mixed with deuterium-substituted compounds than when a single compound is used, which has a close interfacial adhesion between the interfaces, thereby increasing energy transfer between layers and thus high driving voltage. Will be lowered.

Therefore, as the driving voltage decreases, it is judged to have high efficiency and long life, and it is expected to solve the short life problem due to the high driving voltage which is a problem in the OLED device.

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, it is obvious that the same effect can be obtained.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics 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 scope of protection of the present invention should be interpreted by the above claims, and all descriptions within the scope equivalent thereto should be construed as being included in the scope of the present invention.

Claims (15)

One or more organic material layers comprising a composition containing a mixture of a first electrode, a compound represented by the following [Formula 1] and a compound represented by the following [Formula 2], and a second electrode in a sequentially stacked form Organic electric device:
[Formula 1]

In Chemical Formula 1
1) Ar ₁ To Ar ₃ is the same or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of , 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, C ₅ ~ C ₂₀ heterocyclic ring C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of groups ; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, and the heteroaryl group in the C ₅ ~ C ₆₀ having at least one of S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Halogen group, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C of the arylamine group with one or more substituents selected from the ₆₀ heteroaryl group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ of _30; Or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ aryl group substituted with deuterium, C of ₈ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ An alkyl group , wherein at least one of Ar ₁ to Ar ₃ includes one or more deuterium, and when Ar ₂ is a substituted or unsubstituted fluorene group, Ar ₃ includes one or more deuterium,
2) R ₁ And Each R ₂ is independently the same or different and is a hydrogen atom ; heavy hydrogen; halogen; Nitro group ; Nitrile group ; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C ₂ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group, a substituted or unsubstituted C ₆ ~ C _60; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₂ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, or substituted heteroaryl, unsubstituted C ₅ ~ C ₆₀ group having from S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ aryl group substituted with deuterium, C of ₈ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ An alkyl group , wherein R ₁ And R ₂ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or heterocycle,
3) L is nitro, nitrile, halogen, alkyl group, alkoxy group and substituted with one or more substituents selected from the group consisting of an amino group or unsubstituted arylene group, a C ₆ ~ C _60; Or a C ₅ to C ₆₀ hetero arylene group unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, alkyl, alkoxy and amino groups ,
4) a is an integer of 1 to 4, b is an integer of 1 to 3, c is an integer of 0 to 2,
(2)

In Chemical Formula 2
1) Ar ₁ To Ar ₃ is the same or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of , 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, C ₅ ~ C ₂₀ heterocyclic ring C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of groups ; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, a heteroaryl group of C ₅ ~ C ₆₀ with at least one of S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Halogen group, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C ₃₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ arylamine group of C with one or more substituents selected from the ₆₀ heteroaryl group the group consisting of substituted or unsubstituted C ₆ ~ C _60; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ of the alkoxy group, C ₆ ~ substituted by an aryl group, a heavy hydrogen of the C _20, C ₆ ~ C ₂₀ aryl group, a C ₈ ~ C C ₁ ~ C ₅₀ Alkyl group unsubstituted or substituted with a substituent selected from the group consisting of ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group, Wherein at least one of Ar ₁ to Ar ₃ includes one or more deuterium,
2) the R ₁ To Each R ₄ is independently the same or different and is a hydrogen atom ; heavy hydrogen; halogen; Nitro group ; Nitrile group ; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C ₂ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group, a substituted or unsubstituted C ₆ ~ C _60; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₂ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, or substituted heteroaryl, unsubstituted C ₅ ~ C ₆₀ group having from S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₈ C ₁ ~ C ₅₀ alkyl group unsubstituted or substituted with a substituent selected from the group consisting of-C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group Where R ₁ To R ₄ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or a heterocycle,
3) R ' And R ″ are the same as or different from each other independently, and are hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl an amine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of Alkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ hetero C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ hetero Selected from the group consisting of cyclic, nitrile and acetylene groups A C ₁ to C ₅₀ alkyl group unsubstituted or substituted with a selected substituent, wherein R ' And R ″ may be bonded to each other to form a saturated or unsaturated aliphatic ring, heterocycle, or spiro compound,
4) a is an integer of 1 to 3, and b, c, and d are integers of 1 to 4, respectively. The method of claim 1,
At least one of Ar ₁ , Ar ₂ , and Ar ₃ is independently any one selected from the group consisting of: wherein at least one of a to v is not 0;

here,
a is an integer from 0 to 5, b is an integer from 0 to 7, c is an integer from 0 to 4, d is an integer from 0 to 5, e is an integer from 0 to 6, f is 0 to 5 It is an integer of, g is an integer of 0-4, h is an integer of 0-4, i is an integer of o-4, j is an integer of 0-4, k is an integer of 0-5. L is an integer from 0 to 2, m is an integer from 0 to 5, n is an integer from 0 to 4, o, p, and r are integers from 0 to 3, s and t are integers from 0 to 5, u and v is an integer of 0-4. The method of claim 1,
Ar ₁ , Ar ₂ , and Ar ₃ Wherein at least one of is independently selected from the group consisting of:

The method of claim 1,
The compound represented by the above [Formula 1] is characterized in that selected from the group consisting of, an organic electric device:

. The method of claim 1,
The compound represented by the above [Formula 2] is characterized in that selected from the group consisting of, an organic electric device:

6. The method according to any one of claims 1 to 5,
The composition of the organic material, characterized in that to form the organic layer by a solution process (soluble process). 6. The method according to any one of claims 1 to 5,
The organic material layer, characterized in that used as a light emitting layer, a hole injection layer, or a hole transport layer. 8. The electronic device of claim 7, wherein the organic electroluminescent element is any one of an organic electroluminescent element (OLED), an organic solar cell, an organic photoconductor (OPC), and an organic transistor (organic TFT). An organic electric device composition comprising a mixture of a compound represented by the following [Formula 1] and a compound represented by the following [Formula 2]:
[Formula 1]

In Chemical Formula 1
1) Ar ₁ To Ar ₃ is the same or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of , 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, C ₅ ~ C ₂₀ heterocyclic ring C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of groups ; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, and the heteroaryl group in the C ₅ ~ C ₆₀ having at least one of S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Halogen group, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C of the arylamine group with one or more substituents selected from the ₆₀ heteroaryl group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ of _30; Or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ aryl group substituted with deuterium, C of ₈ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ An alkyl group , wherein at least one of Ar ₁ to Ar ₃ includes one or more deuterium, and when Ar ₂ is a substituted or unsubstituted fluorene group, Ar ₃ includes one or more deuterium,
2) R ₁ And Each R ₂ is independently the same or different and is a hydrogen atom ; heavy hydrogen; halogen; Nitro group ; Nitrile group ; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C ₂ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group, a substituted or unsubstituted C ₆ ~ C _60; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₂ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, or substituted heteroaryl, unsubstituted C ₅ ~ C ₆₀ group having from S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ aryl group substituted with deuterium, C of ₈ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ An alkyl group , wherein R ₁ And R ₂ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or heterocycle,
3) L is nitro, nitrile, halogen, alkyl group, alkoxy group and substituted with one or more substituents selected from the group consisting of an amino group or unsubstituted arylene group, a C ₆ ~ C _60; Or a C ₅ to C ₆₀ hetero arylene group unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, alkyl, alkoxy and amino groups ,
4) a is an integer of 1 to 4, b is an integer of 1 to 3, c is an integer of 0 to 2,
(2)

In Chemical Formula 2
1) Ar ₁ To Ar ₃ is the same or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl group of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of , 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, C ₅ ~ C ₂₀ heterocyclic ring C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of groups ; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, a heteroaryl group of C ₅ ~ C ₆₀ with at least one of S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; Halogen group, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C ₃₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ arylamine group of C with one or more substituents selected from the ₆₀ heteroaryl group the group consisting of substituted or unsubstituted C ₆ ~ C _60; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ of the alkoxy group, C ₆ ~ substituted by an aryl group, a heavy hydrogen of the C _20, C ₆ ~ C ₂₀ aryl group, a C ₈ ~ C C ₁ ~ C ₅₀ Alkyl group unsubstituted or substituted with a substituent selected from the group consisting of ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group, Wherein at least one of Ar ₁ to Ar ₃ includes one or more deuterium,
2) the R ₁ To Each R ₄ is independently the same or different and is a hydrogen atom ; heavy hydrogen; halogen; Nitro group ; Nitrile group ; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C ₂ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group, a substituted or unsubstituted C ₆ ~ C _60; Hydrogen, deuterium, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₈ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl A C ₂ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted with one or more substituents selected from the group or unsubstituted, and O, N, or substituted heteroaryl, unsubstituted C ₅ ~ C ₆₀ group having from S; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; Hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₆ to C ₃₀ aryloxy group ; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₈ C ₁ ~ C ₅₀ alkyl group unsubstituted or substituted with a substituent selected from the group consisting of-C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group Where R ₁ To R ₄ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or a heterocycle,
3) R ' And R ″ are the same as or different from each other independently, and are hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl an amine group, C ₁ ~ alkyl group of C ₂₀ thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C cycloalkyl of ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of Alkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₂ ~ C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ hetero C ₆ ~ C ₆₀ aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group; C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ hetero Selected from the group consisting of cyclic, nitrile and acetylene groups A C ₁ to C ₅₀ alkyl group unsubstituted or substituted with a selected substituent, wherein R ' And R ″ may be bonded to each other to form a saturated or unsaturated aliphatic ring, heterocycle, or spiro compound,
4) a is an integer of 1 to 3, and b, c, and d are integers of 1 to 4, respectively. The method of claim 9,
At least one of Ar ₁ , Ar ₂ , and Ar ₃ is independently any one selected from the group consisting of: wherein at least one of a to v is not 0, the composition for an organic electric device :

here,
a is an integer from 0 to 5, b is an integer from 0 to 7, c is an integer from 0 to 4, d is an integer from 0 to 5, e is an integer from 0 to 6, f is 0 to 5 It is an integer of, g is an integer of 0-4, h is an integer of 0-4, i is an integer of o-4, j is an integer of 0-4, k is an integer of 0-5. L is an integer from 0 to 2, m is an integer from 0 to 5, n is an integer from 0 to 4, o, p, and r are integers from 0 to 3, s and t are integers from 0 to 5, u and v is an integer of 0-4. The method of claim 9,
Ar ₁ , Ar ₂ , and Ar ₃ Wherein at least one is independently selected from the group consisting of:

The method of claim 9,
Compound represented by the above [Formula 1] is selected from the group consisting of, the composition for an organic electric device:

. The method of claim 9,
The compound represented by the above [Formula 2] is characterized in that selected from the group consisting of, the composition for an organic electric device:

The method of claim 1,
Organic compound device, characterized in that any compound in the composition is mixed in the range of 90% by weight or less of the total weight of the composition. The method of claim 9,
Any one compound in the composition is characterized in that the mixture in the range of 90% by weight or less of the total weight of the composition, the composition for an organic electric device.

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