KR102507368B1 - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

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

Description

Organic compound and organic electroluminescent device using the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to a novel compound having excellent light emitting ability, electron transport ability, etc. It relates to an organic electroluminescent device with improved characteristics.

Research on organic electroluminescent devices, which led to blue electroluminescence using an anthracene single crystal in 1965 from Bernanose's observation of organic thin film emission in the 1950s, was divided into a hole layer and a functional layer of light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure is presented. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

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

Materials for forming the light emitting layer of the organic electroluminescent 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.

Until now, NPB, BCP, Alq ₃ , etc. have been widely known as materials used in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials. . In particular, phosphorescent materials that have a great advantage in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ as blue, green, and red dopant materials. is being used as 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 have low glass transition temperatures and very poor thermal stability, so they are not satisfactory in terms of lifespan in organic light emitting devices. Therefore, there is a demand for the development of light emitting materials having excellent performance.

Japanese Laid-Open 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, hole transport, luminescence, electron transport, electron injection, etc. The purpose.

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

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

In Formula 1,

A is a 6-membered aromatic ring or a 6-membered heteroaromatic ring;

B is a nitrogen-containing heteroaryl group having 5 to 60 nuclear atoms,

X ₁ to X ₄ are the same as or different from each other, and are each independently N or C(R ₁ ), at least one of which is C(R ₁ ),

R ₁ is hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group , C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ It is selected from the group consisting of an arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring, wherein R ₁ is plural, they are the same as or different from each other,

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

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

In addition, the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound represented by Formula 1. An electroluminescent device is provided. Here, at least one of the organic material layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an auxiliary electron transport layer, an electron transport layer, and an electron injection layer, It is preferable that it is a light emitting layer, an electron transport auxiliary layer, or an electron transport layer. In this case, the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer.

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

In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent host material or an electron transport layer material, an organic electric field having excellent light emitting performance, low driving voltage, high efficiency and long lifetime compared to conventional host materials or electron transport layer materials. A light emitting device can be manufactured, and a full color display panel with improved performance and lifespan can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

)의 C2 위치에 전자 끌개기(EWG)가 연결된 구조를 기본 골격을 하며, 이러한 기본 골격에 다양한 치환기가 도입된 상기 화학식 1로 표시된다. The novel compound according to the present invention is a pyrrolocarbazole moiety,

) has a structure in which an electron withdrawing group (EWG) is connected to the C2 position of the basic skeleton, and is represented by the above formula (1) in which various substituents are introduced to this basic skeleton.

As a conventional compound, if there are no substituents at the C2 and C3 positions of the pyrrolocarbazole moiety (see Compound I below), it can be used as a high-efficiency material for devices, but since the binding force of the C2-C3 bond is weaker than other parts, the device There was a disadvantage that the life of the was reduced. In order to compensate for this, when benzene is bonded to the C2 position (see Compound II below), the lifetime of the device is improved by 2 to 2.5 times, but the efficiency tends to decrease by 30 to 40%. The reason for this is that when an aryl group having an electro-donating property is substituted at the C2-C3 position where the band bond is weak in the pyrrolocarbazole moiety having a strong hole accepting property, hole mobility ) becomes stronger and the charge balance in the molecule can be broken. Therefore, in the present invention, in order to develop a novel compound having superior properties compared to the conventional compounds, the durability of the compound is achieved by binding a heteroaryl group having an electro-withdrawing property to the C2-C3 position of the pyrrolocarbazole moiety. , and through this, it is possible to improve the life characteristics of the device and improve the efficiency characteristics (see Evaluation Example 2 below).

Since the compound represented by Formula 1 has an electron withdrawing group bonded to the C2 position of the structurally weak pyrrolocarbazole moiety, the compound has excellent thermal stability, luminescence, hole transport, hole injection, etc. great. Therefore, when the compound represented by Chemical Formula 1 according to the present invention is applied to an organic electroluminescent device, the driving voltage, current efficiency, lifespan, and the like of the device can be improved. In this case, since an electron withdrawing group having high electron absorption is bonded to the compound represented by Chemical Formula 1, the entire molecule has a bipolar characteristic, and thus the bonding force between holes and electrons can be increased. The compound represented by Chemical Formula 1 can exhibit excellent light emitting properties, and thus can be usefully applied as a material for a blue, green or red phosphorescent light emitting layer of an organic electroluminescent device.

The compound represented by Chemical Formula 1 can significantly increase the molecular weight of the compound by introducing various substituents, particularly aryl and/or heteroaryl groups, into the basic skeleton, thereby improving the glass transition temperature, thereby improving conventional light emitting materials. [Example: 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] may have higher thermal stability. In addition, electron transport ability may be improved according to the characteristics of the substituent bonded to the basic skeleton. Therefore, the compound represented by Chemical Formula 1 according to the present invention has a certain level of electron mobility or higher, and can be used as a material for an electron transport layer of an organic electroluminescent device.

Meanwhile, in the phosphorescent light emitting layer of the organic electroluminescent device, the triplet energy gap of the host material should be higher than that of the dopant. 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, the energy level can be adjusted higher than that of the dopant by introducing a specific substituent into the condensed indole derivative (pyrrolocarbazole moiety) having a wide singlet energy level and a high triplet energy level. Therefore, it can be used as a host material.

Furthermore, 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 light emitting device including the compound represented by Chemical Formula 1 according to the present invention can be greatly improved, and as a result, the performance of the full color organic light emitting panel can be maximized.

As described above, the compound represented by Chemical Formula 1 can improve the phosphorescent properties of the organic EL device, as well as improve electron injection/transport capability, luminous efficiency, driving voltage, lifetime characteristics, and the like. 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), an electron transport auxiliary layer material and an electron transport layer material, more preferably Preferably, it can be used as a material for a phosphorescent light emitting layer.

That is, when the compound of Formula 1 according to the present invention is used as an electron injection/transport layer material or a blue, green and/or red phosphorescent host material of an organic electroluminescent device, compared to a conventional organic material layer material (eg, CBP), organic Efficiency and lifetime of the 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.

Specifically, in the compound represented by Formula 1 according to the present invention, 'one electron withdrawing group (EWG, B)' is connected to the terminal 5-membered ring of the 'pyrrolocarbazole moiety', and the pyrrolocarbazole moiety It is a structure in which various substituents are bonded to 5-membered rings in Tee.

In the compound represented by Formula 1, A is a 6-membered aromatic ring or a 6-membered heteroaromatic ring, and constitutes a pyrrolocarbazole moiety.

Preferably, A may be a 6-membered aromatic ring.

At this time, the structure of the pyrrolocarbazole moiety may be different depending on the binding position of the 6-membered aromatic ring. The compound represented by Formula 1 may be a compound represented by any one of Formulas 2 to 7 below.

In Chemical Formulas 2 to 7, B, X ₁ to X ₄ , Ar ₁ , and Ar ₂ are each as defined in Chemical Formula 1 above.

In the compound represented by Formula 1, X ₁ to X ₄ are the same as or different from each other, and are each independently N or C(R ₁ ), and at least one of them is C(R ₁ ).

Preferably, all of X ₁ to X ₄ may be C(R ₁ ).

Here, R ₁ is hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cyclo Alkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryl Oxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a phosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring, wherein R ₁ is plural In case, they are the same or different.

Preferably, the plurality of R ₁ is hydrogen or a C ₁ to C ₄₀ alkyl group, or one R ₁ and another R ₁ may be bonded to each other to form a condensed aromatic ring.

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

Preferably, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ ~ C ₆₀ aryloxy group, C ₆ ~ C ₆₀ arylsilyl group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, and It may be selected from the group consisting of C ₆ ~ C ₆₀ arylamine groups.

In the compound of Formula 1, B where the electron withdrawing group is located may be a nitrogen-containing heteroaryl group having 5 to 60 nuclear atoms having high electron withdrawing property. Such a heteroaryl group may contain only nitrogen (N) as a hetero atom, or may further contain O or S together with N.

Preferably, B may be a substituent represented by Formula 8 below.

In Formula 8, * means a moiety bonded to Formula 1.

Y ₁ to Y ₅ are the same as or different from each other, and are each independently N or C(R ₂ ), and at least one of them is N.

Preferably, at least two of Y ₁ to Y ₅ are N, and the rest may be C(R ₂ ).

In this case, when R ₂ is plural, they are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₃ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkyl boron group, C ₆ It is selected from the group consisting of ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group, and C ₆ ~C ₆₀ arylamine group, or a condensed ring with an adjacent group can form In particular, one R ₂ and another R ₂ may bond to each other to form a condensed ring.

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

The substituent represented by Chemical Formula 8 may be represented by any one of the substituents represented by Chemical Formulas A1 to A15.

In Formulas A1 to A15, R ₂ is as defined in Formula 8 above.

m is an integer from 0 to 4; In this case, when m is 0, it means that hydrogen is not substituted with R ₃ , and when m is an integer of 1 to 4, it means that one or more hydrogen atoms are substituted with R ₃ . When these R ₃ are plural, they are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ It is selected from the group consisting of an arylboron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or may form a condensed ring with an adjacent group. there is. At this time, one R ₃ and the other R ₃ or one R ₃ and one R ₂ may combine with each other to form a condensed ring.

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

Preferably, the R ₃ are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or one R ₃ and the other one R ₃ or one R ₃ and one R ₂ may combine with each other to form a condensed ring.

According to an example of the present invention, the compound represented by Chemical Formula 1 may be prepared as a final compound from Synthesis Formula 2 or 3 after intermediate (C2-PC) is prepared through Synthesis Formula 1 below.

[Synthetic formula 1]

[Synthetic Formula 2]

[Synthetic Formula 3]

In Synthesis Formulas 1 to 3, A and B, X ₁ to X ₄ , Ar ₁ , and Ar ₂ are as defined in Formula 1, and X is any one of group 17 elements of the periodic table.

Compounds represented by Formula 1 according to the present invention described above include compounds A-1 to A-8, B-1 to B-8, C-1 to C-8, D-1 to D-8, A compound represented by any one of E-1 to E-8, F-1 to F-8, and G-1 to G-8 may be more specific. However, the compound represented by Formula 1 of the present invention is not limited to 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 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, “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, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

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

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include a linear, branched or cyclic structure. Examples of such 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, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

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

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.

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.

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

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, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and at least one organic material layer among them is represented by Formula 1 above. compounds may be included. Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer, an electron transport auxiliary layer or an electron transport layer.

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

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

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

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

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like can be used.

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, and the light emitting auxiliary 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 1] C2-PC- 1 of synthesis

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

5-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 2500 ml of 1,4-Dioxane were mixed and heated at 130 °C for 12 Stir for an hour.

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 5-(4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl)-1H-indole (93.0 g, yield 75%) was obtained.

^1H -NMR: δ 1.24 (s, 12H), 6.50 (d, 1H), 7.30 (d, 1H), 7.51 (d, 1H), 7.63 (d, 1H), 7.98 (s, 1H), 10.1 ( b, 1H)

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

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (93.0 g, 382.6 mmol), 1-bromo-2-nitrobenzene (92.7 g) under nitrogen stream , 459.1 mmol), Pd(PPh ₃ ) ₄ (22.1 g, 19.1 mmol), K ₂ CO ₃ (105.8 g, 765.2 mmol), 1000 ml of 1,4-Dioxane, and 200 ml of H ₂ O 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 5-(2-nitrophenyl)-1H-indole (73.8 g, yield 81%).

^1H -NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.67-7.77 (m, 3H), 7.87-8.05 (m, 4H), 10.1 (b, 1H)

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

5-(2-nitrophenyl)-1H-indole (73.8 g, 309.9 mmol), Iodobenzene (75.9 g, 371.9 mmol), Cu (9.8 g, 154.9 mmol), K ₂ CO ₃ (85.7 g, 619.8 mmol) under nitrogen stream ) and Nitrobenzene 1500 ml were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and purified by column chromatography (Hexane:EA = 5:1 (v/v)) to obtain 5-(2-nitrophenyl)-1-phenyl- 1H-indole (66.2 g, yield 68%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.50-7.72 (m, 7H), 7.88-7.89 (m, 2H), 8.00-8.03 (m, 2H), 8.13 (d, 1H), 8.30 (d , 1H)

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

₁₂ Stir for an hour.

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 3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (25.0 g, yield 42 %) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.20 (dd, 1H), 7.50-7.62 (m, 8H), 7.94-7.96 (m, 2H), 8.19 (d, 1H), 8.53 (b, 1H) )

<Step 5> C2-PC- 1 of synthesis

3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (25.0 g, 88.5 mmol) and 2-chloro-3-phenylquinoxaline (23.4 g, 97.3 mmol), aluminum chloride (AlCl ₃ ) ( 13.0 g, 97.3 mmol), 1,2-dichloroethane (ο-DCE) 500 ml was added and stirred for 12 hours.

After completion of the reaction, 1,2-dichloroethane was removed, extraction was performed with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 4:1 (v/v)) to obtain C2-PC-1 (27.6 g, yield 64%).

^1H -NMR: δ 6.80 (s, 1H), 7.20 (dd, 1H), 7.32 (dd, 2H), 7.50-7.67 (m, 10H), 7.79-7.80 (m, 2H), 8.03 (d, 2H) ), 8.19 (d, 1H), 8.62 (b, 1H)

[ preparation example 2] C2-PC- 2 of synthesis

Except for using 2-chloro-4-phenylquinazoline (23.4 g, 97.3 mmol) instead of 2-chloro-3-phenylquinoxaline in <Step 5>, the same procedure as in Preparation Example 1 was performed, and the target compound C2-PC- 2 (31.0 g, yield 72%) was obtained.

^1H -NMR: δ 6.80 (s, 1H), 7.20 (dd, 1H), 7.49-7.65 (m, 11H), 7.80-7.84 (m, 4H), 7.94-7.96 (m, 2H), 8.13-8.19 (m, 2H), 8.58 (b, 1H)

[ preparation example 3] C2-PC- 3 of synthesis

Except for using 2-chloro-4,6-diphenylpyrimidine (26.0 g, 97.3 mmol) instead of 2-chloro-3-phenylquinoxaline in <Step 5>, the same procedure as in Preparation Example 1 was performed to obtain the target compound, C2- PC-3 (23.6 g, yield 52%) was obtained.

^1H -NMR: δ 6.80 (s, 1H), 7.20 (dd, 1H), 7.49-7.63 (m, 13H), 7.94-7.96 (m, 6H), 8.19 (d, 1H), 8.58 (b, 1H) ), 8.73 (s, 1H)

[ preparation example 4] C2-PC- 4 of synthesis

Same procedure as in Preparation Example 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (26.1 g, 97.3 mmol) was used instead of 2-chloro-3-phenylquinoxaline in <Step 5>. was performed to obtain the target compound, C2-PC-4 (28.6 g, yield 63%).

^1H -NMR: δ 6.80 (s, 1H), 7.20 (dd, 1H), 7.50-7.63 (m, 13H), 7.94-7.96 (m, 2H), 8.19 (d, 1H), 8.36-8.38 (m , 4H), 8.58 (b, 1H)

[ preparation example 5] C2-PC- 5 of synthesis

In <Step 2>, 1-bromo-2-nitronaphthalene (115.7 g, 459.1 mmol) was used instead of 1-bromo-2-nitrobenzene, and in <Step 5>, 2-chloro-4 instead of 2-chloro-3-phenylquinoxaline, Except for using 6-diphenyl-1,3,5-triazine (26.1 g, 97.3 mmol), the same procedure as in Preparation Example 1 was performed to obtain the target compound, C2-PC-5 (21.7 g, yield 48%) got

^1H -NMR: δ 6.80 (s, 1H), 7.50-7.65 (m, 15H), 7.94-7.99 (m, 3H), 8.37-8.40 (m, 4H), 8.54 (d, 1H), 8.71 (b) , 1H)

[ preparation example 6] C2-PC- 6 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 2500 ml of 1,4-Dioxane were mixed and heated at 130 °C for 12 Stir for an hour.

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 (104.2 g, yield 84%) was obtained.

^1H -NMR: δ 1.20 (s, 12H), 6.56 (d, 1H), 7.14 (d, 1H), 7.37-7.42 (m, 2H), 7.63 (d, 1H), 8.34 (b, 1H)

<Step 2> 4-(2- nitrophenyl )-1H- indole synthesis of

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (104.2 g, 428.4 mmol), 1-bromo-2-nitrobenzene (103.9 g) under nitrogen stream , 514.2 mmol), Pd(PPh ₃ ) ₄ (24.8 g, 21.4 mmol), K ₂ CO ₃ (118.4 g, 856.9 mmol), 1,4-Dioxane 1000 ml, and H ₂ O 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 4-(2-nitrophenyl)-1H-indole (86.8 g, yield 85%).

^1H -NMR: δ 6.56 (d, 1H), 7.14 (d, 1H), 7.56 (dd, 1H), 7.72-7.73 (m, 2H), 7.89-8.03 (m, 4H), 8.32 (b, 1H) )

<Step 3> 4-(2- nitrophenyl )-1-phenyl-1H- indole synthesis of

4-(2-nitrophenyl)-1H-indole (86.8 g, 364.2 mmol), Iodobenzene (89.2 g, 437.0 mmol), Cu (11.6 g, 182.1 mmol), K ₂ CO ₃ (100.7 g, 728.4 mmol) under nitrogen stream ) and Nitrobenzene 1500 ml were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, it was extracted with ethyl acetate, then water was removed with MgSO ₄ , and purified by column chromatography (Hexane:EA = 5:1 (v/v)) to obtain 4-(2-nitrophenyl)-1-phenyl- 1H-indole (64.1 g, yield 56%) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.50-7.72 (m, 8H), 7.89 (dd, 1H), 8.00-8.04 (m, 3H), 8.22 (d, 1H)

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

4-(2-nitrophenyl)-1-phenyl-1H-indole (64.1 g, 204.0 mmol), triphenylphosphine (133.7 g, 509.9 mmol), and 1000 ml of 1,2-dichlorobenzene were added under a nitrogen stream, followed by stirring 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 3-phenyl-3,6-dihydropyrrolo[2,3-c]carbazole (41.5 g, yield 72 %) was obtained.

^1H -NMR: δ 6.52 (d, 1H), 7.20 (dd, 1H), 7.50-7.63 (m, 9H), 7.94 (d, 1H), 8.19 (d, 1H), 8.57 (b, 1H)

<Step 5> C2-PC- 6 of synthesis

3-phenyl-3,6-dihydropyrrolo[2,3-c]carbazole (41.5 g, 146.8 mmol) and 2-chloro-4-phenylquinazoline (38.9 g, 161.5 mmol), aluminum chloride (21.5 g, 161.5 mmol) under a nitrogen stream. mmol) and 500 ml of 1,2-dichloroethane were added and stirred for 12 hours.

After completion of the reaction, 1,2-dichloroethane was removed, extraction was performed with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:MC = 4:1 (v/v)) to obtain C2-PC-6 (43.6 g, yield 61%).

¹ H-NMR: δ 6.80 (s, 1H), 7.20 (dd, 1H), 7.49-7.65 (m, 12H), 7.80-7.84 (m, 4H), 7.94 (d, 1H), 8.13-8.19 (m , 2H), 8.59 (b, 1H)

[ preparation example 7] C2-PC- 7 of synthesis

Same procedure as in Preparation Example 6, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (43.2 g, 161.5 mmol) was used instead of 2-chloro-4-phenylquinazoline in <Step 5>. was carried out to obtain the target compound, C2-PC-7 (43.7 g, yield 58%).

^1H -NMR: δ 6.80 (s, 1H), 7.20 (dd, 1H), 7.50 -7.63 (m, 14H), 7.94 (d, 1H), 8.19 (d, 1H), 8.36-8.37 (m, 4H) ), 8.63 (b, 1H)

[ synthesis example 1] Synthesis of B-1

C2-PC-2 (3.3 g, 6.7 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2.75 g, 8.0 mmol), NaH (0.16 g, 6.7 mmol) and 25 ml of DMF were mixed and stirred at room temperature for 1 hour. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound B-1 (4.0 g, yield 76%).

Mass (Theory: 793.93, Measured: 793 g/mol)

[ synthesis example 2] Synthesis of B-2

2-chloro-4-(dibenzo[b,d]furan-4- instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound B-2 (3.8 g, yield 71%) ) was obtained.

Mass (Theory: 807.92, Measured: 807 g/mol)

[ synthesis example 3] Synthesis of B-3

2-chloro-4-(dibenzo[b,d]furan-3- instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound B-3 (3.9 g, yield 72%) ) was obtained.

Mass (Theory: 807.92, Measured: 807 g/mol)

[ synthesis example 4] Synthesis of B-4

C2-PC-2 (3.3 g, 6.7 mmol), 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5- under nitrogen stream triazine (3.4 g, 8.0 mmol), Pd(OAc) ₂ (0.15 g, 0.67 mmol), P-( t -bu) ₃ (0.33 ml, 1.34 mmol), NaO t -Bu (1.3 g, 13.4 mmol) and 25 ml of xylene was mixed and stirred at 140°C for 3 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound B-4 (4.1 g, yield 70%).

Mass (Theory: 870.03, Measured: 870 g/mol)

[ synthesis example 5] Synthesis of B-5

2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound B-5 (3.4 g, yield 70%).

Mass (Theory: 717.84, Measured: 717 g/mol)

[ synthesis example 6] Synthesis of B-6

2-chlorothiochromeno[4,3,2-de]quinazoline ( Except for using 2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound B-6 (3.5 g, yield 73%).

Mass (Theory: 720.85, Measured: 720 g/mol)

[ synthesis example 7] Synthesis of B-7

2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) instead of 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Except for using, the same procedure as in Synthesis Example 4 was performed to obtain the target compound B-7 (3.5 g, yield 75%).

Mass (Theory: 690.81, Measured: 690 g/mol)

[ synthesis example 8] Synthesis of B-8

2-chloro-4-phenylbenzo[4,5]thieno[ Except for using 3,2-d] pyrimidine (2.4 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound B-8 (3.6 g, yield 71%).

Mass (Theory: 746.89, Measured: 746 g/mol)

[ synthesis example 9] Synthesis of A-1

Except for using C2-PC-1 instead of C2-PC-2, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-1 (3.5 g, yield 65%).

Mass (Theory: 793.93, Measured: 793 g/mol)

[ synthesis example 10] Synthesis of A-2

Use C2-PC-1 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound A-2 (3.3 g, yield 62%).

Mass (Theory: 807.92, Measured: 807 g/mol)

[ synthesis example 11] Synthesis of A-3

Use C2-PC-1 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound A-3 (3.6 g, yield 67%).

Mass (Theory: 807.92, Measured: 807 g/mol)

[ synthesis example 12] Synthesis of A-4

Except for using C2-PC-1 instead of C2-PC-2, the same procedure as in Synthesis Example 4 was performed to obtain the target compound A-4 (4.1 g, yield 71%).

Mass (Theory: 870.03, Measured: 870 g/mol)

[ synthesis example 13] Synthesis of A-5

Use C2-PC-1 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-5 (2.5 g, yield 53). %) was obtained.

Mass (Theory: 717.84, Measured: 711 g/mol)

[ synthesis example 14] Synthesis of A-6

C2-PC-1 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chlorothiochromeno[4,3,2-de]quinazoline (2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound A-6 (3.3 g, yield 68%). ) was obtained.

Mass (Theory: 720.85, Measured: 720 g/mol)

[ synthesis example 15] Synthesis of A-7

C2-PC-1 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound A-7 (3.2 g, yield 69%).

Mass (Theory: 690.81, Measured: 690 g/mol)

[ synthesis example 16] Synthesis of A-8

C2-PC-1 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (2.4 g, 8.0 mmol) was used, but the same procedure as in Synthesis Example 4 was performed to obtain the target compound, A- 8 (3.1 g, yield 62%) was obtained.

Mass (Theory: 746.89, Measured: 746 g/mol)

[ synthesis example 17] Synthesis of C-1

Except for using C2-PC-3 instead of C2-PC-2, the same procedure as in Synthesis Example 1 was performed to obtain the target compound C-1 (3.9 g, yield 71%).

Mass (Theory: 819.55, Measured: 819 g/mol)

[ synthesis example 18] Synthesis of C-2

Use C2-PC-3 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound C-2 (3.6 g, yield 64%).

Mass (Theory: 833.54, Measured: 833 g/mol)

[ synthesis example 19] Synthesis of C-3

Use C2-PC-3 instead of C2-PC-2, 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4-(dibenzo[b,d]furan-3- Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound C-3 (3.7 g, yield 66%) ) was obtained.

Mass (Theory: 833.54, Measured: 833 g/mol)

[ synthesis example 20] Synthesis of C-4

Except for using C2-PC-3 instead of C2-PC-2, the same procedure as in Synthesis Example 4 was performed to obtain the target compound C-4 (3.7 g, yield 61%).

Mass (Theory: 895.65, Measured: 895 g/mol)

[ synthesis example 21] Synthesis of C-5

Use C2-PC-3 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound C-5 (3.4 g, yield 69). %) was obtained.

Mass (Theory: 743.46, Measured: 743 g/mol)

[ synthesis example 22] Synthesis of C-6

C2-PC-3 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chlorothiochromeno[4,3,2-de]quinazoline (2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound C-6 (3.7 g, yield 73%). ) was obtained.

Mass (Theory: 746.47, Measured: 746 g/mol)

[ synthesis example 23] Synthesis of C-7

C2-PC-3 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound C-7 (3.6 g, yield 74%).

Mass (Theory: 716.43, Measured: 716 g/mol)

[ synthesis example 24] Synthesis of C-8

C2-PC-3 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (2.4 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound, C- 8 (4.0 g, yield 78%) was obtained.

Mass (Theory: 772.51, Measured: 772 g/mol)

[ synthesis example 25] Synthesis of D-1

Except for using C2-PC-4 instead of C2-PC-2, the same procedure as in Synthesis Example 1 was performed to obtain the target compound D-1 (3.7 g, yield 68%).

Mass (Theory: 820.95, Measured: 820 g/mol)

[ synthesis example 26] Synthesis of D-2

Use C2-PC-4 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead. Except for using chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound D-2 (3.7 g, yield 67%).

Mass (Theory: 834.94, Measured: 834 g/mol)

[ synthesis example 27] Synthesis of D-3

Use C2-PC-4 instead of C2-PC-2, 2-chloro-4-(dibenzo[b,d]furan-3- instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound D-3 (3.9 g, yield 69%) ) was obtained.

Mass (Theory: 834.94, Measured: 834 g/mol)

[ synthesis example 28] Synthesis of D-4

Except for using C2-PC-4 instead of C2-PC-2, the same procedure as in Synthesis Example 4 was performed to obtain the target compound D-4 (3.5 g, yield 59%).

Mass (Theory: 897.05, Measured: 897 g/mol)

[ synthesis example 29] Synthesis of D-5

Use C2-PC-4 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead. Except for using chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound D-5 (3.6 g, yield 73). %) was obtained.

Mass (Theory: 744.86, Measured: 744 g/mol)

[ synthesis example 30] Synthesis of D-6

Use C2-PC-4 instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chlorothiochromeno[4,3,2-de]quinazoline (2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound D-6 (3.6 g, yield 72%). ) was obtained.

Mass (Theory: 747.87, Measured: 747 g/mol)

[ synthesis example 31] Synthesis of D-7

Use C2-PC-4 instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound D-7 (3.4 g, yield 70%).

Mass (Theory: 717.83, Measured: 717 g/mol)

[ synthesis example 32] Synthesis of D-8

Use C2-PC-4 instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (2.4 g, 8.0 mmol) was used, but the same procedure as in Synthesis Example 4 was performed to obtain the target compound, D- 8 (3.7 g, yield 72%) was obtained.

Mass (Theory: 773.91, Measured: 773 g/mol)

[ synthesis example 33] Synthesis of E-1

C2-PC-5 (3.8 g, 6.7 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2.75 g, 8.0 mmol), NaH (0.16 g, 6.7 mmol) and 25 ml of DMF were mixed and stirred at room temperature for 1 hour. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound E-1 (3.6 g, yield 62%).

Mass (Theory: 871.01, Measured: 871 g/mol)

[ synthesis example 34] Synthesis of E-2

2-chloro-4-(dibenzo[b,d]furan-4- instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-2 (3.3 g, yield 55%) ) was obtained.

Mass (Theory: 885.00, Measured: 885 g/mol)

[ synthesis example 35] Synthesis of E-3

2-chloro-4-(dibenzo[b,d]furan-3- instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-3 (3.7 g, yield 63%) ) was obtained.

Mass (Theory: 885.00, Measured: 885 g/mol)

[ synthesis example 36] Synthesis of E-4

C2-PC-5 (3.8 g, 6.7 mmol), 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5- under nitrogen stream triazine (3.4 g, 8.0 mmol), Pd(OAc) ₂ (0.15 g, 0.67 mmol), P-( t -bu) ₃ (0.33 ml, 1.34 mmol), NaO t -Bu (1.3 g, 13.4 mmol) and 25 ml of xylene was mixed and stirred at 140°C for 3 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the target compound E-4 (4.2 g, yield 66%).

Mass (Theory: 947.11, Measured: 947 g/mol)

[ synthesis example 37] Synthesis of E-5

2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-5 (2.8 g, yield 52%).

Mass (Theory: 794.92, Measured: 794 g/mol)

[ synthesis example 38] Synthesis of E-6

2-chlorothiochromeno[4,3,2-de]quinazoline ( Except for using 2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 36 was performed to obtain the target compound E-6 (3.8 g, yield 71%).

Mass (Theory: 797.93, Measured: 797 g/mol)

[ synthesis example 39] Synthesis of E-7

2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) instead of 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Except for using, the same procedure as in Synthesis Example 36 was performed to obtain the target compound E-7 (3.8 g, yield 74%).

Mass (Theory: 767.89, Measured: 767 g/mol)

[ synthesis example 40] Synthesis of E-8

2-chloro-4-phenylbenzo[4,5]thieno[ Except for using 3,2-d] pyrimidine (2.4 g, 8.0 mmol), the same procedure as in Synthesis Example 36 was performed to obtain the target compound E-8 (4.0 g, yield 73%).

Mass (Theory: 823.97, Measured: 823 g/mol)

[ synthesis example 41] Synthesis of F-1

Except for using C2-PC-6 instead of C2-PC-2, the same procedure as in Synthesis Example 1 was performed to obtain the target compound F-1 (3.8 g, yield 71%).

Mass (Theory: 793.93, Measured: 793 g/mol)

[ synthesis example 42] Synthesis of F-2

Use C2-PC-6 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound, F-2 (4.0 g, yield 73%).

Mass (Theory: 807.92, Measured: 807 g/mol)

[ synthesis example 43] Synthesis of F-3

Use C2-PC-6 instead of C2-PC-2, 2-chloro-4-(dibenzo[b,d]furan-3- instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound F-3 (4.1 g, yield 75%) ) was obtained.

Mass (Theory: 807.92, Measured: 807 g/mol)

[ synthesis example 44] Synthesis of F-4

Except for using C2-PC-6 instead of C2-PC-2, the same procedure as in Synthesis Example 4 was performed to obtain the target compound F-4 (3.6 g, yield 61%).

Mass (Theory: 870.03, Measured: 870 g/mol)

[ synthesis example 45] Synthesis of F-5

Use C2-PC-6 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound F-5 (3.5 g, yield 72 %) was obtained.

Mass (Theory: 717.84, Measured: 711 g/mol)

[ synthesis example 46] Synthesis of F-6

C2-PC-6 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chlorothiochromeno[4,3,2-de]quinazoline (2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound F-6 (3.6 g, yield 74%). ) was obtained.

Mass (Theory: 720.85, Measured: 720 g/mol)

[ synthesis example 47] Synthesis of F-7

C2-PC-6 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound F-7 (3.6 g, yield 77%).

Mass (Theory: 690.81, Measured: 690 g/mol)

[ synthesis example 48] Synthesis of F-8

C2-PC-6 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (2.4 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound, F- 8 (3.8 g, yield 76%) was obtained.

Mass (Theory: 746.89, Measured: 746 g/mol)

[ synthesis example 49] Synthesis of G-1

Except for using C2-PC-7 instead of C2-PC-2, the same procedure as in Synthesis Example 1 was performed to obtain the target compound G-1 (3.5 g, yield 64%).

Mass (Theory: 820.95, Measured: 820 g/mol)

[ synthesis example 50] Synthesis of G-2

Use C2-PC-7 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound, G-2 (4.0 g, yield 72%).

Mass (Theory: 834.94, Measured: 834 g/mol)

[ synthesis example 51] Synthesis of G-3

Use C2-PC-7 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was followed This was carried out to obtain the target compound, G-3 (4.1 g, yield 73%).

Mass (Theory: 834.94, Measured: 834 g/mol)

[ synthesis example 52] Synthesis of G-4

Except for using C2-PC-7 instead of C2-PC-2, the same procedure as in Synthesis Example 4 was performed to obtain the target compound G-4 (3.8 g, yield 64%).

Mass (Theory: 897.05, Measured: 897 g/mol)

[ synthesis example 53] Synthesis of G-5

Use C2-PC-7 instead of C2-PC-2, and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2- Except for using chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol), the same procedure as in Synthesis Example 1 was performed to obtain the target compound G-5 (3.3 g, yield 66). %) was obtained.

Mass (Theory: 744.86, Measured: 744 g/mol)

[ synthesis example 54] Synthesis of G-6

C2-PC-7 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chlorothiochromeno[4,3,2-de]quinazoline (2.2 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound, G-6 (3.1 g, yield 61%). ) was obtained.

Mass (Theory: 747.87, Measured: 747 g/mol)

[ synthesis example 55] Synthesis of G-7

C2-PC-7 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound G-7 (3.0 g, yield 63%).

Mass (Theory: 717.83, Measured: 717 g/mol)

[ synthesis example 56] Synthesis of G-8

C2-PC-7 is used instead of C2-PC-2, and 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Instead, except for using 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (2.4 g, 8.0 mmol), the same procedure as in Synthesis Example 4 was performed to obtain the target compound, G- 8 (3.5 g, yield 67%) was obtained.

Mass (Theory: 773.91, Measured: 773 g/mol)

[ Example 1 to 35] green organic electric field Fabrication of light emitting device

Compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, E-1 to E-5, F-1 synthesized in the Synthesis Example to F-5 and G-1 to G-5 were subjected to high-purity sublimation purification by a commonly known method, and then a green organic electroluminescent device was manufactured 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 cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes and vacuum evaporator The substrate was transferred to

m-MTDATA (60 nm)/TCTA (80 nm)/ 90% of each compound A-1 to A-5, B-1 to B-5, C-1 to C-5, D on the prepared ITO transparent electrode -1 to D-5, E-1 to E-5, F-1 to F-5, G-1 to G-5 + 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 fabricate an organic electroluminescent device.

[ comparative example 1] Green organic electric field Fabrication of light emitting device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound A-1 as a 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 35 and Comparative Example 1 are as follows.

[ evaluation example One]

For each of the green organic electroluminescent devices manufactured in Examples 1 to 35 and Comparative Example 1, driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. .

Sample host drive voltage
(V) emission peak
(nm) current efficiency
(cd/A) Example 1 A-1 6.77 517 41.3 Example 2 A-2 6.7 515 41.2 Example 3 A-3 6.51 518 41.2 Example 4 A-4 6.77 518 38.9 Example 5 A-5 6.7 515 41.3 Example 6 B-1 6.51 515 41.2 Example 7 B-2 6.77 518 41.3 Example 8 B-3 6.7 515 41.3 Example 9 B-4 6.77 515 41.2 Example 10 B-5 6.7 515 38.9 Example 11 C-1 6.51 518 41.3 Example 12 C-2 6.77 518 41.3 Example 13 C-3 6.7 515 41.2 Example 14 C-4 6.51 515 38.9 Example 15 C-5 6.77 518 41.3 Example 16 D-1 6.7 515 41.3 Example 17 D-2 6.66 518 41.3 Example 18 D-3 6.81 517 41.2 Example 19 D-4 6.68 518 41.2 Example 20 D-5 6.66 518 38.9 Example 21 E-1 6.7 518 41.3 Example 22 E-2 6.7 517 41.3 Example 23 E-3 6.77 518 41.3 Example 24 E-4 6.7 518 41.2 Example 25 E-5 6.51 515 41.3 Example 26 F-1 6.77 515 41.3 Example 27 F-2 6.7 518 41.2 Example 28 F-3 6.51 515 38.9 Example 29 F-4 6.77 515 41.3 Example 30 F-5 6.7 515 42.0 Example 31 G-1 6.66 515 41.3 Example 32 G-2 6.81 515 41.2 Example 33 G-3 6.68 518 41.2 Example 34 G-4 6.5 515 38.9 Example 35 G-5 6.6 515 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, and E-1 synthesized in the Synthesis Example. to E-5, F-1 to F-5, and G-1 to G-5 as a light emitting layer host (Examples 1 to 35) are green organic light emitting devices using conventional CBP as a light emitting layer host. It was found that current efficiency and driving voltage were excellent compared to (Comparative Example 1).

[ Example 36 to 56] red organic electric field Fabrication of light emitting device

Compounds A-6 to A-8, B-6 to B-8, C-6 to C-8, D-6 to D-8, E-6 to E-8, F-6 synthesized in the above Synthesis Example to F-8 and G-6 to G-8 were sublimated to high purity by a commonly known method, and then a red organic electroluminescent device was manufactured 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 cleaned 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-6 to A-8, B-6 to B-8, C-6 to C-8, D -6 to D-8, E-6 to E-8, F-6 to F-8, G-6 to G-8 + 10% of (piq) ₂ Ir(acac) (300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to fabricate an organic electroluminescent device.

[ comparative example 2]

A red organic electroluminescent device was manufactured in the same manner as in Example 36, except that CBP was used instead of Compound A-6 as a host material when forming the light emitting layer.

[ comparative example 3]

A red organic electroluminescent device was manufactured in the same manner as in Example 36, except that Compound I was used instead of Compound A-6 as a host material when forming the light emitting layer.

[ comparative example 4]

A red organic electroluminescent device was manufactured in the same manner as in Example 36, except that Compound II was used instead of Compound A-6 as a host material when forming the light emitting layer.

The structures of (piq) ₂ Ir(acac), Compound I and Compound II used in Examples 36 to 56 and Comparative Examples 2 to 4 are as follows.

[ evaluation example 2]

The driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured for each of the red organic EL devices manufactured in Examples 36 to 56 and Comparative Examples 2 to 4, and the results are shown in Table 2 below.

Sample host driving voltage
(V) current efficiency
(cd/A) Example 36 A-6 4.62 15.2 Example 37 A-7 4.63 13.4 Example 38 A-8 4.81 10.8 Example 39 B-6 4.63 13.2 Example 40 B-7 4.81 11.5 Example 41 B-8 4.81 12.3 Example 42 C-6 4.64 11.9 Example 43 C-7 4.64 12.5 Example 44 C-8 4.53 11.5 Example 45 D-6 4.55 12.3 Example 46 D-7 4.64 11.9 Example 47 D-8 4.87 12.5 Example 48 E-6 4.54 13.2 Example 49 E-7 4.81 11.5 Example 50 E-8 4.81 12.3 Example 51 F-6 4.64 11.9 Example 52 F-7 4.55 12.5 Example 53 F-8 4.64 11.5 Example 54 G-6 4.87 12.5 Example 55 G-7 4.54 13.2 Example 56 G-8 4.81 11.5 Comparative Example 2 CBP 5.25 8.2 Comparative Example 3 Compound I 5.01 10.5 Comparative Example 4 Compound II 5.52 6.8

As shown in Table 2, the compounds A-6 to A-8, B-6 to B-8, C-6 to C-8, D-6 to D-8, E-6 synthesized in the above Synthesis Example. to E-8, F-6 to F-8, and G-6 to G-8 as the light emitting layer host, the red organic electroluminescent device (Examples 36 to 56) uses conventional CBP, Compound I, and Compound II as the light emitting layer host. It was found that the current efficiency and driving voltage were excellent compared to the used red organic light emitting devices (Comparative Examples 2 to 4).

[ Example 57 to 91] blue organic electric field Fabrication of light emitting device

Compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, E-1 to E-5, F-1 synthesized in the Synthesis Example to F-5 and G-1 to G-5 were subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.

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)/95% AND + 5% DS-405 (Doosan Electronics) (30 nm)/ each compound A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, E-1 to E-5, F-1 to F-5, G- 1 to G-5 (5 nm)/Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to prepare an organic electroluminescent device.

[ comparative example 5] Blue organic electric field Fabrication of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 57, except that the electron transport auxiliary layer material was not included and Alq ₃ , the electron transport layer material, was deposited in 30 nm instead of 25 nm.

[ comparative example 6] Blue organic electric field Fabrication of light emitting device

An organic electroluminescent device was manufactured in the same manner as in Example 57, except that BCP was used as the electron transport auxiliary layer material instead of Compound A-1 as the electron transport auxiliary layer material.

The structure of AND used in Examples 57 to 91 and Comparative Examples 5 and 6 is as follows.

[ evaluation example 3]

For each of the blue organic electroluminescent devices prepared in Examples 57 to 91 and Comparative Examples 5 and 6, the driving voltage, current efficiency, emission peak, and lifetime (T ₉₇ ) at a current density of 10 mA/cm 2 were measured, and The results are shown in Table 3 below.

Sample electron transport auxiliary layer drive voltage
(V) current efficiency
(cd/A) emission peak
(nm) life span
(hr, T ₉₇ ) Example 57 A-1 4.3 6.0 459 37 Example 58 A-2 5.3 6.0 459 39 Example 59 A-3 5.3 5.9 459 44 Example 60 A-4 5.1 6.3 459 43 Example 61 A-5 5.2 5.9 459 48 Example 62 B-1 5.2 6.2 459 38 Example 63 B-2 4.3 6.1 459 37 Example 64 B-3 4.3 6.0 459 39 Example 65 B-4 5.3 5.9 451 44 Example 66 B-5 5.1 6.3 459 43 Example 67 C-1 5.3 5.9 459 48 Example 68 C-2 5.2 6.2 459 49 Example 69 C-3 5.0 6.1 459 41 Example 70 C-4 4.8 6.1 462 39 Example 71 C-5 5.1 6.0 463 44 Example 72 D-1 5.0 6.0 460 43 Example 73 D-2 4.8 6.0 459 48 Example 74 D-3 5.0 6.0 459 49 Example 75 D-4 5.3 6.0 459 41 Example 76 D-5 5.3 5.9 459 42 Example 77 E-1 5.2 6.2 451 47 Example 78 E-2 4.3 6.1 459 43 Example 79 E-3 4.3 6.1 451 48 Example 80 E-4 5.3 6.0 469 43 Example 81 E-5 5.1 6.0 461 48 Example 82 F-1 5.3 6.0 461 49 Example 83 F-2 5.2 6.0 459 41 Example 84 F-3 5.0 6.2 451 42 Example 85 F-4 4.8 6.1 469 47 Example 86 F-5 5.1 6.0 461 47 Example 87 G-1 4.8 5.9 451 43 Example 88 G-2 5.1 6.2 459 48 Example 89 G-3 5.0 6.1 451 43 Example 90 G-4 4.8 6.1 469 48 Example 91 G-5 5.0 6.0 461 49 Comparative Example 5 - 4.8 6.0 461 49 Comparative Example 6 BCP 5.3 5.9 458 28

As shown in Table 3, the compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, and E-1 synthesized in the Synthesis Example. to E-5, F-1 to F-5, and G-1 to G-5 as electron transport auxiliary layer materials (Examples 57 to 91) using no electron transport auxiliary layer material. It was found that current efficiency and lifespan were greatly improved compared to the blue organic light emitting device (Comparative Example 5).

In addition, the blue organic electroluminescent device (Examples 57 to 91) has excellent driving voltage and current efficiency compared to the conventional blue organic electroluminescent device using CBP as an electron transport auxiliary layer material (Comparative Example 6), and life span. It was found that this markedly improved.

[ Example 92 to 98] blue organic electric field Fabrication of light emitting device

Compounds A-4, B-4, C-4, D-4, E-4, F-4, and G-4 synthesized in Synthesis Example were subjected to high-purity sublimation purification by a commonly known method, as follows. A blue organic electroluminescent device was fabricated.

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)/95% AND + 5% DS-405 (Doosan Electronics) (30 nm)/Compound A- 4, B-4, C-4, D-4, E-4, F-4, G-4 (30 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to form an organic electroluminescent device. produced.

[ comparative example 7]

A blue organic electroluminescent device was fabricated in the same manner as in Example 92, except that Compound A-4 was not used as the electron transport layer material.

[ evaluation example 4]

Driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured for each of the blue organic electroluminescent devices prepared in Examples 92 to 98 and Comparative Example 7, and the results are shown in Table 4 below. .

Sample electron transport layer drive voltage
(V) current efficiency
(cd/A) emission peak
(nm) Example 92 A-4 4.7 5.7 461 Example 93 B-4 4.2 6.0 457 Example 94 C-4 4.7 5.8 457 Example 95 D-4 4.2 5.8 457 Example 96 E-4 4.2 5.8 461 Example 97 F-4 4.2 5.8 461 Example 98 G-4 4.3 5.7 463 Comparative Example 7 _ 4.7 5.6 458

As shown in Table 4, the blue organic field using the compounds A-4, B-4, C-4, D-4, E-4, F-4, G-4 synthesized in the above Synthesis Example for the electron transport layer It was found that the driving voltage and current efficiency of the light emitting devices (Examples 92 to 98) were further improved compared to the blue organic light emitting device (Comparative Example 7) without using the electron transport layer material.

As such, when the compound according to the present invention is used as an electron transport auxiliary layer material and an electron transport layer material as well as the light emitting layer material (host material), it was confirmed that the driving voltage and current efficiency are improved, and furthermore, the lifetime characteristics are greatly improved. .

Claims (8)

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

In Formula 1,
A is a 6-membered aromatic ring or a 6-membered heteroaromatic ring;
X ₁ to X ₄ are the same as or different from each other, and are each independently N or C(R ₁ ), at least one of which is C(R ₁ ),
R ₁ is hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group , C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ It is selected from the group consisting of an arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent group to form a condensed ring, wherein R ₁ is plural, they are the same as or different from each other,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, or may form a condensed ring with an adjacent group, ,
An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron of the above R ₁ , Ar ₁ and Ar ₂ Group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ arylamine group to be substituted with one or more substituents selected from the group consisting of In this case, when the substituents are plural, they may be the same as or different from each other,
B is a substituent represented by Formula 8 below,
[Formula 8]

In Formula 8,
* means a part bonded to Formula 1,
Y ₁ to Y ₅ are the same as or different from each other, and are each independently N or C(R ₂ ), wherein, when R ₂ is plural, they are the same as or different from each other;
R ₂ is hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ It is selected from the group consisting of an arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or may form a condensed ring with an adjacent group,
An _alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, Arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy Group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ may be substituted with one or more substituents selected from the group consisting of an arylamine group, wherein the substituent When is plural, they may be the same as or different from each other. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 2 to 7 below.
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 2 to 7,
B, X ₁ to X ₄ , Ar ₁ and Ar ₂ are as defined in claim 1. delete According to claim 1,
The substituent represented by Formula 8 is a compound represented by any one of the substituents represented by Formulas A1 to A15.

In the above formulas A1 to A15,
R ₂ is as defined in claim 1;
m is an integer from 0 to 4;
R ₃ is hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ It is selected from the group consisting of an arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or may form a condensed ring with an adjacent group,
An _alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, Arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy Group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ may be substituted with one or more substituents selected from the group consisting of an arylamine 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 C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ ~ C ₆₀ Aryloxy group, C ₆ ~ C ₆₀ arylsilyl group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C A compound selected from the group consisting of ₆₀ arylamine groups. Including an anode, a cathode and one or more organic material layers interposed between the anode and the cathode,
An organic electroluminescent device in which at least one of the one or more organic material layers contains the compound according to any one of claims 1, 2, and 4 to 5. According to claim 6,
An organic electroluminescent device wherein the organic material layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. According to claim 7,
The organic material layer containing the compound is a phosphorescent light emitting layer, an electron transport auxiliary layer or an electron transport layer organic electroluminescent device.