KR20130096334A - Organic electronic element, and a compound for the same - Google Patents

Abstract

PURPOSE: A compound for an organic electronic device is provided to obtain a blue light with high efficiency and improved color purity, thereby decreasing a driving voltage and remarkably increasing luminous efficiency and lifetime when used as a light emitting host or a hole transfer material for an organic electronic device. CONSTITUTION: An organic electronic device successively includes a first electrode, an organic material layer of one or more layer, including a compound represented by chemical formula 1, and a second electrode. In chemical formula 1, each of R1-R6 is hydrogen, deuterium, tritium, a halogen, an amino group, a nitrile group, a nitro group, a hydroxy group, a C5-60 heteroaryl group, a substituted or non-substituted C1-30 alkoxy group, a substituted or non-substituted C6-C30 aryloxy group, a substituted or non-substituted amino group, a substituted or non-substituted C5-60 arylthio group, or a substituted or non-substituted C1-50 alkyl group; and L is selected from a substituted or non-substituted C6-60 arylene group, a substituted or non-substituted heteroarylene, and a divalent or trivalent substituted or non-substituted aliphatic hydrocarbon.

Description

ORGANIC ELECTRONIC ELEMENT, AND A COMPOUND FOR THE SAME

The present invention relates to a hole injection layer and a hole transport layer material having a low driving voltage, high luminous efficiency and lifetime, and an organic electric element including the same. More particularly, the present invention relates to a novel compound which can be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material and a passivation (kepping) material, and an organic electric device including 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 (electron injection) in addition to the emitting layer (EML). layer, 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.

An object of the present invention is to improve low-voltage driving, high luminous efficiency, and device life of an electroluminescent device of an organic electric device. More specifically, an object of the present invention is to provide a compound having a structure in which a tertiary amine is substituted for a substituted or unsubstituted carbazole derivative, an organic electric device using the same, and an electronic device including the organic electric device. .

In order to achieve the above object, the present invention, in one aspect, a compound having a structure in which tertiary amine is substituted in a substituted or unsubstituted carbazole derivative, and hole injection, hole transport, electron injection comprising the same in an organic electric device , Electron transport, luminescent materials and passivation (kepping) materials.

In another aspect, the present invention in the form of sequentially stacking the first electrode, at least one organic layer comprising a compound having a structure having a tertiary amine substituted in the substituted or unsubstituted carbazole derivatives, and the second electrode It provides an organic electric device comprising.

In another aspect, the present invention provides a compound represented by the following formula (1).

[Formula 1]

In another aspect, the present invention provides a compound represented by any one of the following formula (2).

(2)

(3)

[Formula 4]

[Chemical Formula 5]

[Formula 6]

The organic electroluminescent device using the compound of the present invention exhibits the increased efficiency, the driving voltage drop, the increase in lifespan, and the increase in thermal stability. The compound of the present invention may be used alone as a light emitting material or as a host or a dopant in a host / dopant, and may be used as a hole injection layer or a hole transport layer.

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 assigned to the same components as much as possible even though they are shown in 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 describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

Various studies are being conducted on organic materials inserted into a hole transport layer or a buffer layer for excellent life characteristics of organic electronic devices, for example, organic electronic devices (see SA Van Slyke et al., Appl. Phys. Lett). , 69, 2160, 1996) .As a result, a hole injection layer material having high uniformity and low crystallinity is required in forming a thin film after deposition while providing high hole transfer characteristics from an anode to an organic layer (Refer to Youngkyoo Kim et al., Appl. Phys. Lett., 82, 2200, 2003).

Delays penetration of metal oxides into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electric device (see CO Poon et al., Appl. Phys. Lett., 82, 155, 2003). There is a need for the development of a hole injection layer material having stable characteristics, that is, a high glass transition temperature, for Joule heating generated during driving (see Shizuo Tokito, Appl. Phys. Lett., 70 (15), 1929, 1997). 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 according to the characteristics of the uniformity of the surface of the thin film when the device is driven (see C.-H. Chen et al. / Synthetic Metals 143). (2004) 215-220).

In addition, the deposition method is the mainstream in the formation of the organic electric element, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

In particular, as panel sizes of mobile phones and tablet PCs are enlarged, a major overcoming problem of the organic light emitting diode is to overcome the problems of power consumption and lifespan.

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. For example, naphthyl, fluorene, phenanthrene, and the like. 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. Increasing the driving voltage lowers the driving voltage, but results in a drastic reduction in life. 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.

Therefore, in the present invention, in order to solve such a part, a substituted or unsubstituted carbazole by using a material having a good lifespan, without introducing a plate-like molecular structure which adversely affects the lifespan and lowering the driving voltage. By using a compound having a structure in which a tertiary amine is substituted in a derivative, a method of lowering a driving voltage is proposed.

On the other hand, according to the research results of the present inventors it was confirmed that the compound substituted with deuterium shows a lot of thermodynamic behavior compared to the unsubstituted compound. Among these thermodynamic properties, when the iridium compound is substituted with deuterium, the intermolecular half 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 has been confirmed that the light emission efficiency may be higher due to the weakening of the Derbals force.

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. (Electropolar polarizability) can be reduced, and the thin film volume can be increased by weakening the intermolecular interaction (Buckingham, AD; Hentschel, HGEJ Polym. Sci. 1980, 18, 853. ). These characteristics can make the effect of lowering the crystallinity of the thin film, that is, the amorphous (Amorphous) state, and in general, in order to increase the OLED lifetime and driving characteristics, it was determined that it will be very effective to implement the necessary amorphous state (Chem: Chem. Rev. 2007, 107, 953-1010 953 ).

In more detail, the compound having a structure in which tertiary amines are substituted for carbazole derivatives was used 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.

As a result of the research and development of the inventors, the present invention provides a compound having a structure in which tertiary amines are substituted with substituted or unsubstituted carbazole derivatives so as to meet the requirements of organic materials while maintaining the excellent properties of the organic material layers of the organic electronic device. To provide.

The present invention provides a compound represented by the following formula (1).

In Formula 1,

(1) R ₁ to R ₆ are the same as or different from each other, and a hydrogen atom ; Deuterium ; Tritium ; Halogen ; Amino group ; Nitrile group ; Nitro group ; Hydroxyl group ; 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, Substituted by 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, deuterium Or substituted with one or more substituents selected from the group consisting of a C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₅ to C ₂₀ heterocyclic group, or an aryl group unsubstituted C ₆ ~ C _60; Deuterium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl group, In the group consisting of C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group a heteroaryl group of C ₅ ~ C ₆₀ being unsubstituted or substituted with one or more substituents having at least one of O, N, and S; 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, C ₂ alkoxy group ~ C ₃₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C ₆₀ heteroaryl group unsubstituted or substituted with one or more substituents selected from the group yirwojin C ₁ ~ C ₃₀ of the; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted C ₆ ~ C ₃₀ aryloxy group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted amino group ; 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, C ₂ - heterocycloalkyl group of C _30, C ₆ ~ C ₆₀ Of an aryl group, a C ₆ ~ C ₂₀ aryl group, C ₃ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from a heteroaryl group the group yirwojin C for ₅ ~ C ₆₀ aryl come Cy substituted with deuterium; Or 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 ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ It is a C ₁ ~ C ₅₀ alkyl group unsubstituted or substituted with a substituent selected from the group consisting of an aryl alkenyl group, a C ₅ ~ C ₂₀ heterocyclic group, a nitrile group and an acetylene group.

R ₁ to R ₂ may be bonded to groups adjacent to each other to form a saturated or unsaturated aliphatic ring or heterocycle. N of carbazole may also be bonded to an adjacent group together with a substituent linked to it to form a ring.

2) L is a C ₆ ~ C ₆₀ of unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and amino group Arylene group ; A heteroaryl group of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and by one or more substituents selected from the group consisting of amino group-substituted or unsubstituted C ₅ ~ C ₆₀ of; And a group selected from divalent or trivalent substituted or unsubstituted aliphatic hydrocarbons , It is an integer of n = 0-2.

Specifically, L is selected from the group consisting of phenyl group, biphenyl group, 1-naphthalyl group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group, fluorenyl group and the like.

In defining the substituents corresponding to L above, the substituents described above should be interpreted to include not only the divalent radicals of these substituents when o = 1 but also the trivalent radicals of these substituents when n = 3.

3 ) Ar ₁ and Ar ₂ are the same as or different from each other, and each independently halogen ; Nitrile group ; Nitro group ; 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 -C20 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, deuterium substituted C Substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₂₀ aryl group, C ₈ to C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group an aryl group of a C ₆ ~ C _60; An aryl group of a C ₆ ~ C ₆₀ substituted with heavy hydrogen; With 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 group, deuterium One of a substituted C ₆ -C ₂₀ aryl group, C ₈ -C ₂₀ arylalkyl group, C ₈ -C ₂₀ arylalkenyl group, C ₅ -C ₂₀ heterocyclic group, nitrile group and acetylene group a heteroaryl group of the above substituted with a substituent or unsubstituted, and O, N, S, and C ₅ ~ C ₆₀ having at least one of; 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 A C ₁ to C ₃₀ alkoxy group unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, and C ₃ to C ₆₀ heteroaryl groups ; 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups hwandoen C ₆ ~ C ₃₀ Ah reel 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 Unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups Amino 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 Unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups aryl come Sy of the C ₅ ~ C _60; 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 ₈ to C ₂₀ arylalkyl group, C ₈ to C _It is a C ₁ ~ C ₅₀ alkyl group unsubstituted or substituted with a substituent selected from the group consisting of ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group.

4) It is an integer of l = 1-4, an integer of m = 1-3, an integer of p = 1-3, and an integer of q = 1-4. is an integer of o = 1 or 2.

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

The term "alkyl" or "alkyl group ", as used herein, unless otherwise specified, has from 1 to 60 carbon atoms, 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 specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxy group" as used in the present invention has, unless otherwise stated, 1 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used in the present invention, each have 6 to 60 carbon atoms, but are 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 an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

In addition, as used herein, the term "substituted" in "substituted or unsubstituted" is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ C ₂₀ -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 - a cycloalkyl group of C _20, C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, a C ₈ - arylalkenyl group, a silane group, a boron group, a germanium group of C _20, C ₅ It means substituted with one or more substituents selected from the group consisting of ~ C ₂₀ heterocyclic group, and is not limited to these substituents.

More specifically, the present invention provides a compound represented by the following Formula 2 to Formula 6 of the compound of Formula 1.

R ₂ to R ₆ , L, Ar ₁ to Ar ₂ , n, o, p, and q of Formulas 2 to 6 are the same as defined in Formula 1.

More specifically, the present invention provides any one of compounds represented by the following Chemical Formula 7 among the compounds represented by Chemical Formulas 1 to 6.

The compounds represented by Formula 1 may be one of the compounds shown in Formula 7, but are not limited thereto. In this case, since the substituents of the compounds represented by the formula (1) are practically difficult to illustrate all the compounds in a broad relationship, the exemplary compounds have been described by way of example, but the compounds represented by the formula (1) not shown in the formula (1) also Some can be configured.

Meanwhile, the compound having the structural formula may be used in a solution process. In other words, the composition containing the compound may form an organic material layer of the organic electric device described below 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.

As described above, according to the results of the present inventors, the present invention provides a compound represented by Chemical Formula 1. The compound 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, i.e., the requirement of a hole injection layer material having a high glass transition temperature, and withstanding the deposition method in the formation of an organic electric device. It is possible to meet the requirements of materials with high heat resistance.

Example

Hereinafter, the present invention will be described in more detail through Preparation Examples and Experimental Examples. However, the following Production Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example

Hereinafter, preparation or synthesis examples of the compounds belonging to Chemical Formula 1 will be described. However, some of the compounds belonging to Formula 1 will be exemplarily described since the number of compounds belonging to Formula 1 is large. 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.

(1) General Synthesis Method of Chemical Formulas 1, 2, 3, 4, 5

(2) Starting material synthesis

1) Starting material Sub1 Synthesis of

① Synthesis of Starting Material Sub1-2: 3-bromo-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) were added respectively, followed by stirring under reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was purified by silica gel column and recrystallized to obtain 481-166 (67%) of Sub1-1. Sub1-1 (48.66 g, 200 mmol) was dissolved in 600 mL of methylene chloride, and then 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 gave 47.7 (74%) of Sub1-2. Again, NBS was added and reacted to obtain Sub1-3.

② Synthesis of Starting Material Sub1-6: 2-bromo-9-phenyl-9H-carbazole

To a 2-liter round bottom flask, add phenylboronic acid (76.61 g, 628 mmol), THF (700 mL), H ₂ O (350 mL) and dissolve 4-bromo-1-iodo-2-nitrobenzene (227 g , 690 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order, and the reaction was performed at 80 ° C. for 24 hours. After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The obtained organic layer was purified by silica gel column (methylene chloride: hexane = 1: 3) to obtain 80.4 g (46%) of Sub1-4. Triethyl phosphate was added to the obtained Sub1-4 and heated to reflux for 14 hours at 160 ° C to 165 ° C. After the reaction was completed, the remaining triehtyl phosphite was removed by distillation under reduced pressure, and the resulting solid was diluted with MeOH: H ₂ O = 1: 1 mixed solvent and filtered. The resulting solid is washed with MeOH: H ₂ O = 1: 1 mixed solvent and petroleum ether. The solid was dissolved in methylene chloride, dried over MgSO ₄ , concentrated and purified by silica gel to give Sub1-5. (petroleum ether: methylene chloride = 2: 1) Sub1-5 (80.4 g, 327 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) and NaO t -Bu (86.5 g, 900 mmol) were added respectively and then stirred and refluxed at 100 ° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated and the resulting organic was purified by silica gel column and recrystallized to give 48.66 g (46%) of Sub1-6.

2) Starting material Sub2 Synthesis of

① Synthesis of starting material Sub2-3: 2-bromo-d5-9- (naphthalen-2-yl) -9H-carbazole

In a 2 L round bottom flask, add d5-phenylboronic acid (76.61 g, 590 mmol), THF (700 mL), H ₂ O (350 mL) and dissolve 4-bromo-1-iodo-2-nitrobenzene (227 g, 690 mmol). ), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. After the reaction is completed, the mixture is extracted using methylene chloride, water and brine, and the organic layer is dried over MgSO ₄ . The obtained organic layer was purified by silica gel column (methylene chloride: hexane = 1: 3) to obtain 79.8 g (45%) of Sub2-1. Into the obtained Sub2-1 triehtyl phosphate and heated to reflux for 14 hours at 160 ℃ ~ 165 ℃. After the reaction is completed, the remaining triehtyl phosphite is removed by distillation under reduced pressure, and diluted with MeOH: H ₂ O = 1: 1 mixed solvent, and the resulting solid is filtered. The resulting solid is washed with MeOH: H ₂ O = 1: 1 mixed solvent and petroleum ether. The solid was dissolved in methylene chloride, dried over MgSO ₄ , concentrated and purified by silica gel column to obtain Sub 2-2. (petroleum ether: methylene chloride = 2: 1) Sub 2-2 (79.8 g, 347 mmol) and 2-bromonaphthalene (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) and NaO t -Bu (86.5 g, 900 mmol) were added respectively, followed by stirring under reflux at 100 ° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated and the resulting organic was purified by silica gel column and recrystallized to give 60.74 g (54%) of Sub2-3.

② Synthesis of Starting Sub2-6: 3-bromo-d5-9- (naphthalen-2-yl) -9H-carbazole

In a 2 L round bottom flask, add d5-phenylboronic acid (76.61 g, 628 mmol), THF (700 mL), H ₂ O (350 mL), and dissolve 4-bromo-2-iodo-1-nitrobenzene (227 g, 690 mmol). ), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The obtained organic layer was purified by silica gel column (methylene chloride: hexane = 1: 3) to obtain 79.6 g (62%) of Sub2-4. Triehtyl phosphate was added to the obtained 2-4 and heated to reflux for 14 hours at 160 ℃ ~ 165 ℃. After the reaction is completed, the remaining triehtyl phosphite is removed by distillation under reduced pressure, and diluted with MeOH: H ₂ O = 1: 1 mixed solvent, and the resulting solid is filtered. The resulting solid is washed with MeOH: H ₂ O = 1: 1 mixed solvent and petroleum ether. The solid was dissolved in methylene chloride, dried over MgSO ₄ , concentrated and purified by silica gel column to obtain Sub2-5. (petroleum ether: methylene chloride = 2: 1) Sub2-5 (79.6 g, 327 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) and NaO t -Bu (86.5 g, 900 mmol) were added respectively, followed by stirring under reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated and the resulting organic was purified by silica gel column and recrystallized to obtain 49.05 g (46%) of Sub2-6.

3) Starting material Sub3 Synthesis of

① Synthesis of starting material Sub3-3: 2-bromo-9- (naphthalene-2-yl) -7-d-carbazole

In a 2L round bottom flask, add 4-d-phenylboronic acid (77.2 g, 628mmol), THF (700 mL), H ₂ O (350 mL) and dissolve 4-bromo-1-iodo-2-nitrobenzene (227g, 690 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The obtained organic layer was purified by silica gel column (methylene chloride: hexane = 1: 3) to obtain 75 g (43%) Sub 3-1. Into the obtained 3-1 triehtyl phosphate and heated to reflux for 14 hours at 160 ℃ ~ 165 ℃. After the reaction is completed, the remaining triehtyl phosphite is removed by distillation under reduced pressure, and diluted with MeOH: H ₂ O = 1: 1 mixed solvent, and the resulting solid is filtered. The resulting solid is washed with MeOH: H ₂ O = 1: 1 mixed solvent and petroleum ether. The solid was dissolved in methylene chloride, dried over MgSO ₄ , concentrated and purified by silica gel column to obtain Sub3-2. (petroleum ether: methylene chloride = 2: 1) Sub3-2 (75 g, 267 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) and NaO t -Bu (86.5 g, 900 mmol) were added respectively, followed by stirring under reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated and the resulting organic was purified by silica gel column and recrystallized to obtain 49.05 g (46%) of Sub2-6.

② Synthesis of Starting Material Sub3-6: 3-bromo-9- (naphthalene-2-yl) -7-d-carbazole)

In a 2L round bottom flask, add 4-d-phenylboronic acid (77.2 g, 628mmol), THF (700 mL), H ₂ O (350 mL) and dissolve 4-bromo-1-iodo-2-nitrobenzene (227g, 690 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The obtained organic layer was purified by silica gel column (methylene chloride: hexane = 1: 3) to obtain 74.6 g (43%) Sub 3-4. Into the obtained Sub3-4 triehtyl phosphate and heated to reflux for 14 hours at 160 ℃ ~ 165 ℃. After the reaction is completed, the remaining triehtyl phosphite is removed by distillation under reduced pressure, and diluted with MeOH: H ₂ O = 1: 1 mixed solvent, and the resulting solid is filtered. The resulting solid is washed with MeOH: H ₂ O = 1: 1 mixed solvent and petroleum ether. The solid was dissolved in methylene chloride, dried over MgSO ₄ , concentrated and purified by silica gel column to obtain Sub 3-5. (petroleum ether: methylene chloride = 2: 1) Sub 3-5 (74.6 g, 267 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) and NaO t -Bu (86.5 g, 900 mmol) were added respectively, followed by stirring under reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was purified by silica gel column and recrystallized to obtain 49.3 g (46%) of Sub2-6.

4) Starting material Sub4 Synthesis of

① Synthesis of Starting Material Sub4-1: 2-bromo-9- (naphthalene-2-yl) -6- (5dphenyl) -9H-carbazole

                                                  Sub4-1

Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a ₂ L round bottom flask, and then 2-bromo-6-iodo-9- (naphthalene-2 -yl) -9H-carbazole (258g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. . After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The resulting organic layer was purified by silica gel column to give 92.1 g (66%) of product.

② Synthesis of Starting Material Sub4-2: 3-bromo-9- (naphthalene-2-yl) -6- (5dphenyl) -9H-carbazole

                                                     Sub4-2

Phenyl-d5-boronic acid (43.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a ₂ L round bottom flask, and then 2-bromo-6-iodo-9- (naphthalene-2 -yl) -9H-carbazole (258g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. . After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The resulting organic layer was purified by silica gel column to give 87 g (63%) of product.

4) Starting material Sub5 Synthesis of

① Synthesis of Starting Material Sub5-1: 9- (biphenyl-4-yl) -2-bromo-6- (7dnaphthalen-1-yl) -9H-carbazole

                                                     Sub5-1

7dnaphthalen-2-ylboronic acid (61.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a 2 L round bottom flask, and 9- (biphenyl-4-yl) -2-bromo- 6-iodo-9H-carbazole (258g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. . After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The resulting organic layer was purified by silica gel column to give 74.1 g (40.4%) of product.

② Synthesis of Starting Material Sub5-2: 9- (biphenyl-4-yl) -3-bromo-6- (7dnaphthalen-1-yl) -9H-carbazole

                                                     Sub5-2

7dnaphthalen-2-ylboronic acid (61.8 g, 345 mmol), THF (700 mL), H ₂ O (350 mL) was added to a 2 L round bottom flask, and 9- (biphenyl-4-yl) -3-bromo- 6-iodo-9H-carbazole (258g, 518 mmol), NaOH (42 g, 1035 mmol) and Pd (PPh ₃ ) ₄ (20 g, 17.3 mmol) were added in this order and the reaction proceeds at 80 ° C. for 24 hours. . After completion of the reaction, the mixture was extracted using methylene chloride, water and brine, and the organic layer was dried over MgSO ₄ . The resulting organic layer was purified by silica gel column to give 80 g (43.6%) of product.

(3) General synthesis method of intermediates 2-1 and 2-2

1) Synthesis of Intermediate 2-1

Compound 1 (1 equivalent), amine compound (1 equivalent), Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 equivalent), NaO t -Bu (6 equivalent) in a round bottom flask Add toluene (10.5 mL / 1 mmol) and 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 by silica gel column and recrystallized to obtain a product.

2) Synthesis of Intermediate 2-2

1-2 rounds of compound (1 equiv), amine compound (2 equiv), Pd ₂ (dba) ₃ (0.06 ~ 0.1 mmol), PPh ₃ (0.2 equiv), NaO t -Bu (6 equiv) Add toluene (10.5 mL / 1 mmol) and 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 by silica gel column and recrystallized to obtain a product.

3) Example of specific intermediate synthesis

2-A:  N- (4- bromophenyl ) -9,9- dimethyl -N- phenyl -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (14.3 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol ), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) was synthesized using the synthesis method of Intermediate 2-1, 2-2 (13.6 g, yield: 62). %) Got.

2-B:  N- (4- bromophenyl ) -9,9- dimethyl -N- ( naphthalen -One- yl ) -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N- (naphthalene-1-yl) -9H-fluoren-2-amine (14.3 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis of Intermediate 2-1, 2-2 13.2 g (yield: 60%) were obtained.

2-C:  N- (4- bromophenyl ) -9,9- dimethyl -N- ( naphthalen -2- yl ) -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N- (naphthalene-2-yl) -9H-fluoren-2-amine (14.3 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis of Intermediate 2-1, 2-2 12.8 g (yield: 60%) were obtained.

2-D:  N- ( biphenyl -4- yl ) -N- (4- bromophenyl ) -9,9- dimethyl -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (18.1g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis of Intermediates 2-1, 2-2 15.8 g (yield: 61%) were obtained.

2-E:  N- (4- bromophenyl ) -N- (9,9- dimethyl -9H- fluoren -2- yl ) phenanthren -9- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) phenanthren-9-amine (17.9g, 50 mmol), Pd ₂ (dba) ₃ ( 2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) using 14.9 synthesis of the intermediates 2-1, 2-2 g (yield: 55%) was obtained.

2-F:  N- (4- bromophenyl ) -N- (3 ', 5'- diphenylbiphenyl -4- yl ) -9,9- dimethyl -9H- fluoren -2- yl ) phenanthren -9- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (3 ', 5' - diphenylbiphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-yl) phenanthren-9-amine (21.9 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) 10.4 g (yield: 35%) was obtained using the synthesis method of 2-1 and 2-2.

2-G:  N- (4- bromophenyl ) -9,9- dimethyl -N- (4- phenylnaphthalen -One- yl ) -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N- (4-phenylnaphthalen-1-yl) -9H-fluoren-2-amine (20.6 g, 50 mmol), Pd ₂ (dba ) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) Using 12.8 g (yield: 45%) was obtained.

2-H:  N- (4- bromophenyl ) -9,9- dimethyl -N- (4- ( naphthalen -One- yl ) phenyl ) -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), 9,9-dimethyl-N- (4- (naphthalen-1-yl) phenyl) -9H-fluoren-2-amine (20.6 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) was prepared as the intermediate 2-1, 2-2 Using the synthesis method of 12.5 g (yield: 44%) was obtained.

2-I:  N- (4- bromophenyl ) -N- (4- isopropylphenyl ) -9,9- dimethyl -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (4-isopropylphenyl) -9,9-dimethyl-9H-fluoren-2-amine (16.4 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) were synthesized using the synthesis of Intermediate 2-1, 2-2. (Yield: 58%) was obtained.

2-J:  N- (4- bromophenyl ) -N- (4- 메틸oxyphenyl ) -9,9- dimethyl -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (4-methoxyphenyl) -9,9-dimethyl-9H-fluoren-2-amine (23.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) were prepared using the synthesis of the intermediates 2-1 and 2-2 using 11.8 g. (Yield: 50%) was obtained.

2-K:  4-((4- bromophenyl ) (9,9- dimethyl -9H- fluoren -2- yl ) amino ) benzonitrile

1,4-dibromobenzene (11.8 g, 50 mmol), 4- (9,9-dimethyl-9H-fluoren-2-ylamino) benzonitrile (15.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol) and toluene (525 mL) were synthesized using the synthesis of the intermediates 2-1, 2-2 (12.6 g (yield: 54%).

2-L:  N- ( biphenyl -4- yl ) -N- (4- bromophenyl ) -9,9'- spirobi [ fluoren ]-2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (biphenyl-4-yl) -9,9'-spirobi [fluoren] -2-amine (24.2 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis of Intermediate 2-1, 2-2 11.8 g (yield 37%) were obtained.

2-M:  N- (4- bromophenyl ) -N- (9,9- 피덴 -9H- fluoren -2- yl ) -9,9- 피덴 -9H- fluoren -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), bis (9,9-diphenyl-9H-fluoren-2-yl) amine (32.5 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol ), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol) and toluene (525 mL) were synthesized using the synthesis of the intermediates 2-1 and 2-2, yielding 14.1 g (yield: 35 %) Got.

2-N:  N- (4- bromophenyl ) -N- (4- fluorophenyl ) -9,9'- spirobi [ fluoren ]-2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (4-fluorophenyl) -9,9'-spirobi [fluoren] -2-amine (21.3 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol) and toluene (525 mL) were prepared using the synthesis of the intermediates 2-1 and 2-2 using 15.7 g. (Yield 54%) was obtained.

2-O:  N- (4- bromophenyl ) -N- (9,9- dimethyl -9H- fluoren -2- yl ) -5- phenylthiophen -2- amine

1,4-dibromobenzene (11.8 g, 50 mmol), N- (9,9-dimethyl-9H-fluoren-2-yl) -5-phenylthiophen-2-amine (18.4 g, 50 mmol), Pd ₂ (dba ) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) was prepared by the synthesis of Intermediate 2-1, 2-2. Using 15.7 g (yield: 60%) was obtained.

2-P:  5- bromo - N1 , N3 - bis (9,9- dimethyl -9H- fluoren -2- yl ) - N1 , N3 - diphenylbenzene -1,3- diamine

1,3,5-tribromobenzene (7.9 g, 25 mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (14.2 g, 50 mmol), Pd ₂ (dba) ₃ (2.3 g, 2.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO t -Bu (14.42 g, 150 mmol), toluene (525 mL) using the synthesis of Intermediates 2-1, 2-2 9.8 g (Yield) : 54%).

L is specifically selected from the group consisting of a biphenyl group, 1- naphthal group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group, fluorenyl group, etc. The method is the same as the synthesis method of 2-1-6.

compound FD-MS compound FD-MS 2-A m / z = 439.09 (C ₂₇ H ₂₂ BrN = 440.37) 2-B m / z = 489.43 (C ₃₁ H ₂₄ BrN = 490.43) 2-C m / z = 489.11 (C ₃₁ H ₂₄ BrN = 489.11) 2-D m / z = 515.12 (C ₃₃ H ₂₆ BrN = 516.47) 2-E m / z = 481.14 (C ₃₀ H ₂₈ BrN = 482.45) 2-F m / z = 469.10 (C ₂₈ H ₂₄ BrNO = 470.40) 2-G m / z = 464.09 (C ₂₈ H ₂₁ BrN ₂ = 465.38) 2-H m / z = 565.14 (C ₃₇ H ₂₈ BrN = 566.53) 2-I m / z = 481.14 (C ₃₀ H ₂₈ BrN = 482.45) 2-J m / z = 469.10 (C ₂₈ H ₂₄ BrNO = 470.40) 2-K m / z = 464.09 (C ₂₈ H ₂₁ BrN ₂ = 465.38) 2-L m / z = 637.14 (C ₄₃ H ₂₈ BrN = 638.59) 2-M m / z = 803.22 (C ₅₆ H ₃₈ BrN = 804.81) 2-N m / z = 579.10 (C ₃₇ H ₂₃ BrFN = 580.49) 2-O m / z = 521.08 (C ₃₁ H ₂₄ BrNS = 522.50) 2-P m / z = 722.23 (C ₄₈ H ₃₉ BrN ₂ = 723.74)

4) Final Compound Synthesis

Synthetic method

Sub1-B (OH) _2, or Sub2-B (OH) ₂ or Sub3-B (OH) ₂ or Sub4-B (OH) ₂ or Sub5-B (OH), compound ₂ To a round bottom flask was added (1 eq) Add 2-1 or 2-2 (1.1 equiv), Pd (PPh ₃ ) ₄ (0.03-0.05 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 by silica gel column and recrystallized to obtain a product.

compound FD-MS compound FD-MS 1-1 m / z = 602.27 (C ₄₅ H ₃₄ N ₂ = 602.76) 1-2 m / z = 652.29 (C ₄₉ H ₃₆ N ₂ = 652.82) 1-3 m / z = 652.29 (C ₄₉ H ₃₆ N ₂ = 652.82) 1-4 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.86) 1-5 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88) 1-6 m / z = 804.35 (C ₆₁ H ₄₄ N ₂ = 805.02) 1-7 m / z = 778.33 (C ₅₉ H ₄₂ N ₂ = 778.98) 1-8 m / z = 834.31 (C ₆₁ H ₄₂ N ₂ S = 835.06) 1-9 m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.00) 1-10 m / z = 703.30 (C ₅₂ H ₃₇ N ₃ = 703.87) 1-11 m / z = 734.37 (C ₅₅ H ₄₆ N ₂ = 734.97) 1-12 m / z = 682.30 (C ₅₀ H ₃₈ N ₂ O = 682.85) 1-13 m / z = 703.30 (C ₅₂ H ₃₇ N ₃ = 703.87) 1-14 m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) 1-15 m / z = 708.26 (C ₅₁ H ₃₆ N ₂ S = 708.91) 1-16 m / z = 966.40 (C ₇₄ H ₅₀ N ₂ = 967.20) 1-17 m / z = 792.29 (C ₅₉ H ₃₇ FN ₂ = 792.94) 1-18 m / z = 760.29 (C ₅₅ H ₄₀ N ₂ S = 760.98) 1-19 m / z = 684.26 (C ₄₉ H ₃₆ N ₂ S = 684.89) 1-20 m / z = 885.41 (C ₆₆ H ₅₁ N ₃ = 886.13) 1-21 m / z = 652.29 (C ₄₉ H ₃₆ N ₂ = 652.82) 1-22 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88) 1-23 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88) 1-24 m / z = 728.32 (C ₅₅ H ₄₀ N ₂ = 728.92) 1-25 m / z = 752.32 (C ₅₇ H ₄₀ N ₂ = 752.94) 1-26 m / z = 854.37 (C ₆₅ H ₄₆ N ₂ = 855.07) 1-27 m / z = 828.35 (C ₆₃ H ₄₄ N ₂ = 829.04) 1-28 m / z = 884.32 (C ₆₅ H ₄₄ N ₂ S = 885.12) 1-29 m / z = 852.35 (C ₆₅ H ₄₄ N ₂ = 853.06) 1-30 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.93) 1-31 m / z = 784.38 (C ₅₉ H ₄₈ N ₂ = 785.03) 1-32 m / z = 732.31 (C ₅₄ H ₄₀ N ₂ O = 732.91) 1-33 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.93) 1-34 m / z = 805.33 (C ₆₅ H ₄₂ N ₂ = 851.04) 1-35 m / z = 758.28 (C ₅₅ H ₃₈ N ₂ S = 758.97) 1-36 m / z = 1016.41 (C ₇₈ H ₅₂ N ₂ = 1017.26) 1-37 m / z = 842.31 (C ₆₃ H ₃₉ FN ₂ = 843.00) 1-38 m / z = 810.31 (C ₅₉ H ₄₂ N ₂ S = 811.04) 1-39 m / z = 734.28 (C ₅₃ H ₃₈ N ₂ S = 734.95) 1-40 m / z = 935.42 (C ₇₀ H ₅₃ N ₃ = 936.19) 1-41 m / z = 985.44 (C ₇₄ H ₅₅ N ₃ = 986.25) 1-42 m / z = 1035.46 (C ₇₈ H ₅₇ N ₃ = 1036.31) 1-43 m / z = 985.44 (C ₇₄ H ₅₅ N ₃ = 986.25) 1-44 m / z = 1061.47 (C ₈₀ H ₅₉ N ₃ = 1062.34) 1-45 m / z = 1143.46 (C ₈₄ H ₆₁ N ₃ S = 1144.47) 1-46 m / z = 652.29 (C ₄₉ H ₃₆ N ₂ = 652.82) 1-47 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88) 1-48 m / z = 702.30 (C ₅₃ H ₃₈ N ₂ = 702.88)

1-49 m / z = 723.32 (C ₅₅ H ₄₀ N ₂ = 728.92) 1-50 m / z = 752.32 (C ₅₇ H ₄₀ N ₂ = 752.94) 1-51 m / z = 854.37 (C ₆₅ H ₄₆ N ₂ = 855.07) 1-52 m / z = 828.35 (C ₆₃ H ₄₄ N ₂ = 829.04) 1-53 m / z = 884.32 (C ₆₅ H ₄₄ N ₂ S = 855.12) 1-54 m / z = 852.35 (C ₆₅ H ₄₄ N ₂ = 853.06) 1-55 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.93) 1-56 m / z = 784.38 (C ₅₉ H ₄₈ N ₂ = 785.03) 1-57 m / z = 732.31 (C ₅₄ H ₄₀ N ₂ O = 732.91) 1-58 m / z = 753.31 (C ₅₆ H ₃₉ N ₃ = 753.93) 1-59 m / z = 850.33 (C ₆₅ H ₄₂ N ₂ = 851.04) 1-60 m / z = 758.28 (C ₅₅ H ₃₈ N ₂ S = 758.97) 1-61 m / z = 1016.41 (C ₇₈ H ₅₂ N ₂ = 1017.26) 1-62 m / z = 842.31 (C ₆₃ H ₃₉ FN ₂ = 843.00) 1-63 m / z = 810.31 (C ₅₉ H ₄₂ N ₂ S = 811.04) 1-64 m / z = 734.28 (C ₅₃ H ₃₈ N ₂ S = 734.95) 1-65 m / z = 935.42 (C ₇₀ H ₅₃ N ₃ = 936.19) 1-66 m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.86) 1-67 m / z = 728.32 (C ₅₅ H ₄₀ N ₂ = 728.92) 1-68 m / z = 728.32 (C ₅₅ H ₀₄ N ₂ = 728.92) 1-69 m / z = 754.33 (C ₅₇ H ₄₂ N ₂ = 754.96) 1-70 m / z = 778.33 (C ₅₉ H ₄₂ N ₂ = 778.98) 1-71 m / z = 880.38 (C ₆₇ H ₄₈ N ₂ = 881.11) 1-72 m / z = 854.37 (C ₆₅ H ₄₆ N ₂ = 855.07) 1-73 m / z = 910.34 (C ₆₇ H ₄₆ N ₂ S = 911.16) 1-74 m / z = 878.37 (C ₆₇ H ₄₆ N ₂ = 879.10) 1-75 m / z = 779.33 (C ₅₈ H ₄₁ N ₃ = 779.97) 1-76 m / z = 810.40 (C ₆₁ H ₅₀ N ₂ = 811.06) 1-77 m / z = 758.33 (C ₅₆ H ₄₂ N ₂ O = 758.95) 1-78 m / z = 779.33 (C ₅₈ H ₄₁ N ₃ = 779.97) 1-79 m / z = 876.35 (C ₆₇ H ₄₄ N ₂ = 877.08) 1-80 m / z = 784.29 (C ₅₇ H ₄₀ N ₂ S = 758.01) 1-81 m / z = 1042.43 (C ₈₀ H ₅₄ N ₂ = 1043.30) 1-82 m / z = 868.33 (C ₆₅ H ₄₁ FN ₂ = 869.03) 1-83 m / z = 836.32 (C ₆₁ H ₄₄ N ₂ S = 837.08) 1-84 m / z = 760.29 (C ₅₅ H ₄₀ N ₂ S = 760.98) 1-85 m / z = 961.44 (C ₇₂ H ₅₅ N ₃ = 962.23) 1-86 m / z = 607.30 (C ₄₅ H ₂₉ D ₅ N ₂ = 607.80) 1-87 m / z = 707.33 (C ₅₃ H ₃₃ D ₅ N ₂ = 707.91) 1-88 m / z = 659.33 (C ₄₉ H ₂₉ D ₇ N ₂ = 659.87) 1-89 m / z = 709.35 (C ₅₃ H ₃₁ D ₇ N ₂ = 709.93) 1-90 m / z = 763.39 (C ₅₇ H ₃₃ D ₉ N ₂ = 764.01) 1-91 m / z = 607.30 (C ₄₅ H ₂₉ D ₅ N ₂ = 607.80) 1-92 m / z = 659.33 (C ₄₉ H ₂₉ D ₇ N ₂ = 659.87) 1-93 m / z = 659.33 (C ₄₉ H ₂₉ D ₇ N ₂ = 659.87) 1-94 m / z = 687.36 (C ₅₁ H ₂₉ D ₉ N ₂ = 687.92) 1-95 m / z = 711.36 (C ₅₃ H ₂₉ D ₉ N ₂ = 711.94) 2-1 m / z = 606.30 (C ₄₅ H ₃₀ D ₄ N ₂ = 606.79) 2-2 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 2-3 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 2-4 m / z = 682.33 (C ₅₁ H ₃₄ D ₄ N ₂ = 682.89) 2-5 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 2-6 m / z = 808.38 (C ₆₁ H ₄₀ D ₄ N ₂ = 809.04) 2-7 m / z = 782.36 (C ₅₉ H ₃₈ D ₄ N ₂ = 783.00) 2-8 m / z = 838.33 (C ₆₁ H ₃₈ D ₄ N ₂ S = 839.09) 2-9 m / z = 806.36 (C ₆₁ H ₃₈ D ₄ N ₂ = 807.02) 2-10 m / z = 707.32 (C ₅₂ H ₃₃ D ₄ N ₃ = 707.89) 2-11 m / z = 738.39 ₄ (C ₅₅ H ₄₂ D ₄ N ₂ = 738.99) 2-12 m / z = 686.32 (C ₅₀ H ₃₄ D ₄ N ₂ O = 686.87) 2-13 m / z = 707.32 (C ₅₂ H ₃₃ D ₄ N ₃ = 707.89) 2-14 m / z = 804.34 (C ₆₁ H ₃₆ D ₄ N ₂ = 805.01) 2-15 m / z = 712.29 (C ₅₁ H ₃₂ D ₄ N ₂ S = 712.93) 2-16 m / z = 970.42 (C ₇₄ H ₄₆ D ₄ N ₂ = 971.23) 2-17 m / z = 796.32 (C ₅₉ H ₃₃ D ₄ FN ₂ = 796.96) 2-18 m / z = 764.32 (C ₅₅ H ₃₆ D ₄ N ₂ S = 765.01) 2-19 m / z = 688.29 (C ₄₉ H ₃₂ D ₄ N ₂ S = 688.91) 2-20 m / z = 899.43 (C ₆₆ H ₄₇ D ₄ N ₃ = 890.16) 2-21 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 2-22 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 2-23 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 2-24 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 2-25 m / z = 756.34 (C ₅₇ H ₃₆ D ₄ N ₂ = 756.97) 2-26 m / z = 858.39 (C ₆₅ H ₄₂ D ₄ N ₂ = 859.10) 2-27 m / z = 832.38 (C ₆₃ H ₄₀ D ₄ N ₂ = 833.06) 2-28 m / z = 888.35 (C ₆₅ H ₄₀ D ₄ N ₂ S = 889.15) 2-29 m / z = 856.38 (C ₆₅ H ₄₀ D ₄ N ₂ = 857.08) 2-30 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95) 2-31 m / z = 788.41 (C ₅₉ H ₄₄ D ₄ N ₂ = 789.05) 2-32 m / z = 736.34 (C ₅₄ H ₃₆ D ₄ N ₂ O = 736.93) 2-33 m / z = 757.34 (C ₅₆ H ₃₄ D ₄ N ₃ = 757.95) 2-34 m / z = 854.36 (C ₆₅ H ₃₈ D ₄ N ₂ = 855.07) 2-35 m / z = 762.30 (C ₅₅ H ₃₄ D ₄ N ₂ S = 762.99) 2-36 m / z = 1020.44 (C ₇₈ H ₄₈ D ₄ N ₂ = 1021.29) 2-37 m / z = 846.33 (C ₆₃ H ₃₅ D ₄ FN ₂ = 847.02) 2-38 m / z = 814.33 (C ₅₉ H ₃₈ D ₄ N ₂ S = 815.07) 2-39 m / z = 738.30 (C ₅₃ H ₃₄ D ₄ N ₂ S = 738.97) 2-40 m / z = 939.45 (C ₇₀ H ₄₉ D ₄ N ₃ = 940.21) 2-41 m / z = 989.46 (C ₇₄ H ₅₁ D ₄ N ₃ = 990.27) 2-42 m / z = 1039.48 (C ₇₈ H ₅₃ D ₄ N ₃ = 1040.33) 2-43 m / z = 989.46 (C ₇₄ H ₅₁ D ₄ N ₂ = 990.27) 2-44 m / z = 1065.50 (C ₈₀ H ₅₅ D ₄ N ₃ = 1066.37) 2-45 m / z = 1 147.48 (C ₈₄ H ₅₇ D ₄ N ₃ S = 1148.5)

2-46 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 2-47 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 2-48 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 2-49 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 2-50 m / z = 756.34 (C ₅₇ H ₃₆ D ₄ N ₂ = 756.97) 2-51 m / z = 858.39 (C ₆₅ H ₄₁ D ₄ N ₂ = 859.10) 2-52 m / z = 832.38 (C ₆₃ H ₄₀ D ₄ N ₂ = 833.06) 2-53 m / z = 888.35 (C ₆₅ H ₄₀ D ₄ N ₂ S = 889.15) 2-54 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 857.08) 2-55 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95) 2-56 m / z = 788.41 (C ₅₉ H ₄₄ D ₄ N ₂ = 789.05) 2-57 m / z = 736.34 (C ₅₄ H ₃₆ D ₄ N ₂ O = 736.93) 2-58 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95) 2-59 m / z = 854.36 (C ₆₅ H ₃₈ D ₄ N ₂ = 855.07) 2-60 m / z = 762.30 (C ₅₅ H ₃₄ D ₄ N ₂ S = 762.99) 2-61 m / z = 1020.44 (C ₇₈ D ₄ N ₂ = 1021.29) 2-62 m / z = 846.33 (C ₆₃ H ₃₅ D ₄ FN ₂ = 847.02) 2-63 m / z = 814.33 (C ₅₉ H ₃₈ D ₄ N ₂ S = 815.07) 2-64 m / z = 738.30 (C ₅₃ H ₃₄ D ₄ N ₂ S = 738.97) 2-65 m / z = 939.45 (C ₇₀ H ₄₉ D ₄ N ₃ = 940.21) 2-66 m / z = 682.23 (C ₅₁ H ₃₄ D ₄ N ₂ = 682.89) 2-67 m / z = 732.34 (C ₅₃ H ₃₆ D ₄ N ₂ = 732.94) 2-68 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 2-69 m / z = 758.36 (C ₅₇ H ₃₈ D ₄ N ₂ = 758.98) 2-70 m / z = 782.36 (C ₅₉ H ₃₈ D ₄ N ₂ = 783.00) 2-71 m / z = 884.41 (C ₆₇ H ₄₄ D ₄ N ₂ = 885.14) 2-72 m / z = 858.39 (C ₆₅ H ₄₂ D ₄ N ₂ = 859.10) 2-73 m / z = 914.36 (C ₆₇ H ₄₂ D ₄ N ₂ S = 915.19) 2-74 m / z = 882.39 (C ₆₇ H ₄₂ D ₄ N ₂ = 883.12) 2-75 m / z = 783.36 (C ₅₈ H ₃₇ D ₄ N ₃ = 783.99) 2-76 m / z = 814.42 (C ₆₁ H ₄₆ D ₄ N ₂ = 815.09) 2-77 m / z = 762.35 (C ₅₆ H ₃₈ D ₄ N ₂ O = 762.97) 2-78 m / z = 783.36 (C ₅₈ H ₃₇ D ₄ N ₃ = 783.99) 2-79 m / z = 880.38 (C ₆₇ H ₄₀ D ₄ N ₂ = 881.10) 2-80 m / z = 788.32 (C ₅₇ H ₃₆ D ₄ N ₂ S = 789.03) 2-81 m / z = 1046.45 (C ₈₀ H ₅₀ D ₄ N ₂ = 1047.32) 2-82 m / z = 872.35 (C ₆₅ H ₃₇ D ₄ FN ₂ = 873.06) 2-83 m / z = 840.35 (C ₆₁ H ₄₀ D ₄ N ₂ S = 841.11) 2-84 m / z = 764.32 (C ₅₅ H ₃₆ D ₄ N ₂ S = 765.01) 2-85 m / z = 965.46 (C ₇₂ H ₅₁ D ₄ N ₃ = 966.25) 2-86 m / z = 611.33 (C ₄₅ H ₂₅ D ₉ N ₂ = 611.82) 2-87 m / z = 711.36 (C ₅₃ H ₂₉ D ₉ N ₂ = 711.94) 2-88 m / z = 663.36 (C ₄₅ H ₂₅ D ₁₁ N ₂ = 663.89) 2-89 m / z = 713.37 (C ₅₃ H ₂₇ D ₁₁ N ₂ = 713.95) 2-90 m / z = 767.42 (C ₅₇ H ₂₉ D ₁₃ N ₂ = 768.04) 2-91 m / z = 611.33 (C ₄₅ H ₂₅ D ₉ N ₂ = 611.82) 2-92 m / z = 663.36 (C ₄₉ H ₂₅ D ₁₁ N ₂ = 663.89) 2-93 m / z = 663.36 (C ₄₉ H ₂₅ D ₁₁ N ₂ = 663.89) 2-94 m / z = 691.39 (C ₅₁ H ₂₅ D ₁₃ N ₂ = 691.94) 2-95 m / z = 715.39 (C ₅₃ H ₂₅ D ₁₃ N ₂ = 715.96) 3-1 m / z = 603.28 (C ₄₅ H ₃₃ DN ₂ = 603.77) 3-2 m / z = 653.29 (C ₄₉ H ₃₅ DN ₂ = 653.83) 3-3 m / z = 653.29 (C ₄₉ H ₃₅ DN ₂ = 653.83) 3-4 m / z = 679.31 (C ₅₁ H ₃₇ DN ₂ = 679.87) 3-5 m / z = 703.31 (C ₅₃ H ₃₇ DN ₂ = 703.89) 3-6 m / z = 805.36 (C ₆₁ H ₄₃ DN ₂ = 806.02) 3-7 m / z = 779.34 (C ₅₉ H ₄₁ DN ₂ = 779.98) 3-8 m / z = 835.31 (C ₆₁ H ₄₁ DN ₂ S = 836.07) 3-9 m / z = 803.34 (C ₆₁ H ₄₁ DN ₂ = 804.01) 3-10 m / z = 704.31 (C ₅₂ H ₃₆ DN ₃ = 704.88) 3-11 m / z = 735.37 (C ₅₅ H ₄₅ DN ₂ = 735.97) 3-12 m / z = 683.30 (C ₅₀ H ₃₇ DN ₂ O = 683.36) 3-13 m / z = 704.31 (C ₅₂ H ₃₆ DN ₃ = 704.88) 3-14 m / z = 801.33 (C ₆₁ H ₃₉ DN ₂ = 801.99) 3-15 m / z = 709.27 (C ₅₁ H ₃₅ DN ₂ S = 709.92) 3-16 m / z = 967.40 (C ₇₄ H ₄₉ DN ₂ = 968.21) 3-17 m / z = 793.30 (C ₅₃ H ₃₆ DFN ₂ = 793.94) 3-18 m / z = 761.30 (C ₅₅ H ₃₉ DN ₂ S = 761.99) 3-19 m / z = 685.27 (C ₄₉ H ₃₅ DN ₂ S = 685.89) 3-20 m / z = 886.41 (C ₆₆ H ₅₀ DN ₃ = 887.14) 3-21 m / z = 653.29 (C ₄₉ H ₃₅ DN ₂ = 653.83) 3-22 m / z = 703.31 (C ₅₃ H ₃₇ DN ₂ = 703.89) 3-23 m / z = 703.31 (C ₅₃ H ₃₇ DN ₂ = 703.89) 3-24 m / z = 729.33 (C ₅₅ H ₃₉ DN ₂ = 729.93) 3-25 m / z = 753.33 (C ₅₇ H ₃₉ DN ₂ = 753.95) 3-26 m / z = 855.37 (C ₆₅ H ₄₅ DN ₂ = 856.08) 3-27 m / z = 829.36 (C ₆₃ H ₄₃ DN ₂ = 830.04) 3-28 m / z = 885.33 (C ₆₅ H ₄₃ DN ₂ S = 886.13) 3-29 m / z = 853.36 (C ₆₅ H ₄₃ DN ₂ = 854.06) 3-30 m / z = 754.32 (C ₅₆ H ₃₈ DN ₃ = 754.94) 3-31 m / z = 785.39 (C ₅₉ H ₄₇ DN ₂ = 786.03) 3-32 m / z = 733.32 (C ₅₄ H ₃₉ DN ₂ O = 733.91) 3-33 m / z = 754.32 (C ₅₆ H ₃₈ DN ₃ = 754.94) 3-34 m / z = 851.34 (C ₆₅ H ₄₁ DN ₂ = 852.05) 3-35 m / z = 759.28 (C ₅₅ H ₃₇ DN ₂ S = 759.97) 3-36 m / z = 1017.42 (C ₇₈ H ₅₁ DN ₂ = 1018.27) 3-37 m / z = 843.32 (C ₆₃ H ₃₈ DFN ₂ = 844.00) 3-38 m / z = 811.31 (C ₅₉ H ₄₁ DN ₂ S = 812.05) 3-39 m / z = 735.28 (C ₅₃ H ₃₇ DN ₂ S = 735.95) 3-40 m / z = 936.43 (C ₇₀ H ₅₂ DN ₃ = 937.20) 3-41 m / z = 986.45 (C ₇₄ H ₅₄ DN ₃ = 987.25) 3-42 m / z = 1036.46 (C ₇₈ H ₅₆ DN ₃ = 1037.31)

3-43 m / z = 986.45 (C ₇₄ H ₅₄ DN ₃ = 987.25) 3-44 m / z = 1062.48 (C ₈₀ H ₅₈ DN ₃ = 1063.35) 3-45 m / z = 1144.46 (C ₈₄ H ₆₀ DN ₃ S = 1145.5) 3-46 m / z = 653.29 (C ₄₉ H ₃₅ DN ₂ = 653.83) 3-47 m / z = 703.31 (C ₅₃ H ₃₇ DN ₂ = 703.89) 3-48 m / z = 703.31 (C ₅₃ H ₃₇ DN ₂ = 703.89) 3-49 m / z = 729.33 (C ₅₅ H ₃₉ DN ₂ = 729.93) 3-50 m / z = 753.33 (C ₅₇ H ₃₉ DN ₂ = 753.95) 3-51 m / z = 855.37 (C ₆₅ H ₄₅ DN ₂ = 856.08) 3-52 m / z = 829.36 (C ₆₃ H ₄₃ DN ₂ = 830.04) 3-53 m / z = 885.33 (C ₆₅ H ₄₃ DN ₂ S = 886.13) 3-54 m / z = 853.36 (C ₆₅ H ₄₃ DN ₂ = 854.06) 3-55 m / z = 754.32 (C ₅₆ H ₃₈ DN ₃ = 754.94) 3-56 m / z = 785.39 (C ₅₉ H ₄₇ DN ₂ = 786.03) 3-57 m / z = 733.32 (C ₅₄ H ₃₉ DN ₂ O = 733.91) 3-58 m / z = 754.32 (C ₅₆ H ₃₈ DN ₃ = 754.94) 3-59 m / z = 851.34 (C ₆₅ H ₄₁ DN ₂ = 852.05) 3-60 m / z = 759.28 (C ₅₅ H ₃₇ DN ₂ S = 759.97) 3-61 m / z = 1017.42 (C ₇₈ H ₅₁ DN ₂ = 1018.27) 3-62 m / z = 843.32 (C ₆₃ H ₃₈ DFN ₂ = 844.00) 3-63 m / z = 811.31 (C ₅₉ H ₄₁ DN ₂ S = 812.05) 3-64 m / z = 735.28 (C ₅₃ H ₃₇ DN ₂ S = 735.95) 3-65 m / z = 936.43 (C ₇₀ H ₅₂ DN ₃ = 937.20) 3-66 m / z = 679.31 (C ₅₁ H ₃₇ DN ₂ = 679.87) 3-67 m / z = 729.33 (C ₅₅ H ₃₉ DN ₂ = 729.93) 3-68 m / z = 729.33 (C ₅₅ H ₃₉ DN ₂ = 729.93) 3-69 m / z = 755.34 (C ₅₇ H ₄₁ DN ₂ = 755.96) 3-70 m / z = 779.34 (C ₅₉ H ₄₁ DN ₂ = 779.98) 3-71 m / z = 881.39 (C ₆₇ H ₄₇ DN ₂ = 882.12) 3-72 m / z = 855.37 (C ₆₅ H ₄₅ DN ₂ = 856.08) 3-73 m / z = 911.34 (C ₆₇ H ₄₅ DN ₂ O = 603.77) 3-74 m / z = 879.37 (C ₆₇ H ₄₅ DN ₂ = 880.10) 3-75 m / z = 780.34 (C ₅₈ H ₄₀ DN ₃ = 780.97) 3-76 m / z = 811.40 (C ₆₁ H ₄₉ DN ₂ = 812.07) 3-77 m / z = 759.34 (C ₅₆ H ₄₁ DN ₂ O = 759.95) 3-78 m / z = 780.34 (C ₅₈ H ₄₀ DN ₃ = 780.97) 3-79 m / z = 877.36 (C ₆₇ H ₄₃ DN ₂ = 878.09) 3-80 m / z = 785.30 (C ₅₇ H ₃₉ DN ₂ S = 786.01) 3-81 m / z = 1043.43 (C ₈₀ H ₅₃ DN ₂ = 1044.30) 3-82 m / z = 869.33 (C ₆₅ H ₄₀ DFN ₂ = 870.04) 3-83 m / z = 837.33 (C ₆₁ H ₄₃ DN ₂ S = 838.09) 3-84 m / z = 761.30 (C ₅₅ H ₃₉ DN ₂ S = 761.99) 3-85 m / z = 962.45 (C ₇₂ H ₅₄ DN ₃ = 963.23) 3-86 m / z = 608.31 (C ₄₅ H ₂₈ D ₆ N ₂ = 608.80) 3-87 m / z = 708.34 (C ₅₃ H ₃₂ D ₆ N ₂ = 708.92) 3-88 m / z = 660.34 (C ₄₉ H ₂₈ D ₈ N ₂ = 660.87) 3-89 m / z = 710.35 (C ₅₃ H ₃₀ D ₈ N ₂ = 710.93) 3-90 m / z = 764.40 (C ₅₇ H ₃₂ D ₁₀ N ₂ = 765.02) 3-91 m / z = 608.31 (C ₄₅ H ₂₈ D ₆ N ₂ = 608.80) 3-92 m / z = 660.34 (C ₄₉ H ₂₈ D ₈ N ₂ = 660.87) 3-93 m / z = 660.34 (C ₄₉ H ₂₈ D ₈ N ₂ = 660.87) 3-94 m / z = 688.37 (C ₅₁ H ₂₈ D ₁₀ N ₂ = 688.92) 3-95 m / z = 712.37 (C ₅₃ H ₂₈ D ₁₀ N ₂ = 712.94) 4-1 m / z = 683.33 (C ₅₁ H ₃₃ D ₅ N ₂ = 683.89) 4-2 m / z = 733.35 (C ₅₅ H ₃₅ D ₅ N ₂ = 733.95) 4-3 m / z = 733.35 (C ₅₅ H ₃₅ D ₅ N ₂ = 733.95) 4-4 m / z = 759.37 (C ₅₇ H ₃₇ D ₅ N ₂ = 759.99) 4-5 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) 4-6 m / z = 885.41 (C ₆₇ H ₄₃ D ₅ N ₂ = 886.14) 4-7 m / z = 859.40 (C ₆₅ H ₄₁ D ₅ N ₂ = 860.10) 4-8 m / z = 915.37 (C ₆₇ H ₄₁ D ₅ N ₂ S = 916.19) 4-9 m / z = 883.40 (C ₆₇ H ₄₁ D ₅ N ₂ = 884.13) 4-10 m / z = 784.36 (C ₅₈ H ₃₆ D ₅ N ₃ = 785.00) 4-11 m / z = 815.43 (C ₆₁ H ₄₅ D ₅ N ₂ = 816.09) 4-12 m / z = 763.36 (C ₅₆ H ₃₇ D ₅ N ₂ O = 763.98) 4-13 m / z = 784.36 (C ₅₈ H ₃₆ D ₅ N ₃ = 785.00) 4-14 m / z = 881.38 (C ₆₇ H ₃₉ D ₅ N ₂ = 882.11) 4-15 m / z = 789.32 (C ₅₇ H ₃₅ D ₅ N ₂ S = 790.04) 4-16 m / z = 1047.46 (C ₈₀ H ₄₉ D ₅ N ₂ = 1048.33) 4-17 m / z = 873.36 (C ₆₅ H ₃₆ D ₅ FN ₂ = 874.06) 4-18 m / z = 841.35 (C ₆₁ H ₃₉ D ₅ N ₂ S = 842.11) 4-19 m / z = 765.32 (C ₅₅ H ₃₅ D ₅ N ₂ S = 766.02) 4-20 m / z = 966.47 (C ₇₂ H ₅₀ D ₅ N ₃ = 967.26) 4-21 m / z = 733.35 (C ₅₅ H ₃₅ D ₅ N ₂ = 733.95) 4-22 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) 4-23 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) 4-24 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) 4-25 m / z = 833.38 (C ₆₃ H ₃₉ D ₅ N ₂ = 834.07) 4-26 m / z = 935.43 (C ₇₁ H ₄₅ D ₅ N ₂ = 936.20) 4-27 m / z = 909.41 (C ₆₉ H ₄₃ D ₅ N ₂ = 910.16) 4-28 m / z = 965.39 (C ₇₁ H ₄₃ D ₅ N ₂ S = 966.25) 4-29 m / z = 933.41 (C ₇₁ H ₄₃ D ₅ N ₂ = 934.19) 4-30 m / z = 834.38 (C ₆₂ H ₃₈ D ₅ N ₃ = 835.06) 4-31 m / z = 865.44 (C ₆₅ H ₄₇ D ₅ N ₂ = 866.15) 4-32 m / z = 813.38 (C ₆₀ H ₃₉ D ₅ N ₂ O = 814.03) 4-33 m / z = 835.06 (C ₆₂ H ₃₈ D ₅ N ₃ = 835.06) 4-34 m / z = 931.40 (C ₇₁ H ₄₁ D ₅ N ₂ = 932.17) 4-35 m / z = 839.34 (C ₆₁ H ₃₇ D ₅ N ₂ S = 840.10) 4-36 m / z = 1097.48 (C ₈₄ H ₅₁ D ₅ N ₂ = 1098.39) 4-37 m / z = 923.37 (C ₆₉ H ₃₈ D ₅ FN ₂ = 924.12) 4-38 m / z = 891.37 (C ₆₅ H ₄₁ D ₅ N ₂ S = 892.17) 4-39 m / z = 815.34 (C ₅₉ H ₃₇ D ₅ N ₂ S = 816.07)

4-40 m / z = 1016.49 (C ₇₆ H ₅₂ D ₅ N ₃ = 1017.32) 4-41 m / z = 1066.50 (C ₈₀ H ₅₄ D ₅ N ₃ = 1067.38) 4-42 m / z = 1116.52 (C ₈₄ H ₅₆ D ₅ N ₃ = 117.43) 4-43 m / z = 1066.50 (C ₈₀ H ₅₄ D ₅ N ₃ = 1067.38) 4-44 m / z = 1142.53 (C ₈₆ H ₅₈ D ₅ N ₃ = 1143.47) 4-45 m / z = 1224.52 (C ₉₀ H ₆₀ D ₅ N ₃ S = 1225.6) 4-46 m / z = 733.35 (C ₅₅ H ₃₅ D ₅ N ₂ = 733.95) 4-47 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) 4-48 m / z = 783.37 (C ₅₉ H ₃₇ D ₅ N ₂ = 784.01) 4-49 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) 4-50 m / z = 833.38 (C ₆₃ H ₃₉ D ₅ N ₂ = 834.07) 4-51 m / z = 935.43 (C ₇₁ H ₄₅ D ₅ N ₂ = 936.20) 4-52 m / z = 909.41 (C ₆₉ H ₄₃ D ₅ N ₂ = 910.16) 4-53 m / z = 965.39 (C ₇₁ H ₄₃ D ₅ N ₂ S = 966.25) 4-54 m / z = 933.41 (C ₇₁ H ₄₃ D ₅ N ₂ = 934.19) 4-55 m / z = 834.38 (C ₆₂ H ₃₈ D ₅ N ₃ = 835.06) 4-56 m / z = 865.44 (C ₆₅ H ₄₇ D ₅ N ₂ = 866.15) 4-57 m / z = 813.38 (C ₆₀ H ₃₉ D ₅ N ₂ O = 814.03) 4-58 m / z = 834.38 (C ₆₂ H ₃₈ D ₅ N ₃ = 835.06) 4-59 m / z = 931.40 (C ₇₁ H ₄₁ D ₅ N ₂ = 932.17) 4-60 m / z = 839.34 (C ₆₁ H ₃₇ D ₅ N ₂ S = 840.10) 4-61 m / z = 1097.48 (C ₈₄ H ₅₁ D ₅ N ₂ = 1098.39) 4-62 m / z = 923.37 (C ₆₉ H ₃₈ D ₅ FN ₂ = 924.12) 4-63 m / z = 891.37 (C ₆₅ H ₄₁ D ₅ N ₂ S = 892.17) 4-64 m / z = 815.34 (C ₅₉ H ₃₇ D ₅ N ₂ S = 816.07) 4-65 m / z = 1016.49 (C ₇₆ H ₅₂ D ₅ N ₃ = 1017.32) 4-66 m / z = 759.37 (C ₅₇ H ₃₇ D ₅ N ₂ = 759.99) 4-67 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) 4-68 m / z = 809.38 (C ₆₁ H ₃₉ D ₅ N ₂ = 810.05) 4-69 m / z = 835.40 (C ₆₃ H ₄₁ D ₅ N ₂ = 836.08) 4-70 m / z = 859.40 (C ₆₅ H ₄₁ D ₅ N ₂ = 860.10) 4-71 m / z = 961.44 (C ₇₃ H ₄₇ D ₅ N ₂ = 962.24) 4-72 m / z = 935.43 (C ₇₁ H ₄₅ D ₅ N ₂ = 936.20) 4-73 m / z = 991.40 (C ₇₃ H ₄₅ D ₅ N ₂ S = 992.29) 4-74 m / z = 959.43 (C ₇₃ H ₄₅ D ₅ N ₂ = 960.22) 4-75 m / z = 860.39 (C ₆₄ H ₄₀ D ₅ N ₃ = 861.09) 4-76 m / z = 891.46 (C ₆₇ H ₄₉ D ₅ N ₂ = 892.19) 4-77 m / z = 839.39 (C ₆₂ H ₄₁ D ₅ N ₂ O = 840.07) 4-78 m / z = 860.39 (C ₆₄ H ₄₀ D ₅ N ₃ = 861.09) 4-79 m / z = 957.41 (C ₇₃ H ₄₃ D ₅ N ₂ = 958.21) 4-80 m / z = 865.35 (C ₆₃ H ₃₉ D ₅ N ₂ S = 866.13) 4-81 m / z = 1123.49 (C ₈₆ H ₅₃ D ₅ N ₂ = 1124.42) 4-82 m / z = 949.39 (C ₇₁ H ₄₀ D ₅ FN ₂ = 950.16) 4-83 m / z = 917.39 (C ₆₇ H ₄₃ D ₅ N ₂ S = 918.21) 4-84 m / z = 841.35 (C ₆₁ H ₃₉ D ₅ N ₂ S = 842.11) 4-85 m / z = 1042.50 (C ₇₈ H ₅₄ D ₅ N ₃ = 1043.35) 4-86 m / z = 688.37 (C ₅₁ H ₂₈ D ₁₀ N ₂ = 688.92) 4-87 m / z = 738.38 (C ₅₅ H ₃₀ D ₁₀ N ₂ = 738.98) 4-88 m / z = 738.38 (C ₅₅ H ₃₀ D ₁₀ N ₂ = 738.98) 4-89 m / z = 764.40 (C ₅₇ H ₃₂ D ₁₀ N ₂ = 765.02) 4-90 m / z = 788.40 (C ₅₉ H ₃₂ D ₁₀ N ₂ = 789.04) 4-91 m / z = 688.37 (C ₅₁ H ₂₈ D ₁₀ N ₂ = 688.92) 4-92 m / z = 740.39 (C ₅₅ H ₂₈ D ₁₂ N ₂ = 740.99) 4-93 m / z = 740.39 (C ₅₅ H ₂₈ D ₁₂ N ₂ = 740.99) 4-94 m / z = 768.42 (C ₅₇ H ₂₈ D ₁₄ N ₂ = 769.04) 4-95 m / z = 792.42 (C ₅₉ H ₂₈ D ₁₄ N ₂ = 793.06) 5-1 m / z = 735.36 (C ₅₅ H ₃₃ D ₇ N ₂ = 735.96) 5-2 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) 5-3 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) 5-4 m / z = 811.39 (C ₆₁ H ₃₇ D ₇ N ₂ = 812.06) 5-5 m / z = 835.39 (C ₆₃ H ₃₇ D ₇ N ₂ = 836.08) 5-6 m / z = 938.21 (C ₇₁ H ₄₃ D ₇ N ₂ = 938.21) 5-7 m / z = 911.43 (C ₆₉ H ₄₁ D ₇ N ₂ = 912.18) 5-8 m / z = 967.40 (C ₇₁ H ₄₁ D ₇ N ₂ O = 968.26) 5-9 m / z = 935.43 (C ₇₁ H ₄₁ D ₇ N ₂ = 936.20) 5-10 m / z = 836.39 (C ₆₂ H ₃₆ D ₇ N ₃ = 837.07) 5-11 m / z = 867.46 (C ₆₅ H ₄₅ D ₇ N ₂ = 868.16) 5-12 m / z = 815.39 (C ₆₀ H ₃₇ D ₇ N ₂ O = 816.05) 5-13 m / z = 836.39 (C ₆₂ H ₃₆ D ₇ N ₃ = 837.07) 5-14 m / z = 933.41 (C ₇₁ H ₃₉ D ₇ N ₂ = 934.18) 5-15 m / z = 841.35 (C ₆₁ H ₃₅ D ₇ N ₂ S = 842.11) 5-16 m / z = 1099.49 (C ₈₄ H ₄₉ D ₇ N ₂ = 1100.40) 5-17 m / z = 925.38 (C ₆₉ H ₃₆ D ₇ FN ₂ = 926.13) 5-18 m / z = 894.18 (C ₆₅ H ₃₉ D ₇ N ₂ S = 894.18) 5-19 m / z = 817.35 (C ₅₉ H ₃₅ D ₇ N ₂ S = 818.09) 5-20 m / z = 1018.50 (C ₇₆ H ₅₀ D ₇ N ₃ = 1019.33) 5-21 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) 5-22 m / z = 835.39 (C ₆₃ H ₃₇ D ₇ N ₂ = 836.08) 5-23 m / z = 835.39 (C ₆₃ H ₃₇ D ₇ N ₂ = 836.08) 5-24 m / z = 861.41 (C ₆₅ H ₃₉ D ₇ N ₂ = 862.12) 5-25 m / z = 885.41 (C ₆₇ H ₃₉ D ₇ N ₂ = 886.14) 5-26 m / z = 987.46 (C ₇₅ H ₄₅ D ₇ N ₂ = 988.27) 5-27 m / z = 961.44 (C ₇₃ H ₄₃ D ₇ N ₂ = 962.23) 5-28 m / z = 1017.41 (C ₇₅ H ₄₃ D ₇ N ₂ S = 1018.3) 5-29 m / z = 985.44 (C ₇₅ H ₄₃ D ₇ N ₂ = 986.26) 5-30 m / z = 886.41 (C ₆₆ H ₃₈ D ₇ N ₃ = 887.13) 5-31 m / z = 917.47 (C ₆₉ H ₄₇ D ₇ N ₂ = 918.22) 5-32 m / z = 865.40 (C ₆₄ H ₃₉ D ₇ N ₂ O = 866.11) 5-33 m / z = 886.41 (C ₆₆ H ₃₈ D ₇ N ₃ = 887.13) 5-34 m / z = 983.43 (C ₇₅ H ₄₁ D ₇ N ₂ = 984.24) 5-35 m / z = 891.37 (C ₆₅ H ₃₇ D ₇ N ₂ S = 892.17) 5-36 m / z = 1 149.50 (C ₈₈ H ₅₁ D ₇ N ₂ = 1150.46)

5-37 m / z = 943.40 (C ₇₃ H ₃₈ D ₇ FN ₂ = 976.19) 5-38 m / z = 943.40 (C ₆₉ H ₄₁ D ₇ N ₂ S = 944.24) 5-39 m / z = 867.37 (C ₆₃ H ₃₇ D ₇ N ₂ S = 868.14) 5-40 m / z = 1068.51 (C ₈₀ H ₅₂ D ₇ N ₃ = 1069.39) 5-41 m / z = 1118.53 (C ₈₄ H ₅₄ D ₇ N ₃ = 1119.45) 5-42 m / z = 1168.55 (C ₈₈ H ₅₆ D ₇ N ₃ = 1169.51) 5-43 m / z = 1118.53 (C ₈₄ H ₅₄ D ₇ N ₂ = 1119.45) 5-44 m / z = 1194.56 (C ₉₀ H ₅₈ D ₇ N ₃ = 1195.54) 5-45 m / z = 1276.55 (C ₉₄ H ₆₀ D ₇ N ₃ S = 1277.7) 5-46 m / z = 785.38 (C ₅₉ H ₃₅ D ₇ N ₂ = 786.02) 5-47 m / z = 835.39 (C ₆₃ H ₃₇ D ₇ N ₂ = 836.08) 5-48 m / z = 835.39 (C ₆₃ H ₃₇ D ₇ N ₂ = 836.08) 5-49 m / z = 861.41 (C ₆₅ H ₃₉ D ₇ N ₂ = 862.12) 5-50 m / z = 885.41 (C ₆₇ H ₃₉ D ₇ N ₂ = 886.14) 5-51 m / z = 987.46 (C ₇₅ H ₄₅ D ₇ N ₂ = 988.27) 5-52 m / z = 961.44 (C ₇₃ H ₄₃ D ₇ N ₂ = 962.23) 5-53 m / z = 1017.41 (C ₇₅ H ₄₃ D ₇ N ₂ S = 1018.3) 5-54 m / z = 985.44 (C ₇₅ H ₄₃ D ₇ N ₂ = 986.26) 5-55 m / z = 886.41 (C ₆₆ H ₃₈ D ₇ N ₃ = 887.13) 5-56 m / z = 917.47 (C ₆₉ H ₄₇ D ₇ N ₂ = 918.22) 5-57 m / z = 865.40 (C ₆₄ H ₃₉ D ₇ N ₂ O = 866.11) 5-58 m / z = 886.41 (C ₆₆ H ₃₈ D ₇ N ₃ = 887.13) 5-59 m / z = 983.43 (C ₇₅ H ₄₁ D ₇ N ₂ = 984.24) 5-60 m / z = 891.37 (C ₆₅ H ₃₇ D ₇ N ₂ S = 892.17) 5-61 m / z = 1 149.50 (C ₈₈ H ₅₁ D ₇ N ₂ = 1150.46) 5-62 m / z = 975.40 (C ₇₃ H ₃₈ D ₇ FN ₂ = 976.19) 5-63 m / z = 943.40 (C ₆₉ H ₄₁ D ₇ N ₂ S = 944.24) 5-64 m / z = 867.37 (C ₆₃ H ₃₇ D ₇ N ₂ S = 868.14) 5-65 m / z = 1068.51 (C ₈₀ H ₅₂ D ₇ N ₃ = 1069.39) 5-66 m / z = 811.39 (C ₆₁ H ₃₇ D ₇ N ₂ = 812.06) 5-67 m / z = 861.41 (C ₆₅ H ₃₉ D ₇ N ₂ = 862.12) 5-68 m / z = 861.41 (C ₆₅ H ₃₉ D ₇ N ₂ = 862.12) 5-69 m / z = 887.43 (C ₆₇ H ₄₁ D ₇ N ₂ = 888.15) 5-70 m / z = 911.43 (C ₆₉ H ₄₁ D ₇ N ₂ = 912.18) 5-71 m / z = 1013.47 (C ₇₇ H ₄₇ D ₇ N ₂ = 1014.31) 5-72 m / z = 987.46 (C ₇₅ H ₄₅ D ₇ N ₂ = 988.27) 5-73 m / z = 1043.43 (C ₇₇ H ₄₅ D ₇ N ₂ S = 1044.4) 5-74 m / z = 1011.46 (C ₇₇ H ₄₅ D ₇ N ₂ = 1012.29) 5-75 m / z = 912.42 (C ₆₈ H ₄₀ D ₇ N ₃ = 913.16) 5-76 m / z = 943.49 (C ₇₁ H ₄₉ D ₇ N ₂ = 944.26) 5-77 m / z = 891.42 (C ₆₆ H ₄₁ D ₇ N ₂ O = 892.14) 5-78 m / z = 912.42 (C ₆₈ H ₄₀ D ₇ N ₃ = 913.16) 5-79 m / z = 1009.44 (C ₇₇ H ₄₃ D ₇ N ₂ = 1010.28) 5-80 m / z = 917.38 (C ₆₇ H ₃₉ D ₇ N ₂ S = 918.20) 5-81 m / z = 1175.52 (C ₉₀ H ₅₃ D ₇ N ₂ = 1176.50) 5-82 m / z = 1001.42 (C ₇₅ H ₄₀ D ₇ FN ₂ = 1002.2) 5-83 m / z = 969.41 (C ₇₁ H ₄₃ D ₇ N ₂ S = 970.28) 5-84 m / z = 893.38 (C ₆₅ H ₃₉ D ₇ N ₂ S = 894.18) 5-85 m / z = 1094.53 (C ₈₂ H ₅₄ D ₇ N ₃ = 1095.42) 5-86 m / z = 740.39 (C ₅₅ H ₂₈ D ₁₂ N ₂ = 740.99) 5-87 m / z = 790.41 (C ₅₉ H ₃₀ D ₁₂ N ₂ = 791.05) 5-88 m / z = 790.41 (C ₅₉ H ₃₀ D ₁₂ N ₂ = 791.05) 5-89 m / z = 816.43 (C ₆₁ H ₃₂ D ₁₂ N ₂ = 817.09) 5-90 m / z = 840.43 (C ₆₃ H ₃₂ D ₁₂ N ₂ = 841.11) 5-91 m / z = 740.39 (C ₅₅ H ₂₈ D ₁₂ N ₂ = 740.99) 5-92 m / z = 792.42 (C ₅₉ H ₂₈ D ₁₄ N ₂ = 793.06) 5-93 m / z = 792.42 (C ₅₉ H ₂₈ D ₁₄ N ₂ = 793.06) 5-94 m / z = 820.45 (C ₆₁ H ₂₈ D ₁₆ N ₂ = 821.11) 5-95 m / z = 844.45 (C ₆₃ H ₂₈ D ₁₆ N ₂ = 845.14) 6-1 m / z = 606.30 (C ₄₅ H ₃₀ D ₄ N ₂ = 606.79) 6-2 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 6-3 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 6-4 m / z = 682.33 (C ₅₁ H ₃₄ D ₄ N ₂ = 682.89) 6-5 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 6-6 m / z = 808.38 (C ₆₁ H ₄₀ D ₄ N ₂ = 809.04) 6-7 m / z = 782.36 (C ₅₉ H ₃₈ D ₄ N ₂ = 783.00) 6-8 m / z = 838.33 (C ₆₁ H ₃₈ D ₄ N ₂ S = 839.09) 6-9 m / z = 806.36 (C ₆₁ H ₃₈ D ₄ N ₂ = 807.02) 6-10 m / z = 707.32 (C ₅₂ H ₃₃ D ₄ N ₃ = 707.89) 6-11 m / z = 738.39 (C ₅₅ H ₄₂ D ₄ N ₂ = 738.99) 6-12 m / z = 686.32 (C ₅₀ H ₃₄ D ₄ N ₂ O = 686.87) 6-13 m / z = 707.32 (C ₅₂ H ₃₃ D ₄ N ₃ = 707.89) 6-14 m / z = 808.37 (C ₆₁ H ₃₂ D ₈ N ₂ = 809.03) 6-15 m / z = 712.29 (C ₅₁ H ₃₂ D ₄ N ₂ S = 712.93) 6-16 m / z = 974.45 (C ₇₄ H ₄₂ D ₈ N ₂ = 975.25) 6-17 m / z = 796.32 (C ₅₉ H ₃₃ D ₄ FN ₂ = 796.96) 6-18 m / z = 764.32 (C ₅₅ H ₃₆ D ₄ N ₂ S = 765.01) 6-19 m / z = 688.29 (C ₄₉ H ₃₂ D ₄ N ₂ S = 688.91) 6-20 m / z = 893.46 (C ₆₆ H ₄₃ D ₈ N ₃ = 894.18) 6-21 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 6-22 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 6-23 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 6-24 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 6-25 m / z = 756.34 (C ₅₇ H ₃₆ D ₄ N ₂ = 756.97) 6-26 m / z = 858.39 (C ₆₅ H ₄₂ D ₄ N ₂ = 859.10) 6-27 m / z = 832.38 (C ₆₃ H ₄₀ D ₄ N ₂ = 833.06) 6-28 m / z = 888.35 (C ₆₅ H ₄₀ D ₄ N ₂ S = 889.15) 6-29 m / z = 856.38 (C ₆₅ H ₄₀ D ₄ N ₂ = 857.08) 6-30 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95) 6-31 m / z = 788.41 (C ₅₉ H ₄₄ D ₄ N ₂ = 789.05) 6-32 m / z = 736.34 (C ₅₄ H ₃₆ D ₄ N ₂ O = 736.93) 6-33 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95)

6-34 m / z = 858.39 (C ₆₅ H ₃₄ D ₈ N ₂ = 859.09) 6-35 m / z = 762.30 (C ₅₅ H ₃₄ D ₄ N ₂ S = 762.99) 6-36 m / z = 1024.46 (C ₇₈ H ₄₄ D ₈ N ₂ = 1025.31) 6-37 m / z = 846.33 (C ₆₃ H ₃₅ D ₄ FN ₂ = 847.02) 6-38 m / z = 814.33 (C ₅₉ H ₃₈ D ₄ N ₂ S = 815.07) 6-39 m / z = 738.30 (C ₅₃ H ₃₄ D ₄ N ₂ S = 738.97) 6-40 m / z = 943.47 (C ₇₀ H ₄₅ D ₈ N ₃ = 944.24) 6-41 m / z = 993.49 (C ₇₄ H ₄₇ D ₈ N ₃ = 994.30) 6-42 m / z = 1043.51 (C ₇₈ H ₄₉ D ₈ N ₃ = 1044.36) 6-43 m / z = 993.49 (C ₇₄ H ₄₇ D ₈ N ₃ = 994.30) 6-44 m / z = 1069.52 (C ₈₀ H ₅₁ D ₈ N ₃ = 1070.39) 6-45 m / z = 1 151.51 (C ₈₄ H ₅₃ D ₈ N ₃ S = 1152.5) 6-46 m / z = 656.31 (C ₄₉ H ₃₂ D ₄ N ₂ = 656.85) 6-47 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 6-48 m / z = 706.33 (C ₅₃ H ₃₄ D ₄ N ₂ = 706.91) 6-49 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 6-50 m / z = 756.34 (C ₅₇ H ₃₆ D ₄ N ₂ = 756.97) 6-51 m / z = 858.39 (C ₆₅ H ₄₂ D ₄ N ₂ = 859.10) 6-52 m / z = 832.38 (C ₆₃ H ₄₀ D ₄ N ₂ = 833.06) 6-53 m / z = 889.35 (C ₆₅ H ₄₀ D ₄ N ₂ S = 889.15) 6-54 m / z = 856.38 (C ₆₅ H ₄₀ D ₄ N ₂ = 857.08) 6-55 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95) 6-56 m / z = 788.41 (C ₅₉ H ₄₄ D ₄ N ₂ = 789.05) 6-57 m / z = 736.34 (C ₅₄ H ₃₆ D ₄ N ₂ O = 736.93) 6-58 m / z = 757.34 (C ₅₆ H ₃₅ D ₄ N ₃ = 757.95) 6-59 m / z = 854.36 (C ₆₅ H ₃₈ D ₄ N ₂ = 855.07) 6-60 m / z = 762.30 (C ₅₅ H ₃₄ D ₄ N ₂ S = 762.99) 6-61 m / z = 1024.46 (C ₇₈ H ₄₄ D ₈ N ₂ = 1025.31) 6-62 m / z = 846.33 (C ₆₃ H ₃₅ D ₄ FN ₂ = 847.02) 6-63 m / z = 841.33 (C ₅₉ H ₃₈ D ₄ N ₂ S = 815.07) 6-64 m / z = 738.30 (C ₅₃ H ₃₄ D ₄ N ₂ S = 738.97) 6-65 m / z = 943.47 (C ₇₀ H ₄₅ D ₈ N ₃ = 944.24) 6-66 m / z = 682.33 (C ₅₁ H ₃₄ D ₄ N ₂ = 682.89) 6-67 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 6-68 m / z = 732.34 (C ₅₅ H ₃₆ D ₄ N ₂ = 732.94) 6-69 m / z = 758.36 (C ₅₇ H ₃₈ D ₄ N ₂ = 758.98) 6-70 m / z = 782.36 (C ₅₉ H ₃₈ D ₄ N ₂ = 783.00) 6-71 m / z = 884.41 (C ₆₇ H ₄₄ D ₄ N ₂ = 885.14) 6-72 m / z = 858.39 (C ₆₅ H ₄₂ D ₄ N ₂ = 859.10) 6-73 m / z = 914.36 (C ₆₇ H ₄₂ D ₄ N ₂ S = 915.19) 6-74 m / z = 882.39 (C ₆₇ H ₄₂ D ₄ N ₂ = 883.12) 6-75 m / z = 783.36 (C ₅₈ H ₃₇ D ₄ N ₂ = 783.99) 6-76 m / z = 814.42 (C ₆₁ H ₄₆ D ₄ N ₂ = 815.09) 6-77 m / z = 762.35 (C ₅₆ H ₃₈ D ₄ N ₂ O = 762.97) 6-78 m / z = 783.36 (C ₅₈ H ₃₇ D ₄ N ₃ = 783.99) 6-79 m / z = 880.38 (C ₆₇ H ₄₀ D ₄ N ₂ = 881.10) 6-80 m / z = 788.32 (C ₅₇ H ₃₆ D ₄ N ₂ S = 789.03) 6-81 m / z = 1050.48 (C ₈₀ H ₄₆ D ₈ N ₂ = 1051.35) 6-82 m / z = 872.35 (C ₆₅ H ₃₇ D ₄ FN ₂ = 873.06) 6-83 m / z = 840.35 (C ₆₁ H ₄₀ D ₄ N ₂ S = 841.11) 6-84 m / z = 764.32 (C ₅₅ H ₃₆ D ₄ N ₂ S = 765.01) 6-85 m / z = 969.49 (C ₇₂ H ₄₇ D ₈ N ₂ = 970.28) 6-86 m / z = 611.33 (C ₄₅ H ₂₅ D ₉ N ₂ = 611.82) 6-87 m / z = 611.34 (C ₄₉ H ₂₇ D ₉ N ₂ = 661.88) 6-88 m / z = 661.34 (C ₄₉ H ₂₇ D ₉ N ₂ = 661.88) 6-89 m / z = 700.44 (C ₅₁ H ₁₆ D ₂₂ N ₂ = 701.00) 6-90 m / z = 711.36 (C ₅₃ H ₂₉ D ₉ N ₂ = 711.94) 6-91 m / z = 611.33 (C ₄₅ H ₂₅ D ₉ N ₂ = 611.82) 6-92 m / z = 633.36 (C ₄₉ H ₂₅ D ₁₁ N ₂ = 663.89) 6-93 m / z = 663.36 (C ₄₉ H ₂₅ D ₁₁ N ₂ = 663.89) 6-94 m / z = 691.39 (C ₅₁ H ₂₅ D ₁₃ N ₂ = 691.94) 6-95 m / z = 715.39 (C ₅₃ H ₂₅ D ₁₃ N ₂ = 715.96)

On the other hand, each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.

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 a substituent 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 electronic 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 in various applications in organic electric devices 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 electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that at least one organic material layer is formed using the above-described compounds.

It is apparent that the same effect can be obtained even when the compounds of the present invention are used in other organic material layers of the organic electric device, for example, a light emission auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer.

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 an 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 the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, 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

Evaluation of manufacturing of organic electric device

Hereinafter, the compounds were synthesized according to the synthesis method described above, and the examples in which the compounds were applied to an organic material layer of an organic electroluminescent device, for example, an organic electroluminescent device, were compared with those of commonly used compounds.

Using various compounds obtained through synthesis as a hole transport layer, an organic electroluminescent device was manufactured according to a conventional method. First, 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter 2T-NATA) as a hole injection layer on the ITO layer (anode) formed on the glass substrate first The film was vacuum deposited to form a thickness of 10 nm.

Subsequently, the developed material was vacuum-deposited to a thickness of 30 nm as a major transport compound to form a hole transport layer. After the hole transport layer was formed, the developed material was measured by the hole transport layer, and a light emitting layer having a 45 nm-thick BD-052X (Idemitus) doped with 7% on the hole transport layer (where BD-052X was a blue fluorescent dopant) 9,10-di (naphthalene-2-anthracene (AND)) was used as the light emitting host material.

(1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a hole blocking layer to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to an electron injection layer at a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.

Comparative Example  (One): NPB

compound Driving voltage electric current
(mA / cm ² ) Luminance
(cd / m < 2 & efficiency
(cd / A) T (90) Chromaticity coordinates Comparative Example (1) Comparative Example (1) 6.3 7.0 300.0 4.3 75.4 (0.15, 0.15) Example (1) Compound (1-1) 5.3 6.7 300.0 4.5 145.8 (0.15,
014) Example (2) Compound (1-2) 5.8 5.7 300.0 5.2 107.0 (0.15, 0.15) Example (3) Compound (1-3) 5.8 6.4 300.0 4.7 146.8 (0.15, 0.14) Example (4) Compound (1-4) 5.1 6.3 300.0 4.7 132.1 (0.15, 0.13) Example (5) Compound (1-5) 5.5 5.7 300.0 5.3 91.5 (0.15, 0.13) Example (6) Compound (1-6) 5.9 5.8 300.0 5.2 146.8 (0.15, 0.14) Example (7) Compound (1-7) 5.5 6.0 300.0 5.0 94.1 (0.15, 0.15) Example (8) Compound (1-8) 4.9 6.3 300.0 4.8 137.4 (0.15, 0.13) Example (9) Compound (1-9) 4.7 5.9 300.0 5.1 133.7 (0.15, 0.15) Example (10) Compound (1-10) 5.6 5.9 300.0 5.1 132.4 (0.15, 0.13) Example (11) Compound (1-11) 5.0 6.9 300.0 4.4 105.9 (0.15, 0.14) Example (12) Compound (1-12) 5.1 6.6 300.0 4.6 122.9 (0.15, 0.13) Example (13) Compound (1-13) 4.9 6.0 300.0 5.0 91.4 (0.15, 0.14) Example (14) Compound (1-14) 4.9 6.0 300.0 5.0 113.2 (0.15, 0.13) Example (15) Compound (1-15) 5.3 6.3 300.0 4.7 126.8 (0.15, 0.15) Example (16) Compound (1-16) 5.7 5.6 300.0 5.3 129.7 (0.15, 0.14) Example (17) Compound (1-18) 5.2 6.2 300.0 4.9 95.1 (0.15, 0.15) Example (18) Compound (1-19) 5.0 5.8 300.0 5.2 142.1 (0.15, 0.14) Example (19) Compound (1-20) 5.6 6.6 300.0 4.6 115.8 (0.15, 0.13) Example (20) Compound (1-24) 4.7 5.7 300.0 5.3 107.0 (0.15, 0.15) Example (21) Compound (1-29) 4.5 6.0 300.0 5.0 128.7 (0.15, 0.13) Example (22) Compound (1-34) 5.2 6.2 300.0 4.8 141.9 (0.15, 0.15) Example (23) Compound (1-35) 4.8 6.3 300.0 4.8 119.4 (0.15, 0.14) Example (24) Compound (1-36) 5.5 6.3 300.0 4.8 147.9 (0.15, 0.15) Example (25) Compound (1-40) 5.8 6.3 300.0 4.8 126.2 (0.15, 0.15) Example (26) Compound (1-41) 5.8 7.0 300.0 4.3 138.6 (0.15, 0.14) Example (27) Compound (1-44) 5.8 6.0 300.0 5.0 141.5 (0.15, 0.13) Example (28) Compound (1-49) 5.1 6.4 300.0 4.7 123.9 (0.15, 0.15)

Example (29) Compound (1-51) 5.0 6.6 300.0 4.5 100.7 (0.15, 0.14) Example (30) Compound (1-54) 4.8 5.8 300.0 5.2 122.2 (0.15, 0.15) Example (31) Compound (1-59) 4.9 5.9 300.0 5.1 107.5 (0.15, 0.14) Example (32) Compound (1-69) 5.0 5.7 300.0 5.3 135.1 (0.15, 0.13) Example (33) Compound (1-72) 5.2 6.1 300.0 5.0 96.4 (0.15, 0.13) Example (34) Compound (1-74) 4.6 5.7 300.0 5.3 113.4 (0.15, 0.14) Example (35) Compound (1-79) 4.9 5.6 300.0 5.3 108.8 (0.15, 0.15) Example (36) Compound (2-1) 4.9 6.7 300.0 4.5 142.3 (0.15, 0.13) Example (37) Compound (2-2) 5.1 6.7 300.0 4.5 119.3 (0.15, 0.14) Example (38) Compound (2-3) 5.1 6.8 300.0 4.4 134.5 (0.15, 0.15) Example (39) Compound (2-4) 4.9 5.5 300.0 5.5 135.7 (0.15, 0.13) Example (40) Compound (2-5) 5.0 6.3 300.0 4.8 128.0 (0.15, 0.14) Example (41) Compound (2-6) 5.0 5.5 300.0 5.5 97.9 (0.15, 0.15) Example (42) Compound (2-7) 5.0 5.5 300.0 5.4 104.0 (0.15, 0.15) Example (43) Compound (2-8) 4.8 5.7 300.0 5.3 140.4 (0.15, 0.14) Example (44) Compound (2-9) 4.3 5.2 300.0 5.7 113.0 (0.15, 0.14) Example (45) Compound (2-10) 5.2 6.4 300.0 4.7 138.3 (0.15, 0.13) Example (46) Compound (2-11) 5.2 6.4 300.0 4.7 134.5 (0.15, 0.14) Example (47) Compound (2-12) 4.7 5.4 300.0 5.6 125.6 (0.15, 0.15) Example (48) Compound (2-13) 5.1 6.8 300.0 4.4 112.3 (0.15, 0.13) Example (49) Compound (2-14) 5.0 6.2 300.0 4.8 120.2 (0.15, 0.14) Example (50) Compound (2-15) 4.9 5.6 300.0 5.4 113.1 (0.15, 0.15) Example (51) Compound (2-16) 4.6 5.3 300.0 5.7 148.5 (0.15, 0.14) Example (52) Compound (2-18) 5.2 5.8 300.0 5.2 122.9 (0.15, 0.13) Example (53) Compound (2-19) 4.9 5.6 300.0 5.4 99.5 (0.15, 0.13) Example (54) Compound (2-20) 5.1 5.8 300.0 5.2 94.7 (0.15, 0.13) Example (55) Compound (2-24) 4.7 6.9 300.0 4.3 113.6 (0.15, 0.15) Example (56) Compound (2-29) 4.3 5.5 300.0 5.4 92.9 (0.15, 0.15) Example (57) Compound (2-34) 4.9 6.7 300.0 4.5 142.0 (0.15, 0.14) Example (58) Compound (2-35) 5.0 5.5 300.0 5.4 145.5 (0.15, 0.13) Example (59) Compound (2-36) 4.9 6.9 300.0 4.4 146.3 (0.15, 0.15)

Example (60) Compound (2-40) 4.9 6.1 300.0 4.9 94.7 (0.15, 0.14) Example (61) Compound (2-41) 4.6 6.8 300.0 4.4 105.0 (0.15, 0.13) Example (62) Compound (2-44) 4.6 6.5 300.0 4.6 116.6 (0.15, 0.15) Example (63) Compound (2-49) 4.9 6.4 300.0 4.7 112.3 (0.15, 0.14) Example (64) Compound (2-51) 5.1 6.6 300.0 4.5 146.0 (0.15, 0.15) Example (65) Compound (2-54) 4.4 5.5 300.0 5.4 121.5 (0.15, 0.14) Example (66) Compound (2-59) 5.0 5.8 300.0 5.2 129.4 (0.15, 0.13) Example (67) Compound (2-69) 4.9 6.3 300.0 4.8 104.7 (0.15, 0.13) Example (68) Compound (2-72) 4.8 5.8 300.0 5.2 94.6 (0.15, 0.14) Example (69) Compound (2-74) 4.3 5.5 300.0 5.5 110.0 (0.15, 0.15) Example (70) Compound (2-79) 4.7 6.3 300.0 4.7 97.8 (0.15, 0.14) Example (71) Compound (3-1) 5.3 5.8 300.0 5.1 142.0 (0.15, 0.13) Example (72) Compound (3-2) 5.1 7.0 300.0 4.3 106.3 (0.15, 0.13) Example (73) Compound (3-3) 4.8 6.1 300.0 4.9 149.8 (0.15, 0.15) Example (74) Compound (3-4) 4.9 5.7 300.0 5.2 131.9 (0.15, 0.15) Example (75) Compound (3-5) 5.2 6.8 300.0 4.4 108.6 (0.15, 0.14) Example (76) Compound (3-6) 5.0 6.6 300.0 4.6 126.9 (0.15, 0.14) Example (77) Compound (3-7) 5.2 5.4 300.0 5.6 128.7 (0.15, 0.13) Example (78) Compound (3-8) 5.2 5.4 300.0 5.6 139.4 (0.15, 0.13) Example (79) Compound (3-9) 4.2 5.4 300.0 5.6 146.3 (0.15, 0.14) Example (80) Compound (3-10) 5.1 5.7 300.0 5.3 148.1 (0.15, 0.15) Example (81) Compound (3-11) 5.2 6.0 300.0 5.0 149.1 (0.15, 0.14) Example (82) Compound (3-12) 5.2 5.8 300.0 5.2 102.8 (0.15, 0.14) Example (83) Compound (3-13) 4.8 5.5 300.0 5.4 142.9 (0.15, 0.13) Example (84) Compound (3-14) 4.8 5.6 300.0 5.4 111.6 (0.15, 0.14) Example (85) Compound (3-15) 5.0 5.8 300.0 5.2 105.9 (0.15, 0.15) Example (86) Compound (3-16) 5.0 6.8 300.0 4.4 149.9 (0.15, 0.15) Example (87) Compound (3-18) 5.2 5.6 300.0 5.3 143.9 (0.15, 0.13) Example (88) Compound (3-19) 5.1 6.1 300.0 4.9 103.7 (0.15, 0.14) Example (89) Compound (3-20) 5.1 5.5 300.0 5.4 102.8 (0.15, 0.15) Example (90) Compound (3-24) 4.6 6.4 300.0 4.7 144.5 (0.15, 0.13) Example (91) Compound (3-29) 4.0 5.4 300.0 5.5 99.8 (0.15, 0.14) Example (92) Compound (3-34) 4.7 6.5 300.0 4.6 104.7 (0.15, 0.14) Example (93) Compound (3-35) 5.1 6.6 300.0 4.5 129.0 (0.15, 0.13) Example (94) Compound (3-36) 4.8 5.4 300.0 5.6 142.7 (0.15, 0.15) Example (95) Compound (3-40) 4.7 5.3 300.0 5.7 134.0 (0.15, 0.14) Example (96) Compound (3-41) 5.2 5.7 300.0 5.3 90.7 (0.15, 0.15) Example (97) Compound (3-44) 5.0 5.6 300.0 5.4 146.2 (0.15, 0.13) Example (98) Compound (3-49) 4.9 6.0 300.0 5.0 136.2 (0.15, 0.13) Example (99) Compound (3-51) 5.2 5.3 300.0 5.6 96.5 (0.15, 0.15)

Example (100) Compound (3-54) 4.0 5.4 300.0 5.6 94.8 (0.15, 0.14) Example (101) Compound (3-59) 4.9 5.4 300.0 5.6 122.6 (0.15, 0.13) Example (102) Compound (3-69) 4.8 5.6 300.0 5.3 126.6 (0.15, 0.14) Example (103) Compound (3-72) 4.8 5.8 300.0 5.2 107.7 (0.15, 0.14) Example (104) Compound (3-74) 4.4 5.6 300.0 5.3 115.6 (0.15, 0.15) Example 105 Compound (3-79) 4.8 5.3 300.0 5.7 130.1 (0.15, 0.14) Example 106 Compound (4-1) 5.5 6.7 300.0 4.4 102.4 (0.15, 0.13) Example 107 Compound (4-2) 5.0 5.8 300.0 5.2 111.8 (0.15, 0.15) Example 108 Compound (4-3) 5.4 6.4 300.0 4.7 140.0 (0.15, 0.14) Example 109 Compound (4-4) 4.8 5.6 300.0 5.4 116.5 (0.15, 0.15) Example (110) Compound (4-5) 5.2 6.1 300.0 4.9 108.7 (0.15, 0.13) Example (111) Compound (4-6) 5.2 6.0 300.0 5.0 125.7 (0.15, 0.14) Example (112) Compound (4-7) 5.4 6.2 300.0 4.9 108.9 (0.15, 0.13) Example (113) Compound (4-8) 5.3 6.1 300.0 4.9 127.5 (0.15, 0.14) Example 114 Compound (4-9) 4.6 5.6 300.0 5.3 135.5 (0.15, 0.15) Example 115 Compound (4-10) 5.5 6.3 300.0 4.8 143.0 (0.15, 0.14) Example 116 Compound (4-11) 5.3 6.3 300.0 4.7 145.5 (0.15, 0.13) Example 117 Compound (4-12) 5.4 6.3 300.0 4.8 112.7 (0.15, 0.13) Example 118 Compound (4-13) 5.4 6.0 300.0 5.0 103.9 (0.15, 0.14) Example (119) Compound (4-14) 4.9 5.7 300.0 5.3 109.3 (0.15, 0.15) Example 120 Compound (4-15) 5.5 6.5 300.0 4.6 132.0 (0.15, 0.15) Example (121) Compound (4-16) 5.3 5.8 300.0 5.2 106.2 (0.15, 0.14) Example (122) Compound (4-18) 5.3 6.3 300.0 4.8 130.1 (0.15, 0.15) Example (123) Compound (4-19) 5.3 6.3 300.0 4.7 127.3 (0.15, 0.13) Example 124 Compound (4-20) 5.1 6.6 300.0 4.5 118.8 (0.15, 0.14) Example (125) Compound (4-24) 4.9 6.3 300.0 4.7 120.1 (0.15, 0.13) Example 126 Compound (4-29) 4.9 5.6 300.0 5.4 126.3 (0.15, 0.13) Example (127) Compound (4-34) 5.2 6.4 300.0 4.7 137.1 (0.15, 0.14) Example 128 Compound (4-35) 4.9 5.7 300.0 5.3 109.6 (0.15, 0.15) Example (129) Compound (4-36) 4.9 6.0 300.0 5.0 139.7 (0.15, 0.14) Example 130 Compound (4-40) 4.9 6.9 300.0 4.4 135.0 (0.15, 0.15) Example 131 Compound (4-41) 5.5 5.7 300.0 5.3 122.2 (0.15, 0.13) Example 132 Compound (4-44) 5.2 6.9 300.0 4.4 101.5 (0.15, 0.14) Example (133) Compound (4-49) 5.1 6.0 300.0 5.0 105.6 (0.15, 0.15) Example 134 Compound (4-51) 5.6 6.6 300.0 4.5 96.6 (0.15, 0.14) Example (135) Compound (4-54) 4.9 5.6 300.0 5.3 91.7 (0.15, 0.15) Example 136 Compound (4-59) 4.9 5.9 300.0 5.1 102.9 (0.15, 0.14) Example (137) Compound (4-69) 5.3 6.7 300.0 4.5 94.6 (0.15, 0.14) Example (138) Compound (4-72) 5.3 6.2 300.0 4.8 106.2 (0.15, 0.14) Example (139) Compound (4-74) 4.8 6.0 300.0 5.0 122.0 (0.15, 0.13) Example 140 Compound (4-79) 4.8 5.7 300.0 5.2 95.7 (0.15, 0.14) Example 141 Compound (5-1) 4.9 7.0 300.0 4.3 145.0 (0.15, 0.13) Example 142 Compound (5-2) 5.0 6.2 300.0 4.8 110.1 (0.15, 0.15) Example 143 Compound (5-3) 5.5 6.3 300.0 4.8 94.7 (0.15, 0.14) Example 144 Compound (5-4) 4.9 6.2 300.0 4.8 111.9 (0.15, 0.13) Example 145 Compound (5-5) 5.0 6.7 300.0 4.5 113.7 (0.15, 0.13) Example (146) Compound (5-6) 5.6 5.7 300.0 5.3 149.4 (0.15, 0.14) Example (147) Compound (5-7) 5.4 6.3 300.0 4.8 135.4 (0.15, 0.13) Example (148) Compound (5-8) 5.3 5.9 300.0 5.0 123.7 (0.15, 0.15) Example 149 Compound (5-9) 4.7 5.8 300.0 5.2 133.6 (0.15, 0.13) Example (150) Compound (5-10) 5.2 6.6 300.0 4.5 91.8 (0.15, 0.14) Example 151 Compound (5-11) 4.9 6.0 300.0 5.0 134.0 (0.15, 0.13) Example 152 Compound (5-12) 5.3 6.7 300.0 4.5 117.0 (0.15, 0.13) Example 153 Compound (5-13) 5.1 6.4 300.0 4.7 99.9 (0.15, 0.14) Example 154 Compound (5-14) 5.0 6.0 300.0 5.0 137.2 (0.15, 0.13) Example (155) Compound (5-15) 5.5 5.6 300.0 5.3 99.9 (0.15, 0.15) Example 156 Compound (5-16) 5.5 6.3 300.0 4.8 121.6 (0.15, 0.13)

Example (157) Compound (5-18) 5.5 6.9 300.0 4.4 105.6 (0.15, 0.13) Example 158 Compound (5-19) 5.2 5.9 300.0 5.1 128.0 (0.15, 0.14) Example 159 Compound (5-20) 4.8 6.2 300.0 4.8 145.9 (0.15, 0.14) Example 160 Compound (5-24) 5.2 5.9 300.0 5.0 129.3 (0.15, 0.15) Example 161 Compound (5-29) 4.8 5.9 300.0 5.1 143.1 (0.15, 0.13) Example 162 Compound (5-34) 5.0 6.0 300.0 5.0 148.7 (0.15, 0.14) Example 163 Compound (5-35) 5.1 5.7 300.0 5.2 91.9 (0.15, 0.14) Example 164 Compound (5-36) 5.5 5.7 300.0 5.3 145.3 (0.15, 0.14) Example (165) Compound (5-40) 5.5 6.4 300.0 4.7 129.9 (0.15, 0.13) Example 166 Compound (5-41) 5.0 5.8 300.0 5.1 130.0 (0.15, 0.13) Example 167 Compound (5-44) 5.4 5.7 300.0 5.3 90.9 (0.15, 0.14) Example 168 Compound (5-49) 5.2 6.1 300.0 4.9 118.9 (0.15, 0.15) Example (169) Compound (5-51) 4.9 5.8 300.0 5.2 101.8 (0.15, 0.14) Example 170 Compound (5-54) 4.9 6.4 300.0 4.7 121.5 (0.15, 0.13) Example 171 Compound (5-59) 4.9 6.4 300.0 4.7 146.6 (0.15, 0.14) Example 172 Compound (5-69) 5.0 5.7 300.0 5.3 100.3 (0.15, 0.14) Example (173) Compound (5-72) 5.1 6.0 300.0 5.0 116.6 (0.15, 0.14) Example 174 Compound (5-74) 4.7 5.8 300.0 5.2 131.7 (0.15, 0.15) Example (175) Compound (5-79) 5.3 6.2 300.0 4.8 123.9 (0.15, 0.13) Example (176) Compound (6-1) 5.0 6.3 300.0 4.7 111.5 (0.15, 0.14) Example (177) Compound (6-2) 5.1 6.7 300.0 4.4 104.1 (0.15, 0.14) Example (178) Compound (6-3) 5.3 6.8 300.0 4.4 90.6 (0.15, 0.14) Example (179) Compound (6-4) 5.2 6.0 300.0 5.0 139.1 (0.15, 0.15) Example 180 Compound (6-5) 5.0 5.6 300.0 5.4 128.9 (0.15, 0.14) Example (181) Compound (6-6) 5.2 6.7 300.0 4.5 145.5 (0.15, 0.15) Example 182 Compound (6-7) 5.5 5.7 300.0 5.3 98.1 (0.15, 0.14) Example (183) Compound (6-8) 5.4 6.5 300.0 4.6 104.4 (0.15, 0.14) Example 184 Compound (6-9) 5.4 5.6 300.0 5.4 103.6 (0.15, 0.14) Example (185) Compound (6-10) 5.3 5.9 300.0 5.1 107.8 (0.15, 0.13) Example (186) Compound (6-11) 5.3 5.6 300.0 5.3 140.6 (0.15, 0.14) Example (187) Compound (6-12) 5.1 6.7 300.0 4.5 140.4 (0.15, 0.14) Example (188) Compound (6-13) 5.4 5.6 300.0 5.4 122.1 (0.15, 0.14) Example (189) Compound (6-14) 5.2 6.2 300.0 4.8 130.1 (0.15, 0.15) Example 190 Compound (6-15) 5.7 5.7 300.0 5.3 98.2 (0.15, 0.14) Example (191) Compound (6-16) 5.1 6.5 300.0 4.6 112.9 (0.15, 0.13) Example (192) Compound (6-18) 5.1 6.1 300.0 4.9 116.8 (0.15, 0.14) Example (193) Compound (6-19) 4.9 7.0 300.0 4.3 105.7 (0.15, 0.14) Example 194 Compound (6-20) 5.3 6.6 300.0 4.6 113.6 (0.15, 0.14) Example (195) Compound (6-24) 5.7 7.0 300.0 4.3 130.3 (0.15, 0.15) Example (196) Compound (6-29) 4.9 5.9 300.0 5.1 99.6 (0.15, 0.14) Example (197) Compound (6-34) 4.9 6.3 300.0 4.8 138.1 (0.15, 0.13) Example (198) Compound (6-35) 5.4 5.7 300.0 5.3 104.8 (0.15, 0.14) Example (199) Compound (6-36) 5.7 6.3 300.0 4.8 95.4 (0.15, 0.14) Example (200) Compound (6-40) 5.0 6.0 300.0 5.0 105.9 (0.15, 0.15) Example 201 Compound (6-41) 5.3 5.9 300.0 5.1 134.6 (0.15, 0.14) Example 202 Compound (6-44) 5.1 5.9 300.0 5.0 133.1 (0.15, 0.15) Example (203) Compound (6-49) 5.3 5.6 300.0 5.3 101.0 (0.15, 0.14) Example 204 Compound (6-51) 5.3 5.8 300.0 5.2 138.4 (0.15, 0.13) Example (205) Compound (6-54) 5.1 5.6 300.0 5.4 97.3 (0.15, 0.15) Example 206 Compound (6-59) 5.0 6.0 300.0 5.0 102.3 (0.15, 0.14) Example (207) Compound (6-69) 5.7 5.6 300.0 5.3 92.7 (0.15, 0.14) Example 208 Compound (6-72) 5.3 6.7 300.0 4.5 134.4 (0.15, 0.15) Example (209) Compound (6-74) 5.7 5.8 300.0 5.1 103.8 (0.15, 0.13) Example 210 Compound (6-79) 5.3 6.4 300.0 4.7 95.5 (0.15, 0.14)

As can be seen from the results of the above table, the organic electric element using the organic electric element material of the present invention is used as a light emitting host and hole transporting material of the organic electric element because the blue light emission with improved color purity is obtained. The luminous efficiency and lifespan can be significantly improved.

It is apparent that the same effect can be obtained even when the compounds of the present invention are used in other organic material layers of the organic electric device, for example, a light emission auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, 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 construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

Claims (11)

An organic electric device comprising a first electrode, at least one organic material layer including a compound represented by Formula 1, and a second electrode in a sequentially stacked form:

[Formula 1]
In Formula 1,
(1) R ₁ to R ₆ are the same as or different from each other, and a hydrogen atom ; Deuterium ; Tritium ; Halogen ; Amino group ; Nitrile group ; Nitro group ; Hydroxyl group ; 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, Substituted by 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, deuterium Or substituted with one or more substituents selected from the group consisting of a C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₅ to C ₂₀ heterocyclic group, or Unsubstituted C ₆ ~ C ₆₀ aryl group ; Deuterium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl group, In the group consisting of C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group A C ₅ to C ₆₀ heteroaryl group which is unsubstituted or substituted with one or more substituents and has at least one of O, N, and S ; 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, C ₂ C ₁ -C ₃₀ alkoxy group unsubstituted or substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₃ -C ₆₀ heteroaryl group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted C ₆ ~ C ₃₀ aryloxy group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted amino group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or aryl come Sy of the unsubstituted C ₅ ~ C ₆₀ ring; Or 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 ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ An arylalkenyl group, a C ₅ ~ C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted or unsubstituted C ₁ ~ C ₅₀ Alkyl group , wherein R ₁ ~ R ₂ is bonded to a group adjacent to each other To form a saturated or unsaturated aliphatic ring or heterocycle, and N of carbazole may combine with an adjacent group together with a substituent connected to it to form a ring,
2) L is a C ₆ ~ C ₆₀ of unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and amino group Arylene group ; C ₅ -C ₆₀ heteroarylene group unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group and amino group; And divalent or trivalent substituted or unsubstituted aliphatic hydrocarbons ,
3 ) Ar ₁ and Ar ₂ are the same as or different from each other, and each independently halogen ; Nitrile group ; Nitro group ; 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 -C20 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, deuterium substituted C Substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₂₀ aryl group, C ₈ to C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group C ₆ ~ C ₆₀ aryl group ; C ₆ ~ C ₆₀ aryl group substituted with deuterium ; With 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 group, deuterium One of a substituted C ₆ -C ₂₀ aryl group, C ₈ -C ₂₀ arylalkyl group, C ₈ -C ₂₀ arylalkenyl group, C ₅ -C ₂₀ heterocyclic group, nitrile group and acetylene group A C ₅ to C ₆₀ heteroaryl group unsubstituted or substituted with the above substituents and having at least one of O, N, and S ; 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 C ₁ -C ₃₀ alkoxy group unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ -C ₆₀ aryl groups, C ₃ -C ₆₀ heteroaryl groups ; 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups Ring C ₆ ~ 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 Unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups Amino 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 Unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups aryl come Sy of the C ₅ ~ C _60; 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 ₈ to C ₂₀ arylalkyl group, C ₈ to C C ₁ ~ C ₅₀ Alkyl group unsubstituted or substituted with a substituent selected from the group consisting of ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group,
4) an integer of l = 1-4, an integer of m = 1-3, an integer of p = 1-3, an integer of q = 1-4, an integer of n = 0-2, and an integer of o = 1 or 2 ,
5) wherein the hetero compound comprises one or more heteroatoms selected from the group consisting of N, O, and S. The method according to claim 1,
The compound is an organic electric device, characterized in that the compound represented by any one of the following formulas (2) to (6):

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]
here,
R ₂ to R ₆ , L, Ar ₁ to Ar ₂ , n, o, p, q are as defined in claim 1. The method according to claim 1 or 2,
The L is selected from the group consisting of a phenyl group, a biphenyl group, 1- naphthal group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group, fluorenyl group, organic Electrical elements. The organic electroluminescence device according to claim 1 or 2, wherein the compound is a compound selected from the group consisting of:

The method according to claim 1 or 2,
The organic electroluminescent device, characterized in that to form the organic material layer by a solution process (soluble process). The method according to claim 1 or 2,
The organic layer is an organic electroluminescent device, characterized in that used as a light emitting layer, a hole injection layer, or a hole transport layer. The electronic device of claim 6, wherein the organic electric element is one of an organic electroluminescent element (OLED), an organic solar cell, an organic photoconductor (OPC), and an organic transistor (organic TFT). A compound represented by the following formula (1):

[Formula 1]
In Formula 1,
(1) R ₁ to R ₆ are the same as or different from each other, and a hydrogen atom ; Deuterium ; Tritium ; Halogen ; Amino group ; Nitrile group ; Nitro group ; Hydroxyl group ; 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, Substituted by 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, deuterium Or substituted with one or more substituents selected from the group consisting of a C ₆ to C ₂₀ aryl group, a C ₈ to C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₅ to C ₂₀ heterocyclic group, or Unsubstituted C ₆ ~ C ₆₀ aryl group ; Deuterium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl group, In the group consisting of C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group A C ₅ to C ₆₀ heteroaryl group which is unsubstituted or substituted with one or more substituents and has at least one of O, N, and S ; 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, C ₂ C ₁ -C ₃₀ alkoxy group unsubstituted or substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₃ -C ₆₀ heteroaryl group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted C ₆ ~ C ₃₀ aryloxy group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted amino group ; 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, C ₂ Substituted with one or more substituents selected from the group consisting of -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₃ -C ₆₀ heteroaryl group or Unsubstituted C ₅ -C ₆₀ arylthio group; Or 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 ₈ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ An arylalkenyl group, a C ₅ ~ C ₂₀ heterocyclic group, a nitrile group and an acetylene group substituted or unsubstituted C ₁ ~ C ₅₀ Alkyl group , wherein R ₁ ~ R ₂ is bonded to a group adjacent to each other To form a saturated or unsaturated aliphatic ring or heterocycle, and N of carbazole may combine with an adjacent group together with a substituent connected to it to form a ring,
2) L is a C ₆ ~ C ₆₀ of unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and amino group Arylene group ; C ₅ -C ₆₀ heteroarylene group unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group and amino group; And divalent or trivalent substituted or unsubstituted aliphatic hydrocarbons ,
3 ) Ar ₁ and Ar ₂ are the same as or different from each other, and each independently halogen ; Nitrile group ; Nitro group ; 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 -C20 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, deuterium substituted C Substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₂₀ aryl group, C ₈ to C ₂₀ aryl alkenyl group, silane group, boron group, germanium group, C ₅ ~ C ₂₀ heterocyclic group C ₆ ~ C ₆₀ aryl group ; C ₆ ~ C ₆₀ aryl group substituted with deuterium ; With 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 group, deuterium One of a substituted C ₆ -C ₂₀ aryl group, C ₈ -C ₂₀ arylalkyl group, C ₈ -C ₂₀ arylalkenyl group, C ₅ -C ₂₀ heterocyclic group, nitrile group and acetylene group A C ₅ to C ₆₀ heteroaryl group unsubstituted or substituted with the above substituents and having at least one of O, N, and S ; 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 C ₁ -C ₃₀ alkoxy group unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ -C ₆₀ aryl groups, C ₃ -C ₆₀ heteroaryl groups ; 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups Ring C ₆ ~ 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 Unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups Amino 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 Unsubstituted or substituted with one or more substituents selected from the group consisting of ₃₀ heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, C ₆ to C ₂₀ aryl groups substituted with deuterium, C ₃ to C ₆₀ heteroaryl groups aryl come Sy of the C ₅ ~ C _60; 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 ₈ to C ₂₀ arylalkyl group, C ₈ to C C ₁ ~ C ₅₀ Alkyl group unsubstituted or substituted with a substituent selected from the group consisting of ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group,
4) an integer of l = 1-4, an integer of m = 1-3, an integer of p = 1-3, an integer of q = 1-4, an integer of n = 0-2, and an integer of o = 1 or 2 ,
5) wherein the hetero compound comprises one or more heteroatoms selected from the group consisting of N, O, and S. The method according to claim 8,
A compound represented by any one of the following formulas (2) to (6):

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]
here,
R ₂ to R ₆ , L, Ar ₁ to Ar ₂ , n, o, p, q are as defined in claim 8. The method according to claim 8 or 9,
Wherein L is selected from the group consisting of phenyl group, biphenyl group, 1-naphthalyl group, 2-naphthyl group, pyridyl group, stilbene, anthracenyl group, phenanthrene group, pyrenyl group, fluorenyl group . The compound of claim 8 or 9, selected from the group consisting of:

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