KR102530095B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same, and more particularly, to a novel compound having excellent hole injecting and transporting ability, electron injecting and transporting ability, and light emitting ability, and by including the same in one or more organic material layers. , It relates to an organic electroluminescent device with improved characteristics such as high luminous efficiency, low driving voltage, and long lifespan.

Description

Organic light emitting compound and organic electroluminescent device using the same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel compound having excellent hole injecting and transporting ability, electron injecting and transporting ability, and light emitting ability, and including the same in at least one organic material layer. By doing so, it relates to an organic electroluminescent device with improved characteristics such as luminous efficiency, driving voltage, and lifetime.

Research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices'), starting with Bernanose's observation of organic thin film emission in the 1950s and leading to blue electroluminescence using anthracene single crystal in 1965, was conducted in 1987. (Tang) proposed an organic EL device with a laminated structure divided into a hole layer and a functional layer of a light emitting layer. Since then, in order to make a high-efficiency, long-life organic EL device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

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

Materials for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the light emitting color. In addition, yellow and orange light emitting materials are also used as light emitting materials for implementing 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 may be divided into a phosphorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to 4 times compared to fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Until now, NPB, BCP, Alq ₃ and the like represented by the following chemical formulas have been widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant/host materials for light emitting materials. . In particular, as a phosphorescent material that has a great advantage in terms of efficiency improvement among light emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ are used as blue, green, and red dopant materials. It is being used. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional materials are advantageous in terms of light emitting properties, but have low glass transition temperatures and very poor thermal stability, so they are not satisfactory in terms of lifetime in organic EL devices.

Japanese Unexamined Patent Publication No. 2001-160489

In order to solve the above problems, an object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device and has excellent hole injection and transport capabilities, electron injection and transport capabilities, and luminescent performance. .

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

In order to achieve the above object, the present invention provides a compound represented by Formula 1 below.

In Formula 1,

X ₁ and X ₂ are the same as or different from each other, and are each independently N(Ar ₁ ) or C(Ar ₂ )(Ar ₃ ), wherein at least one of X ₁ and X ₂ is N(Ar ₁ );

Ar ₁ to Ar ₃ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or is combined with an adjacent group to form a condensed ring. can;

Y ₁ to Y ₁₂ are the same as or different from each other, and are each independently N or C;

a to c are each independently an integer of 0 to 4, and when a to c are each independently an integer of 1 to 3, R ₁ to R ₃ are the same as or different from each other, and each independently deuterium, a halogen, a cyano group, Nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, 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 aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group And C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, or may be combined with adjacent groups to form a condensed ring, wherein when R ₁ to R ₃ are plural, they are the same or different;

However, at least one of R ₁ to R ₃ is selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms;

An _{alkyl group} , an _alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, and an arylsilyl group of Ar 1 to Ar ₃ , R ₁ to R 3 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, 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 aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ arylamine group to be substituted with one or more substituents selected from the group consisting of In this case, when the substituents are plural, they may be the same as or different from each other.

In addition, the present invention includes an anode, a 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 includes organic electroluminescence containing the compound represented by Formula 1 above. provide a small

Here, the one or more organic material layers may include a hole injection layer, a hole transport layer, a light emitting layer, a lifespan improvement layer, an electron transport layer, and an electron injection layer. It may be a transport layer, an electron transport layer, a light emitting layer, or a lifespan improvement layer.

Since the compound represented by Chemical Formula 1 according to the present invention has excellent thermal stability and emission characteristics, it can be used as a material for an organic layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 of the present invention is applied to an organic electroluminescent device, an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long lifespan can be manufactured, and furthermore, performance and lifespan are improved. Improved full color display panels can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New compounds

The novel compound according to the present invention is a 5-membered heterocyclic moiety in which benzene is condensed with dibenzoazepine (5H-dibenzo[b,f]azepine) or dibenzocycloheptene (5H-dibenzo[a,d]cycloheptene). moiety) is condensed to form a basic skeleton, and is characterized in that it is represented by Formula 1 above.

More specifically, the compound represented by Formula 1 may be obtained by condensation of an indole moiety to dibenzoazepine (5H-dibenzo[b,f]azepine) or dibenzocycloheptene (5Hdibenzo[a,d]cycloheptene). ) is condensed with an indole moiety, and each N is substituted with an aryl group (specifically, a phenyl group), a heteroaryl group, or an arylamine group as a basic skeleton. .

Since the compound represented by Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices [eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], it has excellent thermal stability as well as a high glass transition temperature. In addition, it has excellent hole injection ability, hole transport ability, and luminous ability. Therefore, when the compound of Chemical Formula 1 is applied to the organic material layer of the organic electroluminescent device, the driving voltage, efficiency, and lifetime of the device can be improved.

More specifically, the compound represented by Formula 1 according to the present invention may have excellent hole transport and/or electron transport capabilities as various substituents are introduced to the non-N benzene ring of the basic skeleton. Accordingly, the compound of Chemical Formula 1 may be used as an organic material layer (specifically, a hole transport layer) of an organic EL device having hole mobility or electron mobility of a certain level or higher.

In addition, the compound of Formula 1 according to the present invention has a high electron absorption such as an aryl group, a nitrogen-containing heteroaryl group (eg, a pyridine group, a pyrimidine group, a triazine group, etc.) or an arylamine group on the benzene ring of the basic skeleton. When electron withdrawing (EWG) is combined, since the entire molecule has a bipolar characteristic, the bonding force between holes and electrons can be increased. Accordingly, the compound of Chemical Formula 1 can exhibit excellent light emitting properties, and thus can be usefully applied as a material for a blue, green or red phosphorescent light emitting layer of an organic electroluminescent device.

On the other hand, in the compound of Formula 1 according to the present invention, when carbon and nitrogen are directly bonded (C-N bond), the bond structure is distorted or the conjugate may be broken compared to when carbon and carbon are directly bonded (C-C bond). Therefore, the compound of Formula 1 can expand the conjugation system by arranging the carbon of the basic skeleton and the carbon of the electron withdrawing group (EWG) to be bonded, and thus, a light emitting material with a long wavelength or an auxiliary light emitting material having a long conjugated system. can be applied as

In general, in a phosphorescent layer of an organic electroluminescent device, a triplet energy gap of a host material should be higher than a triplet energy gap of a dopant material. That is, in order to effectively provide phosphorescent light emission from the dopant, the lowest excited state of the host must have higher energy than the lowest emission state of the dopant. In the compound represented by Formula 1, a specific substituent (eg, an aryl group, a heteroaryl group, an arylamine group) is introduced into a condensed indole moiety having a wide singlet energy level and a high triplet energy level, thereby increasing the energy level. It can be adjusted higher than the dopant and can be used as a host material.

As such, the compound represented by Chemical Formula 1 can improve not only the phosphorescent properties of the organic electroluminescent device but also the hole injection/transport capability, luminous efficiency, driving voltage, and lifetime characteristics, etc., depending on the type of substituent introduced. Accordingly, the electron transport ability and the like can be improved. Therefore, the compound of Formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and/or red phosphorescent host material), a hole and electron transport layer material, and a hole and electron injection layer material. , a lifespan improving layer material, more preferably a phosphorescent light emitting layer material, a hole and electron transport layer material, and a lifespan improving layer material.

In addition, the compound of Formula 1 is introduced with various substituents, in particular, an aryl group and/or a heteroaryl group to the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, thereby improving conventional light emitting materials ( For example, CBP) may have higher thermal stability. In addition, the compound represented by Chemical Formula 1 is effective in inhibiting crystallization of the organic material layer. Therefore, the performance and lifetime characteristics of the organic EL device including the compound of Formula 1 according to the present invention can be greatly improved. As a result, the organic light emitting device having improved performance and lifespan characteristics can maximize the performance of a full-color organic light emitting panel.

That is, when the compound of Formula 1 according to the present invention is used as a hole and electron injection/transport layer material or a blue, green and/or red phosphorescent host material of an organic electroluminescent device, a conventional organic material layer material (eg, CBP) In comparison, the efficiency and lifetime of the organic EL device can be greatly improved. In addition, the lifespan of the organic light emitting device can be improved to maximize the performance of the full color organic light emitting panel.

A novel compound according to the present invention is a compound represented by Formula 1 above.

More specifically, in the compound represented by Formula 1, X ₁ and X ₂ are the same as or different from each other, and each independently represents N(Ar ₁ ) or C(Ar ₂ )(Ar ₃ ). At this time, at least one of X ₁ and X ₂ is N(Ar ₁ ).

Ar ₁ to Ar ₃ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or is combined with an adjacent group to form a condensed ring. can Preferably, Ar ₁ to Ar ₃ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, or a heteroaryl having 5 to 60 nuclear atoms. It is selected from the group consisting of a group and a C ₆ ~ C ₆₀ arylamine group, or may be bonded to an adjacent group to form a condensed ring.

Y ₁ to Y ₁₂ are the same as or different from each other, and are each independently N or C. Preferably, all of Y ₁ to Y ₁₂ are C.

a to c are each independently an integer of 0 to 4; At this time, when a to c are each independently 0, it means that hydrogen is not substituted with each of the substituents R ₁ to R ₃ . In addition, when a to c are each independently an integer of 1 to 4, R ₁ to R ₃ are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 nuclear atoms to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ A group consisting of a C ₄₀ alkyl boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group It is selected from, or may be bonded to an adjacent group to form a condensed ring, wherein, when R ₁ to R ₃ are each plural, they are the same or different. Preferably, R ₁ to R ₃ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, or a heteroaryl having 5 to 60 nuclear atoms. It is selected from the group consisting of a group and a C ₆ ~ C ₆₀ arylamine group, or may be bonded to an adjacent group to form a condensed ring. However, at least one of R ₁ to R ₃ is selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

In this case, an _{alkyl group} , an alkenyl group, an alkynyl group, _a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, or an aryl of Ar 1 to Ar ₃ , R ₁ to R 3 A silyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, At least one substituent selected from the group consisting of C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ arylamine group In this case, when the substituents are plural, they may be the same as or different from each other.

The compound represented by Formula 1 may be embodied by Formula 2 or 3 below.

In Formulas 2 and 3,

Ar ₁ to Ar ₃ , Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are each as defined in Formula 1 above.

More specifically, the compound represented by Formula 2 may be embodied in any one of Formulas 4 to 7 below.

In Formulas 4 to 7,

Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are each as defined in Formula 1 above.

d and e are each independently an integer of 0 to 5, and f is an integer of 0 to 4. At this time, when d to f are each independently 0, it means that hydrogen is not substituted with each of the substituents R ₄ to R ₆ . In addition, when d and e are each independently an integer of 1 to 5, and f is an integer of 1 to 4, R ₄ to R ₆ are the same as or different from each other, and each independently deuterium, a C ₁ to C ₄₀ alkyl group, It is selected from the group consisting of a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring, wherein R When ₄ to R ₆ are each plural, they are the same or different.

In addition, the compound represented by Formula 3 may be embodied by any one of Formulas 8 to 11 below.

In Formulas 8 to 11,

Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are each as defined in Formula 1 above.

f is an integer from 0 to 4; At this time, when f is 0, it means that hydrogen is not substituted with the substituent R ₆ . In addition, when f is an integer of 1 to 4, R ₆ is each independently deuterium, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ It is selected from the group consisting of C ₆₀ arylamine groups, or may be combined with an adjacent group to form a condensed ring, wherein when R ₆ is plural, they are the same or different.

In the compound represented by Formula 1, at least one of Ar ₁ to Ar ₃ and R ₁ to R ₃ may be a substituent represented by Formula 12 below.

In Formula 12,

* means a part bonded to Formula 1 above.

L ₁ is a single bond, or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms.

Z ₁ to Z ₅ are the same as or different from each other, and are each independently N or C(R ₇ ), provided that at least one of Z ₁ to Z ₅ is N, wherein, when R ₇ is plural, they are the same as or It is different.

R ₇ is hydrogen, deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ It is selected from the group consisting of ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring.

At this time, the arylene group and heteroarylene group of L ₁ , an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group of R ₇ , Arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl having 5 to 60 nuclear atoms group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron At least one selected from the group consisting of a C ₆ ~ C ₆₀ arylboron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group It may be substituted with a substituent, and in this case, when the substituent is plural, they may be the same as or different from each other.

The substituent represented by Chemical Formula 12 may be more specifically exemplified by any one of the substituents represented by Chemical Formulas A1 to A15. However, it is not particularly limited thereto.

In Chemical Formulas A1 to A15, L ₁ and R ₇ are each as defined in Chemical Formula 12 above.

n is an integer from 0 to 4; At this time, when n is 0, it means that hydrogen is not substituted with the substituent R ₈ . In addition, when n is an integer of 1 to 4, R ₈ is each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, It is selected from the group consisting of a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring, At this time, when R ₈ is plural, they are the same as or different from each other.

In this case, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, and an arylboron of the R ₈ Group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group , C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group , C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group , C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ may be substituted with one or more substituents selected from the group consisting of arylamine group, wherein the substituent is In case of plural, they may be the same as or different from each other.

As such, the compounds represented by Formula 1 according to the present invention are compounds A-1 to A-10, B-1 to B-10, C-1 to C-10, D-1 to D-10, Any one of E-1 to E-10 and F-1 to F-10 may be more specific. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyl include, but are not limited to, ethynyl and 2-propynyl.

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; and 2-furanyl; N-imidazolyl; 2-isoxazolyl; 2-pyridinyl; 2-pyrimidinyl and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. can include Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms.

In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are N, O, S or a heteroatom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "alkyl boron" means boron substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron" means boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with an aryl having 6 to 60 carbon atoms.

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 of the present invention can be variously synthesized by referring to the synthesis process in the following examples.

2. organic electric field light emitting element

The present invention provides an organic electroluminescent device including the compound represented by Formula 1 above.

More specifically, the organic electroluminescent device according to the present invention includes an anode, a 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. includes the compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a lifespan improvement layer, an electron transport layer, and an electron injection layer, and at least one organic material layer among them is a compound represented by Formula 1 above. can include Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer, or a lifespan improvement layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material (preferably, a phosphorescent host material), wherein the compound of Formula 1 may be included as the host material. In addition, the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but a non-limiting example 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, an electron injection layer, and a cathode are sequentially stacked. . In this case, a light emitting auxiliary layer may be interposed between the hole transport layer and the light emitting layer, and a lifespan improvement layer may be interposed between the light emitting layer and the electron transport layer. In addition, an electron injection layer may be additionally stacked on the electron transport layer. At least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the lifespan improvement layer, the electron transport layer, and the electron injection layer may include the compound represented by Formula 1, and preferably the hole transport layer, the electron transport layer, At least one of the light emitting layer and the lifespan improvement layer may include the compound represented by Formula 1 above. Here, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

On the other hand, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode with materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Formula 1. there is.

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

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but may be a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet.

In addition, as an anode material, metals such as vanadium, chromium, copper, zinc, 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 SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, as the negative electrode material, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; and multi-layered materials such as LiF/Al or LiO2/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 to illustrate the present invention, and the present invention is not limited by the following examples.

[ preparation example One] EIAz - 1 of synthesis

<Step 1> 5-phenyl-5H- dibenzo[b,f]azepine synthesis of

5H-dibenzo[b,f]azepine (100 g, 517.5 mmol), iodobenzene (126.7 g, 621.0 mmol), Cu (16.4 g, 258.7 mmol), K ₂ CO ₃ (143.0 g, 1,035.0 mmol) and Nitrobenzene (1000 ml) was mixed and stirred at 210 °C for 12 hours.

After the reaction was completed, the mixture was extracted with ethyl acetate, concentrated, and recrystallized with ethanol to obtain 5-phenyl-5H-dibenzo[b,f]azepine (100.4 g, yield 72%).

¹ H-NMR: δ 6.63-6.81 (m, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.20 (d, 2H), 7.26-7.45 (m, 8H)

<Step 2> 6-phenyl-6,10b- dihydro - 1aH - dibenzo[b,f]oxyreno [2,3-d] azepine synthesis of

5-phenyl-5H-dibenzo[b,f]azepine (100.4 g, 372.6 mmol), meta- chloroperoxybenzoic acid (mCPBA) (77.2 g, 447.1 mmol), silica (200.7 g), NaOCl under a nitrogen stream (200.7 g) and acetonitrile (ACN) (1000 ml) were mixed and stirred at 80°C for 2 hours.

After the reaction was completed, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was recrystallized with ethanol to obtain 6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine (84.0 g, yield 79%).

^1H -NMR: δ 4.31 (s, 2H), 6.63-6.81 (m, 3H), 7.24-7.53 (m, 10H)

<Step 3> 5-phenyl-5H- dibenzo[b,f]azepin -10(11H)- of one synthesis

6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine (84.0 g, 294.3 mmol), lithium iodide(LiI) (47.3 g, 353.2 mmol) under nitrogen stream and chloroform (CHL) (840 ml) were mixed and stirred at 60°C for 1 hour.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and recrystallized from ethanol to obtain 5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one (68.0 g, yield 81%) got

^1H -NMR: δ 3.42 (d, 1H), 4.21 (d, 1H), 6.62-6.74 (m, 3H), 7.25-7.40 (m, 7H), 7.51-7.59 (m, 2H), 8.10 (d , 1H)

<Step 4> 5-phenyl-10,11-(5- chloro -1H- indole )-5H- dibenzo[b,f]azepin synthesis of

5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one (68.0 g, 238.4 mmol) and (4-chlorophenyl)hydrazine under a nitrogen stream (37.4 g, 262.3 mmol) and acetic acid (700 ml) were added, followed by stirring at 120°C for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 3:1 (v/v)) to obtain 5-phenyl-10,11-(5-chloro-1H-indole)-5H-dibenzo[b ,f]azepin (66.5 g, yield 71%) was obtained.

^1H -NMR: δ 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 6.98 (d, 1H), 7.16-7.20 (m, 4H), 7.38 (d, 1H), 7.54 (d , 1H), 7.68 (s, 1H), 8.83 (d, 1H), 11.36 (b, 1H)

<Step 5> 5-phenyl-10,11-(5- chloro -1-phenyl-1H- indole Synthesis of )-5H-dibenzo[b,f]azepin

5-phenyl-10,11-(5-chloro-1H-indole)-5H-dibenzo[b,f]azepin (66.5 g, 169.3 mmol), iodobenzene (41.4 g, 203.1 mmol), Cu (5.4 g, 84.6 mmol), K ₂ CO ₃ (46.8 g, 338.6 mmol) and nitrobenzene (665 ml) were mixed and stirred at 210° C. for 12 hours.

After the reaction was completed, the mixture was extracted with dichloromethane, and MgSO ₄ was added thereto and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 5:1 (v/v)) to obtain 5-phenyl-10,11-(5-chloro-1-phenyl-1H-indole)-5H -dibenzo[b,f]azepin (58.0 g, yield 73%) was obtained.

¹ H-NMR: δ 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 7.16-7.20 (m, 5H), 7.45-7.69 (m, 8H), 8.83 (d, 1H)

<Step 6> EIAz - 1 of synthesis

5-phenyl-10,11-(5-chloro-1-phenyl-1H-indole)-5H-dibenzo[b,f]azepin (57.8 g, 123.6 mmol), 4,4,4',4 under nitrogen flow ',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (34.5 g, 135.9 mmol), Pd(dppf)Cl ₂ (10.8 g, 12.4 mmol) , KOAc (34.9 g, 370.7 mmol) and 1,4-Dioxane (600 ml) were mixed and 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 purification was performed by column chromatography (Hexane:EA = 4:1 (v/v)) to obtain EIAz-1 (56.1 g, yield 81%). got it

^1H -NMR: δ 1.24 (s, 12H), 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 7.16-7.20 (m, 4H), 7.45-7.60 (m, 8H), 7.71 (d, 1h), 8.83 (d, 1H)

[ preparation example 2] EIAz - 2 of synthesis

<Step 1> 1-(4- chlorophenyl )-1H- indole synthesis of

1H-indole (100 g, 854.0 mmol), 1-chloro-4-iodobenzene (244.3 g, 1024.8 mmol), Cu (27.2 g, 427.0 mmol), K ₂ CO ₃ (236.1 g, 1.70 mol) and nitrobenzene under a nitrogen stream. (3000 ml) and stirred at 210° C. for 12 hours.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and purified by column chromatography (Hexane:EA = 8:1 (v/v)) to obtain 1-(4-chlorophenyl)-1H-indole ( 163.3 g, yield 84%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 6.87 (dd, 1H), 7.33-7.37 (m, 3H), 7.49 (d, 2H), 7.60 (d, 1H), 7.93-7.94 (m, 2H) )

<Step 2> 2- chloro -5H- dibenzo[b,f]azepine synthesis of

1-(4-chlorophenyl)-1H-indole (163.3g, 717.4 mmol) and polyphosphoric acid (PPA) (817 g) were mixed under a nitrogen stream and stirred at 100°C for 12 hours.

After the reaction was completed, the mixture was extracted from water and filtered to obtain 2-chloro-5H-dibenzo[b,f]azepine (49 g, yield 30%).

^1H -NMR: δ 6.57 (d, 1H), 6.81 (dd, 1H), 6.99-7.09 (m, 4H), 7.17 (s, 1H), 7.25 (d, 1H), 8.21 (d, 1H), 8.42 (b, 1H)

<Step 3> 2- chloro -5-phenyl-5H- dibenzo[b,f]azepine synthesis of

2-chloro-5H-dibenzo[b,f]azepine (49 g, 215.2 mmol), iodobenzene (52.7 g, 258.1 mmol), Cu (6.8 g, 107.6 mmol), K ₂ CO ₃ (59.5 g, 430 mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210 °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:EA = 7:1 (v/v)) to obtain 2-chloro-5-phenyl-5H-dibenzo[ b,f]azepine (52.3 g, yield 80%) was obtained.

¹ H-NMR: δ 6.57-6.63 (m, 4H), 6.80-6.81 (m, 2H), 6.99-7.09 (m, 4H), 7.17-7.25 (m, 4H)

<Step 4> 3- chloro -6-phenyl-6,10b- dihydro - 1aH - dibenzo[b,f]oxyreno Synthesis of [2,3-d]azepine

2-chloro-5-phenyl-5H-dibenzo[b,f]azepine (52.3 g, 172.1 mmol), meta- chloroperoxybenzoic acid (35.6 g, 206.5 mmol), silica (104.6 g), NaOCl under a nitrogen stream (104.6 g) and acetonitrile (550 ml) were mixed and stirred at 80°C for 2 hours.

After the reaction was completed, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was recrystallized with ethanol to obtain 3-chloro-6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine (45.1 g, yield 82%) got

¹ H-NMR: δ 4.20 (s, 2H), 6.63-6.56 (m, 4H), 6.74-6.81 (m, 2H), 7.11-7.20 (m, 5H), 7.31 (s, 1H)

<Step 5> 2- chloro -5-phenyl-5H- dibenzo[b,f]azepin -10(11H)- of one synthesis

3-chloro-6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine (45.1 g, 141.1 mmol), lithium iodide (22.7 g, 169.3 mmol) under nitrogen stream ) and chloroform (500 ml) were mixed and stirred at 60° C. for 1 hour.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and recrystallized from ethanol to obtain 2-chloro-5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one (38.4 g, Yield 85%) was obtained.

^1H -NMR: δ 3.80 (s, 2H), 6.45 (d, 1H), 6.63 (d, 2H), 6.74-6.81 (m, 2H), 6.92 (dd, 1H), 7.05 (d, 1H), 7.18-7.20 (m, 3H), 7.39 (dd, 1H), 7.54 (d, 1H)

<Step 6> 2- chloro -5-phenyl-10,11-(1-phenyl-1H- indole Synthesis of )-5H-dibenzo[b,f]azepin

2-chloro-5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one (38.4 g, 120.0 mmol) and 1,1-diphenylhydrazine (24.3 g, 131.9 mmol), acetic acid under a nitrogen stream (400 ml) was added and stirred at 120°C for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 3:1 (v/v)) to obtain 2-chloro-5-phenyl-10,11-(1-phenyl-1H-indole)-5H -dibenzo[b,f]azepin (42.8 g, yield 76%) was obtained.

¹ H-NMR: δ 6.63-6.69 (m, 4H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 4H), 7.42-7.58 (m, 7H), 7.71-7.76 (m, 2H) , 8.17 (d, 1H), 8.83 (d, 1H)

<Step 7> EIAz - 2 of synthesis

2-chloro-5-phenyl-10,11-(1-phenyl-1H-indole)-5H-dibenzo[b,f]azepin (42.8 g, 91.1 mmol), 4,4,4',4 under nitrogen flow ',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (25.5 g, 100.3 mmol), Pd(dppf)Cl ₂ (8.0 g, 9.1 mmol) , KOAc (25.7 g, 273.5 mmol) and 1,4-Dioxane (400 ml) were mixed and stirred at 130 °C for 12 hours.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and purified by column chromatography (Hexane:EA = 4:1 (v/v)) to obtain EIAz-2 (39.9 g, yield 78%). got it

^1H -NMR: δ 1.24 (s, 12H), 6.63-6.69 (m, 4H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 3H), 7.41-7.58 (m, 9H), 7.71 (d, 1H), 8.17 (d, 1H), 8.83 (d, 1H)

[ preparation example 3] EIAz - 3 of synthesis

<Step 1> 5-H- Dibenzo[a,d]cycloheptene synthesis of

5-dibenzosuberenone (100g, 484.9 mmol) and N ₂ H _{2 ·} H ₂ O (830 mL) were mixed under a nitrogen stream, and the reaction vessel was sealed and stirred at 180°C for 15 hours.

After the reaction was completed, the mixture was cooled to room temperature, extracted with ethyl acetate, dried with MgSO ₄ , and precipitated with methanol to obtain 5-H-Dibenzo[a,d]cycloheptene (69.9 g, yield 75%).

¹ H-NMR: δ 3.51 (s, 2H), 6.99 (s, 2H), 7.07 (d, 2H), 7.18 (dd, 2H), 7.26 (dd, 2H), 7.38 (d, 2H)

<Step 2> 5,5- dimethyl -5-H- Dibenzo[a,d]cycloheptene synthesis of

5-H-Dibenzo[a,d]cycloheptene (69.9g, 363.7 mmol) and DMSO (1000 mL) were mixed under a nitrogen stream, and methyl iodide (MeI) (103.2g, 727.3mmol), KI (6.64g, 40.0 mmol) was added dropwise, and the reaction temperature was lowered to 0°C. After adding KOH (85.7g, 1,527.3 mmol) and stirring at 0°C for 15 minutes, the temperature was raised to room temperature and stirred for 15 hours. After adding methyl iodide (34.6g, 243.6 mmol) again, the mixture was stirred at 60°C for 7 hours.

After the reaction was completed, extraction was performed with ethyl acetate, water was removed with MgSO ₄ , and 5,5-dimethyl-5-H-Dibenzo[ a,d] cycloheptene (51.3 g, yield 62%) was obtained.

^1H -NMR: δ 1.72 (s, 6H), 6.99 (s, 2H), 7.22-7.30 (m, 6H), 7.42 (d, 2H)

<Step 3> 6,6- dimethyl -6,10b- dihydro - 1aH - dibenzo[b,f]oxyreno Synthesis of [2,3-d]cycloheptene

5,5-dimethyl-5-H-Dibenzo[a,d]cycloheptene (51.3 g, 225.5 mmol), meta- chloroperoxybenzoic acid (46.7 g, 270.6 mmol), silica (102.7 g), NaOCl under a nitrogen stream (102.7 g) and acetonitrile (513.4 ml) were mixed and stirred at 80°C for 2 hours.

After the reaction was completed, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was recrystallized with ethanol to obtain 6,6-dimethyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]cycloheptene (41.6 g, yield 78%) .

^1H -NMR: δ 1.72 (s, 6H), 4.20 (s, 2H) 6.99 (s, 2H), 7.20-7.30 (m, 6H), 7.59 (d, 2H)

<Step 4> 5,5- dimethyl -5-H- Dibenzo[a,d]cycloheptane -10(11H)- of one synthesis

6,6-dimethyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]cycloheptene (41.6 g, 175.9 mmol), lithium iodide (28.2 g, 211.0 mmol) and chloroform (500 ml) was mixed and stirred at 60 °C for 1 hour.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and recrystallized from ethanol to obtain 5,5-dimethyl-5-H-Dibenzo[a,d]cycloheptane-10(11H)-one (31.2 g, Yield 75%) was obtained.

^1H -NMR: δ 1.72 (s, 6H), 3.81 (s, 2H) 7.18 (dd, 1H), 7.38-7.44 (m, 4H), 7.54-7.56 (m, 2H), 7.86 (d, 1H)

<Step 5> EIAz - 3 of synthesis

5,5-dimethyl-5-H-Dibenzo[a,d]cycloheptane-10(11H)-one (31.2 g, 131.2 mmol), phenylhydrazine (15.7 g, 145.1 mmol), and acetic acid (350 ml) under a nitrogen stream. After putting the mixture was stirred at 120 ° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 3:1 (v/v)) to obtain EIAz-3 (26.5 g, yield 65%).

^1H -NMR: δ 1.72 (s, 6H), 7.06-7.08 (m, 2H), 7.33-7.44 (m, 7H), 7.56-7.60 (m, 2H), 7.71 (d, 1H), 11.36 (b) , 1H)

[ preparation example 4] EIAz Synthesis of -4

<Step 1> to <Step 4>

The same procedures as <Step 1> to <Step 4> of Preparation Example 3 were performed.

<Step 5> EIAz - 4 of synthesis

5,5-dimethyl-5-H-Dibenzo[a,d]cycloheptane-10(11H)-one (31.2 g, 131.2 mmol) and naphthalen-1-ylhydrazine (23.0 g, 145.1 mmol), acetic acid under a nitrogen atmosphere (350 ml) was added and stirred at 120°C for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 3:1 (v/v)) to obtain EIAz-4 (26.1 g, yield 55%).

^1H -NMR: δ 1.72 (s, 6H), 7.33-7.36 (m, 6H), 7.60-7.71 (m, 6H), 8.16 (d, 1H), 8.51 (d, 1H), 11.36 (b, 1H) )

[ preparation example 5] EIAz Synthesis of -5

<Step 1> to <Step 4>

The same procedures as <Step 1> to <Step 4> of Preparation Example 3 were performed.

<Step 5> 5,5- dimethyl -10,11-(5- chloro -1H- indole Synthesis of )-5-H-Dibenzo[a,d]cycloheptene

5,5-dimethyl-5-H-Dibenzo[a,d]cycloheptane-10(11H)-one (31.2 g, 131.2 mmol) and (4-chlorophenyl)hydrazine (20.7 g, 145.1 mmol), acetic acid under a nitrogen stream After adding acid (350 ml), the mixture was stirred at 120°C for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 4:1 (v/v)) to obtain 5,5-dimethyl-10,11-(5-chloro-1H-indole)-5-H -Dibenzo[a,d]cycloheptene (26.8 g, yield 59%) was obtained.

^1H -NMR: δ 1.72 (s, 6H), 6.98 (d, 1H), 7.33-7.38 (m, 7H), 7.60 (d, 1H), 7.68-7.71 (m, 2H), 11.36 (b, 1H) )

<Step 6> 5,5- dimethyl -10,11-(5- chloro -1-phenyl-1H- indole Synthesis of )-5-H-Dibenzo[a,d]cycloheptene

5,5-dimethyl-10,11-(5-chloro-1H-indole)-5-H-Dibenzo[a,d]cycloheptene (26.8 g, 77.8 mmol), iodobenzene (19.2 g, 93.4 mmol) under nitrogen stream , Cu (2.5 g, 38.9 mmol), K ₂ CO ₃ (21.5 g, 155.6 mmol) and nitrobenzene (300 ml) were mixed and stirred at 210 °C for 12 hours.

After the reaction was completed, the mixture was extracted with dichloromethane, and MgSO ₄ was added thereto and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 4:1 (v/v)) to obtain 5,5-dimethyl-10,11-(5-chloro-1-phenyl-1H-indole) -5-H-Dibenzo[a,d]cycloheptene (24.5 g, yield 75%) was obtained.

^1H -NMR: δ 1.72 (s, 6H), 7.18 (d, 1H), 7.33-7.38 (m, 6H), 7.45-7.71 (m, 9H)

<Step 7> EIAz - 5 of synthesis

5,5-dimethyl-10,11-(5-chloro-1-phenyl-1H-indole)-5-H-Dibenzo[a,d]cycloheptene (24.5 g, 58.4 mmol), 4,4, 4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (16.3 g, 64.2 mmol), Pd(dppf)Cl ₂ (5.1 g , 5.8 mmol), KOAc (16.5 g, 175.1 mmol) and 1,4-Dioxane (200 ml) were mixed and 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 purification was performed by column chromatography (Hexane:EA = 5:1 (v/v)) to obtain EIAz-5 (23.3 g, yield 78%). got it

^1H -NMR: δ 1.24 (s, 12H), 1.72 (s, 6H), 7.33-7.36 (m, 6H), 7.45-7.50 (m. 3H), 7.58-7.60 (m, 5H), 7.71-7.72 (m, 2H)

[ synthesis example 1] Synthesis of A-1

EIAz-1 (3.8 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (PPh ₃ ) synthesized in Preparation Example 1 under a nitrogen stream ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol), and toluene/EtOH/H ₂ 0 (50/30/20 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, extraction was performed with MC, water was removed with MgSO ₄ , and purification was performed by recrystallization to obtain the target compound A-1 (3.5 g, yield 71%).

Mass (Theory: 740.89, Measured: 740 g/mol)

[ synthesis example 2] Synthesis of A-2

Synthesis except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The same procedure as in Example 1 was performed to obtain the target compound A-2 (3.3 g, yield 73%).

Mass (Theory: 665.78, Measured: 665 g/mol)

[ synthesis example 3] Synthesis of A-3

Same as Synthesis Example 1 except for using 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The process was performed to obtain the target compound A-3 (3.8 g, yield 77%).

Mass (Theory: 740.89, Measured: 740 g/mol)

[ synthesis example 4] Synthesis of A-4

It is recommended to use 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-4 (3.5 g, yield 70%).

Mass (Theory: 741.88, Measured: 741 g/mol)

[ synthesis example 5] Synthesis of A-5

It is recommended to use 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. A target compound, A-5 (3.6 g, yield 72%) was obtained by performing the same process as in Synthesis Example 1 except for the above.

Mass (Theory: 741.88, Measured: 741 g/mol)

[ synthesis example 6] Synthesis of A-6

It is recommended to use 4-(biphenyl-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-6 (3.7 g, yield 68%).

Mass (Theory: 816.98, Measured: 816 g/mol)

[ synthesis example 7] Synthesis of A-7

2-(biphenyl-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.4 g) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine , 8.0 mmol), but the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-7 (4.3 g, yield 79%).

Mass (Theory: 817.97, Measured: 817 g/mol)

[ synthesis example 8] Synthesis of A-8

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine ) The target compound A-8 (3.6 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1 except for using.

Mass (Theory: 817.97, Measured: 817 g/mol)

[ synthesis example 9] Synthesis of A-9

The target compound was obtained by performing the same procedure as in Synthesis Example 1, except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Phosphorus A-9 (1.9 g, yield 67%) was obtained.

Mass (Theory: 638.75, Measured: 638 g/mol)

[ synthesis example 10] Synthesis of A-10

The same procedure as in Synthesis Example 1 was performed except for using 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Compound A-10 (3.5 g, yield 70%) was obtained.

Mass (Theory: 736.9, Measured: 736 g/mol)

[ synthesis example 11] Synthesis of B-1

EIAz-2 (3.8 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (PPh ₃ ) synthesized in Preparation Example 2 under a nitrogen stream ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol), and toluene/EtOH/H ₂ 0 (50/30/20 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, extraction was performed with MC, water was removed with MgSO ₄ , and purification was performed by recrystallization to obtain the target compound B-1 (3.2 g, yield 65%).

Mass (Theory: 740.89, Measured: 740 g/mol)

[ synthesis example 12] Synthesis of B-2

Synthesis except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The same procedure as in Example 11 was performed to obtain the target compound B-2 (3.1 g, yield 70%).

Mass (Theory: 665.78, Measured: 665 g/mol)

[ synthesis example 13] Synthesis of B-3

Same as Synthesis Example 11 except for using 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The process was performed to obtain the target compound B-3 (3.7 g, yield 75%).

Mass (Theory: 740.89, Measured: 740 g/mol)

[ synthesis example 14] Synthesis of B-4

It is recommended to use 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 11 was performed to obtain the target compound B-4 (3.4 g, yield 68%).

Mass (Theory: 741.88, Measured: 741 g/mol)

[ synthesis example 15] Synthesis of B-5

It is recommended to use 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 11 was performed to obtain the target compound B-5 (3.6 g, yield 73%).

Mass (Theory: 741.88, Measured: 741 g/mol)

[ synthesis example 16] Synthesis of B-6

It is recommended to use 4-(biphenyl-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 11 was performed to obtain the target compound B-6 (3.9 g, yield 71%).

Mass (Theory: 816.98, Measured: 816 g/mol)

[ synthesis example 17] Synthesis of B-7

2-(biphenyl-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.4 g) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine , 8.0 mmol), but the same procedure as in Synthesis Example 11 was performed to obtain the target compound B-7 (4.1 g, yield 75%).

Mass (Theory: 817.97, Measured: 817 g/mol)

[ synthesis example 18] Synthesis of B-8

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine ) The target compound B-8 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 11 except for using.

Mass (Theory: 817.97, Measured: 817 g/mol)

[ synthesis example 19] Synthesis of B-9

The target compound was obtained by performing the same procedure as in Synthesis Example 11, except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Phosphorus B-9 (3.2 g, yield 74%) was obtained.

Mass (Theory: 638.75, Measured: 638 g/mol)

[ synthesis example 20] Synthesis of B-10

Purpose Compound B-10 (3.4 g, yield 69%) was obtained.

Mass (Theory: 736.9, Measured: 736 g/mol)

[ synthesis example 21] Synthesis of C-1

EIAz-3 (2.1 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (OAc) ₂ synthesized in Preparation Example 3 under a nitrogen stream (0.08 g, 0.34 mmol), P( t -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and incubated at 110℃ for 5 hours. while stirring. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound C-1 (2.8 g, yield 68%).

Mass (Theory: 615.76, Measured: 615 g/mol)

[ synthesis example 22] Synthesis of C-2

Synthesis except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The same procedure as in Example 21 was performed to obtain the target compound C-2 (2.3 g, yield 64%).

Mass (Theory: 540.65, Measured: 540 g/mol)

[ synthesis example 23] Synthesis of C-3

Same as Synthesis Example 21 except for using 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The process was performed to obtain the target compound C-3 (3.0 g, yield 73%).

Mass (Theory: 615.76, Measured: 615 g/mol)

[ synthesis example 24] Synthesis of C-4

It is recommended to use 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 21 was performed to obtain the target compound C-4 (2.7 g, yield 65%).

Mass (Theory: 616.75, Measured: 616 g/mol)

[ synthesis example 25] Synthesis of C-5

It is recommended to use 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 21 was performed to obtain the target compound C-5 (2.9 g, yield 70%).

Mass (Theory: 616.75, Measured: 616 g/mol)

[ synthesis example 26] Synthesis of C-6

It is recommended to use 4-(biphenyl-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 21 was performed to obtain the target compound C-6 (3.1 g, yield 66%).

Mass (Theory: 691.85, Measured: 691 g/mol)

[ synthesis example 27] Synthesis of C-7

2-(biphenyl-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.4 g) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine , 8.0 mmol) to obtain the target compound C-7 (3.3 g, yield 72%) in the same manner as in Synthesis Example 21 except for using.

Mass (Theory: 692.84, Measured: 692 g/mol)

[ synthesis example 28] Synthesis of C-8

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine ) The same procedure as in Synthesis Example 21 was performed except for using, to obtain the target compound C-8 (3.5 g, yield 75%).

Mass (Theory: 692.84, Measured: 692 g/mol)

[ synthesis example 29] Synthesis of C-9

The target compound was obtained by performing the same procedure as in Synthesis Example 21, except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Phosphorus C-9 (2.5 g, yield 73%) was obtained.

Mass (Theory: 513.62, Measured: 513 g/mol)

[ synthesis example 30] Synthesis of C-10

Purpose Compound C-10 (2.8 g, yield 68%) was obtained.

Mass (Theory: 611.8, Measured: 611 g/mol)

[ synthesis example 31] Synthesis of D-1

EIAz-4 (2.4 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (OAc) ₂ synthesized in Preparation Example 4 under a nitrogen stream (0.08 g, 0.34 mmol), P( t -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and incubated at 110℃ for 5 hours. while stirring. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound D-1 (3.2 g, yield 72%).

Mass (Theory: 665.82, Measured: 665 g/mol)

[ synthesis example 32] Synthesis of D-2

Synthesis except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The same procedure as in Example 31 was performed to obtain the target compound D-2 (3.0 g, yield 75%).

Mass (Theory: 590.71, Measured: 590 g/mol)

[ synthesis example 33] Synthesis of D-3

Same as Synthesis Example 31 except for using 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The process was performed to obtain the target compound D-3 (3.1 g, yield 70%).

Mass (Theory: 665.82, Measured: 665 g/mol)

[ synthesis example 34] Synthesis of D-4

It is recommended to use 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 31 was performed to obtain the target compound D-4 (3.0 g, yield 68%).

Mass (Theory: 666.81, Measured: 666 g/mol)

[ synthesis example 35] Synthesis of D-5

It is recommended to use 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 31 was performed to obtain the target compound D-5 (3.3 g, yield 74%).

Mass (Theory: 666.81, Measured: 666 g/mol)

[ synthesis example 36] Synthesis of D-6

It is recommended to use 4-(biphenyl-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 31 was performed to obtain the target compound D-6 (3.6 g, yield 72%).

Mass (Theory: 741.91, Measured: 741 g/mol)

[ synthesis example 37] Synthesis of D-7

2-(biphenyl-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.4 g) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine , 8.0 mmol) was performed in the same manner as in Synthesis Example 31 to obtain the target compound D-7 (3.5 g, yield 70%).

Mass (Theory: 742.90, Measured: 742 g/mol)

[ synthesis example 38] Synthesis of D-8

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine ) The target compound D-8 (3.4 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 31 except for using.

Mass (Theory: 742.90, Measured: 742 g/mol)

[ synthesis example 39] Synthesis of D-9

The target compound was obtained by performing the same procedure as in Synthesis Example 31, except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Phosphorus D-9 (2.8 g, yield 75%) was obtained.

Mass (Theory: 563.68, Measured: 563 g/mol)

[ synthesis example 40] Synthesis of D-10

Purpose Compound D-10 (3.2 g, yield 72%) was obtained.

Mass (Theory: 661.83, Measured: 661 g/mol)

[ synthesis example 41] Synthesis of E-1

EIAz-5 (3.4 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (PPh ₃ ) synthesized in Preparation Example 5 under a nitrogen stream ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol), and toluene/EtOH/H ₂ 0 (50/30/20 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, extraction was performed with MC, water was removed with MgSO ₄ , and purification was performed by recrystallization to obtain the target compound E-1 (3.2 g, yield 68%).

Mass (Theory: 691.86, Measured: 691 g/mol)

[ synthesis example 42] Synthesis of E-2

Synthesis except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The same procedure as in Example 41 was performed to obtain the target compound E-2 (3.1 g, yield 75%).

Mass (Theory: 616.75, Measured: 616 g/mol)

[ synthesis example 43] Synthesis of E-3

Same as Synthesis Example 41 except for using 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. The process was performed to obtain the target compound E-3 (3.2 g, yield 69%).

Mass (Theory: 691.86, Measured: 691 g/mol)

[ synthesis example 44] Synthesis of E-4

It is recommended to use 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 41 was performed to obtain the target compound E-4 (3.4 g, yield 73%).

Mass (Theory: 692.85, Measured: 692 g/mol)

[ synthesis example 45] Synthesis of E-5

It is recommended to use 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 41 was performed to obtain the target compound E-5 (3.2 g, yield 70%).

Mass (Theory: 692.85, Measured: 692 g/mol)

[ synthesis example 46] Synthesis of E-6

It is recommended to use 4-(biphenyl-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Except for the same procedure as in Synthesis Example 41 was performed to obtain the target compound E-6 (3.3 g, yield 65%).

Mass (Theory: 767.95, Measured: 767 g/mol)

[ synthesis example 47] Synthesis of E-7

2-(biphenyl-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (3.4 g) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine , 8.0 mmol) to obtain the target compound E-7 (3.6 g, yield 70%) in the same manner as in Synthesis Example 41 except for using.

Mass (Theory: 768.94, Measured: 768 g/mol)

[ synthesis example 48] Synthesis of E-8

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine ) The target compound E-8 (3.8 g, yield 74%) was obtained by performing the same procedure as in Synthesis Example 41 except for using.

Mass (Theory: 768.94, Measured: 768 g/mol)

[ synthesis example 49] Synthesis of E-9

The target compound was obtained by performing the same procedure as in Synthesis Example 41, except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine. Phosphorus E-9 (2.7 g, yield 68%) was obtained.

Mass (Theory: 589.72, Measured: 589 g/mol)

[ synthesis example 50] Synthesis of E-10

Purpose Compound E-10 (3.3 g, yield 72%) was obtained.

Mass (Theory: 687.87, Measured: 687 g/mol)

[ synthesis example 51] Synthesis of F-1

EIAz-1 (3.8 g, 6.7 mmol), N,N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd synthesized in Preparation Example 1 under a nitrogen stream (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol), and toluene/EtOH/H ₂ 0 (50/30/20 ml) were mixed and stirred at 110°C for 5 hours. did After the reaction was completed, extraction was performed with MC, water was removed with MgSO ₄ , and purification was performed by recrystallization to obtain the target compound, F-1 (3.9 g, yield 65%).

Mass (Theory: 906.12, Measured: 906 g/mol)

[ synthesis example 52] F- 2 of synthesis

Instead of N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine, N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) was used. Except for the use, the same procedure as in Synthesis Example 51 was performed to obtain the target compound F-2 (3.6 g, yield 66%).

Mass (Theory: 803.99, Measured: 804 g/mol)

[ synthesis example 53] F- 3 of synthesis

EIAz-2 (3.8 g, 6.7 mmol), N,N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd synthesized in Preparation Example 2 under nitrogen stream (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol), and toluene/EtOH/H ₂ 0 (50/30/20 ml) were mixed and stirred at 110°C for 5 hours. did After the reaction was completed, extraction was performed with MC, water was removed with MgSO ₄ , and purification was performed by recrystallization to obtain the target compound, F-3 (4.2 g, yield 70%).

Mass (Theory: 906.12, Measured: 906 g/mol)

[ synthesis example 54] F- 4 of synthesis

N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine instead of N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine N-(4'-bromobiphenyl- Except for using 4-yl) -N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol), the same procedure as in Synthesis Example 53 was performed to obtain the target compound F-4 (3.4 g, yield 63%). got it

Mass (Theory: 803.99, Measured: 804 g/mol)

[ synthesis example 55] Synthesis of F-5

EIAz-3 (2.1 g, 6.7 mmol), N,N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd synthesized in Preparation Example 3 under a nitrogen stream (OAc) ₂ (0.08 g, 0.34 mmol), P( t -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and heated to 110 It was stirred for 5 hours at °C. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound F-5 (3.5 g, yield 66%).

Mass (Theory: 780.99, Measured: 780 g/mol)

[ synthesis example 56] Synthesis of F-6

Instead of N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine, N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) was used. Except for the use, the same procedure as in Synthesis Example 55 was performed to obtain the target compound F-6 (3.0 g, yield 65%).

Mass (Theory: 678.86, Measured: 678 g/mol)

[ synthesis example 57] Synthesis of F-7

EIAz-4 (2.4 g, 6.7 mmol), N,N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd synthesized in Preparation Example 4 under nitrogen stream (OAc) ₂ (0.08 g, 0.34 mmol), P( t -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and heated to 110 It was stirred for 5 hours at °C. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound, F-7 (3.3 g, yield 60%).

Mass (Theory: 831.05, Measured: 831 g/mol)

[ synthesis example 58] Synthesis of F-8

Instead of N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine, N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) was used. Except for the use, the same procedure as in Synthesis Example 57 was performed to obtain the target compound F-8 (3.5 g, yield 71%).

Mass (Theory: 728.92, Measured: 728 g/mol)

[ synthesis example 59] Synthesis of F-9

EIAz-5 (3.4 g, 6.7 mmol), N,N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd synthesized in Preparation Example 5 under a nitrogen stream (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol), and toluene/EtOH/H ₂ 0 (50/30/20 ml) were mixed and stirred at 110°C for 5 hours. did After the reaction was completed, extraction was performed with MC, water was removed with MgSO ₄ , and purification was performed by recrystallization to obtain the target compound, F-9 (3.8 g, yield 67%).

Mass (Theory: 857.09, Measured: 857 g/mol)

[ synthesis example 60] Synthesis of F-10

Instead of N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine, N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) was used. Except for the use, the same procedure as in Synthesis Example 59 was performed to obtain the target compound F-10 (3.2 g, yield 64%).

Mass (Theory: 754.96, Measured: 754 g/mol)

[ Example 1 to 45] green organic electric field Manufacture of Light-Emitting Devices

Compounds A-1 to A-8, A-10, B-1 to B-8, B-10, C-1 to C-8, C-10, D-1 to D-8 synthesized in Synthesis Examples; D-10, E-1 to E-8, and E-10 were sublimated to high purity by a commonly known method, and then a green organic electroluminescent device was prepared according to the following procedure.

First, a 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, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes and vacuum evaporator The substrate was transferred to

m-MTDATA (60 nm) / TCTA (80 nm) / 90% of each compound A-1 to A-8, A-10, B-1 to B-8, B- on the ITO transparent electrode prepared as above 10, C-1 to C-8, C-10, D-1 to D-8, D-10, E-1 to E-8, E-10 + 10% of Ir(ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare an organic light emitting device.

[ comparative example 1] Green organic electric field Manufacture of Light-Emitting Devices

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound A-1 as the light emitting host material when forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , CBP, Alq ₃ and BCP used in Examples 1 to 45 and Comparative Example 1 are as follows.

[ evaluation example One]

Driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured for the green organic electroluminescent devices prepared in Examples 1 to 45 and Comparative Example 1, respectively, and the results are shown in Tables 1 and 2 below. was

Sample host Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 A-1 6.86 518 38.9 Example 2 A-2 6.48 518 41.3 Example 3 A-3 6.48 517 41.3 Example 4 A-4 6.86 515 41.3 Example 5 A-5 6.77 518 41.2 Example 6 A-6 6.66 518 38.9 Example 7 A-7 6.65 517 41.3 Example 8 A-8 6.77 515 41.2 Example 9 A-10 6.77 518 38.9 Example 10 B-1 6.66 518 41.3 Example 11 B-2 6.65 517 41.3 Example 12 B-3 6.77 515 41.3 Example 13 B-4 6.66 518 41.2 Example 14 B-5 6.66 518 38.9 Example 15 B-6 6.81 517 41.3 Example 16 B-7 6.68 515 41.3 Example 17 B-8 6.66 518 41.3 Example 18 B-10 6.70 518 41.2 Example 19 C-1 6.66 517 42.2 Example 20 C-2 6.66 515 42.0 Example 21 C-3 6.81 518 39.7 Example 22 C-4 6.68 518 38.9 Example 23 C-5 6.66 518 41.3 Example 24 C-6 6.70 517 41.3 Example 25 C-7 6.70 515 43.1 Example 26 C-8 6.51 518 43.5 Example 27 C-10 6.77 518 41.4 Example 28 D-1 6.70 517 43.1 Example 29 D-2 6.51 515 41.3 Example 30 D-3 6.77 515 41.3 Example 31 D-4 6.46 515 41.3 Example 32 D-5 6.51 515 41.2 Example 33 D-6 6.77 518 38.9 Example 34 D-7 6.70 518 41.3 Example 35 D-8 6.51 517 41.3 Example 36 D-10 6.77 515 41.3

Sample host Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 37 E-1 6.86 518 41.2 Example 38 E-2 6.77 517 42.0 Example 39 E-3 6.66 518 39.7 Example 40 E-4 6.66 517 38.9 Example 41 E-5 6.77 518 41.3 Example 42 E-6 6.70 518 41.3 Example 43 E-7 6.51 518 43.1 Example 44 E-8 6.77 517 41.3 Example 45 E-10 6.77 518 38.9 Comparative Example 1 CBP 6.93 516 38.2

As shown in Tables 1 and 2, the green organic electroluminescent device (Examples 1 to 45) using the compound according to the present invention in the light emitting layer is compared to the green organic electroluminescent device (Comparative Example 1) using the conventional CBP in the light emitting layer. It was confirmed that the current efficiency and driving voltage were excellent.

[ Example 46 to 50] red organic electric field Manufacture of Light-Emitting Devices

Compounds A-9, B-9, C-9, D-9, and E-9 synthesized in Synthesis Example were subjected to high-purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was prepared according to the following procedure. .

First, a 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, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes and vacuum evaporator The substrate was transferred to

m-MTDATA (60 nm) / TCTA (80 nm) / 90% of compounds A-9, B-9, C-9, D-9, E-9 + 10% of ( piq) ₂ Ir(acac) (300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in this order to prepare an organic electroluminescent device.

[ comparative example 2]

A red organic electroluminescent device was manufactured in the same manner as in Example 46, except that CBP was used instead of Compound A-9 as the light emitting host material when forming the light emitting layer.

The structure of (piq) ₂ Ir(acac) used in Examples 46 to 50 and Comparative Example 2 is as follows.

[ evaluation example 2]

For the organic electroluminescent devices prepared in Examples 46 to 50 and Comparative Example 2, driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below.

Sample host Driving voltage (V) Current efficiency (cd/A) Example 46 A-9 4.94 12.5 Example 47 B-9 4.81 10.8 Example 48 C-9 4.64 13.2 Example 49 D-9 4.87 11.9 Example 50 E-9 4.78 13.1 Comparative Example 2 CBP 5.25 8.2

As shown in Table 3, the red organic electroluminescent device (Examples 46 to 50) using the compound according to the present invention in the light emitting layer has current efficiency compared to the red organic light emitting device (Comparative Example 2) using the conventional CBP in the light emitting layer. And it was confirmed that the driving voltage was excellent.

[ Example 51 to 60] organic electric field Manufacture of Light-Emitting Devices

Compounds F-1 to F-10 synthesized in Synthesis Example were subjected to high-purity sublimation purification by a conventionally known method, and an organic electroluminescent device was prepared according to the following procedure.

First, a 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, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes. Afterwards, the substrate was transferred to a vacuum layering machine.

m-MTDATA (60 nm)/ each compound F-1 to F-10 (80 nm)/ DS-H522 + 5% of DS-501 (Doosan Electronics Co., Ltd., 30 nm)/ BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to prepare an organic light emitting device.

[ comparative example 3] organic electric field Manufacture of Light-Emitting Devices

An organic electroluminescent device was manufactured in the same manner as in Example 51, except that NPB was used instead of Compound F-1 as the hole transport layer material when forming the hole transport layer.

The structure of the NPB used in Comparative Example 3 is as follows.

[ evaluation example 3]

The driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured for the organic electroluminescent devices prepared in Examples 51 to 60 and Comparative Example 3, respectively, and the results are shown in Table 4 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 51 F-1 4.9 21.1 Example 52 F-2 4.6 19.4 Example 53 F-3 4.8 20.0 Example 54 F-4 4.3 19.3 Example 55 F-5 4.8 19.2 Example 56 F-6 4.6 21.1 Example 57 F-7 4.8 19.4 Example 58 F-8 4.3 20.0 Example 59 F-9 4.6 19.3 Example 60 F-10 4.8 19.2 Comparative Example 3 NPB 5.2 18.1

As shown in Table 4, the organic electroluminescent device (Examples 51 to 60) using the compound according to the present invention as a hole transport layer has higher current efficiency than the organic electroluminescent device (Comparative Example 3) using a conventional NPB as a hole transport layer. And it was confirmed that the driving voltage was excellent.

[ Example 61 to 100] blue organic electric field Manufacture of Light-Emitting Devices

Compounds A-1 to A-8, B-1 to B-8, C-1 to C-8, D-1 to D-8, and E-1 to E-8 synthesized in Synthesis Example were prepared by commonly known methods. After sublimation purification with high purity, a blue organic electroluminescent device was prepared as follows.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After the distilled water cleaning is finished, ultrasonic cleaning is performed with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, the substrate is transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/AND + 5% DS-405 (Doosan Electronics) (30 nm)/each compound A- 1 to A-8, B-1 to B-8, C-1 to C-8, D-1 to D-8, E-1 to E-8 (5 nm) / Alq ₃ (25 nm) / LiF (1 nm)/Al (200 nm) were laminated in this order to prepare an organic electroluminescent device.

[ comparative example 4] Blue organic electric field Manufacture of Light-Emitting Devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 61, except that the lifespan improvement layer was not included and Alq ₃ , an electron transport layer material, was deposited in a thickness of 30 nm instead of 25 nm.

[ comparative example 5] Blue organic electric field Manufacture of Light-Emitting Devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 61, except for using BCP instead of Compound A-1 as a material for the lifespan improvement layer when forming the lifespan improvement layer.

The structure of AND used in Examples 61 to 100 and Comparative Examples 4 and 5 is as follows.

[ evaluation example 4]

For the organic electroluminescent devices prepared in Examples 61 to 100 and Comparative Examples 4 and 5, respectively, the driving voltage, current efficiency, emission wavelength and lifetime (T ₉₇ ) at a current density of 10 mA/cm 2 were measured, and the results are shown in Tables 5 and 6 below.

Sample life improvement layer Driving voltage (V) Current efficiency (cd/A) Emission peak (nm) Life (hr, T ₉₇ ) Example 61 A-1 4.3 6.2 459 38 Example 62 A-2 4.2 6.1 451 37 Example 63 A-3 4.4 6.1 460 32 Example 64 A-4 4.3 6.0 461 39 Example 65 A-5 4.3 6.1 461 44 Example 66 A-6 4.2 6.3 462 45 Example 67 A-7 4.7 6.1 463 32 Example 68 A-8 4.3 6.1 457 39 Example 69 B-1 4.6 6.2 459 38 Example 70 B-2 4.5 6.0 459 37 Example 71 B-3 4.8 6.1 459 32 Example 72 B-4 4.3 6.1 451 39 Example 73 B-5 4.4 6.3 459 44 Example 74 B-6 4.3 6.0 459 45 Example 75 B-7 4.2 6.2 459 45 Example 76 B-8 4.2 6.1 451 32 Example 77 C-1 4.3 6.1 460 39 Example 78 C-2 4.7 6.0 460 38 Example 79 C-3 4.2 6.1 459 37 Example 80 C-4 4.8 6.2 459 32 Example 81 C-5 4.9 6.1 451 39 Example 82 C-6 4.5 6.1 460 44 Example 83 C-7 4.3 6.0 461 42 Example 84 C-8 4.2 6.0 461 44 Example 85 D-1 4.2 6.0 462 43 Example 86 D-2 4.9 6.2 463 48 Example 87 D-3 4.6 6.4 460 49 Example 88 D-4 4.3 6.0 459 41 Example 89 D-5 4.6 6.0 459 48 Example 90 D-6 4.3 6.0 451 49 Example 91 D-7 4.1 6.2 460 41 Example 92 D-8 4.3 6.4 461 42

Sample life improvement layer Driving voltage (V) Current efficiency (cd/A) Emission peak (nm) Life (hr, T ₉₇ ) Example 93 E-1 4.2 6.3 461 47 Example 94 E-2 4.4 6.4 462 43 Example 95 E-3 4.8 6.2 463 48 Example 96 E-4 4.4 6.1 469 49 Example 97 E-5 4.7 6.0 461 41 Example 98 E-6 4.5 6.0 462 48 Example 99 E-7 4.9 6.0 463 49 Example 100 E-8 4.6 6.0 469 41 Comparative Example 4 - 4.7 5.6 458 32 Comparative Example 5 BCP 5.3 5.9 458 28

As shown in Tables 5 and 6, the blue organic electroluminescent device (Examples 61 to 100) using the compound according to the present invention in the lifetime improvement layer is a blue organic EL device without using the lifetime improvement layer (Comparative Example 4 ), it was confirmed that the current efficiency and lifespan were excellent, and the driving voltage current efficiency was excellent compared to the blue organic electroluminescent device (Comparative Example 5) using the conventional BCP for the lifespan improvement layer, and the lifespan was significantly improved. I was able to confirm.

[ Example 101 to 110] blue organic electric field Manufacture of Light-Emitting Devices

Compounds A-1, A-6, B-1, B-6, C-1, C-6, D-1, D-6, E-1, E-6 synthesized in Synthesis Example were prepared by commonly known methods. After sublimation purification with high purity, a blue organic electroluminescent device was prepared as follows.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After the distilled water cleaning is finished, ultrasonic cleaning is performed with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, the substrate is transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/AND + 5% DS-405 (Doosan Electronics) (30 nm)/each compound A- 1, A-6, B-1, B-6, C-1, C-6, D-1, D-6, E-1, E-6 (30 nm) / LiF (1 nm) / Al ( 200 nm) to prepare an organic electroluminescent device.

[ comparative example 6] Blue organic electric field Manufacture of Light-Emitting Devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 101, except that Alq ₃ was used instead of Compound A-1 as the electron transport layer material when forming the electron transport layer.

[ evaluation example 5]

Driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured for the organic electroluminescent devices prepared in Examples 101 to 110 and Comparative Example 6, respectively, and the results are shown in Table 7 below.

Sample electron transport layer Driving voltage (V) Current efficiency (V) Emission peak (nm) Example 101 A-1 4.2 6.3 462 Example 102 A-6 4.0 6.1 460 Example 103 B-1 4.1 5.8 457 Example 104 B-6 4.6 5.8 463 Example 105 C-1 4.5 6.1 460 Example 106 C-6 4.6 5.8 457 Example 107 D-1 4.5 5.8 463 Example 108 D-6 4.2 5.8 462 Example 109 E-1 4.0 6.0 460 Example 110 E-6 4.1 6.1 463 Comparative Example 6 - 4.7 5.6 458

As shown in Table 7, the blue organic electroluminescent device (Examples 101 to 110) using the compound according to the present invention in the electron transport layer is driven compared to the blue organic electroluminescent device (Comparative Example 4) without using the electron transport layer. It was confirmed that the voltage and current efficiency were excellent.

As such, it was confirmed that the driving voltage and current efficiency of the organic field generating device using the compound represented by Formula 1 according to the present invention in the lifespan improvement layer or the electron transport layer can be improved, and furthermore, the lifespan characteristics can be greatly improved.

Claims (9)

delete delete delete delete A compound characterized by being represented by Formula 8:
[Formula 8]

In Formula 8,
Ar ₁ is selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms;
Y ₁ to Y ₁₂ are the same as or different from each other, and are each independently N or C;
a to c are each independently an integer of 0 to 4, and when a to c are each independently an integer of 1 to 3, R ₁ to R ₃ are the same as or different from each other, and each independently deuterium, a halogen, a cyano group, It is selected from the group consisting of a nitro group, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group, or an adjacent group may combine to form a condensed ring, wherein, when R ₁ to R ₃ are each plural, they are the same or different;
The Ar ₁ , R ₁ to R ₃ alkyl group, aryl group, heteroaryl group, and arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, It may be substituted with one or more substituents selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ ~ C ₆₀ , wherein when the substituents are plural, they are the same as or different from each other,
However, at least one of Ar ₁ , R ₁ to R ₃ is a substituent represented by Formula 12 below,
[Formula 12]

In Formula 12,
* means a moiety bonded to Formula 8;
L ₁ is a single bond, or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Z ₁ to Z ₅ are the same as or different from each other, and are each independently N or C(R ₇ ), provided that at least one of Z ₁ to Z ₅ is N, wherein, when the R ₇ is plural, they are the same as or different;
R ₇ is selected from the group consisting of hydrogen, heavy hydrogen, a C ₁ ~ C ₄₀ alkyl group, and a C ₆ ~ C ₆₀ aryl group, or may combine with an adjacent group to form a condensed ring;
The arylene group and heteroarylene group of L ₁ , the alkyl group and aryl group of R ₇ are each independently composed of deuterium, halogen, cyano, C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. It may be substituted with one or more substituents selected from the group, and in this case, when the substituents are plural, they may be the same as or different from each other.
delete According to claim 5,
A compound characterized in that the substituent of Formula 12 is represented by any one of the substituents represented by the following Formulas A1 to A15:

In the above formulas A1 to A15,
L ₁ and R ₇ are each as defined in claim 5;
n is an integer of 0 to 4, and when n is an integer of 1 to 4, each R ₈ is independently selected from the group consisting of deuterium, a C ₁ to C ₄₀ alkyl group, and a C ₆ to C ₆₀ aryl group, wherein When the R ₈ is plural, they may be the same as or different from each other. Including an anode, a cathode and one or more organic material layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic material layers contains the compound according to any one of claims 5 or 7. According to claim 8,
An organic electroluminescent device, wherein the one or more organic material layers containing the compound are selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a lifespan improvement layer, an electron transport layer, and an electron injection layer.