KR102197609B1 - Organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including a novel compound having excellent hole transporting ability and luminous ability in one or more organic material layers.

Description

Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including a novel compound containing an amine group having excellent hole injection ability, hole transporting ability, and light emitting ability as a material of an organic material layer.

With the observation of Bernanose's organic thin-film emission in the 1950s as the starting point, research on an organic electroluminescent (EL) device (hereinafter simply referred to as'organic EL device') followed by blue electroluminescence using an anthracene single crystal in 1965 was continued. In 1987, by Tang, an organic EL device having a laminated structure divided into a hole layer and a functional layer of a light emitting layer was presented. Since then, in order to improve the efficiency and lifetime of the organic EL device, it has been developed in the form of introducing a characteristic organic material layer in the device, and it has also led to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. Materials used as the organic material layer may be classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like according to their functions.

The light-emitting material may be classified into blue, green, and red light-emitting materials according to the light emission color. In addition, it can be classified into yellow and orange light-emitting materials necessary to realize better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of a phosphorescent material can theoretically improve the luminous efficiency of up to four times compared to fluorescence, interest is focused on not only phosphorescent dopants but also phosphorescent host materials.

To date, the hole injection layer and the hole transport layer. As materials used as the hole blocking layer and the electron transport layer, NPB, BCP, Alq ₃ and the like represented by the following formula are widely known, and anthracene derivatives are reported as fluorescent dopant/host materials as light emitting materials. In particular, among light-emitting materials, phosphorescent materials that have great advantages in terms of efficiency improvement include metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) _2, etc., and these are blue and green. , Is used as a red dopant material. Until now, CBP has shown excellent properties as a phosphorescent host material.

However, conventional light-emitting materials are good in terms of light emission characteristics, but because of low glass transition temperature and low thermal stability, they are not at a satisfactory level in terms of lifespan in an organic EL device. Accordingly, there is a need for development of an organic electroluminescent device including a light emitting material having excellent performance.

On the other hand, in order to put the organic electroluminescent device into practical use and to improve its properties, not only the device is composed of an organic material layer having a multilayer structure as described above, but also the material of the device, particularly, a hole transport material, must have thermally and electrically stable properties. Because, when a voltage is applied, molecules with low thermal stability due to heat generated from the device have low crystal stability, resulting in a rearrangement phenomenon, and eventually local crystallization occurs, resulting in the presence of a heterogeneous part, which causes the electric field to concentrate on this part. This is because it causes deterioration and destruction of the device. Therefore, in consideration of the above points, the conventionally used hole transport material is m-MTDATA [4, 4′,4″-tris(N-3-methylphenyl-N-phenylamino)-triphenylamine, 2-TNATA [4, 4′,4″-tris(N-(naphthylene-2-yl)-N-phenylamino)-triphenylamine],TPD [N, N′-diphenyl-N, N′-di( 3-methylphenyl)-4, 4'-diaminobiphenyl] and NPB [N, N'-di(naphthalen-1-yl)-N, N'-diphenylbenzidine].

However, m-MTDATA and 2-TNATA had a problem in realizing full color because the glass transition temperature (Tg) was low at 78°C and 108°C, respectively, and many problems occurred in the process of mass-producing, and TPD and NPB were also problematic. Since the glass transition temperature (Tg) is as low as 60°C and 96°C, respectively, there is a fatal disadvantage of shortening the life of the device for the same reason. Accordingly, there is a need for development of an organic electroluminescent device capable of improving thermal stability and improving the luminous efficiency and power efficiency of the organic electroluminescent device by having excellent hole transport capability.

An object of the present invention is to provide a compound capable of being used as a material for a light-emitting layer, a material for a hole-transport layer, and a material for a hole injection layer because of excellent hole injection capability, hole transport capability, and light emission capability.

In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the above-described novel compound.

In order to achieve the above object, the present invention is a positive electrode; cathode; And one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers comprises a compound represented by the following formula (1). .

In Formula 1,

Y ₁ to Y ₄ are the same as or different from each other, and each independently N or CR ₃ , provided that at least one of Y ₁ and Y ₂ , Y ₂ and Y ₃ , and Y ₃ and Y ₄ is CR ₃ , To form a condensed ring represented by the following formula (2);

In Chemical Formula 2,

The dotted line is the site where condensation takes place;

Y ₅ to Y ₈ are the same as or different from each other, and each independently N or CR ₄ , provided that at least one of Y ₅ to Y ₈ is CR _4, wherein at least one of one or more R ₄ is represented by the following Formula 3 It is a displayed substituent;

In Chemical Formula 3,

L is a single bond, or is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms,

R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nuclear atom It is selected from the group consisting of a heterocycloalkyl group of 3 to 40, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, provided that L, R _a And R _b may be combined with an adjacent substituent to form a condensed ring;

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cyclo Alkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or It is selected from the group consisting of an unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryloxy group, and a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, or They form or form a condensed ring with an adjacent group,

R ₃ and R ₄ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cyclo Alkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or Unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₆₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~ C ₆₀ arylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, or they form a condensed ring with an adjacent group, or To form,

X ₁ and X ₂ are the same as or different from each other, and each independently O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ ) It is selected from, provided that at least one of X ₁ and X ₂ is N (Ar ₁ );

Ar ₁ to Ar ₅ are the same or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, the number of substituted or unsubstituted nuclear atoms 3 to 40 heterocycloalkyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkyl Oxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted C ₁ ~C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~C ₆₀ arylsilyl group, substituted or unsubstituted C ₁ ~ group of the C ₄₀ alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine It is selected from the group consisting of an oxide group or a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group;

In the above L, the arylene group and the heteroarylene group are each independently deuterium, halogen, cyano, a C ₁ ~ C ₄₀ alkyl group, a C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C _Consisting of an aryl group of ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ to C ₄₀ , an aryloxy group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ It may be substituted with one or more selected from the group. At this time, when a plurality of substituents are introduced, the plurality of substituents are the same or different from each other;

In the above R ₁ to R ₄ , R _a , R _b , Ar ₁ to Ar ₅ , the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, arylamine group are each independently Deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms Heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ selected from the aryl group consisting of an amine group in the C ₆₀ It may be substituted with one or more. At this time, when a plurality of substituents are introduced, the plurality of substituents are the same or different from each other.

According to a preferred embodiment of the present invention, one or more organic material layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, an electron blocking layer, and a light emitting layer.

Specifically, the organic electroluminescent device may include a light emission auxiliary layer formed of the compound represented by Chemical Formula 1 between the hole transport layer and the emission layer.

Since the organic electroluminescent device of the present invention contains the compound of Formula 1 having excellent heat resistance, hole injection ability, hole transporting ability, and luminous ability in at least one or more organic material layers, the light emitting performance, driving voltage, lifetime, efficiency, etc. The side surface can be greatly improved, and further, it can be effectively applied to a full color display panel.

Hereinafter, the present invention will be described.

The present invention is characterized in that a compound represented by Formula 1 is used as at least one component of one or more organic material layers interposed between an anode and a cathode of an organic electroluminescent device.

Here, the one or more organic material layers containing the compound may be selected from the group consisting of a hole injection layer, an electron blocking layer, and a light emitting layer, preferably a light emitting layer, more preferably between the hole transport layer and the light emitting layer, as a light emitting auxiliary layer. It is used.

In general, the light emitting auxiliary layer material may be defined as a material having a relatively good hole mobility and a triplet energy of 2.5 eV or more. Includes cores such as carbazole, phenyl, fluorene, and hetero-cyclic ring having a high T1 as intrinsic properties, and triphenyl amine as a substituent ), terphenyl (Terphenyl), biphenyl (Biphenyl) has a structural feature that is provided with an electron-rich moiety. In order to have such high hole mobility and triplet energy of 2.5 eV or more, the LUMO value must be increased at the same time, so it can also be used as an electron blocking layer.

In the present invention, the compound of Formula 1, which is used as a component of one or more organic layers, has an arylamine moiety directly bonded to the end of a moiety in which an indole-based moiety, etc. is condensed, or Or, it is bonded through a linking group (L) to form a basic skeleton, and has a structure in which various substituents are bonded to this basic skeleton.

The compound represented by Formula 1 can improve the phosphorescent properties of the device, and at the same time, improve the hole injection/transport ability, luminous efficiency, driving voltage, life characteristics, durability, etc., and also, depending on the type of the introduced substituent, Transportation capacity and the like can also be improved. Accordingly, the compound of Formula 1 is used as an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (phosphorescent host material), a hole transport layer material, an electron blocking layer material and a light emitting layer material, more preferably a hole transport layer material and a light emitting layer material. Can be used.

More specifically, the compound represented by Formula 1 includes a moiety in which an indole-based moiety and an indole-based moiety are condensed (see Formulas 4 to 9 below), and thus the existing wide singlet energy level and high triplet It can have an energy level. In addition, the arylamine moiety is directly introduced into the moiety in which the indole-based moieties are condensed or introduced through a linking group (L) (see Formulas 10 to 15 below), so that the energy level is effectively controlled while maintaining the triplet energy. , Hole blocking ability and hole injection/transport ability can be maximized. The compound of Formula 1 can be usefully applied as a material for a hole transport layer and a light emitting layer of an organic EL device.

In addition, the compound represented by Formula 1 has various substituents, in particular, aryl groups and/or heteroaryl groups are introduced to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, which results in higher thermal thermal properties than conventional light-emitting materials. It can have stability. Accordingly, the organic electroluminescent device including the compound represented by Chemical Formula 1 of the present invention can greatly improve durability and lifespan characteristics.

Furthermore, when the compound represented by Formula 1 is used as a hole transport layer of an organic electroluminescent device or a blue fluorescent, green, and/or red phosphorescent light emitting layer material, it can exhibit remarkably superior effects in terms of efficiency and lifespan compared to conventional NPB. . Accordingly, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic electroluminescent device, and further, improving the lifespan of the organic electroluminescent device can maximize the performance of the full-color organic light emitting panel.

More specifically, the compound according to the present invention is in the indole-based moiety of Formula 1 wherein at least one of Y ₁ and Y ₂ , Y ₂ and Y ₃ , and Y ₃ and Y ₄ is indole of Formula 2 It is bonded to the system moiety, and at the same time in Formula 2, at least one of Y ₅ to Y ₈ is directly bonded to the arylamine moiety represented by Formula 3 or has a structure connected through a linking group (L).

In the compound represented by Formula 1 of the present invention, the R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, A substituted or unsubstituted C ₃ ~C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₆ ~C ₆₀ aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 60 atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, and a substituted or unsubstituted C ₆ to C _It is selected from the group consisting of ₆₀ arylamine groups, or they form or form a condensed ring with an adjacent group.

More specifically, the R ₁ and R ₂ are preferably selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, Hydrogen, deuterium, and phenyl groups are more preferable.

In addition, Y ₁ to Y ₄ are each independently N or CR ₃ , and at this time, when two or more of Y ₁ to Y ₄ are CR ₃ , a plurality of R ₃ are the same or different from each other. However, at least one of Y ₁ and Y ₂ , Y ₂ and Y ₃ , and Y ₃ and Y ₄ is CR ₃ to form a condensed ring represented by the following formula (2).

For example, in Y ₁ and Y ₂ , Y ₂ and Y ₃ , and Y ₃ and Y ₄ , when both Y ₁ and Y ₂ are CR ₃ , and condensed with each other to form a condensed ring represented by Formula 2, the following formula A compound represented by 4 or Formula 9 may be formed.

In Formula 2, the dotted line indicates a site where condensation occurs with the compound of Formula 1.

In addition, the Y ₅ to Y ₈ are the same as or different from each other, and each independently N or CR _4, wherein when two or more of Y ₅ to Y ₈ are CR ₄ , a plurality of R ₄ are the same or different from each other. However, at least one of Y ₅ to Y ₈ is CR ₄ , wherein at least one of the one or more R ₄ is a substituent represented by Formula 3 above.

According to a preferred example of the present invention, all of Y ₁ to Y ₄ may be CR _3, and all of Y ₅ to Y ₈ may be CR ₄ .

At this time, a plurality of R ₃ and a plurality of R ₄ are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C _{A 3} to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted 5 to 60 nuclear atom Heteroaryl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₆₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted Or an unsubstituted C ₆ ~ C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group selected from the group consisting of, or these adjacent groups and Condensed rings may or may not be formed. However, at least one of the plurality of R ₄ is a substituent represented by Chemical Formula 3.

In Formula 3, L is a single bond, or is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, or They can form condensed rings with adjacent groups.

Wherein the L arylene group and heteroarylene group are each independently deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C _Consisting of an aryl group of ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ to C ₄₀ , an aryloxy group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ It may be substituted with one or more substituents selected from the group. In this case, when a plurality of substituents are introduced, the plurality of substituents may be the same or different from each other.

In the present invention, L is a single bond, or a phenylene group, a biphenylene group, a fluorenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, or It is preferably selected from the group consisting of a quinolinylene group and a carbazolylene group.

In addition, R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted It is selected from the group consisting of a heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, or It is possible to form a condensed ring with a group to be formed.

In the above R _a and R _b , the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ may be substituted with one or more substituents selected from the group consisting of arylphosphine oxide group and C ₆ ~ C ₆₀ arylamine group. In this case, when a plurality of substituents are introduced, the plurality of substituents They can be the same or different.

In the present invention, R _a and R _b are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, a pyridyl group, and a pyrimidine It is preferably selected from the group consisting of a pyrimidinyl group, a quinolyl group, and a carbazolyl group. More preferably, Formula 3 is selected from the group of substituents (U1 to U86) consisting of the following structures. However, it is not limited thereto.

In the compound according to the present invention, X ₁ and X ₂ are the same as or different from each other, and each independently O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ ) (Ar ₅ ) is selected from the group consisting of. For example, when N(Ar ₁ ) is plural, they are the same or different, and if C(Ar ₂ )(Ar ₃ ) is plural, they are the same or different, and Si(Ar ₄ )(Ar ₅ ) is plural In the case of, they may be the same or different from each other.

However, at least one of X ₁ and X ₂ is N (Ar ₁ ), and preferably both of X ₁ and X ₂ are N (Ar ₁ ).

In the compound according to the present invention, the R ₁ to R ₄ , and Ar ₁ to Ar ₅ may each independently be selected from the group consisting of hydrogen and the substituents S1 to S166 below, but are not limited thereto.

At this time, when at least one of Y ₅ to Y ₈ is CR ₄ , at least one of one or more R ₄ is a substituent represented by Formula 3 above.

The compound represented by Formula 1 according to the present invention may be further specified as a compound represented by any one of the following Formulas 4 to 9.

In Chemical Formulas 4 to 9,

X ₁ and X ₂ , Y ₁ to Y ₈ , R ₁ and R ₂ are each as defined in Formula 1.

More specifically, the compound represented by Formula 1 according to the present invention is preferably represented by any one of the following Formulas 10 to 15.

In Formulas 10 to 15,

R ₁ , R _2, Ar ₁ , R _a , R _b and L are each the same as defined in Formula 1, and in this case, when Ar ₁ is plural, they are the same or different from each other.

For a preferred example of the present invention, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C _It is selected from the group consisting of an aryl group of 60, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,

Ar ₁ is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,

L is a single bond, or a phenylene group, a biphenylene group, a fluorenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a quinolinylene group group), selected from the group consisting of carbazolylene group,

R _a and R _b are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group , It is preferably selected from the group consisting of a quinolyl group, and a carbazolyl group.

Specific examples of the compound represented by Formula 1 of the present invention include compounds represented by the following Formulas 1 to 489. However, it is not particularly limited thereto.

"Unsubstituted alkyl" as used in the present invention refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In addition, "unsubstituted cycloalkyl" in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

In addition, in the present invention, "unsubstituted heterocycloalkyl" refers to a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at this time, at least one of the rings Carbons, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.

Further, in the present invention, "unsubstituted aryl" refers to a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In this case, two or more rings may be simply attached to each other (pendant) or attached in a condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.

Further, in the present invention, "unsubstituted heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably Preferably, 1 to 3 carbons are substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, the heteroaryl may be attached in a form in which two or more rings are simply attached to each other (pendant) or condensed, and further includes a condensed form with an aryl group. Non-limiting examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl It is interpreted as including a ring, and also including 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

In addition, in the present invention, "unsubstituted alkyloxy" refers to a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, and is linear, branched, or cyclic ( It is interpreted as including a cyclic) structure. Examples of such alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In addition, in the present invention, "unsubstituted aryloxy" refers to a monovalent functional group represented by R'O-, wherein R'is an aryl having 6 to 60 carbon atoms. Non-limiting examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

In addition, in the present invention, "unsubstituted arylamine" refers to an amine substituted with an aryl having 6 to 60 carbon atoms.

In addition, in the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compound represented by Chemical Formula 1 according to the present invention may be synthesized according to a general synthesis method [ Chem. Rev. , 60 :313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) et al.]. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described later.

In the organic electroluminescent device according to the present invention, at least one of the one or more organic material layers interposed between the anode and the cathode contains the compound represented by Formula 1, and is preferably represented by any one of Formulas 4 to 9 And more preferably one or more compounds represented by any one of Formulas 10 to 15.

In this case, the compound represented by Formula 1 may be used alone or in combination of two or more.

The one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like, and the one or more organic material layers containing the compound of Formula 1 may be a hole transport layer, an electron blocking layer, or a light emitting layer. Preferably, it may be a light emitting layer or a hole transport layer more preferably. Most preferably, between the hole transport layer and the light-emitting layer, it includes a light-emitting auxiliary layer composed of a compound represented by Formula 1, wherein the compound may be a phosphorescent light-emitting auxiliary layer. In this case, due to the compound, luminous efficiency, luminance, power efficiency, thermal stability, and lifetime of the device may be improved.

When the compound represented by Chemical Formula 1 of the present invention is used as a green or red phosphorescent light emitting layer in implementing a phosphorescent device, the compound restricts injection of triplet excitons into the hole-related layer, and at the same time, By having a delta Est (< 0.5 eV) characteristic below a certain level, the triplet excitons are moved to the singlet level, which is transferred to the singlet level of the emission layer to participate in the generation of excitons, and as a result, the triplet excitons are brought to the triplet level of the emission layer. It is transferred and serves to increase the efficiency of the phosphorescent light emitting layer. In addition, preferably, it exhibits a high LUMO value and may also include a hole blocking function.

In addition, the compound represented by Formula 1 of the present invention is used to increase the efficiency of a fluorescent blue device. At this time, the compound has a higher than hole mobility of NPB (higher than hole mobility of NPB), and the triplet energy level is higher than that of the blue fluorescent light emitting layer, preventing the introduction of triplet excitons, and restricting it in the emission layer. The main role is to increase efficiency by converting triplet excitons into singlet excitons through TTF). In addition, preferably, the effect of improving the interface characteristics between the hole-related layer and the light emitting layer may be accompanied, and more preferably, a high LUMO value may be displayed, thereby including a hole blocking function.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, and a non-limiting example thereof may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. Optionally, an electron injection layer may be additionally stacked on the electron transport layer.

In addition, the organic electroluminescent device according to the present invention may have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, as well as a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention is in the art, except that at least one of the organic material layers (e.g., an emission layer, a hole transport layer and/or an electron transport layer) is formed to include the compound represented by Formula 1 It can be manufactured by forming other organic material layers and electrodes using known materials and methods.

The organic material layer including the compound represented by Formula 1 may be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.

As the substrate usable in the present invention, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, etc. may be used, but is not limited thereto.

In addition, as the anode material, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.

In addition, as the negative electrode material, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound IC-1

<Step 1> Synthesis of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

5-bromo-1H-indole (25 g, 0.128 mol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3) under nitrogen stream ,2-dioxaborolane) (48.58 g, 0.191 mol), Pd(dppf)Cl ₂ (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) were mixed, The mixture was stirred at 130° C. for 12 hours.

After the reaction was completed, extraction was performed with ethyl acetate, water was removed with MgSO ₄ , and purified by column chromatography [Hexane: ethyl acetate(EA) = 10:1(v/v)] to obtain 5-(4,4). ,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (22.32 g, yield 72%) was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 6.45 (d, 1H), 7.27 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.95 (s, 1H), 8.21 ( s, 1H)

<Step 2> Synthesis of 5-(5-bromo-2-nitrophenyl)-1H-indole

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (22 g, 90.49 mmol) synthesized in <Step 1> of Preparation Example 1 under a nitrogen stream Was mixed with 2,4-dibromo-1-nitrobenzene (21.18 g, 75.41 mmol), NaOH (9.05 g, 226.24 mmol) and THF/H ₂ O (400 ml/200 ml), and then Pd ( After adding PPh ₃ ) ₄ (4.36 g, 5 mol), the mixture was stirred at 80° C. for 12 hours.

After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added thereto, followed by filtration to obtain an organic layer. After removing the solvent from the obtained organic layer, it was purified by column chromatography [Hexane:EA = 3:1 (v/v)] and 5-(5-bromo-2-nitrophenyl)-1H-indole (9.6 g, yield 40%) ).

<Step 3> Synthesis of 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

5-(5-bromo-2-nitrophenyl)-1H-indole (14.64 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g) obtained in <Step 2> of Preparation Example 1 under a nitrogen stream , 4.62 mmol), K ₂ CO ₃ (6.38 g, 46.17 mmol), Na ₂ SO ₄ (6.56 g, 46.17 mmol), and nitrobenzene (200 ml) were mixed and then stirred at 190° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . After removing the solvent from the water-removed organic layer, 5-(5-bromo-2-nitrophenyl)-1-phenyl was purified by column chromatography [Hexane:methylene chloride(MC) = 3:1 (v/v)] -1H-indole (12.89 g, yield 71%) was obtained.

<Step 4> Synthesis of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole

5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole (6.25 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1 obtained in <Step 3> of Preparation Example 1 under a nitrogen stream After, 2-dichlorobenzene (50 ml) was mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, followed by extraction with dichloromethane to obtain an organic layer. Water was removed from the obtained organic layer using MgSO ₄ and then purified by column chromatography [Hexane:MC = 3:1 (v/v)] to obtain 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2]. -a]carbazole (3.04 g, yield 53%) was obtained.

<Step 5> Synthesis of Compound IC-1

7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (5g, 13.84 mmol), iodobenzene (4.24 g, 20.76 mmol) obtained in <Step 4> of Preparation Example 1 under a nitrogen stream Cu powder (0.09 g, 1.38 mmol), K ₂ CO ₃ (1.91 g, 13.84 mmol), Na ₂ SO ₄ (1.97 g, 13.84 mmol), and nitrobenzene (70ml) were mixed, and then stirred at 190 °C for 12 hours. I did.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography [Hexane:MC = 3:1 (v/v)] to obtain compound IC-1 (3.63 g, yield 60%).

[Preparation Example 2] Synthesis of Compound IC-2

<Step 1> Synthesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Except for using 4-bromo-1H-indole (25 g, 0.128 mol) instead of 5-bromo-1H-indole used in <Step 1> of Preparation Example 1, and <Step 1> of Preparation Example 1 In the same manner, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole was obtained.

<Step 2> Synthesis of 4-(5-bromo-2-nitrophenyl)-1H-indole

In <Step 1> of Preparation Example 2 instead of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole used in <Step 2> of Preparation Example 1 Except for using the synthesized 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (22 g, 90.49 mmol), of Preparation Example 1 Performed in the same manner as in <Step 2> to obtain 4-(2-nitrophenyl)-1H-indole.

<Step 3> Synthesis of 4-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

Instead of the 5-(5-bromo-2-nitrophenyl)-1H-indole used in <Step 3> of Preparation Example 1, 4-(2-nitrophenyl)-1H-indole synthesized in <Step 2> of Preparation Example 2 ( 14.64 g, 46.17 mmol) was carried out in the same manner as in <Step 3> of Preparation Example 1 to obtain 4-(2-nitrophenyl)-1-phenyl-1H-indole.

<Step 4> Synthesis of 9-bromo-3-phenyl-3,6-dihydropyrrolo[2,3-c]carbazole

Instead of 5-(2-nitrophenyl)-1-phenyl-1H-indole used in <Step 4> of Preparation Example 1, 4-(2-nitrophenyl)-1-phenyl- synthesized in <Step 3> of Preparation Example 2 Except for the use of 1H-indole (6.25 g, 15.91 mmol), 9-bromo-3-phenyl-3,6-dihydropyrrolo[2,3-c] was performed in the same manner as in <Step 4> of Preparation Example 1 ]carbazole was obtained.

<Step 5> Synthesis of Compound IC-2

9-bromo-3- synthesized in <Step 4> of Preparation Example 2 instead of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole used in <Step 5> of Preparation Example 1 Except for the use of phenyl-3,6-dihydropyrrolo[2,3-c]carbazole (5g, 13.84 mmol), the compound IC-2 was obtained in the same manner as in <Step 5> of Preparation Example 1.

[Preparation Example 3] Synthesis of Compound IC-3

<Step 1> Synthesis of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

In the same manner as in <Step 1> of Preparation Example 1, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole was obtained.

<Step 2> Synthesis of 5-(5-bromo-2-nitrophenyl)-1H-indole

5-(5-bromo-2-nitrophenyl)-1H-indole was obtained in the same manner as in <Step 2> of Preparation Example 1.

<Step 3> Synthesis of 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

In the same manner as in <Step 3> of Preparation Example 1, 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole was obtained.

<Step 4> Synthesis of 6-bromo-1-phenyl-1,9-dihydropyrrolo[2,3-b]carbazole

6-bromo-1-phenyl-1,9-dihydropyrrolo[2,3-b]carbazole was obtained in the same manner as in <Step 4> of Preparation Example 1.

<Step 5> Synthesis of Compound IC-3

Instead of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole used in <Step 5> of Preparation Example 1, 6-bromo-1-phenyl-1,9-dihydropyrrolo[2,3] Compound IC-3 was obtained in the same manner as in <Step 5> of Preparation Example 1, except that -b]carbazole (5g, 13.84 mmol) was used.

[Preparation Example 4] Synthesis of Compound IC-4

<Step 1> Synthesis of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Except for using 6-bromo-1H-indole (25 g, 0.128 mol) instead of 5-bromo-1H-indole used in <Step 1> of Preparation Example 1, and <Step 1> of Preparation Example 1 In the same manner, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole was obtained.

<Step 2> Synthesis of 6-(5-bromo-2-nitrophenyl)-1H-indole

Instead of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole used in <Step 2> of Preparation Example 1, 6-(4,4,5, Except for the use of 5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (22 g, 90.49 mmol), it was performed in the same manner as in <Step 2> of Preparation Example 1, and 6 -(5-bromo-2-nitrophenyl)-1H-indole was obtained.

<Step 3> Synthesis of 6-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

Instead of 5-(5-bromo-2-nitrophenyl)-1H-indole used in <Step 3> of Preparation Example 1, 6-(5-bromo-2-nitrophenyl)-1H-indole (14.64 g, 46.17 mmol) was used. Except for using, 6-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1.

<Step 4> Synthesis of 8-bromo-1-phenyl-1,5-dihydropyrrolo[3,2-b]carbazole

Instead of 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole used in <Step 4> of Preparation Example 1, 6-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole 8-bromo-1-phenyl-1,5-dihydropyrrolo[3,2-b]carbazole was performed in the same manner as in <Step 4> of Preparation Example 1, except that (6.25 g, 15.91 mmol) was used. Got it.

<Step 5> Synthesis of Compound IC-4

8-bromo-1- synthesized in <Step 4> of Preparation Example 4 instead of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole used in <Step 5> of Preparation Example 1 Except for the use of phenyl-1,5-dihydropyrrolo[3,2-b]carbazole (5g, 13.84 mmol), it was carried out in the same manner as in <Step 5> of Preparation Example 1 to obtain compound IC-4.

[Preparation Example 5] Synthesis of Compound IC-5

<Step 1> Synthesis of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

<Step 1> of Preparation Example 1, except that 6-bromo-1H-indole (25 g, 0.128 mol) was used instead of 5-bromo-1H-indole used in <Step 1> of Preparation Example 1. 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole was obtained in the same manner as described above.

<Step 2> Synthesis of 6-(5-bromo-2-nitrophenyl)-1H-indole

In <Step 1> of Preparation Example 5 instead of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole used in <Step 2> of Preparation Example 1 Except for using the synthesized 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (22 g, 90.49 mmol), Preparation Example 1 In the same manner as in <Step 2>, 6-(5-bromo-2-nitrophenyl)-1H-indole was obtained.

<Step 3> Synthesis of 6-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

Instead of 5-(5-bromo-2-nitrophenyl)-1H-indole used in <Step 3> of Preparation Example 1, 6-(5-bromo-2-nitrophenyl)- synthesized in <Step 2> of Preparation Example 5 Except for using 1H-indole (14.64 g, 46.17 mmol), 6-(5-bromo-2-nitrophenyl)-1-phenyl-1H- in the same manner as in <Step 3> of Preparation Example 1 above. got indole.

<Step 4> Synthesis of 7-bromo-1-phenyl-1,10-dihydropyrrolo[2,3-a]carbazole

6-(5-bromo-2 synthesized in <Step 3> of Preparation Example 5 instead of 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole used in <Step 4> of Preparation Example 1 -nitrophenyl)-1-phenyl-1H-indole (6.25 g, 15.91 mmol) was performed in the same manner as in <Step 4> of Preparation Example 1, and 7-bromo-1-phenyl-1, 10-dihydropyrrolo[2,3-a]carbazole was obtained.

<Step 5> Synthesis of Compound IC-5

Instead of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole used in <Step 5> of Preparation Example 1, 7-bromo-1- synthesized in <Step 4> of Preparation Example 5 Except for the use of phenyl-1,10-dihydropyrrolo[2,3-a]carbazole (5g, 13.84 mmol), it was carried out in the same manner as in <Step 5> of Preparation Example 1 to obtain compound IC-5.

[Preparation Example 6] Synthesis of Compound IC-6

<Step 1> Synthesis of 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

<Step 1> of Preparation Example 1, except that 7-bromo-1H-indole (25 g, 0.128 mol) was used instead of 5-bromo-1H-indole used in <Step 1> of Preparation Example 1. 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole was obtained in the same manner as described above.

<Step 2> Synthesis of 7-(5-bromo-2-nitrophenyl)-1H-indole

In <Step 1> of Preparation Example 6 instead of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole used in <Step 2> of Preparation Example 1 Preparation Example 1, except for using the synthesized 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (22 g, 90.49 mmol) In the same manner as in <Step 2>, 7-(5-bromo-2-nitrophenyl)-1H-indole was obtained.

<Step 3> Synthesis of 7-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

Instead of 5-(5-bromo-2-nitrophenyl)-1H-indole used in <Step 3> of Preparation Example 1, 7-(5-bromo-2-nitrophenyl)- synthesized in <Step 2> of Preparation Example 6 Except for the use of 1H-indole (14.64 g, 46.17 mmol), 7-(5-bromo-2-nitrophenyl)-1-phenyl-1H- was performed in the same manner as in <Step 3> of Preparation Example 1 above. got indole.

<Step 4> Synthesis of 9-bromo-1-phenyl-1,6-dihydropyrrolo[3,2-c]carbazole

Instead of 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole used in <Step 4> of Preparation Example 1, 7-(5-bromo-2 synthesized in <Step 4> of Preparation Example 6 Except for using -nitrophenyl)-1-phenyl-1H-indole (6.25 g, 15.91 mmol), 9-bromo-1-phenyl-1,6 was carried out in the same manner as in <Step 4> of Preparation Example 1 -dihydropyrrolo[3,2-c]carbazole was obtained.

<Step 5> Synthesis of compound IC-6

9-bromo-1- synthesized in <Step 4> of Preparation Example 6 instead of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole used in <Step 5> of Preparation Example 1 Compound IC-6 was synthesized in the same manner as in <Step 5> of Preparation Example 1, except that phenyl-1,6-dihydropyrrolo[3,2-c]carbazole (5g, 13.84 mmol) was used. .

[Preparation Example 7] Synthesis of IC-7

<Step 1> Synthesis of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole was obtained in the same manner as in <Step 1> of Preparation Example 1.

<Step 2> Synthesis of 5-(5-bromo-2-nitrophenyl)-1H-indole

5-(5-bromo-2-nitrophenyl)-1H-indole was obtained in the same manner as in <Step 2> of Preparation Example 1.

<Step 3> Synthesis of 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole

In the same manner as in <Step 3> of Preparation Example 1, 5-(5-bromo-2-nitrophenyl)-1-phenyl-1H-indole was obtained.

<Step 4> Synthesis of 7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole

7-bromo-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole was obtained in the same manner as in <Step 4> of Preparation Example 1.

<Step 5> Synthesis of Compound IC-7

Except for using 2-bromo-4,6-diphenyl-1,3,5-triazine (6.48 g, 20.76 mmol) instead of iodobenzene used in <Step 5> of Preparation Example 1, In the same manner as in <Step 5>, compound IC-7 was obtained.

[Synthesis Example 1] Synthesis of Compound Mat-1

Compound IC-1 (10g, 22.87mmol), N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (9.1g, 25.16mmol) synthesized in Preparation Example 1 under a nitrogen stream , sodium tert-butoxide (6.59g, 68.61mmol), tris(dibenzylideneacetone)dipalladium) (0.65, 0.6861mmol) and tri-tert-butyl phosphine (0.14g, 0.6861mmol) were mixed and refluxed overnight in 220 ml of toluene. Stirred.

After completion of the reaction, the reaction solution was filtered through celite, the solvent was removed, and then purified by column chromatography [Hexane:MC = 4:1 (v/v)] to obtain compound Mat-1 (9.85 g, yield 60%). ).

[Synthesis Example 2] Synthesis of Compound Mat-2

9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl) instead of N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine used in Synthesis Example 1 Except for using -9H-fluoren-2-amine (9.1g, 25.16mmol), it was carried out in the same manner as in Synthesis Example 1 to obtain compound Mat-2.

[Synthesis Example 3] Synthesis of Compound Mat-3

9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl) instead of N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine used in Synthesis Example 1 Compound Mat-3 was synthesized in the same manner as in Synthesis Example 1, except that -9H-fluoren-2-amine (8.1g, 25.16mmol) was used.

[Synthesis Example 4] Synthesis of Compound Mat-4

Compound IC-1 (10g, 22.87mmol), 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid (12.11g) synthesized in Preparation Example 1 under a nitrogen stream , 25.16mmol), tetrakis(triphenylphosphine)palladium(0) (0.79g, 0.6861mmol) and potassium carbonate (9.48g, 68.61mmol) were mixed overnight in 220 ml of 1,4-dioxane and 35 ml of H ₂ O. Stir at reflux.

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the separated organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water was removed, and then purified by column chromatography [Hexane:MC = 3:1 (v/v)] to obtain a compound Mat-4 (12.71 g, yield 70%).

Elemental Analysis: C, 89.25; H, 5.46; N, 5.29/ HRMS [M] ⁺ : 793

[Synthesis Example 5] Synthesis of Compound Mat-5

4-((9,9-diphenyl-9H-fluoren-2-yl) instead of 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2yl)amino)phenylboronic acid used in Synthesis Example 4 Compound Mat-5 was synthesized in the same manner as in Synthesis Example 4, except that (4-(pyridin-2-yl)phenyl)amino)phenylboronic acid (15.26g, 25.16mmol) was used.

Elemental Analysis: C, 88.86; H, 5.04; N, 6.10/ HRMS [M] ⁺ : 919

[Synthesis Example 6] Synthesis of Compound Mat-6

Instead of 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2yl)amino)phenylboronic acid used in Synthesis Example 4, N-(4-bromophenyl)-N-(9,9-dimethyl-9H Except for using -fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (13.1g, 25.16mmol), the compound Mat-6 was prepared in the same manner as in Synthesis Example 4 Synthesized.

Elemental Analysis: C, 89.28; H, 5.68; N, 5.04/ HRMS [M] ⁺ : 834

[Synthesis Example 7] Synthesis of Compound Mat-7

Compound Mat-7 was synthesized in the same manner as in Synthesis Example 1, except that the compound IC-2 (10g, 22.87mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 1. I did.

Elemental Analysis: C, 88.67; H, 5.48; N, 5.85/ HRMS [M] ⁺ : 717

[Synthesis Example 8] Synthesis of Compound Mat-8

Compound IC-2 (10g, 22.87mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (9.12g, 25.16mmol) instead of -2-amine, the synthesis Compound Mat-8 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 86.88; H, 5.33; N, 7.79/ HRMS [M] ⁺ : 718

[Synthesis Example 9] Synthesis of Compound Mat-9

Compound IC-2 (10g, 22.87mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (8.1g, 25.16mmol) instead of -2-amine, the above synthesis Compound Mat-9 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 88.60; H, 5.20; N, 6.20/ HRMS [M] ⁺ : 667

[Synthesis Example 10] Synthesis of Compound Mat-10

Compound Mat-10 was synthesized in the same manner as in Synthesis Example 4, except that the compound IC-2 (10 g, 22.87 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 4 I did.

Elemental Analysis: C, 89.25; H, 5.46; N, 5.29/ HRMS [M] ⁺ : 793

[Synthesis Example 11] Synthesis of Compound Mat-11

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-2 (10 g, 22.87 mmol) synthesized in Preparation Example 2 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2-((9,9-diphenyl-9H-fluoren-2-yl)(4-(pyridin-2-yl)phenyl)amino)phenylboronic acid(15.26) instead of 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) g, 25.16mmol) was synthesized in the same manner as in Synthesis Example 4, except that the compound Mat-11 was used.

Elemental Analysis: C, 88.86; H, 5.04; N, 6.10/ HRMS [M] ⁺ : 918

[Synthesis Example 12] Synthesis of Compound Mat-12

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-2 (10 g, 22.87 mmol) synthesized in Preparation Example 2 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) instead of N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren- Compound Mat-12 was synthesized in the same manner as in Synthesis Example 4, except that 2-amine (13.1g, 25.16mmol) was used.

Elemental Analysis: C, 89.28; H, 5.68; N, 5.04/ HRMS [M] ⁺ : 833

[Synthesis Example 13] Synthesis of Compound Mat-13

Compound Mat-13 was synthesized in the same manner as in Synthesis Example 1, except that the compound IC-3 (10g, 22.87mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 1. I did.

Elemental Analysis: C, 88.67; H, 5.48; N, 5.85/ HRMS [M] ⁺ : 717

[Synthesis Example 14] Synthesis of Compound Mat-14

Compound IC-3 (10g, 22.87mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (9.12g, 25.16mmol) instead of -2-amine, the synthesis Compound Mat-14 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 86.88; H, 5.33; N, 7.79/ HRMS [M] ⁺ : 718

[Synthesis Example 15] Synthesis of Compound Mat-15

Compound IC-3 (10g, 22.87mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (8.1g, 25.16mmol) instead of -2-amine, the above synthesis Compound Mat-15 was synthesized in the same manner as in Example 3.

Elemental Analysis: C, 88.60; H, 5.20; N, 6.20/ HRMS [M] ⁺ : 667

[Synthesis Example 16] Synthesis of Mat-16

Compound Mat-16 was synthesized in the same manner as in Synthesis Example 4, except that the compound IC-3 (10g, 22.87mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 1 I did.

Elemental Analysis: C, 89.25; H, 5.46; N, 5.29/ HRMS [M] ⁺ : 793

[Synthesis Example 17] Synthesis of Compound Mat-17

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-3 (10 g, 22.87 mmol) synthesized in Preparation Example 3 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2-((9,9-diphenyl-9H-fluoren-2-yl)(4-(pyridin-2-yl)phenyl)amino)phenylboronic acid(15.26) instead of 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) g, 25.16mmol) was synthesized in the same manner as in Synthesis Example 4, except that the compound Mat-17 was used.

Elemental Analysis: C, 88.86; H, 5.04; N, 6.10/ HRMS [M] ⁺ : 918

[Synthesis Example 18] Synthesis of Compound Mat-18

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-3 (10 g, 22.87 mmol) synthesized in Preparation Example 3 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) instead of N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren- Compound Mat-18 was synthesized in the same manner as in Synthesis Example 4, except that 2-amine (13.1g, 25.16mmol) was used.

Elemental Analysis: C, 89.28; H, 5.68; N, 5.04/ HRMS [M] ⁺ : 833

[Synthesis Example 19] Synthesis of Compound Mat-19

Compound Mat-19 was synthesized in the same manner as in Synthesis Example 1, except that the compound IC-4 (10g, 22.87mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 1 I did.

Elemental Analysis: C, 88.67; H, 5.48; N, 5.85/ HRMS [M] ⁺ : 717

[Synthesis Example 20] Synthesis of Compound Mat-20

Compound IC-4 (10g, 22.87mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (9.12g, 25.16mmol) instead of -2-amine, the synthesis Compound Mat-20 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 86.88; H, 5.33; N, 7.79/ HRMS [M] ⁺ : 718

[Synthesis Example 21] Synthesis of Compound Mat-21

Compound IC-4 (10g, 22.87mmol) synthesized in Preparation Example 4 was used instead of compound IC-1 used in synthesis 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (8.1g, 25.16mmol) instead of -2-amine, the above synthesis Compound Mat-21 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 88.60; H, 5.20; N, 6.20/ HRMS [M] ⁺ : 667

[Synthesis Example 22] Synthesis of Compound Mat-22

Compound Mat-22 was synthesized in the same manner as in Synthesis Example 4, except that the compound IC-4 (10g, 22.87mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 4 I did.

Elemental Analysis: C, 89.25; H, 5.46; N, 5.29/ HRMS [M] ⁺ : 793

[Synthesis Example 23] Synthesis of Compound Mat-23

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-4 (10 g, 22.87 mmol) synthesized in Preparation Example 4 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2-((9,9-diphenyl-9H-fluoren-2-yl)(4-(pyridin-2-yl)phenyl)amino)phenylboronic acid(15.26) instead of 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) g, 25.16mmol) was synthesized in the same manner as in Synthesis Example 4, except that the compound Mat-23 was used.

Elemental Analysis: C, 88.86; H, 5.04; N, 6.10/ HRMS [M] ⁺ : 918

[Synthesis Example 24] Synthesis of Compound Mat-24

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-4 (10 g, 22.87 mmol) synthesized in Preparation Example 4 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) instead of N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren- Compound Mat-24 was synthesized in the same manner as in Synthesis Example 4, except that 2-amine (13.1g, 25.16mmol) was used.

Elemental Analysis: C, 89.28; H, 5.68; N, 5.04/ HRMS [M] ⁺ : 833

[Synthesis Example 25] Synthesis of Compound Mat-25

Compound Mat-25 was synthesized in the same manner as in Synthesis Example 1, except that the compound IC-5 (10g, 22.87mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 1. I did.

Elemental Analysis: C, 88.67; H, 5.48; N, 5.85/ HRMS [M] ⁺ : 717

[Synthesis Example 26] Synthesis of Compound Mat-26

Compound IC-5 (10g, 22.87mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (9.12g, 25.16mmol) instead of -2-amine, the synthesis Compound Mat-26 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 86.88; H, 5.33; N, 7.79/ HRMS [M] ⁺ : 718

[Synthesis Example 27] Synthesis of Compound Mat-27

Compound IC-5 (10g, 22.87mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (8.1g, 25.16mmol) instead of -2-amine, the above synthesis Compound Mat-27 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 88.60; H, 5.20; N, 6.20/ HRMS [M] ⁺ : 667

[Synthesis Example 28] Synthesis of Compound Mat-28

Compound Mat-28 was synthesized in the same manner as in Synthesis Example 4, except that the compound IC-5 (10g, 22.87mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 4 I did.

Elemental Analysis: C, 89.25; H, 5.46; N, 5.29/ HRMS [M] ⁺ : 793

[Synthesis Example 29] Synthesis of Compound Mat-29

Instead of the compound IC-1 used in Synthesis Example 4, the compound IC-5 (10g, 22.87mmol) used in Preparation Example 5 was used, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren- 2-((9,9-diphenyl-9H-fluoren-2-yl)(4-(pyridin-2-yl)phenyl)amino)phenylboronic acid (15.26) instead of 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) g, 25.16mmol) was synthesized in the same manner as in Synthesis Example 4, except that the compound Mat-29 was used.

Elemental Analysis: C, 88.86; H, 5.04; N, 6.10/ HRMS [M] ⁺ : 918

[Synthesis Example 30] Synthesis of Compound Mat-30

Compound IC-5 (10g, 22.87mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 4, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-) 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) instead of N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren- Compound Mat-30 was synthesized in the same manner as in Synthesis Example 4, except that 2-amine (13.1g, 25.16 mmol) was used.

Elemental Analysis: C, 89.28; H, 5.68; N, 5.04/ HRMS [M] ⁺ : 833

[Synthesis Example 31] Synthesis of Compound Mat-31

Compound Mat-31 was synthesized in the same manner as in Synthesis Example 1, except that compound IC-6 (10g, 22.87mmol) synthesized in Preparation Example 6 was used instead of compound IC-1 used in Synthesis Example 1 I did.

Elemental Analysis: C, 88.67; H, 5.48; N, 5.85/ HRMS [M] ⁺ : 717

[Synthesis Example 32] Synthesis of Compound Mat-32

Compound IC-6 (10g, 22.87mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (9.12g, 25.16mmol) instead of -2-amine, the synthesis Compound Mat-32 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 86.88; H, 5.33; N, 7.79/ HRMS [M] ⁺ : 718

[Synthesis Example 33] Synthesis of Compound Mat-33

Compound IC-6 (10g, 22.87mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 1, and N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren Except for using 9,9-dimethyl-N-(4-(pyridin-2-yl)phenyl)-9H-fluoren-2-amine (8.1g, 25.16mmol) instead of -2-amine, the above synthesis Compound Mat-33 was synthesized in the same manner as in Example 1.

Elemental Analysis: C, 88.60; H, 5.20; N, 6.20/ HRMS [M] ⁺ : 667

[Synthesis Example 34] Synthesis of Compound Mat-34

Compound Mat-34 was synthesized in the same manner as in Synthesis Example 4, except that the compound IC-6 (10g, 22.87mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 4 I did.

Elemental Analysis: C, 89.25; H, 5.46; N, 5.29/ HRMS [M] ⁺ : 793

[Synthesis Example 35] Synthesis of Compound Mat-35

Compound IC-6 (10g, 22.87mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 4, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-) 2-((9,9-diphenyl-9H-fluoren-2-yl)(4-(pyridin-2-yl)phenyl)amino)phenylboronic acid(15.26) instead of 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) g, 25.16mmol) was synthesized in the same manner as in Synthesis Example 4, except that the compound Mat-35 was used.

Elemental Analysis: C, 88.86; H, 5.04; N, 6.10/ HRMS [M] ⁺ : 918

[Synthesis Example 36] Synthesis of Compound Mat-36

Compound IC-6 (10g, 22.87mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 4, and 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-) 2yl)amino)phenylboronic acid (12.11g, 25.16mmol) instead of N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren- Compound Mat-36 was synthesized in the same manner as in Synthesis Example 4, except that 2-amine (13.1g, 25.16mmol) was used.

Elemental Analysis: C, 89.28; H, 5.68; N, 5.04/ HRMS [M] ⁺ : 833

[Synthesis Example 37] Synthesis of Compound Mat-37

Compound Mat-37 was prepared in the same manner as in Synthesis Example 1, except that the compound IC-7 (13.55g, 22.87mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 used in Synthesis Example 1. Synthesized.

Elemental Analysis: C, 85.29; H, 5.08; N, 9.63/ HRMS [M] ⁺ : 872

[Synthesis Example 38] Synthesis of Compound Mat-38

Instead of N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine used in Synthesis Example 1, 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (7.18 g , 25.16mmol) was synthesized in the same manner as in Synthesis Example 1, except that the compound Mat-38 was used.

Elemental Analysis: C, 87.96; H, 5.50; N, 6.55/ HRMS [M] ⁺ : 641

[Synthesis Example 39] Synthesis of Compound Mat-39

Instead of N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine used in Synthesis Example 1, 10-(biphenyl-4-yl)-2-bromo-9,9-dimethyl- Compound Mat-39 was synthesized in the same manner as in Synthesis Example 1, except that 7-(pyridin-2-yl)-9,10-dihydroacridine (13.46g, 25.16mmol) was used.

Elemental Analysis: C, 87.63; H, 5.33; N, 7.05/ HRMS [M] ⁺ : 794

[Example 1] Fabrication of an organic EL device

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and cleaned the substrate for 5 minutes using UV. After that, the substrate was transferred to a vacuum lamination.

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm) / the compound Mat-1 (80 nm) synthesized in Synthesis Example 1 / DS-H522 + 5% DS-501 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) to prepare an organic EL device.

The DS-H522 and DS-501 used for device fabrication are products of Doosan Electronics BG, and the structures of m-MTDATA, TCTA, CBP, Ir(ppy) ₃ , and BCP are as follows.

[Examples 2 to 39] Fabrication of an organic EL device

The same as in Example 1, except that the compounds Mat-2 to Mat-39 each synthesized in Synthesis Examples 2 to 39 were used instead of the compound Mat-1 used as the hole transport layer material when forming the hole transport layer in Example 1 Then, an organic EL device was manufactured.

[Comparative Example 1] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 1, except that NPB was used as the hole transport layer material instead of the compound Mat-1 used as the hole transport layer material when forming the hole transport layer in Example 1. The structure of the used NPB is as follows.

[ Evaluation example One]

For the organic EL devices prepared in Examples 1 to 39 and Comparative Example 1, respectively, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below.

Sample Hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 1 Compound Mat-1 4.1 22.2 Example 2 Compound Mat-2 4.3 20.1 Example 3 Compound Mat-3 4.4 21.3 Example 4 Compound Mat-4 4.0 22.6 Example 5 Compound Mat-5 4.5 19.5 Example 6 Compound Mat-6 4.7 20.1 Example 7 Compound Mat-7 4.3 21.6 Example 8 Compound Mat-8 4.5 20.5 Example 9 Compound Mat-9 4.7 20.6 Example 10 Compound Mat-10 4.4 21.6 Example 11 Compound Mat-11 5.0 20.1 Example 12 Compound Mat-12 5.1 18.6 Example 13 Compound Mat-13 4.3 22.0 Example 14 Compound Mat-14 4.6 21.2 Example 15 Compound Mat-15 4.5 21.2 Example 16 Compound Mat-16 4.4 22.3 Example 17 Compound Mat-17 5.1 18.3 Example 18 Compound Mat-18 5.0 18.9 Example 19 Compound Mat-19 4.5 21.7 Example 20 Compound Mat-20 4.7 21.2 Example 21 Compound Mat-21 4.8 20.8 Example 22 Compound Mat-22 4.5 21.4 Example 23 Compound Mat-23 5.1 18.2 Example 24 Compound Mat-24 5.1 18.5 Example 25 Compound Mat-25 4.3 22.3 Example 26 Compound Mat-26 4.6 21.4 Example 27 Compound Mat-27 4.8 21.6 Example 28 Compound Mat-28 4.2 22.5 Example 29 Compound Mat-29 4.7 20.6 Example 30 Compound Mat-30 4.6 20.2 Example 31 Compound Mat-31 4.2 22.1 Example 32 Compound Mat-32 4.6 21.2 Example 33 Compound Mat-33 4.8 20.0 Example 34 Compound Mat-34 4.2 22.3 Example 35 Compound Mat-35 4.8 21.8 Example 36 Compound Mat-36 5.0 19.2 Example 37 Compound Mat-37 4.5 20.3 Example 38 Compound Mat-38 5.1 18.5 Example 39 Compound Mat-39 4.9 20.3 Comparative Example 1 NPB 5.2 18.1

As shown in Table 1, the organic EL devices of Examples 1 to 39 using the compounds according to the present invention (Mat 1 to Mat 39) as the hole transport layer were compared to the organic EL devices of Comparative Example 1 using the conventional NPB. It was found that the current efficiency and driving voltage exhibited better performance.

[ Example 40] Green Organic Electric field Manufacturing of light emitting devices

Compound 1 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV And transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm)/TCTA (80 nm)/Compound Mat-1 (40 nm)/CBP + 10% Ir(ppy)3 (300 nm)/BCP (10 nm)/ Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) were sequentially stacked to prepare an organic electroluminescent device.

The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP used are as follows.

[Examples 41 to 78] Preparation of green organic electroluminescent device

In Example 1, instead of Mat-1, an organic EL device was manufactured in the same manner as in Example 40, except that the compounds Mat-2 to Mat-39 synthesized in Synthesis Examples 2 to 39, respectively, were used.

[Comparative Example 2] Preparation of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound Mat-1 was not used in Example 1.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples 40 to 78 and Comparative Example 2, respectively, the driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. .

Sample Light-emitting auxiliary layer Driving voltage (V) Current efficiency (cd/A) Example 40 Compound Mat-1 6.70 41.9 Example 41 Compound Mat-2 6.85 42.1 Example 42 Compound Mat-3 6.80 42.1 Example 43 Compound Mat-4 6.80 42.1 Example 44 Compound Mat-5 6.85 42.1 Example 45 Compound Mat-6 6.90 42.1 Example 46 Compound Mat-7 6.95 42.1 Example 47 Compound Mat-8 6.80 42.1 Example 48 Compound Mat-9 6.90 42.1 Example 49 Compound Mat-10 6.80 41.9 Example 50 Compound Mat-11 6.70 42.1 Example 51 Compound Mat-12 6.65 42.1 Example 52 Compound Mat-13 6.70 42.1 Example 53 Compound Mat-14 6.90 42.1 Example 54 Compound Mat-15 6.80 42.1 Example 55 Compound Mat-16 6.70 42.1 Example 56 Compound Mat-17 6.70 42.1 Example 57 Compound Mat-18 6.65 42.1 Example 58 Compound Mat-19 6.70 41.9 Example 59 Compound Mat-20 6.65 42.1 Example 60 Compound Mat-21 6.60 42.1 Example 61 Compound Mat-22 6.60 42.1 Example 62 Compound Mat-23 6.70 42.1 Example 63 Compound Mat-24 6.90 42.1 Example 64 Compound Mat-25 6.80 42.1 Example 65 Compound Mat-26 6.80 42.1 Example 66 Compound Mat-27 6.85 42.1 Example 67 Compound Mat-28 6.85 41.9 Example 68 Compound Mat-29 6.65 42.1 Example 69 Compound Mat-30 6.60 42.1 Example 70 Compound Mat-31 6.70 42.1 Example 71 Compound Mat-32 6.85 42.1 Example 72 Compound Mat-33 6.70 42.1 Example 73 Compound Mat-34 6.80 42.1 Example 74 Compound Mat-35 6.75 42.1 Example 75 Compound Mat-36 6.80 42.1 Example 76 Compound Mat-37 6.80 42.1 Example 77 Compound Mat-38 6.85 42.1 Example 78 Compound Mat-39 6.90 42.1 Comparative Example 2 - 6.93 38.2

As shown in Table 2, the green organic electroluminescent devices manufactured in Examples 1 to 20, respectively, using the compound represented by Formula 1 according to the present invention as a light emitting material, were compared using only CBP as a material of the light emitting layer. Compared to the green organic electroluminescent device of Example 1, the driving voltage was similar, but it was found that the luminous efficiency was improved.

[ Example 79 ~ 117] red organic Electric field Manufacturing of light emitting devices

After the compound synthesized in Synthesis Example was subjected to high-purity sublimation purification by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

First, the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV and a vacuum evaporator. The substrate was transferred to the furnace.

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm)/TCTA (80 nm)/Mat-1 to Mat-39 each compound (40 nm)/CBP + 10% (piq)2Ir(acac) (300nm )/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) were sequentially stacked to prepare an organic electroluminescent device.

The structures of m-MTDATA, TCTA, (piq)2Ir(acac) and CBP used are as follows.

[Comparative Example 3] Fabrication of red organic electroluminescent device

A red organic electroluminescent device was manufactured in the same manner as in Example 79, except that Mat-1 was not used in Example 79.

[Evaluation Example 3]

For the organic electroluminescent devices prepared in Examples 79 to 117 and Comparative Example 3, respectively, driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below. .

Sample Light-emitting auxiliary layer Driving voltage (V) Current efficiency (cd/A) Example 79 Compound Mat-1 5.30 10.9 Example 80 Compound Mat-2 5.30 10.9 Example 81 Compound Mat-3 5.30 10.9 Example 82 Compound Mat-4 5.30 10.9 Example 83 Compound Mat-5 5.30 10.9 Example 84 Compound Mat-6 5.30 10.9 Example 85 Compound Mat-7 5.30 10.9 Example 86 Compound Mat-8 5.30 10.9 Example 87 Compound Mat-9 5.30 10.9 Example 88 Compound Mat-10 5.30 10.9 Example 89 Compound Mat-11 5.30 10.9 Example 90 Compound Mat-12 5.30 10.9 Example 91 Compound Mat-13 5.30 10.9 Example 92 Compound Mat-14 5.30 10.9 Example 93 Compound Mat-15 5.30 10.9 Example 94 Compound Mat-16 5.30 10.9 Example 95 Compound Mat-17 5.30 10.9 Example 96 Compound Mat-18 5.30 10.9 Example 97 Compound Mat-19 5.30 10.9 Example 98 Compound Mat-20 5.30 10.9 Example 99 Compound Mat-21 5.30 10.9 Example 100 Compound Mat-22 5.30 10.9 Example 101 Compound Mat-23 5.30 10.9 Example 102 Compound Mat-24 5.30 10.9 Example 103 Compound Mat-25 5.30 10.9 Example 104 Compound Mat-26 5.30 10.9 Example 105 Compound Mat-27 5.30 10.9 Example 106 Compound Mat-28 5.30 10.9 Example 107 Compound Mat-29 5.30 10.9 Example 108 Compound Mat-30 5.30 10.9 Example 109 Compound Mat-31 5.30 10.9 Example 110 Compound Mat-32 5.30 10.9 Example 111 Compound Mat-33 5.30 10.9 Example 112 Compound Mat-34 5.30 10.9 Example 113 Compound Mat-35 5.30 10.9 Example 114 Compound Mat-36 5.30 10.9 Example 115 Compound Mat-37 5.30 10.9 Example 116 Compound Mat-38 5.30 10.9 Example 117 Compound Mat-39 5.30 10.9 Comparative Example 3 - 5.25 8,2

As shown in Table 3, the red organic electroluminescent devices manufactured in Examples 79 to 117, respectively, using the compound represented by Formula 1 according to the present invention as a light emitting material, were compared using only CBP as a material of the light emitting layer. Compared to the red organic electroluminescent device of Example 3, the driving voltage was similar, but it was found that the luminous efficiency was improved.

[ Example 118 ~ 156] blue organic Electric field Manufacturing of light emitting devices

After the compound synthesized in Synthesis Example was subjected to high-purity sublimation purification by a conventionally known method, a red organic electroluminescent device was manufactured according to the following procedure.

First, the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV and a vacuum evaporator. The substrate was transferred to the furnace.

On the ITO transparent electrode prepared as described above, DS-205 (Doosan Corporation) (80 nm) / NPB (15 nm) / each of the compounds of Mat-1 to Mat-39 (15 nm) / ADN + 5% DS-405 ( Doosan Corporation) (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) were sequentially stacked to manufacture an organic electroluminescent device.

The structure of the ADN used is as follows.

[Comparative Example 4] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 118, except that Mat-1 was not used in Example 118.

[Evaluation Example 4]

For each of the blue organic electroluminescent devices manufactured in Examples 118 to 156 and Comparative Example 4, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 4 below.

Sample Light-emitting auxiliary layer Driving voltage (V) Current efficiency (cd/A) Example 118 Compound Mat-1 5.60 6.9 Example 119 Compound Mat-2 5.60 6.9 Example 120 Compound Mat-3 5.60 6.9 Example 121 Compound Mat-4 5.60 6.9 Example 122 Compound Mat-5 5.60 6.9 Example 123 Compound Mat-6 5.60 6.9 Example 124 Compound Mat-7 5.60 6.9 Example 125 Compound Mat-8 5.60 6.9 Example 126 Compound Mat-9 5.60 6.9 Example 127 Compound Mat-10 5.60 6.9 Example 128 Compound Mat-11 5.60 6.9 Example 129 Compound Mat-12 5.60 6.9 Example 130 Compound Mat-13 5.60 6.9 Example 131 Compound Mat-14 5.60 6.9 Example 132 Compound Mat-15 5.60 6.9 Example 133 Compound Mat-16 5.60 6.9 Example 134 Compound Mat-17 5.60 6.9 Example 135 Compound Mat-18 5.60 6.9 Example 136 Compound Mat-19 5.60 6.9 Example 137 Compound Mat-20 5.60 6.9 Example 138 Compound Mat-21 5.60 6.9 Example 139 Compound Mat-22 5.60 6.9 Example 140 Compound Mat-23 5.60 6.9 Example 141 Compound Mat-24 5.60 6.9 Example 142 Compound Mat-25 5.60 6.9 Example 143 Compound Mat-26 5.60 6.9 Example 144 Compound Mat-27 5.60 6.9 Example 145 Compound Mat-28 5.60 6.9 Example 146 Compound Mat-29 5.60 6.9 Example 147 Compound Mat-30 5.60 6.9 Example 148 Compound Mat-31 5.60 6.9 Example 149 Compound Mat-32 5.60 6.9 Example 150 Compound Mat-33 5.60 6.9 Example 151 Compound Mat-34 5.60 6.9 Example 152 Compound Mat-35 5.60 6.9 Example 153 Compound Mat-36 5.60 6.9 Example 154 Compound Mat-37 5.60 6.9 Example 155 Compound Mat-38 5.60 6.9 Example 156 Compound Mat-39 5.60 6.9 Comparative Example 4 - 5.6 4.8

As shown in Table 4, the blue organic electroluminescent devices manufactured in Examples 118 to 156, respectively, using the compound represented by Formula 1 according to the present invention as a light emitting material, include a conventional blue organic electroluminescent device (Comparative Example It can be seen that the driving voltage is similar to that of the organic electroluminescent device of 4), but the luminous efficiency is improved.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and this also belongs to the scope of the invention. It is natural.

Claims (8)

anode;
cathode; And
Including; one or more organic material layers interposed between the anode and the cathode, including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer,
The one or more organic material layers further include a light emission auxiliary layer disposed between the hole transport layer and the emission layer,
The light-emitting auxiliary layer is an organic electroluminescent device, characterized in that it comprises a compound represented by any one of the following formulas 10, 11, 13 and 14:
[Formula 10]

;
[Formula 11]

;
[Formula 13]

;
[Formula 14]

;
In Formulas 10-11 and 13-14,
L is a single bond, or is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms,
R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nuclear atom It is selected from the group consisting of a heterocycloalkyl group of 3 to 40, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, provided that L, R _a and R _b may be combined with an adjacent substituent to form a condensed ring;
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cyclo Alkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or It is selected from the group consisting of an unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryloxy group, and a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, or They form or form a condensed ring with an adjacent group,
A plurality of Ar ₁ are the same or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, the number of substituted or unsubstituted nuclear atoms 3 to 40 heterocycloalkyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkyl Oxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted C ₁ ~C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~C ₆₀ arylsilyl group, substituted or unsubstituted C ₁ ~ group of the C ₄₀ alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine It is selected from the group consisting of an oxide group or a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group;
In the above L, the arylene group and the heteroarylene group are each independently deuterium, halogen, cyano, a C ₁ ~ C ₄₀ alkyl group, a C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C _Consisting of an aryl group of ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ to C ₄₀ , an aryloxy group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ It may be substituted with one or more selected from the group,
In the above R ₁ to R ₂ , R _a , R _b , Ar ₁ , the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group and arylamine group are each independently deuterium, halogen , Cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl Group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ groups of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ from the aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ aryl group consisting of an amine group of the C ₆₀ of the It may be substituted with one or more selected substituents.
delete delete The method of claim 1,
The plurality of Ar ₁ is the same or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms Organic electroluminescent device, characterized in that the. The method of claim 1, wherein R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ Organic electroluminescent device, characterized in that selected from the group consisting of aryl groups of. The method of claim 1,
remind

An organic electroluminescent device, characterized in that the substituent represented by is selected from the group of substituents consisting of the following structures:

The method of claim 1,
An organic electroluminescent device in which the at least one organic material layer includes an electron blocking layer.
delete