KR102507373B1 - 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 light emitting ability and including the same in one or more organic material layers, thereby providing high luminous efficiency, low driving voltage, long lifespan, etc. It relates to an organic electroluminescent device with improved characteristics.

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 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 into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.

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 light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. 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.

To date, NPB, BCP, Alq _3, etc. represented by the following chemical formula are widely known as materials used as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives as light emitting materials are fluorescent dopant/host materials is being reported as In particular, as a phosphorescent dopant 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 blue, green, and red substrates. It is used as a raw material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional light emitting materials are advantageous in terms of light emitting properties, but are not satisfactory in terms of lifetime in organic EL devices because of their low glass transition temperature and very poor thermal stability. Therefore, there is a demand for the development of light emitting materials having excellent performance.

Japanese Unexamined Patent Publication No. 2001-160489

In order to solve the above problems, the present invention can be applied to an organic electroluminescent device, and to provide a novel organic compound excellent in hole injection and transport ability, electron injection and transport ability, light emitting ability, etc. do.

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.

[Formula 1]

In Formula 1,

L ₁ is a single bond or is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms;

A and B are the same as or different from each other, and are each independently a 6-membered aromatic ring or a 6-membered heteroaromatic ring,

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ Alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or Unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl A boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and It is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring;

a and b are each independently an integer of 0 to 4, and when a and b are each independently an integer of 1 to 4, R ₁ and R ₂ are the same as or different from each other, and each independently deuterium (D), halogen, Cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted Or an unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, or an adjacent group combined to form a condensed ring, provided that when R ₁ and R ₂ are plural, they are the same as or different from each other;

X is N or C(R ₃ );

R ₃ is hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group , A substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted A heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and substituted or unsubstituted C ₆ ~ C ₄₀ aryl It is selected from the group consisting of a silyl group, or may be bonded to an adjacent group to form a condensed ring,

The arylene group and heteroarylene group of L ₁ , Ar ₁ and Ar ₂ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group of R ₁ to R ₃ , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group , Substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted A substituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphos It may be substituted with one or more substituents selected from the group consisting of a pin group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, wherein the substituent When is 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

In this case, the one or more organic material layers may be 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, and is preferably a hole transport layer, an electron transport layer, a light emitting layer, or a lifespan improvement layer. do.

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 material layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material for an organic electroluminescent device, an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long lifespan can be manufactured compared to conventional host materials. Furthermore, a full color display panel with improved performance and lifespan can be manufactured.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

In the novel compound according to the present invention, a 'carbazole moiety' is directly connected to a 'pyrrolo carbazole or pyrazolo carbazole moiety' or connected through a linker to form a basic skeleton. It is characterized in that it is represented by the formula (1). More specifically, in the compound represented by Formula 1, N located at pyrrole or pyrazole of the 'pyrrolocarbazole or pyrazole carbazole moiety' is directly linked to the 'carbazole moiety'. structure as the basic framework.

Since the compound represented by Chemical 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.

In addition, the hole transporting ability and electron transporting ability of the compound of Formula 1 may be improved depending on the characteristics of the substituent bonded to the 'pyrrolocarbazole moiety' or the 'pyrazolocarbazole moiety'. Due to this, the compound of Chemical Formula 1 exhibits a certain level of hole mobility or electron mobility, and thus can be applied to the hole transport layer and the electron transport layer of the organic light emitting device.

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, carbazole) is introduced into a 'pyrrolocarbazole moiety' or 'pyrazolocarbazole moiety' having a wide singlet energy level and a high triplet energy level. As a result, the energy level can be adjusted higher than that of the dopant and can be used as a host material. In particular, when 'carbazole' is introduced into pyrrolocarbazole or pyrazolecarbazole as in the compound of Chemical Formula 1, the energy level is lowered compared to the case where 'known substituents such as aryl' are introduced, resulting in organic electroluminescence. When applied to a device, long-wavelength light emission can be expected.

In addition, in the compound of Formula 1, an electron withdrawing group (EWG) having high electron absorption is introduced into N of the carbazole moiety, so that the entire molecule exhibits bipolar characteristics, thereby increasing the bonding force between holes and electrons. there is. Accordingly, the compound of Chemical Formula 1 can exhibit excellent light emitting properties and can be usefully applied as a material for a blue, green or red phosphorescent light emitting layer of an organic electroluminescent device.

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, 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. , life improvement layer material, more preferably can be used as a phosphorescent light emitting layer material.

In addition, the compound of Formula 1 is introduced with various substituents, particularly 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 such, the organic electroluminescent 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.

In the novel organic compound according to the present invention, the 'carbazole moiety' is connected directly or through a linker to N located at 'pyrrole' of the pyrrolocarbazole moiety or 'pyrazole' of the pyrazole carbazole moiety and has various substituents. As a structure to be introduced, it is represented by the above formula (1).

Specifically, in the compound represented by Formula 1, L ₁ is a single bond, or a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms. selected from the group consisting of Preferably, L ₁ may be a single bond.

A and B are the same as or different from each other, and are each independently a 6-membered aromatic ring or a 6-membered heteroaromatic ring. Preferably, both A and B may be 6-membered aromatic rings.

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ Alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or Unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl A boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and It is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring. Preferably, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, and It is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group. More preferably, Ar ₁ may be a phenyl group or a biphenyl group, and Ar ₂ may be a heteroaryl group containing at least one N and having 5 to 40 nuclear atoms or a C ₆ ~ C ₄₀ arylamine group.

a and b are each independently an integer of 0 to 4; When a and b are each independently 0, it means that hydrogen is not substituted with each of the substituents R ₁ and R ₂ . In addition, when a and b are each independently an integer of 1 to 4, R ₁ and R ₂ are the same as or different from each other, and each independently deuterium (D), halogen, cyano, substituted or unsubstituted C _{1 to} C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted Ringed heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl Silyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or It is selected from the group consisting of an unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring, provided When each of R ₁ and R ₂ is plural, they are identical to or different from each other.

X is N or C(R ₃ ).

R ₃ is hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group , A substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted A heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and substituted or unsubstituted C ₆ ~ C ₄₀ aryl It is selected from the group consisting of a silyl group, or may be combined with an adjacent group to form a condensed ring.

Preferably, R ₁ to R ₃ are the same as or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted It is selected from the group consisting of a C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, or bonded to an adjacent group to form a condensed ring.

In this case, the arylene group and the heteroarylene group of L ₁ , Ar ₁ and Ar ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, aryl of R ₁ to R ₃ An amine group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group, and an aryl silyl group are each independently deuterium (D), halogen, cyano, substituted or Unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ Aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted Or an unsubstituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ It may be substituted with one or more substituents selected from the group consisting of an arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, wherein When the substituents are plural, they may be identical to or different from each other.

The compound represented by Formula 1 may be further embodied by any one of Formulas 2 to 5 below. However, it is not particularly limited thereto.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5, Ar ₂ , a, b, and R ₁ to R ₃ are each as defined in Chemical Formula 1 above.

In the compound represented by Formula 1, at least one of Ar _{1 ,} Ar ₂ , and R ₁ to R ₃ may be a substituent represented by Formula 6 below. Preferably, Ar ₂ may be a substituent represented by Formula 6 below.

[Formula 6]

In Formula 6, * means a moiety bonded to Formula 1.

L ₂ is a single bond, or is selected from the group consisting of a substituted or unsubstituted C ₆ to C ₁₈ arylene group and a substituted or unsubstituted 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 ₄ ). Preferably, at least one of Z ₁ to Z ₅ is N, and the others may be C(R ₄ ). In this case, when the R ₄ is plural, they are the same as or different from each other.

R ₄ is hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group , A substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted A heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and substituted or unsubstituted C ₆ ~ C ₄₀ aryl It is selected from the group consisting of a silyl group, or may be combined with an adjacent group to form a condensed ring.

In this case, the arylene group and the heteroarylene group of L ₂ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, and a heterocycloalkyl group of R ₄ , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted nucleus Heteroaryl group having 5 to 40 atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ An arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, Substituted or unsubstituted C ₁ ~ C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted It may be substituted with one or more substituents selected from the group consisting of a C ₆ ~ C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group. In this case, when the substituents are plural, they are mutually may be the same or different.

The substituent represented by Chemical Formula 6 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, * means a moiety bonded to Chemical Formula 1, and L ₂ and R ₄ are each as defined in Chemical Formula 6 above.

n is an integer from 0 to 4; When n is 0, it means that hydrogen is not substituted with the substituent R ₅ . In addition, when n is an integer of 1 to 4, R ₅ is deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, or a substituted or unsubstituted C ₂ to C ₄₀ alkene Nyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group , A substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted or It is selected from the group consisting of an unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring.

In this case, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkylboron group, and an arylboron of R ₅ Group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted Or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group And it may be substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group. In this case, when the substituents are 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 40 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 40 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 heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl 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 40 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 40 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 40 carbon atoms.

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

In the present invention, "arylphosphine" means a phosphine substituted with an aryl having 6 to 40 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 substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a lifetime improvement layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked. may be a rescue. In this case, 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 lifespan The improvement layer and the light emitting layer may include the compound represented by Chemical 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.

Meanwhile, the organic electroluminescent device of the present invention may 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 includes the compound represented by Chemical 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] CIC - 1 of synthesis

<Step 1> 1-(4- chlorophenyl )-6,7- dihydro -1H- indazol -4(5H)- of one synthesis

6,7-dihydro-1H-indazol-4(5H)-one (100 g, 734.5 mmol), 1-chloro-4-iodobenzene (210.2 g, 881.4 mmol), Cu (23.3 g, 367.2 mmol) under nitrogen stream , K ₂ CO ₃ (203.0 g, 1,469.0 mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210 °C for 12 hours.

After the reaction was completed, it was extracted with ethyl acetate, concentrated, and recrystallized with ethanol to obtain 1-(4-chlorophenyl)-6,7-dihydro-1H-indazol-4(5H)-one (135.9 g, yield 75%). .

^1H -NMR: δ 2.05 (tt, 2H), 2.58 (t, 2H), 2.72 (t, 2H), 7.49 (d, 2H), 7.56 (d, 2H), 8.12 (s, 1H)

<Step 2> 3-(4- chlorophenyl )-10-phenyl-3,10- dihydropyrazolo[4,3-a] Synthesis of carbazole

1-(4-chlorophenyl)-6,7-dihydro-1H-indazol-4(5H)-one (135.9 g, 550.9 mmol) and 1,1-diphenylhydrazine under a nitrogen stream (111.6 g, 605.9 mmol) and acetic acid (1500 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 3-(4-chlorophenyl)-10-phenyl-3,10-dihydropyrazolo[4,3-a ]carbazole (141.0 g, yield 65%) was obtained.

^1H -NMR: δ 7.25-7.58 (m, 12H), 7.94 (d, 1H), 8.32 (d, 1H), 8.37 (s, 1H), 8.55 (d, 1H)

<Step 3> 10-phenyl-3-(4-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan Synthesis of -2-yl)phenyl)-3,10-dihydropyrazolo[4,3-a]carbazole

3-(4-chlorophenyl)-10-phenyl-3,10-dihydropyrazolo[4,3-a]carbazole (141.0 g, 358.1 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (100.01 g, 393.9 mmol), Pd(dppf)Cl ₂ (31.4 g, 35.8 mmol), KOAc (101.1 g, 1074.2 mmol) and 1,4-Dioxane (1500 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 10-phenyl-3-(4-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,10-dihydropyrazolo[4,3-a]carbazole (139.0 g, yield 80%) was obtained.

^1H -NMR: δ 1.24 (s, 12H), 7.25-7.33 (m, 2H), 7.41-7.62 (m, 8H), 7.75 (d, 2H), 7.94 (d, 1H), 8.32 (d, 1H) ), 8.37 (s, 1H), 8.55 (d, 1H)

<Step 4> 3-(2'- nitrobiphenyl -4- yl )-10-phenyl-3,10- dihydropyrazolo[4,3-a] Synthesis of carbazole

10-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,10-dihydropyrazolo[4,3-a] under nitrogen stream carbazole (139.0 g, 286.4 mmol), 1-bromo-2-nitrobenzene (69.4 g, 343.7 mmol), Pd(PPh ₃ ) ₄ (16.6 g, 14.3 mmol), K ₂ CO ₃ (79.2 g, 572.9 mmol) and 1,4-dioxane/H ₂ O (1500 ml/400 ml) were mixed and stirred at 120° C. for 4 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 purified by column chromatography (Hexane:EA = 6:1 (v/v)) to obtain 3-(2'-nitrobiphenyl-4-yl)-10-phenyl-3,10-dihydropyrazolo[ 4,3-a]carbazole (103.2 g, yield 75%) was obtained.

^1H -NMR: δ 7.25-7.68 (m, 11H), 7.79 (d, 2H), 7.90-8.05 (m, 4H), 8.32 (d, 1H), 8.37 (s, 1H), 8.55 (d, 1H) )

<Step 5> CIC - 1 of synthesis

3-(2'-nitrobiphenyl-4-yl)-10-phenyl-3,10-dihydropyrazolo[4,3-a]carbazole (103.2 g, 214.8 mmol) and triphenylphosphine (PPh ₃ ) (140.9 g, 537.1 mmol) and 1,2-dichlorobenzene (1000 ml) were added and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, 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 = 8:1 (v/v)) to obtain CIC-1 (57.8 g, yield 60%).

^1H -NMR: δ 7.23-7.63 (m, 12H), 7.83 (s, 1H), 7.94 (d, 1H), 8.11-8.12 (m, 2H), 8.32 (d, 1H), 8.37 (s, 1H) ), 8.55 (d, 1H), 10.1 (b, 1H)

[ preparation example 2] CIC -2, CIC - 3 of synthesis

<Step 1> 1-(3- chlorophenyl )-6,7- dihydro -1H- indazol -4(5H)- of one synthesis

6,7-dihydro-1H-indazol-4(5H)-one (100 g, 734.5 mmol), 1-chloro-3-iodobenzene (210.2 g, 881.4 mmol), Cu (23.3 g, 367.2 mmol) under a nitrogen stream , K ₂ CO ₃ (203.0 g, 1,469.0 mmol) and nitrobenzene (1000 ml) were 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 1-(3-chlorophenyl)-6,7-dihydro-1H-indazol-4(5H)-one (126.8 g, yield 70%). .

^1H -NMR: δ 2.05 (tt, 2H), 2.58 (t, 2H), 2.72 (t, 2H), 7.39 (dd, 1H), 7.49-7.51 (m, 2H), 7.81 (s, 1H), 8.12 (s, 1H)

<Step 2> 3-(3- chlorophenyl )-10-phenyl-3,10- dihydropyrazolo[4,3-a] Synthesis of carbazole

1-(3-chlorophenyl)-6,7-dihydro-1H-indazol-4(5H)-one (126.8 g, 514.1 mmol) and 1,1-diphenylhydrazine under a nitrogen stream (104.2 g, 565.6 mmol) and acetic acid (1500 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 3-(3-chlorophenyl)-10-phenyl-3,10-dihydropyrazolo[4,3-a ]carbazole (137.7 g, yield 68%) was obtained.

^1H -NMR: δ 7.25-7.58 (m, 11H), 7.81 (s, 1H), 7.94 (d, 1H), 8.32 (d, 1H), 8.37 (s, 1H), 8.55 (d, 1H)

<Step 3> 10-phenyl-3-(3-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan Synthesis of -2-yl)phenyl)-3,10-dihydropyrazolo[4,3-a]carbazole

3-(3-chlorophenyl)-10-phenyl-3,10-dihydropyrazolo[4,3-a]carbazole (137.7 g, 349.6 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (97.7 g, 384.6 mmol), Pd(dppf)Cl ₂ (30.6 g, 34.9 mmol), KOAc (98.7 g, 1048.8 mmol) and 1,4-Dioxane (1500 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 10-phenyl-3-(3-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,10-dihydropyrazolo[4,3-a]carbazole (122.2 g, yield 72%) was obtained.

^1H -NMR: δ 1.24 (s, 12H), 7.25-7.33 (m, 2H), 7.41-7.62 (m, 9H), 7.75 (d, 1H), 7.94 (d, 1H), 8.32 (d, 1H) ), 8.37 (s, 1H), 8.55 (d, 1H)

<Step 4> 3-(2'- nitrobiphenyl -3- yl )-10-phenyl-3,10- dihydropyrazolo[4,3-a] Synthesis of carbazole

10-phenyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,10-dihydropyrazolo[4,3-a] under nitrogen stream carbazole (122.2 g, 251.7 mmol), 1-bromo-2-nitrobenzene (61.0 g, 302.1 mmol), Pd(PPh ₃ ) ₄ (14.5 g, 12.6 mmol), K ₂ CO ₃ (69.6 g, 503.4 mmol) and 1,4-dioxane/H ₂ O (1500 ml/400 ml) were mixed and stirred at 120° C. for 4 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 purified by column chromatography (Hexane:EA = 6:1 (v/v)) to obtain 3-(2'-nitrobiphenyl-3-yl)-10-phenyl-3,10-dihydropyrazolo[ 4,3-a]carbazole (96.8 g, yield 80%) was obtained.

^1H -NMR: δ 7.25-7.67 (m, 12H), 7.90-8.05 (m, 5H), 8.32 (d, 1H), 8.37 (s, 1H), 8.55 (d, 1H)

<Step 5> CIC -2, CIC - 3 of synthesis

3-(2'-nitrobiphenyl-3-yl)-10-phenyl-3,10-dihydropyrazolo[4,3-a]carbazole (96.8 g, 201.4 mmol) and triphenylphosphine (132.0 g, 503.4 mmol) under a nitrogen stream, After adding 1,2-dichlorobenzene (1000 ml), the mixture was stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, 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 = 8:1 (v/v)) to obtain CIC-2 (22.6 g, yield 25%) and CIC-3 (25.3 g, yield 28%) was obtained.

^1H -NMR of CIC-2: δ 7.25-7.63 (m, 13H), 7.94 (d, 1H), 7.98 (s, 1H), 8.12 (d, 1H), 8.32 (d, 1H), 8.37 (s , 1H), 8.55 (d, 1H), 10.1 (b, 1H)

^1H -NMR of CIC-3: δ 7.25-7.63 (m, 13H), 7.94 (d, 1H), 8.11-8.12 (m, 2H), 8.32 (d, 1H), 8.37 (s, 1H), 8.55 (d, 1H), 10.1 (b, 1H)

[ preparation example 3] CIC - 4 of synthesis

<Step 1> 1-(2- bromophenyl )-6,7- dihydro -1H- indol -4(5H)- of one synthesis

6,7-dihydro-1H-indol-4(5H)-one (100 g, 739.9 mmol), 1-bromo-2-iodobenzene (251.2 g, 887.8 mmol), Cu (23.5 g, 369.9 mmol) under nitrogen stream , K ₂ CO ₃ (204.5 g, 1,479.7 mmol) and nitrobenzene (1000 ml) were 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 1-(2-bromophenyl)-6,7-dihydro-1H-indol-4(5H)-one (139.5 g, yield 65%). .

^1H -NMR: δ 1.99 (tt, 2H), 2.58 (t, 2H), 2.76 (t, 2H), 6.66 (d, 1H), 7.15 (d, 1H), 7.34 (dd, 1H), 7.51- 7.60 (m, 3H)

<Step 2> 3-(2- bromophenyl )-10-phenyl-3,10- dihydropyrrolo[3,2-a] Synthesis of carbazole

1-(2-bromophenyl)-6,7-dihydro-1H-indol-4(5H)-one (139.5 g, 480.9 mmol) and 1,1-diphenylhydrazine under a nitrogen stream (97.5 g, 529.0 mmol) and acetic acid (1500 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 3-(2-bromophenyl)-10-phenyl-3,10-dihydropyrrolo[3,2-a ]carbazole (149.3 g, yield 71%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.25-7.34 (m, 3H), 7.45-7.60 (m, 9H), 7.94-7.96 (m, 3H), 8.55 (d, 1H)

<Step 3> 10-phenyl-3-(2-(4,4,5,5- tetramethyl -1,3,2- dioxaborolan Synthesis of -2-yl)phenyl)-3,10-dihydropyrrolo[3,2-a]carbazole

3-(2-bromophenyl)-10-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (149.3 g, 341.4 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (95.4 g, 375.6 mmol), Pd(dppf)Cl ₂ (29.9 g, 34.1 mmol), KOAc (96.4 g, 1024.3 mmol) and 1,4-Dioxane (1500 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 10-phenyl-3-(2-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,10-dihydropyrrolo[3,2-a]carbazole (104.2 g, yield 63%) was obtained.

^1H -NMR: δ 1.24 (s, 12H), 6.52 (d, 1H), 7.25-7.33 (m, 2H), 7.45-7.62 (m, 9H), 7.75 (d, 1H), 7.94-7.96 (m , 3H), 8.55 (d, 1H)

<Step 4> 3-(5'- chloro -2'- nitrobiphenyl -2- yl Synthesis of )-10-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole

10-phenyl-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,10-dihydropyrrolo[3,2-a] under nitrogen stream carbazole (104.2 g, 215.1 mmol), 2-bromo-4-chloro-1-nitrobenzene (61.0 g, 258.1 mmol), Pd(PPh ₃ ) ₄ (12.4 g, 10.8 mmol), K ₂ CO ₃ (59.5 g, 430.2 mmol) and 1,4-dioxane/H ₂ O (1000 ml/250 ml) were mixed and stirred at 120° C. for 4 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 purified by column chromatography (Hexane:EA = 6:1 (v/v)) to obtain 3-(5'-chloro-2'-nitrobiphenyl-2-yl)-10-phenyl-3 ,10-dihydropyrrolo[3,2-a]carbazole (79.6 g, yield 72%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.25-7.34 (m, 2H), 7.45-7.79 (m, 11H), 7.94-7.96 (m, 3H), 8.26-8.31 (m, 2H), 8.55 (d, 1H)

<Step 5> 3-(5'-phenyl-2'- nitrobiphenyl -2- yl Synthesis of )-10-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole

3-(5'-chloro-2'-nitrobiphenyl-2-yl)-10-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (79.6 g, 154.9 mmol), phenylboronic acid (22.7 g, 185.9 mmol), Pd(PPh ₃ ) ₄ (8.9 g, 7.7 mmol), K ₂ CO ₃ (42.8 g, 309.8 mmol) and 1,4-dioxane/H ₂ O (800 ml/200 ml) were mixed and stirred at 120° C. for 4 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 purified by column chromatography (Hexane:EA = 6:1 (v/v)) to obtain 3-(5'-phenyl-2'-nitrobiphenyl-2-yl)-10-phenyl-3 ,10-dihydropyrrolo[3,2-a]carbazole (70.6 g, yield 82%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.25-7.58 (m, 15H), 7.68 (d, 1H), 7.76-7.79 (m, 2H), 7.94-7.96 (m, 4H), 8.38 (d , 1H), 8.55 (d, 1H)

<Step 6> CIC - 4 of synthesis

3-(5'-phenyl-2'-nitrobiphenyl-2-yl)-10-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (70.6 g, 127.0 mmol) and triphenylphosphine (83.3 g) under a nitrogen stream. , 317.5 mmol) and 1,2-dichlorobenzene (800 ml) were added and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, 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 = 8:1 (v/v)) to obtain CIC-4 (35.9 g, yield 54%).

^1H -NMR: δ 6.52 (d, 1H), 7.25-7.69 (m, 17H), 7.77 (d, 1H), 7.87-7.96 (m, 4H), 8.55 (d, 1H), 10.1 (b, 1H) )

[ preparation example 4] CIC - 5 of synthesis

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

4-bromo-1H-indole (100.0 g, 510.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3 ,2-dioxaborolane) (142.5 g, 561.1 mmol), Pd(dppf)Cl ₂ (44.7 g, 51.0 mmol), KOAc (144.1 g, 1.52 mol) and 1,4-Dioxane (2500 ml) were mixed and heated to 130°C. was stirred 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 4-(4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl)-1H-indole (96.7 g, yield 78%) was obtained.

^1H -NMR: δ 1.24 (s, 12H), 6.50 (d, 1H), 7.30 (d, 1H), 7.37-7.43 (M, 2H), 7.63 (d, 1H), 10.1 (b, 1H)

<Step 2> 4-(2- nitronaphthalene -One- yl )-1H- indole synthesis of

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (96.7 g, 397.9 mmol), 1-bromo-2-nitronaphthalene (120.3 g) under nitrogen stream , 477.5 mmol), Pd(PPh ₃ ) ₄ (23.0 g, 20.0 mmol), K ₂ CO ₃ (110.0 g, 795.8 mmol) and 1,4-dioxane/H ₂ O (800 ml/200 ml) were mixed and stirred at 120° C. for 4 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 purified by column chromatography (Hexane:EA = 7:1 (v/v)) to obtain 4-(2-nitronaphthalen-1-yl)-1H-indole (81.4 g, yield 71%) got

^1H -NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.43 (dd, 1H), 7.59 (d, 1H), 7.79-7.83 (m, 3H), 8.22-8.32 (m, 3H) ), 8.81 (d, 1H), 10.1 (b, 1H)

<Step 3> 1-(4- chlorophenyl )-4-(2- nitronaphthalene -One- yl )-1H- indole synthesis of

4-(2-nitronaphthalen-1-yl)-1H-indole (81.4 g, 282.5 mmol), 1-chloro-4-iodobenzene (80.8 g, 339.0 mmol), Cu (9.0 g, 141.2 mmol), K ₂ CO ₃ (78.1 g, 565.0 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 1-(4-chlorophenyl)-4-(2) was purified by column chromatography (Hexane:EA = 6:1 (v/v)). -nitronaphthalen-1-yl)-1H-indole (84.5 g, yield 75%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.37-7.49 (m, 5H), 7.60 (d, 1H), 7.79-7.90 (m, 3H), 8.10 (d, 1H), 8.22-8.32 (m , 3H), 8.81 (d, 1H)

<Step 4> 3-(4- chlorophenyl )-3,6- dihydrobenzo[c]pyrrolo [3,2-g] carbazole synthesis of

1-(4-chlorophenyl)-4-(2-nitronaphthalen-1-yl)-1H-indole (84.5 g, 211.9 mmol), triphenylphosphine (138.9 g, 529.7 mmol), and 1,2-dichlorobenzene (800 ml) was added and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, 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 = 5:1 (v/v)) to obtain 3-(4-chlorophenyl)-3,6-dihydrobenzo[c]pyrrolo[3,2-g ]carbazole (48.2 g, yield 62%) was obtained.

^1H -NMR: δ 6.54 (d, 1H), 7.37 (d, 2H), 7.49 (d, 2H), 7.60-7.67 (m, 6H), 7.94 (d, 1H), 8.16 (d, 1H), 8.54 (d, 1H), 10.1 (b, 1H)

<Step 5> 6-(biphenyl-3- yl )-3-(4- chlorophenyl Synthesis of )-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole

3-(4-chlorophenyl)-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole (48.2 g, 131.4 mmol), 3-bromobiphenyl (36.7 g, 157.6 mmol), Cu (4.2 g, 65.7 mmol), K ₂ CO ₃ (36.3 g, 262.7 mmol) and nitrobenzene (700 ml) were mixed and stirred at 210 °C for 12 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 purified by column chromatography (Hexane:EA = 6:1 (v/v)) to obtain 6-(biphenyl-3-yl)-3-(4-chlorophenyl)-3,6-dihydrobenzo [c]pyrrolo[3,2-g]carbazole (38.2 g, yield 56%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.37-7.52 (m, 12H), 7.60-7.67 (m, 4H), 7.94-7.96 (m, 3H), 8.09 (d, 1H), 8.16 (d , 1H), 8.54 (d, 1H)

<Step 6> 6-(biphenyl-3- yl )-3-(4-(4,4,5,5- tetramethyl Synthesis of -1,3,2-dioxaborolan-2-yl)phenyl)-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole

6-(biphenyl-3-yl)-3-(4-chlorophenyl)-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole (38.2 g, 73.6 mmol), 4,4, 4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (20.5 g, 80.9 mmol), Pd(dppf)Cl ₂ (6.4 g , 7.4 mmol), KOAc (20.8 g, 220.6 mmol) and 1,4-Dioxane (500 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 = 8:1 (v/v)) to obtain 6-(biphenyl-3-yl)-3- (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole (34.1 g, Yield 76%) was obtained.

^1H -NMR: δ 1.24 (s, 12H), 6.52 (d, 1H), 7.41-7.52 (m, 8H), 7.60-7.67 (m, 6H), 7.75 (d, 2H), 7.94-7.96 (m , 3H), 8.09 (s, 1H), 8.16 (d, 1H), 8.54 (d, 1H)

<Step 7> 6-(biphenyl-3- yl )-3-(2'- nitrobiphenyl -4- yl Synthesis of )-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole

6-(biphenyl-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,6-dihydrobenzo[ c]pyrrolo[3,2-g]carbazole (34.1 g, 55.9 mmol), 1-bromo-2-nitrobenzene (13.6 g, 67.1 mmol), Pd(PPh ₃ ) ₄ (3.2 g, 2.8 mmol), K ₂ CO ₃ (15.5 g, 111.8 mmol) and 1,4-dioxane/H ₂ O (500 ml/100 ml) were mixed and stirred at 120° C. for 4 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 purified by column chromatography (Hexane:EA = 7:1 (v/v)) to obtain 6-(biphenyl-3-yl)-3-(2'-nitrobiphenyl-4-yl)- 3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole (26.8 g, yield 79%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.41-7.68 (m, 15H), 7.79 (d, 2H), 7.94-8.09 (m, 7H), 8.16 (d, 1H), 8.54 (d, 1H) )

<Step 8> CIC - 5 of synthesis

6-(biphenyl-3-yl)-3-(2'-nitrobiphenyl-4-yl)-3,6-dihydrobenzo[c]pyrrolo[3,2-g]carbazole (26.8 g, 44.2 mmol) under nitrogen stream After adding triphenylphosphine (29.0 g, 110.4 mmol) and 1,2-dichlorobenzene (300 ml), the mixture was stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, 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 = 5:1 (v/v)) to obtain CIC-5 (14.2 g, yield 56%).

^1H -NMR: δ 6.52 (d, 1H), 7.23-7.29 (m, 2H), 7.41-7.67 (m, 14H), 7.83 (s, 1H), 7.94-7.96 (m, 3H), 8.09-8.16 (m, 4H), 8.54 (d, 1H), 10.1 (b, 1H)

[ synthesis example 1] Synthesis of A-1

CIC-1 (3.0 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol) under nitrogen stream ), 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 stirred at 110 °C for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound A-1 (3.6 g, yield 71%).

Mass (Theory: 754.88, Measured: 754 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 (3.4 g, yield 74%).

Mass (Theory: 679.77, Measured: 679 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 (3.7 g, yield 73%).

Mass (Theory: 754.88, Measured: 754 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 (3.3 g, yield 65%).

Mass (Theory: 755.87, Measured: 755 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. Except for the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-5 (3.1 g, yield 61%).

Mass (Theory: 755.87, Measured: 755 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 (4.1 g, yield 74%).

Mass (Theory: 830.97, Measured: 830 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 (3.9 g, yield 70%).

Mass (Theory: 831.96, Measured: 831 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 (4.0 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1 except for using.

Mass (Theory: 831.96, Measured: 831 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 (2.8 g, yield 64%) was obtained.

Mass (Theory: 652.74, Measured: 652 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 (3.3 g, yield 65%) was obtained.

Mass (Theory: 750.89, Measured: 750 g/mol)

[ synthesis example 11] Synthesis of B-1

CIC-2 (2.1 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol) under nitrogen stream ), 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 stirred at 110 °C for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound B-1 (3.3 g, yield 65%).

Mass (Theory: 754.88, Measured: 754 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 68%).

Mass (Theory: 679.77, Measured: 679 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 (3.4 g, yield 67%).

Mass (Theory: 754.88, Measured: 754 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 (3.6 g, yield 71%).

Mass (Theory: 755.87.88, Measured: 755 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 (3.7 g, yield 74%).

Mass (Theory: 755.87, Measured: 755 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 (3.6 g, yield 65%).

Mass (Theory: 830.97, Measured: 830 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 (3.7 g, yield 66%).

Mass (Theory: 831.96, Measured: 831 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 (3.9 g, yield 70%) was obtained by performing the same procedure as Synthesis Example 11 except for using.

Mass (Theory: 831.96, Measured: 831 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 (3.3 g, yield 75%) was obtained.

Mass (Theory: 652.74, Measured: 652 g/mol)

[ synthesis example 20] Synthesis of B-10

Purpose Compound B-10 (3.6 g, yield 71%) was obtained.

Mass (Theory: 750.9, Measured: 750 g/mol)

[ synthesis example 21] Synthesis of C-1

CIC-3 (2.1 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol) under nitrogen stream ), 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 stirred at 110 °C for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound C-1 (3.5 g, yield 70%).

Mass (Theory: 754.88, Measured: 754 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 (2.8 g, yield 61%).

Mass (Theory: 679.77, Measured: 679 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 (3.1 g, yield 62%).

Mass (Theory: 754.88, Measured: 754 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 (3.2 g, yield 63%).

Mass (Theory: 755.87, Measured: 755 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 (3.4 g, yield 68%).

Mass (Theory: 755.87, Measured: 755 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 (4.0 g, yield 71%).

Mass (Theory: 830.97, Measured: 830 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) was performed in the same manner as in Synthesis Example 21 to obtain the target compound C-7 (4.2 g, yield 75%).

Mass (Theory: 831.96, Measured: 831 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 target compound C-8 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 21 except for using.

Mass (Theory: 831.96, Measured: 831 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 (2.8 g, yield 64%) was obtained.

Mass (Theory: 652.74, Measured: 652 g/mol)

[ synthesis example 30] Synthesis of C-10

Purpose Compound C-10 (3.0 g, yield 60%) was obtained.

Mass (Theory: 750.89, Measured: 750 g/mol)

[ synthesis example 31] Synthesis of D-1

CIC-4 (3.5 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol) under a nitrogen stream ), 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 stirred at 110 °C for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound D-1 (3.6 g, yield 65%).

Mass (Theory: 829.99, Measured: 829 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 60%).

Mass (Theory: 754.88, Measured: 754 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 (3.9 g, yield 70%).

Mass (Theory: 829.99, Measured: 829 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 (3.6 g, yield 65%).

Mass (Theory: 830.98, Measured: 830 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 (3.8 g, yield 68%).

Mass (Theory: 830.98, Measured: 830 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 (4.0 g, yield 66%).

Mass (Theory: 906.08, Measured: 906 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 (3.8 g, yield 62%).

Mass (Theory: 907.07, Measured: 907 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 (4.3 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 31 except for using.

Mass (Theory: 907.07, Measured: 907 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 (3.6 g, yield 74%) was obtained.

Mass (Theory: 727.85, Measured: 727 g/mol)

[ synthesis example 40] Synthesis of D-10

4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine 대신 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol)을 사용하는 것을 제외하고는 합성예 31과 동일한 과정을 수행하여 목적 화합물인 D-10 (3.9 g, 수율 70%)을 얻었다.

Purpose Compound D-10 (3.9 g, yield 70%) was obtained.

Mass (Theory: 826.0, Measured: 826 g/mol)

[ synthesis example 41] Synthesis of E-1

CIC-5 (3.8 g, 6.7 mmol), 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol) under a nitrogen stream ), 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 stirred at 110 °C for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound E-1 (3.7 g, yield 62%).

Mass (Theory: 880.04, Measured: 880 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 (3.2 g, yield 59%).

Mass (Theory: 804.93, Measured: 804 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 (3.8 g, yield 64%).

Mass (Theory: 880.04, Measured: 880 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 (3.6 g, yield 61%).

Mass (Theory: 881.03, Measured: 881 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 (3.9 g, yield 66%).

Mass (Theory: 881.03, Measured: 881 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 (3.8 g, yield 59%).

Mass (Theory: 956.13, Measured: 956 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) was performed in the same manner as in Synthesis Example 41 to obtain the target compound E-7 (3.5 g, yield 54%).

Mass (Theory: 957.12, Measured: 957 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 (3.7 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 41 except for using.

Mass (Theory: 957.12, Measured: 957 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 (3.3 g, yield 63%) was obtained.

Mass (Theory: 777.90, Measured: 777 g/mol)

[ synthesis example 50] Synthesis of E-10

Purpose Compound E-10 (3.9 g, yield 67%) was obtained.

Mass (Theory: 876.05, Measured: 876 g/mol)

[ synthesis example 51] Synthesis of F-1

CIC-1 (3.0 g, 6.7 mmol), N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g) under nitrogen stream , 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 stirred at 110°C for 5 hours. . After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound, F-1 (3.7 g, yield 60%).

Mass (Theory: 920.11, Measured: 920 g/mol)

[ synthesis example 52] F- 2 of synthesis

Except for using N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine Then, the same process as Synthesis Example 51 was performed to obtain the target compound F-2 (3.9 g, yield 62%).

Mass (Theory: 817.98, Measured: 817 g/mol)

[ synthesis example 53] F- 3 of synthesis

CIC-2 (3.0 g, 6.7 mmol), N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g) under a nitrogen stream , 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 stirred at 110°C for 5 hours. . After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound F-3 (3.4 g, yield 55%).

Mass (Theory: 920.11, Measured: 920 g/mol)

[ synthesis example 54] F- 4 of synthesis

N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine N-(4'-bromobiphenyl-4-yl) Except for using -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 62%).

Mass (Theory: 817.98, Measured: 817 g/mol)

[ synthesis example 55] Synthesis of F-5

CIC-3 (3.0 g, 6.7 mmol), N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd(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 stirred at 110 ° C for 5 hours. did After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound F-5 (4.1 g, yield 67%).

Mass (Theory: 920.11, Measured: 920 g/mol)

[ synthesis example 56] Synthesis of F-6

Except for using N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine Then, the same process as in Synthesis Example 55 was performed to obtain the target compound F-6 (3.0 g, yield 54%).

Mass (Theory: 817.98, Measured: 817 g/mol)

[ synthesis example 57] Synthesis of F-7

CIC-4 (3.5 g, 6.7 mmol), N,N-di(biphenyl-4-yl)-4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol), Pd(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 stirred at 110 ° C for 5 hours. did After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound, F-7 (3.7 g, yield 56%).

Mass (Theory: 995.22, Measured: 995 g/mol)

[ synthesis example 58] Synthesis of F-8

Except for using N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine Then, the same procedure as in Synthesis Example 57 was performed to obtain the target compound F-8 (3.5 g, yield 59%).

Mass (Theory: 893.09, Measured: 893 g/mol)

[ synthesis example 59] Synthesis of F-9

CIC-5 (3.8 g, 6.7 mmol), N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (2.74 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g) under a nitrogen stream , 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 stirred at 110°C for 5 hours. . After the reaction was completed, toluene was concentrated, the solid salt was filtered, and purified by recrystallization to obtain the target compound F-9 (3.7 g, yield 53%).

Mass (Theory: 1045.27, Measured: 1045 g/mol)

[ synthesis example 60] Synthesis of F-10

Except for using N-(4'-bromobiphenyl-4-yl)-N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of 4-(biphenyl-4-yl)-6-chloro-2-phenylpyrimidine Then, the same process as in Synthesis Example 59 was performed to obtain the target compound F-10 (3.3 g, yield 52%).

Mass (Theory: 943.14, Measured: 943 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 of the 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, 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 electroluminescent device.

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

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except for using CBP instead of Compound A-1 as a 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]

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

Sample host Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 A-1 6.86 515 41.3 Example 2 A-2 6.48 518 41.2 Example 3 A-3 6.86 515 38.9 Example 4 A-4 6.77 515 41.3 Example 5 A-5 6.66 515 41.2 Example 6 A-6 6.65 515 38.9 Example 7 A-7 6.65 518 41.3 Example 8 A-8 6.77 518 41.3 Example 9 A-10 6.66 515 41.3 Example 10 B-1 6.66 518 41.2 Example 11 B-2 6.51 518 41.3 Example 12 B-3 6.77 518 41.3 Example 13 B-4 6.70 517 41.2 Example 14 B-5 6.51 515 38.9 Example 15 B-6 6.77 515 41.3 Example 16 B-7 6.46 515 41.3 Example 17 B-8 6.51 515 41.3 Example 18 B-10 6.77 518 41.2 Example 19 C-1 6.70 518 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 41.3 Example 23 C-5 6.66 518 41.2 Example 24 C-6 6.70 517 38.9 Example 25 C-7 6.70 515 41.3 Example 26 C-8 6.51 518 41.3 Example 27 C-10 6.77 518 41.3 Example 28 D-1 6.70 517 41.2 Example 29 D-2 6.51 515 42.2 Example 30 D-3 6.77 515 42.0 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 6.70 517 42.0 Example 39 E-3 6.66 518 39.7 Example 40 E-4 6.81 517 41.3 Example 41 E-5 6.68 518 41.3 Example 42 E-6 6.66 517 41.3 Example 43 E-7 6.70 518 41.2 Example 44 E-8 6.70 518 42.0 Example 45 E-10 6.51 518 39.7 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 each compound 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 for using CBP instead of Compound A-9 as a 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 4.81 10.8 Example 47 B-9 4.64 13.2 Example 48 C-9 4.64 11.9 Example 49 D-9 4.64 11.9 Example 50 E-9 4.87 12.5 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 (Doosan Electronics Co., Ltd.) + 5% DS-501 (Doosan Electronics Co., Ltd.) on the ITO transparent electrode prepared as above ) (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm), an organic EL device was prepared in this order.

[ 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 19.2 Example 52 F-2 4.8 21.1 Example 53 F-3 4.7 19.4 Example 54 F-4 4.8 20.0 Example 55 F-5 4.9 19.2 Example 56 F-6 4.8 21.1 Example 57 F-7 4.8 19.4 Example 58 F-8 4.8 19.4 Example 59 F-9 4.9 20.0 Example 60 F-10 4.6 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 high-purity sublimation purification, 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% of 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) / An organic electroluminescent device was prepared by stacking LiF (1 nm)/Al (200 nm) in this order.

[ 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

An organic electroluminescent device was manufactured in the same manner as in Example 61, except for using BCP instead of Compound A-1 as the lifespan improvement layer material 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 4.2 6.1 459 44 Example 62 A-2 4.2 6.1 462 45 Example 63 A-3 4.2 6.2 463 45 Example 64 A-4 4.3 6.2 459 32 Example 65 A-5 4.3 6.4 459 39 Example 66 A-6 4.1 6.3 459 38 Example 67 A-7 4.2 6.3 451 32 Example 68 A-8 4.3 6.2 459 39 Example 69 B-1 4.3 6.2 459 38 Example 70 B-2 4.1 6.4 459 32 Example 71 B-3 4.2 6.3 459 39 Example 72 B-4 4.2 6.3 451 45 Example 73 B-5 4.3 6.3 459 45 Example 74 B-6 4.2 6.5 462 32 Example 75 B-7 4.2 6.4 463 39 Example 76 B-8 4.3 6.3 459 38 Example 77 C-1 4.3 6.4 459 39 Example 78 C-2 4.6 6.3 459 38 Example 79 C-3 4.6 6.4 451 37 Example 80 C-4 4.3 6.3 459 39 Example 81 C-5 4.4 6.2 459 44 Example 82 C-6 4.6 6.2 459 42 Example 83 C-7 4.5 6.4 459 44 Example 84 C-8 4.1 6.4 451 43 Example 85 D-1 4.4 6.3 462 43 Example 86 D-2 4.5 6.3 463 48 Example 87 D-3 4.6 6.2 460 49 Example 88 D-4 4.7 6.2 459 41 Example 89 D-5 4.4 6.3 459 42 Example 90 D-6 4.3 6.4 451 47 Example 91 D-7 4.5 6.2 460 43 Example 92 D-8 4.4 6.3 460 48

Sample life improvement layer Driving voltage (V) Current efficiency (cd/A) Emission peak (nm) Life (hr, T ₉₇ ) Example 93 E-1 4.7 6.4 459 47 Example 94 E-2 4.6 6.4 459 43 Example 95 E-3 4.7 6.2 451 48 Example 96 E-4 4.7 6.2 469 49 Example 97 E-5 4.5 6.2 461 44 Example 98 E-6 4.7 6.2 462 43 Example 99 E-7 4.6 6.4 460 43 Example 100 E-8 4.7 6.5 461 48 Comparative Example 4 - 4.8 6.0 461 49 Comparative Example 5 BCP 5.3 5.9 458 28

As shown in Tables 5 and 6, the blue organic EL device using the lifespan improvement layer according to the present invention (Examples 61 to 100) is an organic EL device without using the lifespan improvement layer (Comparative Example 4) It can be confirmed that the current efficiency and lifespan are excellent compared to the conventional BCP life improvement layer, and the driving voltage and current efficiency are excellent as compared to the blue organic electroluminescent device (Comparative Example 5) using the lifespan improvement layer, as well as the lifespan is 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 high-purity sublimation purification, 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% of 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 (cd/A) Emission peak (nm) Example 101 A-1 4.5 6.3 457 Example 102 A-6 4.5 5.8 463 Example 103 B-1 4.5 5.8 460 Example 104 B-6 4.2 5.8 457 Example 105 C-1 4.5 6.0 463 Example 106 C-6 4.4 5.8 457 Example 107 D-1 4.5 5.8 463 Example 108 D-6 4.2 5.8 457 Example 109 E-1 4.5 5.8 463 Example 110 E-6 4.2 5.8 461 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 6) without using the electron transport layer. It was confirmed that the voltage and current efficiency were excellent.

As such, it can be confirmed that the organic electroluminescent device using the compound represented by Formula 1 according to the present invention in the light emitting layer, lifespan improvement layer, and electron transport layer has improved driving voltage and current efficiency, and further improved lifespan characteristics. there was.

Claims (8)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
L ₁ is a single bond or is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms;
A and B are the same as or different from each other, and are each independently a 6-membered aromatic ring or a 6-membered heteroaromatic ring,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ Alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or Unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl A boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and It is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring;
a and b are each independently an integer of 0 to 4, and when a and b are each independently an integer of 1 to 4, R ₁ and R ₂ are the same as or different from each other, and each independently deuterium (D), halogen, Cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted Or an unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, or an adjacent group combined to form a condensed ring, provided that when R ₁ and R ₂ are plural, they are the same as or different from each other;
X is N;
Arylene group and heteroarylene group of L ₁ , Ar ₁ and Ar ₂ , R ₁ and R ₂ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group , Substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted A substituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphos It may be substituted with one or more substituents selected from the group consisting of a pin group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, wherein the substituent When is plural, they may be the same as or different from each other. According to claim 1,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, and a substituted or unsubstituted C 6 ~ C 40 aryl group. It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine groups,
At this time, the Ar ₁ and Ar ₂ aryl groups, heteroaryl groups, and arylamine groups are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl groups, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted hetero having 5 to 40 nuclear atoms Aryl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or Unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~C ₄₀ aryl It may be substituted with one or more substituents selected from the group consisting of a phosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group. In this case, when the substituents are plural, they may be the same as or different from each other. According to claim 1,
Wherein R ₁ and R ₂ are the same as or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group selected from the group consisting of, or combined with an adjacent group to form a condensed ring can form,
At this time, the alkyl group, aryl group, heteroaryl group and arylamine group of R ₁ and R ₂ are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted substituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted 5 to 40 nuclear atoms A heteroaryl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, Substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ It may be substituted with one or more substituents selected from the group consisting of an arylphosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, wherein when the substituents are plural, they may be the same or different from each other there is. According to claim 1,
The compound represented by Formula 1 is a compound, characterized in that represented by any one of Formulas 3 and 5 below.
[Formula 3]

[Formula 5]

In Formulas 3 and 5,
Ar ₂ , a, b, R ₁ and R ₂ are each as defined in claim 1. According to claim 1,
A compound characterized in that at least one of Ar ₁ and Ar ₂ , R ₁ and R ₂ is a substituent represented by Formula 6 below.
[Formula 6]

In Formula 6,
* means a part bonded to Formula 1,
L ₂ is a single bond or is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₁₈ arylene group and a substituted or unsubstituted 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 ₄ ), wherein, when R ₄ is plural, they are the same as or different from each other;
R ₄ is hydrogen, deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group , A substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted A heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and substituted or unsubstituted C ₆ ~ C ₄₀ aryl It is selected from the group consisting of a silyl group, or may be bonded to an adjacent group to form a condensed ring,
The arylene group and the heteroarylene group of L ₂ , and an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, and an alkyl group of R ₄ A silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group, and an aryl silyl group are each independently deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, Substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted number of nuclear atoms 5 to 40 heteroaryl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl An amine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, a substituted or Unsubstituted C ₁ ~ C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ It may be substituted with one or more substituents selected from the group consisting of ~C ₄₀ arylphosphine oxide group and substituted or unsubstituted C ₆ ~C ₄₀ arylsilyl group, wherein when the substituents are plural, they are the same as each other or can be different According to claim 5,
A compound characterized in that the substituent of Formula 6 is represented by any one of the substituents represented by the following Formulas A1 to A15.

In the above formulas A1 to A15,
* means a part bonded to Formula 1,
L ₂ and R ₄ 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, R ₅ is deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms Group, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphos It is selected from the group consisting of a pinoxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring,
An alkyl group, an _alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkylboron group, an arylboron group, Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ Alkenyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted A substituted C ₆ ~ C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron A substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine oxide group, and a substituted group. Or, it may be substituted with one or more substituents selected from the group consisting of unsubstituted C ₆ ~ C ₄₀ arylsilyl groups. In this case, when the substituents are 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 1 to 6. According to claim 7,
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.